Vacation rentals in Okatie, SC with a pool

Explore 24 vacation rentals, homes, and villas with pools in Okatie, SC for your next getaway or business trip. Step outside to your own private or shared pool and into a home filled with premium amenities such as Air Condition Homes, Best Affordable Homes and Great for Groups. Throughout your stay, unwind poolside, soak up the sun, and enjoy an outdoor space designed for relaxation. With options starting as low as $58 per night and homes offering up to 8 bedrooms and 9 bathrooms, it's easy to book a comfortable, personalized stay. You'll also have access to high-speed Wi-Fi and 24/7 local support, creating a more secure, connected atmosphere for your trip. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, so each trip's more rewarding than the last. Book your next poolside escape with Homes & Villas by Marriott.

24 Homes with Pools in Okatie

Poolside Patio & Gourmet Kitchen: Bluffton Getaway

Bluffton, SC, US
4 Bedrooms 10 Guests
Aug 26 - 28
$468 night

9 Mi to Hilton Head | Kid-Friendly Amenities | Near Golfing, Swimming & Beachcombing Welcome to ‘Palmetto Breeze Retreat’ — an elevated coastal estate crafted for unforgettable family moments. This Bluffton vacation rental is where cannonballs meet cookouts and family time takes center stage. Explore sandy shores, browse charming shops, or tee up on a local course. After, gather everyone for a night swim under the starry Lowcountry sky. One more splash, one more story, one perfect getaway. -- THE PROPERTY -- SLEEPING ARRANGEMENTS- Bedroom 1: 1 king bed- Bedroom 2: 1 king bed- Bedroom 3: 1 queen bed- Bedroom 4: 2 twin beds- Living Room: 1 queen sleeper sofa INDOOR LIVING- 6 Smart TVs- Dining table, breakfast bar- Walk-in closets- Multiple living spaces OUTDOOR LIVING- Screened-in porch w/ seating- Private pool (heated w/ fee)- Gas grill- Dining table- Fenced-in yard w/ lounging chairs KITCHEN- Refrigerator, microwave, stove/oven, dishwasher, air fryer, pressure cooker, rice cooker, blender, toaster- Drip & Keurig coffee makers (coffee provided)- Cooking basics, dishware/flatware GENERAL- Free WiFi- Central A/C & heating, ceiling fans- Linens & towels, trash bags & paper towels- Complimentary toiletries, hair dryer- Washer/dryer, laundry detergent, hangers, iron/board- High chair & stroller- 2 Additional pack & play FAQ- Quiet hours (10:00 PM-8:00 AM)- 2 exterior security cameras (outward facing)- Optional nightly pool heat fee (paid pre-trip, applied to entire stay) ACCESSIBILITY- 2-story home, 1 small step required to enter- 1st-floor bedroom & full bathroom PARKING- Garage (2 vehicles)- Driveway (2 vehicles)- No street parking -- THE LOCATION -- - Near local restaurants & essential shopping- Easy access to family-friendly attractions- 3 miles to Crescent Pointe Golf Club & 5 miles to Hilton Head National Golf Club- 5 miles to Tanger Outlets- 5 miles to Alljoy Beach, 14 miles to Folly Field Beach Park & 17 miles to Coligny Beach Park- 17 miles to Savannah National Wildlife Refuge- 19 miles to Harbour Town Lighthouse- 25 miles to Downtown Savannah- 27 miles to Savannah/Hilton Head International Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking- No pets allowed- No events, parties, or large gatherings- Additional fees and taxes may apply- Photo ID may be required upon check-in- Please observe quiet hours from 10:00 PM to 8:00 AM ADDITIONAL INFORMATION- There is an optional pool heat fee of $35/night (+ fees & taxes, paid pre-trip, applied to entire stay)- This 2-story home requires 1 small step to enter; it features a bedroom and a full bathroom on the 1st floor- Your safety matters. This property features 2 exterior security cameras. Camera 1 is a Ring doorbell camera at the front door facing the entryway, and camera 2 is above the garage facing the driveway. The cameras do not look into any interior spaces. They record video and audio when motion is detected

Grand Palm

Bluffton, SC, US
5 Bedrooms 12 Guests
Aug 26 - 28
$1,662 night

The Grand Palm – Luxurious Marsh-Front Estate in the Heart of Moreland Village Perfectly situated along the serene marsh in Palmetto Bluff’s coveted Moreland Village, The Grand Palm is a spectacular 5-bedroom, 5.5-bathroom estate with a detached carriage house, private pool and hot tub, and sweeping views of the Lowcountry waterways. Thoughtfully designed for families and groups seeking a peaceful escape with elevated comfort, this home blends classic Southern style with modern luxury—making it the ultimate destination for relaxation, connection, and outdoor adventure. Refined Indoor Living • Open-concept great room with soaring ceilings, gas fireplace, and curated designer furnishings • Gourmet chef’s kitchen with high-end appliances, large center island, and walk-in pantry • Formal dining area plus casual bar seating—perfect for entertaining Bedrooms – Sleeps 12 Comfortably Main Level • Primary Suite – KING bed, sitting room with porch access, dual closets, spa-like ensuite with steam shower and soaking tub Second Level • Bedroom 2 – KING bed with private ensuite bath • Bedroom 3 – QUEEN bed with private ensuite bath • Bedroom 4 – QUEEN bed with Jack & Jill bath (shared with Bunk Room) + Bonus Loft Lounge – Cozy upstairs den with Smart TV, perfect for movie nights or game time • Bedroom 5 / Bunk Room – Built-in TWIN bunk beds (sleeps 2), shares bath with Carriage House – Private Guest Retreat • Bedroom 6 – QUEEN bed, living area, full kitchenette, and private ensuite bath—ideal for grandparents or guests seeking added privacy Outdoor Amenities & Marsh-Front Serenity • Expansive screened porch with lounge seating, fireplace, dining area, and direct marsh views • Private pool and hot tub with sun shelf, surrounded by comfortable outdoor seating and wood-burning fireplace • Outdoor shower for rinsing off after a day on the water or evening under the stars • Professionally landscaped backyard with marsh-front ambiance • Bike path access to Moreland and Wilson Village Location Highlights • Walk or bike to Moreland Landing, the Moreland Treehouse, Cole’s Restaurant, The Canteen, and Lake Bales • Steps from fishing, crabbing, kayaking, and boat access at the Moreland Dock • Just 4 miles to Wilson Village for shopping, dining, golf, nightly s’mores, and spa services • Quick access to Palmetto Bluff’s extensive trail system, ideal for biking and exploration • Inquire about golf cart and bike rentals for effortless access to all resort amenities Whether you’re savoring marsh front sunrises, enjoying poolside cocktails, or gathering fireside with loved ones, The Grand Palm is the ultimate setting for an unforgettable Lowcountry escape. Elegant yet approachable, expansive yet cozy, this stunning retreat truly has it all. Modern Amenities • High-speed Wi-Fi • Sonos sound system and Smart TVs throughout • Full-size washer/dryer • Central A/C & heating • Luxury linens, towels, hair dryers & starter amenities • Golf cart-friendly community WHAT’S INCLUDED IF I RESERVE YOUR HOME? MORE THAN YOU’D EXPECT! When you book your stay, you’ll enjoy access to many exclusive Palmetto Bluff Club amenities! ***Only exception is the Blackout Dates for Memorial Day Weekend & July Fourth Weekend!! These blackouts dates are controlled by the Palmetto Bluff Club and are subject to change at their discretion. Club Access & Resort Registration A $30 daily resort fee registers you with the Palmetto Bluff Club (registration opens 30 days before arrival). Fee collected at the time of booking. Once registered, you’ll receive an access card packet upon arrival (at front gate). Use of club pools is $25 per person, per day (children 5 and under are free). Only pay for days when you use the facilities. One fee covers use at multiple pools being used in same day. Payment is taken by Pool Attendant at the time you enter pool. Included Club Amenities Canoe Club Pool: Baby pool, kids’ pool, and large family pool Moreland Pool: Family pool + adults-only junior Olympic lap pool Two Fitness Centers: Canoe Club & Moreland Dining Reservations: Canoe Club & Cole’s (based on availability)….speak with our team for a full list!! Wilson Lawn & Racquet Club: Pickleball, tennis, bocce, and croquet. Check-In at Pro-Shop before playing & pay required fees. Our team can secure your court time prior to your arrival. Golf Access…..Our team will secure your desired tee-times. Check with our team for details. May River Golf Course (book 30 days in advance) Crossroads 9-Hole Course (book 15 days in advance) Guest & Concierge Services Available • Our Guest Services Team is here to support you with everything from booking inquiries and home-specific details to access information and any troubleshooting that may arise during your stay. • Looking to elevate your experience? Our Concierge Team is ready to curate a stay you’ll remember for years to come. Whether you’d like the fridge stocked before arrival, golf cart and/or bikes waiting, dinner reservations secured, or even a private chef or mixologist — we’ve got you covered. Let us take care of the details so you can focus on relaxing and making memories. Our team can handle just about any request to help you elevate your stay!! Make the most of your trip with our premium, personalized services: Custom Trip Planning (start to finish) Golf Cart and/or Bike Rentals Dinner, tee time, and excursion reservations Private chef services In-home spa treatments Water taxis to Savannah or Hilton Head Pre-arrival grocery stocking Daily or mid-stay housekeeping Airport transfers Babysitting services Baby gear rentals (cribs, highchairs, Burleys, etc.) Specialty concierge packages (S’mores Kits, charcuterie boards, holiday kits, and more) Good to Know • Minimum rental age is 25 • Optional trip insurance is available through Rental Guardian—we recommend it, especially during hurricane season (June–November) • Check-In 3:00 p.m. / Check-Out 10:00 a.m. • 50% of Total Balance Due at Booking; Final Balance Due 30 Days Prior to Arrival • If you are Booking within 30 days of your arrival, 100% is due at the time of Booking • Family-friendly (No parties or events allowed) • No smoking and NO Pets Optional Fees • Early Check-in $75/hour / Late Check-out $75/hour (subject to availability)

Marsh view Harbour Town condo with shared pool, close to shops & restaurants

Hilton Head, SC, US
1 Bedrooms 4 Guests
Aug 31 - Sep 2
$68 night

Stoney Creek 268 Stoney Creek Villa 268 offers a scenic marsh view and is just a short walk from the many shops and restaurants of Harbour Town. This cozy loft-style condo, ideal for a small family or couples retreat, features a well-equipped kitchen, dining area with seating for four, and a living room with access out to a private, furnished patio. And when it’s time to cool off, this complex offers a large, shared swimming pool. This Sea Pines vacation rental is located near the Harbour Town Links Golf Course, home of the famed RBC Heritage tournament, with convenient access to waterfront shopping and dining. Additional resort activities include trail rides through Lawton Stables, marina activities at Harbour Town or South Beach , dining, shopping, kayak rentals, and miles of bike paths. Whether you’re looking for the ideal golf getaway or a family fun vacation spot, Lighthouse Villas 1082 is the ideal choice for everyone. <b>RESORT AMENITY</b> -Pool This property’s license number is 26811. <b>THINGS TO KNOW</b> *Phase 2 of the Lighthouse Lane Infrastructure Improvement Project is scheduled to begin in early May 2025, and is estimated to continue through June 2025. Planned work will be conducted Monday-Friday from 7:00 AM to 7:00 PM, excluding major holidays. Weekend and overnight work may be necessary but will be communicated in advance. Heavy machinery and construction vehicles will be traveling to and from the project site. Single-lane road closures and flagging operations will be in place daily, weather permitting. Temporary full lane closures may be required at times. Motorists should expect traffic delays, traffic detours, and be prepared to share the road with bike riders and pedestrians. Sidewalks in the project area will be closed as needed. Pedestrians and bike riders should expect delays and be prepared to stop and follow detours. For safety, bike riders will be required to dismount and walk bikes around the active work zones. Please also note that Harbourtown golf course will be closed from May 10th through mid November for maintenance. Please be aware that the Plantations and Condominium Complexes do not allow trailers, motor homes, motorcycles and/or recreational vehicles and rooftop cargo (i.e. Kayaks, Canoes etc.) other than car top Carriers. Electric bikes are not permitted in the Plantations. License number: 026811,26811

44 Stoney Creek: Sea Pines

Hilton Head Island, SC, US
3 Bedrooms 7 Guests
Sep 12 - 15
$534 night

Welcome to the BESTNEST at 44 Stoney Creek in Sea Pines. Here’s the skinny - just buzz us for more details: Our advertised rates are our very best rates and calendar shows real time availability. We encourage you to book online! • Super stylish, 3 BR/3 BA home, fully renovated and featuring open living plan, all on one level • Each of 3 bedrooms has en suite bath (1 King, 1 King, and 1 Queen + 1 Twin) • Heatable pool with serene lagoon and golf views plus custom evening lightscaping for optimum outdoor ambiance • Circular drive with lots of parking space • Weber gas grill - ready for grilling out! • Password protected WiFi • 4 LED televisions What’s in a BESTNEST: • Our hallmark? CLEANLINESS! Yes, we’re shouting it out and so are our guests- just read our reviews. • Linens: Ahhhhh, yes! Completely comfortable, all cotton bed and bath linens including extra blankets and clean and comfy sleeping pillows, and clean kitchen linens. • Always provided in every BESTNEST in quantity for your stay: beach chairs/umbrellas/sand toys/beach cart, beach towels, a supremely equipped kitchen (in quality and quantity), hand soap, dish soap, kitchen sponges, trash bags, paper towels, tissues and toilet paper, your favorite hair dryer ever, fragrance 350 laundry soap and dryer sheets, ziploc bags, coffee filters, cleaning supplies, loads of quality coat and skirt hangers, and a few surprises. • Always courteous, knowledgeable, and professional, 24/7 guest service. • Allow us to amaze you, again and again. Our FAQ: HOW FAR TO BEACH: Quick drive to the Beach Club in 3 minutes, or to the seasonal Beach Trolley lot. Please read on: BEACH CLUB ACCESS/PARKING Onsite parking AT the Beach Club is permitted for all overnight guests, Labor Day-mid March. From Mid March through end of summer, special Beach Trolleys transport guests from various parking spots within Sea Pines to the Beach Club. Closest Beach Trolley location is at Greenwood Drive and Willow Oak, just off the Fraser Circle. DAY AFTER LABOR DAY THROUGH MARCH, EVERYONE MAY PARK AT THE BEACH CLUB. POOL: Heatable with electricity (cost effective, but ineffective in coldest months of the year). Charge for electric pool heat is  $150.00 for the first day and $50.00 each additional day during March - May and September - November. This charge is non-taxable and non-refundable. ABOUT US: We are proud to have developed a niche concept in vacation rentals on Hilton Head Island: Each and every BESTNEST is outfitted and equipped to exactly the same high standard, no matter the address. Nothing quite compares to a BESTNEST. STR Permit Number: 026999

Amazing Views w/ Private Pool & Amenities

Hilton Head Island, SC, US
3 Bedrooms 8 Guests
Aug 29 - Sep 1
$498 night

30 Stoney Creek Road | Harbour Town Home With Golf View *3 Bedrooms | 3 Full Bathrooms *Sleeps 8 *2 Kings, 2 Fulls *4 TV’s Including 65" SMART TV in LR | Alexa | Wi-Fi *Ceiling Fans in All Rooms *Hair Dryers and Amenities in Each Bathroom *Gas Grill with Spare Propane Tanks *Keurig, Drip Coffee Maker, Toaster, Blender, Mixer and Chopper *View of the Heron Point Golf Course *Large Private Rear Deck for Outdoor Dining *Walk to Harbour Town Marina for Restaurants, Shops and Entertainment *Private Pool {12’ x 20’} with Tiered Deck, Lounge Chairs, and Pool Toys *8 Beach Towels *8 Beach Chairs *4 Adult Bicycles, 2 Kids Bicycles, 1 Tandem and 1 Adult Tricycle *Highchair, Pack & Play Available for Guest Use *Enjoy Daily Rounds of Golf & Children’s Activities with this Home *Beach Gear Credits Included *Guests Have Use of Garage *Point Central Keyless Entry *Access to the Sea Pines Trolley (seasonal) Located in the prestigious Sea Pines Resort on Hilton Head Island, 30 Stoney Creek is a ranch-style residence within easy walking distance of Harbour Town’s iconic lighthouse, diverse shops, fine dining options, and marina. The property boasts a sunlit front pool area surrounded by potted plants and a privacy fence. Featuring a multi-level deck furnished with six chairs, side tables, and a lounge chair, this serene outdoor space offers a peaceful setting for relaxing poolside with family and friends! WOW! That’s what you’ll say as you walk through the front door! You will immediately be captivated by the expansive open floor plan and the stunning panoramic view of the par 5 eleventh hole at Heron Point Golf Course. This home boasts elegant planked flooring, a soaring 20-foot-high vaulted ceiling, and an extensive wall of sliding doors that enhance the bright and spacious living area. The dining space seamlessly connects to both the kitchen and great room. It features a dining table suitable for eight guests, complemented by a wet bar equipped with a sink and wine refrigerator. The adjacent living room offers plush seating with two sofas and three rocking chairs, alongside a 65-inch SMART TV for your entertainment. These areas directly access the private deck through sliding doors where one can relax with incredible views of the golf course. Out on the secluded, back deck are six rocker chairs with a six-foot round glass-topped table with additional seating options next to a Char-Broil gas grill—ideal for al fresco dining while enjoying live action from nearby golfers aiming for the green. This home promises not only outstanding views but also an ambiance perfect for relaxation or hosting gatherings in style. The kitchen is fully outfitted with modern amenities, including stainless-steel appliances. It boasts a full selection of cookware and serving ware, along with all essential staples and supplies provided for your convenience. Seating includes four leather stools at the island and three additional pub chairs at the bar, creating an ideal setup for enjoying casual meals or snacks while admiring the view of the pool through expansive floor-to-ceiling windows. The master suite, positioned in the secluded rear corner of the residence, boasts a king-sized bed with picturesque views of the golf course. It features an expansive walk-in closet, direct access to a private deck, and has a 44" Smart TV alongside a large bureau and a cozy reading chair. The ensuite bathroom has a spacious walk-in shower with bench seating beneath overhead skylights, full length vanity and toilet closet. Adjacent to the living room is the second guest bedroom which also offers another king-sized bed. This room benefits from natural light through sliding doors that open onto the back patio and includes amenities such as a 44” Smart TV and its own private bathroom equipped with another walk-in shower. The third bedroom features two full beds, windows that overlook the swimming pool area along with entertainment provided via a 27’’ TV. Conveniently located next door is an additional bathroom outfitted with both tub and shower facilities, ensuring adequate amenities for all guests of this spacious home. Enjoy all of the amenities provided by the owner including 4 Adult Bicycles, 2 Kids Bicycles, 1 Tandem and 1 Adult Tricycle, beach chairs, beach towels pool toys and floats! Walk or ride your bike to the island’s famous candy-striped lighthouse, the Harbour Town Yacht Basin, the beach at Sea Pines, the Liberty Oak, Harbour Town Golf Links, and countless boutique shops and award-winning restaurants. With a variety of events throughout the year, like The Gregg Russell Family Concerts and the Shrimp Festival, this fun area offers something for everyone. Book your stay today! * Summer Rentals Sat. to Sat. (Weekly only) * September to May: 4 night minimum * Heritage Week 7 night minimum * Additional Charge to Heat the Pool * Pool Size 12’ x 20’ {If the outside temperature is colder than 55 degrees, the pool may not be able to maintain a warmer temperature. If the pool or spa does not reach the desired temperature but is still warming, refunds will NOT be given} *Property May Be Monitored by Exterior Security Cameras *Town of Hilton Head Permit #070280

Harbor Town Golf Views

Hilton Head Island, SC, US
4 Bedrooms 10 Guests
Aug 29 - Sep 2
$478 night

"This four-bedroom, three-bathroom home is located on the 16th fairway of the Harbor Town Golf Course in Sea Pines with views of the 16th green, 17th tee box, and the Calibogue Sound. In the front of the home, there is a private courtyard that leads to the front door entrance. Walking through the French doors you will notice the nautical themed living area just down the hall. The living area consists of the dining room with seating for six, breakfast table with seating for four, and living room with wet bar, TV, and panoramic views of the golf course. From the living area, you can enter the kitchen which has plenty of counter space and storage. The kitchen is equipped with cabinets, countertops, and appliances. Beyond the kitchen is the laundry room which has a washer and dryer and access to the car port. Continuing the first floor you will find the master bathroom. The bathroom has granite countertops, his and her sinks, and a walk-in shower with a bench. The master bedroom is the perfect retreat to relax and has just been updated with a King-sized bed. It has a walk-in closet, a flat-screen TV, and a private sun deck that connects to the back deck. The second floor has three bedrooms. The first bedroom has twin beds with a full bath and granite countertops. The next bedroom has a queen bed with a flat-screen TV and a walk-in closet. Connecting this room to the last bedroom is a shared bathroom with granite countertops and a large sink. Finally, we have the third bedroom. This room has not one but two queen beds with a beautiful private sun porch looking out onto the golf course and sound. As you walk outside the back deck of this home gives you the ultimate Hilton Head experience! A petite pool is in the middle of the large sun deck complete with seating for the whole family and the incredible view of the 16th and 17th of the famous Harbor Town Golf Course. While enjoying the pool and view you can also cookout on the grill and dine at the outdoor table with seating up to six. This home has a coastal flair with a touch of nautical elegance. First Floor Bedroom 1: 1 King (private bath) Second Floor Bedroom 2: 2 Twins (private bath) Bedroom 3: 1 Queen (shared bath) Bedroom 4: 2 Queens (shared bath) - Additional Features ~ Square Footage: 2,950 ~ Pool size: 6.5x15 ~ Parking Spaces: 3 ~ Pool Heat – N/A ~ Neighborhood: Sea Pines Distances ~ Beach: 2.1 mi ~ Coligny: 4.9 mi ~ Harbor Town: 0.8 mi ~ South Beach: 4.1 mi ~ Shelter Cove: 6.9 mi **Sea Pines Rules and Regulations** -Sea Pines Plantation prohibits all trailers, pop-up campers, motorcycles (including three wheelers), large-lifted pickup trucks, extended vans, vans with company signage (visitors in company cars will not be allowed in), work vans, golf carts, and RVs. Boats (prior permission needed), kayaks & surf boards (must be on top of car, no trailer), and large family vans. The only exception would be handicap accessible vans. -Parking along roadsides and off driveways is prohibited -Beach Club parking is not available, the Trolley system must be used to access the beach club. Trolley system does not allow passengers to carry large items such as wagons, chairs or coolers -Vehicle Passes are limited to number of cars able to fit in each driveway, Passes are required to reenter Sea Pines when on a bike, in some cabs, and using Lyft. Try to carry your passes with you when you leave for reentry to avoid any difficult situations at the gate. Bikes can reenter without pass if they take picture of the daily door code posted when they exit. -All animals in the plantation must be on a leash at all times -Do not disturb the wildlife. Wild Animals live in Sea Pines, such as alligators and coyotes. Please be aware of this and do not interact with the wildlife. -Beach parking is prohibited on all roads in Sea Pines. A complimentary beach shuttle service, direct from a designated parking lot to The Sea Pines Beach Club is available for Sea Pines weekly rental guests. *Must have Short Term Weekly vehicle pass issued by Sea Pines CSA." HH STR Permit #27718 Licence number: 27718

Delightful getaway with golf course views, private pool, and high-speed WiFi

Hilton Head, SC, US
4 Bedrooms 9 Guests
Aug 30 - Sep 1
$190 night

Mizzenmast Court 5 Perched on the 16th hole of Harbour Town Golf Links, this island home will be just the place to kick back and watch the golfers pass by each morning with a cup of coffee on the private deck! The beach is just a short trolley ride away, yet you won’t have to leave home base to escape the heat, as you have a private pool right outside to take a quick dip or tan in bliss with a good book. Inside, you will be spoiled by the bright interior, high-end furnishings, and free high-speed WiFi. The open layout of the second floor is perfect for entertaining with a well-equipped kitchen, breakfast bar seating to make meal prep a social event, a wonderful dining area, and a spacious living room complete with a large TV and plush sectional. One bedroom is located on this floor and the other three are on the lower floor, so privacy will be easy to come by. This property’s license number is 27197. <b>Things to Know</b> Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. Free trolley to beach All guests shall abide by The Good Neighbor Policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m. No smoking is permitted anywhere on the premises. Please note E-bikes are not allowed. Please be aware that the Plantations and Condominium Complexes do not allow trailers, motor homes, motorcycles and/or recreational vehicles and rooftop cargo (i.e. Kayaks, Canoes etc.) other than car top Carriers. Electric bikes are not permitted in the Plantations. License number: 27197,027197

1 Buck Island

Hilton Head , SC, US
8 Bedrooms 26 Guests
Aug 26 - 29
$3,500 night

YOUR PRIVATE SANCTUARY AWAITS. Welcome to Buck Island—your 10-acre private island retreat, just a heartbeat off Hilton Head’s legendary coast. This isn’t a vacation. This is an exclusive hideaway over your own Lowcountry Private Island —a escape of wild beauty and barefoot luxury where the outside world disappears, and only your guest list matters. For a few unforgettable days, the entire island is yours. WHERE SECLUSION MEETS CONVENIENCE. Only minutes from Hilton Head’s championship golf, five-star dining, and Harbour Town’s iconic lighthouse—yet worlds apart. ARRIVAL IS PURE VIP. Your private boat captain will meet you and in 5–10 minutes, you’ll glide across the Intracoastal to your personal pier. We’ll arrange your private boat rental, from pontoons to yachts, ready and waiting whenever adventure calls. SECLUSION IS ABSOLUTE. ACCESS IS EFFORTLESS. The Island is the experience. Outside, the island itself becomes your playground. An infinity-edge pool that melts into the marsh horizon. A hot tub beneath ancient live oaks, where Spanish moss sways in the salt breeze. Expansive decks perfect for 100+ guest soirées or intimate candlelit dinners. Hidden hammocks and fire pits tucked among palms and pines. Secret trails where dolphins breach at sunset and the night hums with coastal magic. Whether it’s a milestone celebration, corporate retreat, or once-in-a-lifetime family gathering, Buck Island transforms ordinary escapes into iconic memories. Reserve your dates before this ultra-exclusive retreat vanishes into another family’s legend. THE RESIDENCES — TWO HOMES. ONE ESCAPE. The Main House: A statement in coastal architecture, the Main House welcomes up to 10 guests across five ultra-luxe master suites—each a private sanctuary of comfort and style. Five King Suites, each with spa-caliber ensuites. Floor-to-ceiling windows framing endless Atlantic views. Expansive common areas for dining, entertaining, or simply exhaling. Options for additional guests with air mattresses or flexible configurations. Every detail whispers understated elegance—from handcrafted furnishings to breezy, sunlit spaces that make the outside world melt away. The Guest House: Where luxury meets adventure. The Guest House is a sprawling retreat built for togetherness—perfect for large families, retreats, or groups ready to make memories that stretch late into the night. Six beds across bunks, queens, and private nooks. Expansive great room designed for storytelling and laughter. Wraparound porch for sunrise coffee and evening cocktails. Fully equipped kitchen and communal dining for group feasts. Here, every corner invites connection—sunlight, salt air, and the sound of laughter rolling across the water. JUST OUTSIDE YOUR DOOR, THE ADVENTURE CONTINUES. Infinity Pool & Hot Tub — soak, swim, and savor the view. Outdoor lounges & decks perfect for events, yoga, or weddings. Fire pits, hammocks & secret trails for moments of solitude or celebration. Private dock & water access for boating, kayaking, and paddleboarding. Every sunrise writes a new chapter. Every sunset seals a memory. YOUR ISLAND, YOUR RULES. Whether you’re hosting a once-in-a-lifetime wedding, a corporate leadership retreat, or an unforgettable family reunion, Buck Island adapts to your vision. We provide seamless concierge coordination—chef experiences, excursions, watercraft rentals, event setup, and daily housekeeping—so you can stay fully present in paradise. Because here, luxury isn’t about service. It’s about sovereignty. THERE ARE PRIVATE ISLANDS - AND THEN THERE’S BUCK ISLAND. Ten acres of Lowcountry paradise. Two homes. Infinite memories. Reserve your stay. Because some places aren’t meant to be visited. PLAN YOUR STAY — THE ART OF ISLAND LIVING. Where every moment is tailored to you. At Buck Island, your stay begins long before you arrive. From the moment your reservation is confirmed, our dedicated island concierge team curates every detail to your preferences—ensuring your retreat feels less like a rental, and more like a homecoming to paradise. Whether you’re arriving for a grand family gathering, an executive retreat, or a once-in-a-lifetime celebration, we handle every touchpoint—from dockside champagne welcomes to private chef dinners. Your only task? Decide how much—or how little—you want to do. CULINARY EXPERIENCES. Food is the soul of any great gathering, and at Buck Island, every meal can become a memory. Private Chef Services: Savor five-course Lowcountry dinners, oyster roasts, or tasting menus designed around your tastes. Dockside Dining: Fresh-caught seafood prepared at sunset, served steps from your private pier. Family-Style Feasts: Perfect for reunions—lowcountry boils, BBQs, and beach picnics with every detail handled. On-Island Bar Service: Curated wine lists, craft cocktails, and signature island mixers—because paradise pairs best with a drink in hand. From casual brunches to black-tie banquets, our culinary partners deliver the finest in local and international cuisine. ADVENTURE, WELLNESS & LEISURE. Whether you crave adrenaline or serenity, Buck Island bends to your rhythm. On the Water: Charter a private fishing yacht, sailing excursion, or sunset cruise. Explore the Intracoastal on kayaks and paddleboards, available daily. Arrange dolphin tours or guided eco-adventures through the marshlands. On the Island: Begin your mornings with private yoga sessions on the deck. Book in-villa massages and wellness treatments beneath swaying palms. Enjoy beach games, pickleball, and outdoor movie nights under the stars. Beyond the Island: Tee off at Hilton Head’s world-class championship golf courses. Explore historic Bluffton, Harbour Town shopping, or Savannah’s charm just a short drive away. We’ll coordinate every reservation, every transfer, and every surprise detail—so spontaneity feels seamless. EVENTS & CELEBRATIONS. Some moments deserve an unforgettable setting. Buck Island has hosted everything from intimate elopements to full-scale, 100+ guest soirées. With vast decks, open-air lounges, and cinematic backdrops in every direction, your event is limited only by imagination. Our concierge team partners with elite event planners, photographers, and caterers to orchestrate: Weddings & Vow Renewals Corporate Retreats & Executive Offsite Milestone Birthdays & Anniversaries Luxury Brand Retreats & Private Concerts Every celebration here feels cinematic. Because it is. You’re never more than ten minutes from civilization—but you’ll feel a world away. Your private captain will ferry you to and from Harbour Town Marina as often as you wish, with daily shuttles included. Prefer total control? We’ll arrange a private pontoon, yacht, or center-console vessel exclusively for your party—ready whenever you are. On arrival, you’ll be greeted dockside with a chilled welcome beverage, and a guided island tour before settling in. During your stay, our discreet staff is on call 24/7—visible only when needed, invisible when not. Luxury here means freedom. Privacy. Space to breathe. YOUR LOWCOUNTRY LEGACY AWAITS. Buck Island is more than a destination—it’s an experience that becomes family legend. The kind of place your guests will talk about for years, and your heart will never quite leave. So go ahead—host the reunion, plan the retreat, celebrate the milestone. Or simply disappear for a week and live untethered, barefoot, and beyond the ordinary. *Pet friendly with non-refundable fee. *Pool is heatable with fee.

Professionally decorated townhome with multiple balconies, pool, & washer and dryer

Hilton Head, SC, US
4 Bedrooms 9 Guests
Aug 30 - Sep 2
$283 night

Harbour Town Club Villas 1253 1253 Harbour Town Club is a highly desired, professionally decorated, multi-level townhome right in the heart of Harbour Town in Sea Pines Plantation. This lovely escape is perfect for all looking to real and explore including couples, families, sports enthusiasts, shoppers, adventurers, and readers. The Harbour Town Lighthouse is a leisurely stroll away, offering amazing sights and history. In the same area, you’ll find boat and kayak rentals, sunset cruises, a playground, and restaurants to enjoy. Closer to home, a beautiful outdoor swimming pool is perfect for a splash or two. Harbour Town Club Villas are the perfect vacation spot for the whole family. These villas are located mere steps from everything Sea Pines has to offer: beautiful beaches, horseback riding, a 600-acre forest preserve, two more championship golf courses, the incredible Sea Pines beach club, and bar, South Beach Marina water sports and stores. Rent a bike from one of the local rental shops if you’re planning to stay awhile and explore throughout the day. If you’d prefer a ride to the beach, the cross-island trolley can take you between Harbour Town and the sandy shores (except for winter months). Walk or bike along the golf cart paths before or after hours. If you do so in the evening, behold the incredible sunset over the 18th hole and Calibogue Sound. And that is only Sea Pines! There is still all of the rest of Hilton Head (America’s favorite island per Condé Nast’s annual traveler’s survey), and nearby Bluffton, Daufuskie Island, and Savanah to explore. Pull into your private, covered parking area and ascend a small staircase to the main floor. Floor-to-ceiling windows and sliding glass doors allow ample natural light into the interconnected and nicely decorated living room, kitchen, and dining areas. The living room provides comfortable seating, free WiFi, a TV, and a blue tooth enabled Bose speaker. Just off the living area are the dining room and kitchen. The fully-equipped kitchen is open to the dining area and features saturnia flooring, granite countertops, and stainless steel appliances. A furnished balcony on this floor overlooks the pool terrace and features a gas grill, perfect for outdoor dining and relaxing! This floor also offers two bedrooms, and if you ascend the stairs to the second floor, you’ll find two guest bedrooms with views of the swimming full. Each bedroom offers new mattresses, new wood flooring, and features its own adjoining full bathrooms. The carpeting on the stairs and in the hall was replaced in early 2018, while additional upgrades include the new outside decks, the fridge, and a new bunk bed featured in one of the rooms. Book now for a vacation you’ll remember for the rest of your life! This property’s license number is 26671. <b>Things to Know</b> Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. All guests shall abide by The Good Neighbor Policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m. No smoking is permitted anywhere on the premises. Please note E-bikes are not allowed. Please be aware that the Plantations and Condominium Complexes do not allow trailers, motor homes, motorcycles and/or recreational vehicles and rooftop cargo (i.e. Kayaks, Canoes etc.) other than car top Carriers. Electric bikes are not permitted in the Plantations. License number: 026671,26671

7 Genoa Court

Hilton Head Island, SC, US
6 Bedrooms 16 Guests
Aug 26 - 29
$586 night

Proudly hosted by Island Rentals of Hilton Head, 7 Genoa Court is an extraordinary pet-friendly luxury retreat nestled in the heart of Sea Pines Resort, just moments from the iconic Harbour Town Marina. Thoughtfully designed to accommodate up to 16 guests, this elegant 6-bedroom, 6.5-bath residence offers sophisticated coastal living with premium amenities, expansive gathering spaces, and an unbeatable location. Whether you’re planning a multi-generational family vacation, golf getaway, or group celebration, this exceptional home delivers an elevated Hilton Head experience from the moment you arrive. Inside, timeless coastal elegance meets modern luxury. Beautiful hardwood flooring, soaring ceilings, designer furnishings, and carefully curated finishes create an inviting atmosphere throughout the home. The gourmet kitchen is beautifully appointed with sleek white quartz countertops, black stainless steel appliances, a flat-top range, and generous workspace, making it ideal for everything from casual breakfasts to celebratory dinners. The adjoining dining area and breakfast bar flow seamlessly into the spacious living room, where plush seating and a custom beverage center complete with a wine refrigerator, ice maker, sink, and wine storage create the perfect setting for entertaining. Designed with both comfort and privacy in mind, the home features four luxurious king suites, each with a private ensuite bathroom, along with two custom queen-over-queen bunk suites that are ideal for children or additional guests. Spa-inspired bathrooms offer walk-in showers, double vanities, and upscale finishes, creating private retreats for every member of your group. Outdoor living is equally impressive. The private pool terrace serves as your own secluded oasis, complete with comfortable lounge seating, stylish outdoor furnishings, and beautifully landscaped surroundings. Spend sun-filled afternoons relaxing poolside, gather for evening cocktails under the stars, or choose to heat the pool for year-round enjoyment. On the fourth floor, a second living area with its own beverage center opens onto an expansive rooftop-style deck with comfortable seating, providing the perfect place to enjoy the coastal breeze, morning coffee, or sunset gatherings overlooking the neighborhood. To enhance your stay, the home includes four complimentary adult bicycles from South Beach Bike Rentals, four backpack beach chairs, a complimentary Sea Pines vehicle pass, and convenient access to the seasonal Sea Pines Trolley. From your front door, enjoy a leisurely walk to Harbour Town Marina, where waterfront dining, boutique shopping, live entertainment, and the iconic Harbour Town Lighthouse await. Explore miles of shaded leisure trails, play one of Sea Pines’ renowned championship golf courses, or spend the day relaxing on Hilton Head’s pristine beaches. As a pet-friendly home welcoming up to two well-behaved dogs with an additional pet fee, 7 Genoa Court ensures every member of the family can experience the very best of Hilton Head Island. Combining luxurious accommodations, exceptional amenities, and one of Sea Pines’ most coveted locations, this remarkable residence offers an unforgettable backdrop for creating lifelong memories. *Pool can be heated for an additional fee. * A maximum of 2 well behaved dogs are permitted with payment of an additional pet fee. • 6 Bedrooms | 6.5 Bathrooms • Hosts 16 • 4 Kings, 2 Queen over Queen Bunk Beds • 7 TV’s | Alexa | WiFi | Keurig • Private Pool {18’ x 12’} • 4 Backpack Beach Chairs • 4 Free Adult Bicycles from South Beach Bike Rentals • Walk to Harbour Town Marina for Restaurants, Shops and Entertainment • Pool may be heated for additional cost upon request. • 1 complimentary Sea Pines car pass. Additional passes may be purchased. Three car maximum. • Hospitality Mobile App • Access to the Sea Pines Trolley (seasonal) * All Reservations made for a duration of 1 month (28 Days) or longer are non refundable. Travel Insurance is highly recommended.

Beautifully Decorated and Spacious Home w/ Pool

Hilton Head Island, SC, US
5 Bedrooms 16 Guests
Sep 19 - 22
$778 night

28 Stoney Creek Road | Bella Vista *5 Bedrooms | 4.5 Bathrooms *Sleeps 16 *4 Kings, 2 Pyramid Bunk Beds (XL Twins/Queens), 1 Full Sleeper Sofa *8 TV’s | DVD | Wi-Fi | Gas Grill *Outdoor TV | Pool Table *Beach Gear Credits Included *Enjoy Daily Rounds of Golf & Children’s Activities with this Home *Views of the Heron Point Golf Course *Walk to Harbour Town Marina for Restaurants, Shops and Entertainment *Private Pool {20.5’ x 19’} *8 Beach Towels for Guest Use *Point Central Keyless Entry *Guests Have Use of the 4 Car Garage *2019 Lighthouse Award Winner for New Construction *Perfect Home for Monthly and Off-Season Rentals {please call for extended stay pricing} *Access to the Sea Pines Trolley (seasonal) *5 Car Maximum | *No Parking on the Street The combination of classic and coastal décor accents this well designed Harbour Town gem. This house overlooks number 11 at Heron Point with a million dollar, four hundred yard view to the green of this dog leg par five. This home has three distinct levels, five bedrooms, four and a half baths and sleeps up to 14. There are two king master suites on the first level with three more bedrooms on the third level . The second level is a large game room with a Brunswick slate pool table, 75” SMART TV and a bar that seats five. A large full sleeper sectional accents the room. A sliding barn door separates this room from the rest of the house, or opens up this social setting just six steps from the great room and main living area. Upon entering this home the stunning view takes you through the great room and first covered porch. 10 and 11 foot ceilings accent this open floor plan which flows into the kitchen and dining area. The great room features elegant designs, coastal décor and colors, u shaped seating for eight, and a newly added bar with seating for three to enjoy the 75” SMART TV above the fireplace . The kitchen features a large quartz island with seating for six and flows into the dining area that seats eight with state of the art appliances. One of the unique architectural features are three retractable glass doors opening off the great room and dining room. These doors open to two large covered porches, one with seating for four in a casual setting with a 38” ventilated grill, refrigerator, and granite countertops flanking both sides of the grill for endless entertaining possibilities. The other with a large rectangular slate table and dining for eight. A 75” outdoor SMART TV is visible from both patios and the pool to make weekend afternoons and evenings a sports fest while enjoying all this magnificent home has to offer. The patio also features an outdoor bathroom so the kids never need to enter the house. With these features and a private baby grand shaped pool you may never make it to the beach. The pool offers a gas heater which is available for a fee in the off season to keep the water in the 80’s all year around. A circular paver area down by the golf course with four Adirondack chairs make this house complete for late night gatherings. Less than a half mile walk to the Harbour Town Lighthouse and amenities, but on an incredibly quaint and quiet street makes 28 Stoney Creek the perfect destination to create an abundance of family memories year after year. *Additional Charge to Heat the Pool  {If the outside temperature is colder than 55 degrees, the pool may not be able to maintain a warmer temperature. If the pool does not reach the desired temperature but is still warming, refunds will NOT be given} *4 Night Minimum Stay Required. Summer Rentals Weekly Only (Sat. to Sat.) *5 Car Maximum | *No Parking on the Street *Property May Be Monitored by Exterior Security Cameras *Town of Hilton Head Permit #023369

Harbour Town villa with courtyard view & pool - close to shops & restaurants

Hilton Head, SC, US
2 Bedrooms 6 Guests
Sep 6 - 8
$130 night

Stoney Creek 299 Stoney Creek Villa 299 is a spacious condo located just steps from the shops and restaurants at Harbour Town. It was completely renovated in 2023 with brand-new flooring throughout. Inside, this charming vacation rental features an updated, full kitchen with new appliances and fixtures, a dining room, and a comfortable living area with access to the private, furnished patio with a landscaped view. Its open-concept living space ensures the group chef will never be kept out of lively conversations while whipping up a feast everyone will remember. Indulge together at the dining table while enjoying the view out of the patio door. Afterward, go for a refreshing swim in the large, shared pool before winding down for the night. This Sea Pines vacation rental is near the Harbour Town Links Golf Course, home of the famed RBC Heritage tournament, with convenient access to waterfront shopping and dining. Additional resort activities include trail rides through Lawton Stables, marina activities at Harbour Town or South Beach, dining, shopping, kayak rentals, and miles of bike paths. Whether you’re looking for the ideal golf getaway or a family fun vacation spot, Stoney Creek Villa 299 is the perfect choice for everyone. <b>SHARED AMENITIES</b> -Pool This property’s license number is 28896. <b>THINGS TO KNOW</b> *Phase 2 of the Lighthouse Lane Infrastructure Improvement Project is scheduled to begin in early May 2025, and is estimated to continue through June 2025. Planned work will be conducted Monday-Friday from 7:00 AM to 7:00 PM, excluding major holidays. Weekend and overnight work may be necessary but will be communicated in advance. Heavy machinery and construction vehicles will be traveling to and from the project site. Single-lane road closures and flagging operations will be in place daily, weather permitting. Temporary full lane closures may be required at times. Motorists should expect traffic delays, traffic detours, and be prepared to share the road with bike riders and pedestrians. Sidewalks in the project area will be closed as needed. Pedestrians and bike riders should expect delays and be prepared to stop and follow detours. For safety, bike riders will be required to dismount and walk bikes around the active work zones. Please also note that Harbourtown golf course will be closed from May 10th through mid November for maintenance. Please be aware that the Plantations and Condominium Complexes do not allow trailers, motor homes, motorcycles and/or recreational vehicles and rooftop cargo (i.e. Kayaks, Canoes etc.) other than car top Carriers. Electric bikes are not permitted in the Plantations. License number: 028896,28896

Renovated home with private screened pool, lagoon views & nearby beach access

Hilton Head, SC, US
4 Bedrooms 10 Guests
Aug 31 - Sep 3
$589 night

Carolina Cottage Spend balmy days outside swimming in the screened backyard pool, barbecuing at the lagoon’s edge, or gathering around the outdoor firepit at this fantastic, two-story home. Make your Hilton Head escape one to remember. This cottage is the perfect place for a family getaway, with its secluded location that’s still just a short drive or bike ride from shops, restaurants, and recreational activities. The property is set within easy access of Harbour Town’s businesses and golf courses, as well as the island’s white, sandy beaches. On this quiet street, the tropical flora and fauna of the local landscaping provide gorgeous curb appeal. The Sea Pines Racquet Club and its tennis court are within walking distance of the property, as is the PGA Golf Course. As you arrive, you’ll be greeted by high-speed WiFi with a mesh router and two desk areas to use if you plan to work from home. You’ll find oak hardwood flooring throughout the cottage and a spacious living area featuring overstuffed chairs, a 75-inch TV with a sound bar, and a DVD player for movie nights. The elegant kitchen is separated from the living room by an island breakfast bar, offering polished stainless steel appliances, custom cabinetry, and a wet bar. Enjoy closet organizers in the two downstairs bedrooms and beautifully updated bathrooms. Other amenities include a washer/dryer. This property’s license number is 25911. <b>Things to Know</b> Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. All guests shall abide by The Good Neighbor Policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m. No smoking is permitted anywhere on the premises. Please note E-bikes are not allowed. Please be aware that the Plantations and Condominium Complexes do not allow trailers, motor homes, motorcycles and/or recreational vehicles and rooftop cargo (i.e. Kayaks, Canoes etc.) other than car top Carriers. Electric bikes are not permitted in the Plantations. STR permit no. 025911 License number: 025911,25911

Peaceful villa with large deck and lagoon views, close to Harbour Town

Hilton Head, SC, US
3 Bedrooms 8 Guests
Aug 30 - Sep 1
$118 night

Calibogue Club 2617 Nestled in the serene surroundings of Hilton Head, SC, this charming villa offers tranquil lagoon views from its spacious deck, providing the perfect spot to unwind and enjoy the peaceful ambiance. Just a short walk or bike ride away, you’ll find yourself at Harbour Town, a vibrant area boasting an array of restaurants, shops, and sightseeing opportunities. The complex amenities include a refreshing pool and tennis court, ideal for staying active or simply relaxing under the sun. With close proximity to the beach, you can easily spend your days soaking up the sun and enjoying the coastal breeze. Inside the villa, you’ll find a well-equipped kitchen with modern appliances, a cozy living room with comfortable seating and high ceilings, and a dining area perfect for enjoying meals together. The deck offers a picturesque setting for al fresco dining, complete with patio furniture for relaxing evenings. Whether you choose to explore the nearby attractions or simply relax by the lagoon, this villa provides the perfect retreat for your Hilton Head getaway. Book your stay today and experience the best of coastal living in South Carolina! This property’s license number is 36982. <b>Things to Know</b> Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. All guests shall abide by The Good Neighbor Policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m. No smoking is permitted anywhere on the premises. Please note E-bikes are not allowed. Please be aware that the Plantations and Condominium Complexes do not allow trailers, motor homes, motorcycles and/or recreational vehicles and rooftop cargo (i.e. Kayaks, Canoes etc.) other than car top Carriers. Electric bikes are not permitted in the Plantations. STR permit no. 036982 License number: 036982,35706

120 Club Course Drive - Golfers’ Retreat at Sea Pines | Lagoon & Golf Views | Pool & Spa

Hilton Head Island, SC, US
3 Bedrooms 11 Guests
Sep 1 - 3
$339 night

Indulge in relaxed coastal living at 120 Club Course Drive, nestled within the tranquil ambience of Sea Pines Resort. Embrace captivating lagoon vistas amidst lush greenery and wooded views of the Country Club Golf Course. Immerse yourself in the brand new private pool’s refreshing waters or venture forth to explore the resort’s myriad offerings—from pristine beaches to world-class amenities like tennis and water sports.  Book your perfect Hilton Head Island getaway with Host & Home; Learn More Below! ☆☆ HIGHLIGHTS ☆☆ ✹ 3 bedrooms/ 3.5 bathrooms for up to 10 guests: 1 King En-suite + 1 Queen En-suite + 1 Guest  En-suite with 4 Twins + 1 Trundle set up as bunks + Sleeper Sofa in the Living Room ✹ Pet-friendly: bring your fido along (fees apply)! ✹ Fully equipped hi-end kitchen for your culinary exploits ✹ Brand new pool with tanning ledge and a hot tub for ultimate relaxation (Pool deck completion is April 2025) ✹ Spacious living area w/ large deck and lovely Carolina room with lagoon view ✹ High-speed Wi-Fi w/ 5 smart TVs  ✹ Location: Tranquil part of Sea Pines Resort, Hilton Head Island. ✹ Sports Facilities: Right on the Sea Pines Country Club Golf Course. Easy access to stables, tennis, and pickleball courts (additional fees might apply). ✹ Local Attractions: Within short car ride to Sea Pines Beach Club, Forest Preserve and Fishing charters. Eager to Read More? ☆☆ YOUR SERENE GOLF ESCAPE ☆☆  Welcome to 120 Club Course Drive, your ultimate single level retreat nestled within the serene Sea Pines Resort, right on the edge of a picturesque lagoon, across from the Country Club Golf Course. Experience coastal living at its finest with this meticulously reconstructed property, offering unrivaled comfort and style for your vacation getaway.  ☆☆ LIVING AREA☆☆  Step into a sanctuary of modern elegance in this newly renovated retreat. Redesigned in 2024, the space seamlessly blends contemporary comforts with timeless charm, creating an atmosphere of understated luxury. Every corner has been thoughtfully curated to enhance your stay and make every moment unforgettable. Relax in the stylish living area or step into the inviting Carolina room, which extends to a deck overlooking serene lagoon and golf course views. Whether you’re curled up with a favorite book, hosting a lively game night, or simply soaking in the tranquil surroundings, this space is designed for connection and relaxation. ✓ New plush couches and armchairs for ultimate comfort ✓ Two Smart TVs with cable, perfect for movie nights or catching the game ✓ Spacious Carolina room for year-round enjoyment of nature ✓ Direct access to a deck offering peaceful lagoon and golf course views ✓ Vaulted ceilings that add an open, airy ambiance ✓ Half Bathroom for guests’ convenience ☆☆ KITCHEN AND DINING ☆☆  The home features an open floor plan, seamlessly connecting the living room, dining area, and kitchen so no one is left behind while doing the chef’s chores. Completely renovated in 2024, the kitchen boasts all-new cabinets, countertops, and top-shelf appliances. ✓  Brand new stainless appliances and quartz countertops ✓  Everything necessary to cook and serve most meals ✓  Dripping and Keurig coffee makers ✓  Dining table seats 8 ✓  Kitchen island with additional seating for 4 ✓  Laundry room with full size washer and dryer ☆☆ BEDROOMS  & BATHROOMS ☆☆ Unwind in the comfort of three thoughtfully designed bedrooms, each offering a serene retreat after a day of exploration and adventure. Every detail has been carefully considered to ensure restful nights and rejuvenating mornings. ✓ Primary King En-Suite: A tranquil sanctuary featuring direct deck access, a luxurious soaking tub, and a serene atmosphere for ultimate relaxation. ✓ Queen Suite: A spacious haven with a spa-like bathroom, perfect for indulging in a little extra comfort and privacy. ✓ Cozy Bunk Room: Ideal for families or friends, this charming space features 4 Twin bunk beds with 1 Twin Trundle, an en-suite bathroom, and a cozy ambiance that young and adult alike will love. ✓ For additional sleeping arrangements and different group dynamics, the Living room offers a queen-size sofa sleeper surrounded by nature views, providing a peaceful and flexible option for extra guests. Each sleeping space is outfitted with hotel-grade linens and high-quality new mattresses, ensuring every guest feels pampered and right at home at 120 Club Course Drive.  ☆☆ BACKYARD AND POOL DECK ☆☆ ✹✹ We are in the final stages of transforming our outdoor area into a stunning oasis, complete with a heated pool and luxury spa. The project is expected to be completed by April 2025, and we can’t wait to share the finished results with you! In the meantime, please refer to the contractor-provided renderings for a glimpse of what’s to come. Updated photos will be uploaded as soon as the enhancements are finalized.✹✹ Step into an entertainer’s paradise on the expansive deck overlooking tranquil lagoon and golf course beyond, where comfort and style meet the beauty of the outdoors. Designed with relaxation and connection in mind, this space is perfect for creating unforgettable memories with family and friends. Savor al fresco dining with ample seating and a fully equipped outdoor propane grill station. Gather with sweet tea or your favorite drink on the comfortable outdoor furniture, sharing stories of the day’s adventures and planning tomorrow’s escapades. As the sun sets, let the brand-new luxury hot tub melt away your worries while you unwind under the Lowcountry’s starry skies. Just steps away, the heated pool beckons for refreshing swims by day or peaceful soaks by night. ✓ Large deck with outdoor dining areas ✓ Brand-new built-in hot tub for six guests ✓ Heated pool for year-round enjoyment (heating fees apply) ✓ Fully equipped propane grill station ✓ Three lounge chairs for sunbathing and relaxation ✓ Grassy backyard area ideal for playtime or lawn games Seamlessly blending luxurious amenities with natural beauty, this outdoor haven is designed for both quiet relaxation and lively gatherings, making every moment at 120 Club Course Drive unforgettable. ☆☆ RESORT AMENITIES ☆☆  Immerse yourself in the natural beauty of Sea Pines with long lagoon views and lush greenery all around. Venture out to explore the resort’s pristine beaches and world-class amenities.  Our home grants you access to a myriad of attractions, including the Sea Pines Country Club Golf Course just a stone’s throw away, miles of bike paths, Lawton Stables, and the Sea Pines Forest Preserve. The possibilities for adventure are endless. Community Amenities (additional fees might apply): ✓ Golf ✓ Lawton Stables ✓ Tennis and Pickleball Courts ✓ Sea Pines Forest Preserve ✓ Sea Pines Beach Club (parking limitations during high season apply) ✓ Endless shaded bike and walking paths throughout resort and beyond ☆☆ NEARBY ATTRACTIONS☆☆  Nearby, you’ll find a wealth of attractions to explore, from the beach just a stone’s throw away to charming shops and world-class dining establishments. Here are some of the best activities and attractions.  EXPERIENCES FOR LARGE GROUPS: Enjoy a variety of upscale activities that provide fun and luxurious experiences. ✔ Private guided tours of Sea Pines Forest Preserve (2.1 miles) ✔ Group golf outings at Harbour Town Golf Links (4.2 miles) ✔ Private yacht charters from Shelter Cove Harbour & Marina (4.9 miles) DINING AND SHOPPING: Discover a variety of upscale dining and shopping options to enjoy during your stay. ✔  Coligny Plaza Shopping Center (2.8 miles) ✔  Black Marlin at Palmetto Bay Marina (3.4 miles) ✔  The Crazy Crab - Harbour Town ( 4.2 miles) ✔  Sea Pines Beach Club (4.3 miles) ✔  Shelter Cove Towne Centre (4.9 miles) FAMILY-FRIENDLY ATTRACTIONS: Explore engaging and premium attractions perfect for all ages nearby. ✔ The Sandbox Children’s Museum (2.6 miles) ✔ Pirate’s Island Adventure Golf (4.2 miles) ✔ Coastal Discovery Museum (7.1 miles) All these activities and more are within your reach when you book with us! ☆☆ OTHER THINGS TO KNOW ABOUT 120 CLUB COURSE ☆☆  ✓  Beach Towels Provided ✓  PET POLICY: a dog under 60 pounds is welcome to come with a $300 non-refundable fee ✓  This house has parking for 4 vehicles in the driveway  ✓  This property is in the gated community of Sea Pines and a car pass is required for every vehicle. One paid car pass is included with your reservation.  ✓  Please contact your Host prior to arrival to purchase additional car passes at $17.00 ea per Sea Pines.  ✓  Please park in designated parking areas only.  Please do not park off-site on street, grass, or on pine straw ✓  The Town of Hilton Head Island enforces quiet hours between 10:00 PM and 7:00 AM ✓  The pool does not have safety equipment. All activities at your own risk. ✓  The pool and spa heat are available. Contact the host to order pool and spa heat ✓  The minimum age requirement for renting this property is 25.  ✓  Beach Access can be found at the Sea Pines Beach Club: Located at 87 N. Sea Pines Drive, this is Sea Pines Resort’s organized beach access for the community. Parking at the Sea Pines Beach Club is reserved exclusively for Sea Pines property owners during the season (April through Labor Day) between 8am and 3pm. During the season you would catch the complimentary Sea Pines Trolley service to the Beach Club. Otherwise, renters can park there after 3:00pm. Off Season renters can park at the club without limits. The beach Club features three restaurants including Coast, Oceanfront Dining and restrooms. ☆☆ YOUR STAY - OUR PRIORITY ☆☆ At HOST+HOME, we know that you deserve a vacation, and we have the perfect place for it. Our carefully curated vacation homes are immaculate, safe, and meticulously maintained, ensuring comfort and quality throughout your stay. Enjoy peace of mind with our 24/7 support, available for assistance and maintenance anytime you need. ☆☆ RESERVE YOUR SLICE OF PARADISE ☆☆ Elevate your vacation experience with curated activities, including free and discounted options, to make your stay even more memorable. ★☆ Book Today & Let Us Take Care Of You In Hilton Head Island! ☆★

Private Marshfront Oasis w/ Pool & Sunset Views

Hilton Head Island, SC, US
4 Bedrooms 8 Guests
Aug 29 - Sep 3
$715 night

Welcome to 22 Oyster Landing, a fully remodeled Lowcountry retreat in Sea Pines with sweeping marsh and Calibogue Sound views. Set on over an acre beneath moss-draped oaks, this light-filled home features an open floor plan, white oak floors, and refined coastal style. Enjoy sunsets from the screened porch, patio, or brand-new oversized pool and spa. Four king bedrooms with private baths offer comfort, privacy, and unforgettable Hilton Head living. Welcome to 22 Oyster Landing, a classic Lowcountry home set on a quiet street in Sea Pines Resort with breathtaking views of the marsh and Calibogue Sound. Nestled on more than an acre beneath moss-draped oak trees, this property immediately captures your attention with its privacy, scale, and natural beauty. The sweeping vistas create a true sense of coastal serenity rarely found on the island. From sunrise to sunset, the setting alone makes this home unforgettable. Completely remodeled from top to bottom, the home blends timeless Lowcountry architecture with refined coastal luxury. Wide-plank white oak flooring enhances the open floor plan and light-filled living spaces, making it ideal for large gatherings and relaxed entertaining. Every room has been thoughtfully updated to feel fresh, bright, and welcoming while preserving classic Southern charm. Expansive windows frame stunning water and marsh views throughout the home. Outdoor living is a highlight, with multiple spaces designed to soak in the scenery and evening sunsets. Enjoy the screened-in porch, spacious back patio, or unwind in the brand-new oversized pool and spa overlooking the marsh. The peaceful surroundings and expansive grounds offer a sense of seclusion while still being within Sea Pines. Whether hosting sunset cocktails or enjoying a quiet morning coffee, every moment feels elevated. The home features four spacious king bedrooms, each with its own private ensuite bath, providing comfort and privacy for every guest. With generous indoor and outdoor living areas, this retreat is perfectly suited for families, couples, or groups traveling together. The combination of luxury updates, panoramic views, and a premier Sea Pines location makes this property truly special. Book your stay at 22 Oyster Landing and experience one of the most serene and scenic vacation homes on Hilton Head Island. PROPERTY SPECIFIC DETAILS: * Pool and/or spa heating is available for an additional fee and can be arranged after your booking is confirmed. We kindly ask that heating is ordered in advance of the stay. If the outdoor temperature falls below 60 degrees, the pool heater may not function properly and the pool may not reach the desired temperature. Please note that no refunds will be issued if the pool heating equipment cannot maintain the temperature. * Sea Pines is a gated community in which every vehicle must have a gate pass for entry. One gate pass is included with your reservation at the time of booking. If you require additional passes, please request the exact number needed to ensure they are prepared in advance. Each pass has a fee of $35. All gate passes must be picked up at the host2coast office prior to entry. * Fireplace and garage are not available for guest use. STR Permit # 59952 We want your stay to be all about the memories - not the paperwork. So let’s get the small stuff out of the way early and get back to what matters: your trip! Every reservation is required to complete a quick Guest Portal before check-in. It’s a secure external link we’ll send you shortly after booking, and it’s also where you’ll find all your check-in details - including your all-important door code. The pre-approval process takes just a few minutes and covers three simple steps: 1. Sign the Rental Agreement - a quick electronic signature, no printing required. 2. Guest verification - a fast, standard guest verification. 3. Pick your coverage: Damage Waiver (a small, non-refundable fee covering eligible accidental damage during your stay - our guests’ favorite option, since it takes the stress out of minor mishaps) or Security Deposit (a fully refundable hold, released after checkout as long as everything’s in order). We’ll email your secure portal link before arrival - just a few minutes of your time for a much smoother check-in. Thanks for helping us keep things safe and simple. We can’t wait to host you! Biking is very popular on Hilton Head Island, known for the many award-winning trails. There are recommendations for bike rental companies within your Guest App. You can reserve in advance and they will deliver to you or bring your own! Almost everything you will need is within walking distance, so bring your walking shoes! Sea Pines provides a complimentary seasonal trolley service that helps guests and residents travel around the resort without using a car. The trolley connects major destinations such as Harbour Town, the Sea Pines Beach Club, South Beach Marina, and The Shops at Sea Pines Center, making it easy to access beaches, dining, and shopping throughout the community.

Lovely, water-view townhouse with pool - short walk to Harbour Town & playground

Hilton Head, SC, US
3 Bedrooms 6 Guests
Aug 26 - 30
$332 night

Stoney Creek 272 Stony Creek Villa in Sea Pines is a condo with a cozy atmosphere, making it perfect for a family getaway or a relaxed vacation with friends. This townhouse overlooks a nature-filled marsh abounding with local plants and wildlife. It is a beautiful three-story dwelling with plenty of space for your group. You will be a short walk to Harbour Town, where you can enjoy the activities, restaurants, and shops. The Sea Pines tennis facility is across the street, and the world-famous Harbour Town golf course, home of the RCB-Heritage Tournament, is just a short walk away. Renting a Sea Pines villa gives you many advantages, like the resort’s sailing tours, fishing, crabbing, and water sports, and a beautiful 400-acre nature reserve has trails for biking and jogging. Swimming in the shared pool, playing golf and tennis, and visiting the nearby candy-striped lighthouse are also options. You can get to the town’s shopping and dining destinations pretty quickly, too, by bike or car. The front of this townhouse is tastefully landscaped with trees and foliage, and wide, closely spaced steps lead to the front gate. The villa has carpeted bedrooms and beautiful area rugs in the living and dining areas, with runners in the foyer and hallway. The kitchen has custom white cabinets and granite countertops. Large sliding glass doors flood the living area with natural light. Whether you’re looking for a home away from home, are visiting for the Heritage Golf Tournament, or are more interested in outdoor activities in Sea Pines, book this vacation rental today, and you’ll have ample options at your fingertips. This property’s license number is 26461. <b>Things to Know</b> Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. All guests shall abide by The Good Neighbor Policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m. No smoking is permitted anywhere on the premises. Please note E-bikes are not allowed. *Phase 2 of the Lighthouse Lane Infrastructure Improvement Project is scheduled to begin in early May 2025, and is estimated to continue through June 2025. Planned work will be conducted Monday-Friday from 7:00 AM to 7:00 PM, excluding major holidays. Weekend and overnight work may be necessary but will be communicated in advance. Heavy machinery and construction vehicles will be traveling to and from the project site. Single-lane road closures and flagging operations will be in place daily, weather permitting. Temporary full lane closures may be required at times. Motorists should expect traffic delays, traffic detours, and be prepared to share the road with bike riders and pedestrians. Sidewalks in the project area will be closed as needed. Pedestrians and bike riders should expect delays and be prepared to stop and follow detours. For safety, bike riders will be required to dismount and walk bikes around the active work zones. Please also note that Harbourtown golf course will be closed from May 10th through mid November for maintenance. Please be aware that the Plantations and Condominium Complexes do not allow trailers, motor homes, motorcycles and/or recreational vehicles and rooftop cargo (i.e. Kayaks, Canoes etc.) other than car top Carriers. Electric bikes are not permitted in the Plantations. License number: 26461,026461

200 Olive Shell Court @ Spanish Wells | New Luxury Townhome | Pool Access |

Hilton Head Island, SC, US
4 Bedrooms 8 Guests
Aug 26 - 29
$327 night

200 Olive Shell Court! Located in the luxurious community of The Homes at Olive Shell, this three-story townhome features high-end finishes, 9-foot ceilings, has 4 bedrooms, and a spacious garage. This unit is part of a gated community with amenities like a resort-style pool, walking trails, and lush landscaping. Learn more below ... ☆☆ HIGHLIGHTS ☆☆ ✹ The Homes at Olive Shell Amenities: Community pool with sun loungers, Cornhole sets, and Foosball table! ✹ Multiple Outdoor Areas: Screened in porches provide outdoor areas without any bugs! ✹ Modern Comfort: Accommodates up to 8 guests with 4 bedrooms, including two suites with screened in porch access ✹ Fully equipped kitchen for your culinary exploits ✹ Cozy living area: Complete with a sectional and two arm chairs, perfect for morning coffee or evening downtime ✹ Newly Constructed Units enhance the overall living experience! ☆☆ LIVING AREA ☆☆ Unwind in the comfy living space, designed with comfort and entertainment in mind. A grey sectional plush sofa, two decorative arm chairs, a large flat-screen TV, and stylish decor make it the perfect spot to unwind after a day in the sun. ✓ Indoor-outdoor flow with natural light and deck access ✓ Cozy and comfortable seating, ideal for quality time with family and friends ✓ Smart TV perfect for a movie night! ☆☆ KITCHEN AND DINING ☆☆ Cook up delicious meals in the modern kitchen featuring sleek finishes, top-quality appliances, a large kitchen island, and plenty of counter space. The open concept design provides easy access to the living room and deck. ✓ Stainless steel appliances ✓ Keurig and Drip coffee makers ✓ Everything necessary to cook and serve meals ✓ Cozy dining table with seating for 3 ✓ Additional 3 bar stools at the kitchen island ☆☆ BEDROOMS & BATHROOMS ☆☆ On the second floor, you’ll find the Primary bedroom. This space features a King bed, ensuite with double vanity, walk-in shower, and access to a small screened porch. There is also a convenient half bathroom near the kitchen area. Venture up to the third floor where the remaining bedrooms await. Bedroom 2 features a serene coastal atmosphere with a King bed, en-suite, and access to a private screened in porch deck. Lastly, Bedroom 3 is equipped with a Murphy bed and designated desk area & Bedroom 4 provides a King Bed. Both Bedroom 3 & 4 share a Jack & Jill bathroom. 2nd Floor: ✓ Bedroom 1: 1 King Bed, en-suite bathroom with double vanity, luxurious walk-in shower, access to private screened in porch deck, Smart TV 3rd Floor: ✓ Bedroom 2: 1 King Bed, en-suite bathroom with double vanity, luxurious walk-in shower, access to private screened in porch deck, Smart TV ✓ Bedroom 3: 1 Murphy Bed, designated work area, bathroom shared with Bedroom 4 and has a double vanity, tub/shower combo ✓ Bedroom 4: 1 King Bed, bathroom shared with Bedroom 3 and has a double vanity, tub/shower combo ★☆ OUTDOOR PRIVATE OASIS ☆★ Whether you’re sipping your morning coffee, or unwinding on the comfortable deck, you’ll have a front-row seat to the tranquil beauty of Southern nature. ✓ Multiple screened-in porches to keep the bugs away! ✓ Prime views of Lowcountry nature ☆☆ OLIVE SHELL COMMUNITY AMENITIES ☆☆ ✓ Take a refreshing dip in the shared Community Pool ✓ Play a game of Cornhole on the lawn ✓ Challenge one another in a game of Foosball! ☆☆ NEARBY ATTRACTIONS ☆☆ Nearby, you’ll find a wealth of attractions to explore, from the beach just to charming shops and family-friendly activities. Here are some of the best spots to check out: DINING AND SHOPPING: Discover a variety of upscale dining and shopping options nearby. ✔ South Beach Marina - 10.2 miles ✔ Harbour Town Shops & Lighthouse - 7.8 miles ✔ Shelter Cove Towne Centre - 8.4 miles FAMILY-FRIENDLY ATTRACTIONS: Explore engaging attractions that the whole family will love. ✔ The Sandbox Children’s Museum (5.5 miles) ✔ Pirate’s Island Adventure Golf (7.0 miles) ✔ Coastal Discovery Museum (1.9 miles) ☆☆ OTHER THINGS TO KNOW ☆☆ ✓ Beach towels are provided ✓ This house has parking for 2 vehicles (1 in the driveway, 1 in the garage) ✓ Street parking and parking on grass or pine straw are prohibited by the town. ✓ The Town of Hilton Head Island enforces quiet hours between 10:00 PM and 7:00 AM. ✓ The Olive Shell Community pool does not have safety equipment. All activities are at your own risk. ✓ The minimum age requirement for renting this property is 25. ✓ This townhouse does not allow pets, please plan accordingly.

Luxury Sea Pines Retreat w/ Pool & Golf Views

Hilton Head Island, SC, US
4 Bedrooms 10 Guests
Aug 29 - Sep 2
$520 night

Just a half mile from Harbour Town, 18 Stoney Creek is a 4BR/4BA Sea Pines home with golf course views, private pool, and upscale finishes. The first floor offers a king primary suite and a queen-queen guest room; upstairs features two more bedrooms with en suites. Free WiFi, keyless entry, smart TVs, and modern amenities enhance your stay. Bike 6 minutes or drive to the Sea Pines Beach Club for beach time. Enjoy a vacation reimagined with host2coast, your trusted Hilton Head Island Property Step into the serenity of "A Slice of Heaven" in Sea Pines, a perfect fusion of relaxation and adventure! Welcome to 18 Stoney Creek, a striking 4-bedroom, 4-bath retreat in Sea Pines, where refined comfort meets island ease. Just a half mile from Harbour Town, The Shops at Sea Pines, and the Smith Stearns Tennis Academy, this home enjoys an enviable location that blends peace with proximity. Set on the 11th hole of Heron Point Golf Course, the property presents golf course views and a private backyard pool. Inside, the open living space is designed for gathering: large windows flood rooms with light, multiple dining areas allow for flexibility, and the kitchen is outfitted with quartz countertops and everything you need to cook with ease. On the first floor, the primary suite offers a king bed, private en suite bathroom, and lovely views. A second guest room on the main level features two queen beds with easy access to the hall bath. Upstairs, you’ll find two more guest rooms: one with a king bed, the other with a queen, each with their own en suite baths, offering ideal privacy for all guests. Modern conveniences include free WiFi, smart TVs, keyless entry, a Keurig coffee system, in-unit washer/dryer, and a gas grill for outdoor meals. Beach access is via the Sea Pines Beach Club, about 1.7 miles away or a 6 minute bike ride. Parking at the beach club is limited. Note that pets are not allowed, and the home accommodates up to ten guests. Whether your days are framed by rounds of golf, beach afternoons, or lazy poolside hours, 18 Stoney Creek offers space, style, and a location that keeps you connected to everything Hilton Head Island has to offer. PROPERTY SPECIFIC DETAILS: * Sea Pines is a gated community in which every vehicle must have a gate pass for entry. One gate pass is included with your reservation at the time of booking. If you require additional passes, please request the exact number needed to ensure they are prepared in advance. Each pass has a fee of $35. All gate passes must be picked up at the host2coast office prior to entry. Please note - the garage is not available for guest use. * Pool and/or spa heating is available for an additional fee and can be arranged after your booking is confirmed. We kindly ask that heating is ordered in advance of the stay. If the outdoor temperature falls below 60 degrees, the pool heater may not function properly and the pool may not reach the desired temperature. Please note that no refunds will be issued if the pool heating equipment cannot maintain the temperature. STR Permit # 25340 We want your stay to be all about the memories - not the paperwork. So let’s get the small stuff out of the way early and get back to what matters: your trip! Every reservation is required to complete a quick Guest Portal before check-in. It’s a secure external link we’ll send you shortly after booking, and it’s also where you’ll find all your check-in details - including your all-important door code. The pre-approval process takes just a few minutes and covers three simple steps: 1. Sign the Rental Agreement - a quick electronic signature, no printing required. 2. Guest verification - a fast, standard guest verification. 3. Pick your coverage: Damage Waiver (a small, non-refundable fee covering eligible accidental damage during your stay - our guests’ favorite option, since it takes the stress out of minor mishaps) or Security Deposit (a fully refundable hold, released after checkout as long as everything’s in order). We’ll email your secure portal link before arrival - just a few minutes of your time for a much smoother check-in. Thanks for helping us keep things safe and simple. We can’t wait to host you! Biking is very popular on Hilton Head Island, known for the many award-winning trails. There are recommendations for bike rental companies within your Guest App. You can reserve in advance and they will deliver to you or bring your own! Almost everything you will need is within walking distance, so bring your walking shoes! Sea Pines provides a complimentary seasonal trolley service that helps guests and residents travel around the resort without using a car. The trolley connects major destinations such as Harbour Town, the Sea Pines Beach Club, South Beach Marina, and The Shops at Sea Pines Center, making it easy to access beaches, dining, and shopping throughout the community.

Stay at 1029 Caravel Court

Hilton Head Island, SC, US
1 Bedrooms 2 Guests
Nov 11 - 14
$240 night

Overlooking the iconic Harbour Town Lighthouse and marina, 1029 Caravel Court offers one of the most picturesque waterfront settings on Hilton Head Island. Located inside Sea Pines Resort, this beautifully updated 1-bedroom villa combines stunning views, coastal elegance, and walkable access to Harbour Town’s dining, shopping, and golf. Perfect for couples, this villa provides a front-row seat to unforgettable sunsets and the relaxed charm that makes Harbour Town one of the island’s most beloved destinations. WHY YOU’LL LOVE THIS VILLA: - Located in the heart of Harbour Town inside Sea Pines Resort - Direct views of the Harbour Town Lighthouse and marina - Private balcony overlooking the harbor - King bedroom with marina views - Zero-gravity king bed + zero-gravity sofa - Luxury vinyl plank flooring throughout - Kitchen with granite countertops + stainless steel appliances - Walk-in tiled shower plus additional half bath - Elevator access to second-floor villa - Access to Harbour Town Pool just steps away - Short walk to Harbour Town restaurants, shops, and marina - Sleeps up to 2 guests LIVING & OUTDOOR SPACE: The living room features comfortable seating and panoramic views of the marina and Harbour Town Lighthouse. Sliding glass doors open to a private balcony where guests can enjoy morning coffee or evening cocktails while watching boats drift through the harbor and the sky light up during sunset. KITCHEN & DINING: The updated kitchen includes granite countertops, stainless steel appliances, and everything needed for preparing light meals, snacks, or a relaxing wine-and-cheese evening while taking in the waterfront views. SLEEPING ARRANGEMENTS (2 Guests Max): - Primary Bedroom – King zero-gravity bed with marina and lighthouse views and en-suite bathroom featuring walk-in shower - Additional Half Bath located off living area. RESORT ACCESS & AMENITIES: - Sea Pines and Harbour Town offer some of Hilton Head’s most iconic experiences: - Access to Harbour Town Pool (steps from the villa) - Walk to Harbour Town Lighthouse, marina, and shops - Harbour Town Golf Links and clubhouse nearby - Waterfront dining and live music in Harbour Town - Miles of scenic bike trails throughout Sea Pines - Easy access to Sea Pines beaches and nature preserves THE MYSTAY DIFFERENCE: MyStay redefines the vacation rental experience through effortless stays and genuinely personal hospitality. We believe service should feel welcoming, not corporate — rooted in trust, care, and real connection. Our hands-on local team combines thoughtful touches, professional standards, and responsive support to ensure every stay feels seamless from arrival to departure. With MyStay, you’re not just booking a property — you’re experiencing hospitality done the right way. IMPORTANT NOTES: - 1 Weekly Sea Pines gate pass included (additional passes must be purchased in advance) - Gate passes are mailed approximately 1 month prior to arrival - Harbour Town Pool open March–October and heated/cooled seasonally - Villa located on 2nd floor with elevator access - Primary renter must be 25+ Town of Hilton Head Island STR Permit #077140

240 Olive Shell Court

Hilton Head Island, SC, US
4 Bedrooms 10 Guests
Sep 14 - 17
$299 night

Tucked into the North End of Hilton Head Island, this newly constructed three-story townhome in The Homes at Olive Shell is built for groups who want more than just a place to sleep, think garage game nights, a private plunge pool, and easy access to waterfront restaurants and championship golf. With 9-foot ceilings, high-end finishes, and room for up to 10 guests across four bedrooms, this retreat is perfectly suited for golf trips, family reunions, or a group of friends looking to make the most of the island together. Inside, the living area is bright and open, with a plush gray sectional, a large Smart TV, and coastal décor that invites everyone to unwind after a day in the sun — and a pullout couch keeps the space flexible for extra guests. The modern kitchen carries that same open, easy feel, with sleek stainless steel appliances, a large island, and seating for nine between the dining table and bar stools, so cooking and gathering happen in the same breath, whether it’s morning coffee from the Keurig or a full group dinner. Upstairs, the primary suite offers a king bed, a spa-like en-suite with double vanity and walk-in shower, and its own private screened porch — a quiet spot for morning coffee away from the group. The third floor holds three more bedrooms: a queen suite with its own en-suite bath and screened porch, plus a queen and a king bedroom sharing a Jack-and-Jill bath with a tub/shower combo. Every bedroom comes with its own Smart TV, so there’s a comfortable retreat for everyone in the group. Step outside to your private plunge pool, framed by peaceful Lowcountry views, or settle into one of the home’s multiple screened-in porches to enjoy the outdoors without the bugs. And when it’s time for some friendly competition, head into the spacious garage for a round on the golf simulator — loaded with 160 courses, multiple players, and lifelike graphics — or challenge each other on the arcade machine for an evening the whole group will remember. As part of The Homes at Olive Shell, guests also enjoy a gated community with a resort-style pool, cornhole, foosball, walking trails, and lush Lowcountry landscaping. The North End location puts you close to waterfront favorites like Fish Camp and Skull Creek Dockside, easy access to the island’s best golf courses, and just minutes from the North End Fleet for offshore fishing. Our Host & Home team is dedicated to making every stay feel effortless, from booking through check-out. This home is meticulously maintained and thoughtfully stocked — right down to beach towels, chairs, and a beach cart — so you can settle in and start relaxing the moment you arrive. Whether you’re planning a golf getaway, a multi-family beach trip, or a reunion with friends, 240 Olive Shell Court offers the space, amenities, and island convenience to make it unforgettable. Book your Hilton Head escape today and let the games — and the memories — begin! Other Things To Know ✓ Beach towels, 4 beach chairs, and a beach cart are provided ✓ This house has parking for 2 vehicles (1 in the driveway, 1 in the garage) ✓ Street parking and parking on grass or pine straw are prohibited by the town. ✓ The Town of Hilton Head Island enforces quiet hours between 10:00 PM and 7:00 AM. ✓ The Olive Shell Community pool does not have safety equipment. All activities are at your own risk. ✓ The minimum age requirement for renting this property is 25. ✓ This townhouse does not allow pets, please plan accordingly. ✓ Please note: There is active construction near the home, and occasional noise may be heard.

River Bluff Retreat-Private Dock and Included Cart

Daufuskie Island, SC, US
3 Bedrooms 10 Guests
Aug 26 - 29
$943 night

Welcome to River Bluff Retreat! - 4 passenger golf cart included for any reservations created on or after 12/11/25 - 3 bedrooms, 2.5 baths with hardwood floors - Spacious living area and fully equipped kitchen - Private dock on the Intra-Coastal Waterway - Outdoor pool with lounge chairs and shower - Stunning sunset views from the covered porch - Bring your own boat - Nearby attractions: Bloody Point Lighthouse, Daufuskie Island Beach Escape to River Bluff Retreat, a peaceful 3-bedroom, 2.5-bath vacation home located on the Intra-Coastal Waterway at Marker 40. This captivating retreat features its own dock, making it an ideal spot for boating enthusiasts. Experience breathtaking sunsets and stunning views from the spacious covered porch, perfect for sipping coffee in the morning or enjoying cocktails in the evening. Keep in mind that there is no "BRIDGE" to Daufuskie Island, so your adventure begins with your choice of a private boat, ferry, or your very own vessel. This home is designed for relaxation and enjoyment, boasting luxurious finishes and an outdoor pool facing the intra-coastal. The pool area is equipped with comfortable lounge chairs and an outside shower, providing a perfect sun-soaked retreat. Comfortable Accommodation: - 3 bedrooms and 2.5 bathrooms - Master bedroom with a King bed located on the ground floor - Two additional bedrooms upstairs: one with a queen bed and another with 2 double beds and a bunk bed (double bottom and single top) - Jack and Jill bathroom with separate sink/toilet areas for each bedroom - Cozy sitting room with a daybed and trundle Interior Feeling: - Hardwood floors throughout the two-story home - Open concept living room and kitchen, ideal for entertaining - Fully equipped kitchen with an inviting island - Convenient half bath for guests Outdoor Bliss: - Private dock with 50ft deep water at high tide - Perfect for fishing, with opportunities to catch redfish, speckled trout, and sheepshead right from the backyard - Relaxing outdoor pool area with lounge chairs Delightful Dining: - Enjoy meals with family and friends in the spacious dining area - Explore local flavors at nearby dining options Professional Cleaning: - Thoroughly cleaned and maintained for your comfort and safety Explore the island and rejuvenate your mind and soul. If you’re interested in tasting the unique flavors of rum, bourbon, or vodka, distilled right here on the island, be sure to visit the Daufuskie Island Distillery. Start your day or boost your afternoon at the School Ground Coffee Shop, where you can indulge in gourmet coffee, espresso, lemonade, and more. Tourist Attractions: - Bloody Point Lighthouse (Driving: 3.7 km): Visit this historic beacon and enjoy breathtaking views of Calibogue Sound. - Daufuskie Island Beach (Driving: 4.8 km): Relax on the pristine shores, perfect for sunbathing and peaceful walks. Throughout the year, various activities take place, including farmer’s markets, oyster roasts, 4th of July celebrations, and New Year’s Eve gatherings. For an unforgettable experience, horseback riding is available for all ages. Don’t miss the opportunity to visit the Bloody Point Lighthouse museum and consider taking an afternoon for a self-guided island tour via golf carts. The true gem of the island is its pristine 3-mile beach, boasting endless stretches of sand, crystal-clear waters, vibrant seashells, and abundant wildlife. The beach is never crowded, allowing you to relax, swim, or collect seashells in peace. Bring your own boat and come join us at River Bluff Retreat, where unforgettable memories await you and your loved ones. PLEASE NOTE: Concerned about how to get to our bridgeless island? Daufuskie Rental Group is here to help you with the logistics of booking your passenger only ferry/water taxi, ground transportation shuttle from the dock to your rental, and golf cart rental? (Fees Apply) A 4-passenger golf cart is included with your stay! Please contact us if you need additional golf carts, as discounts are available for DRG guests if booked with our premier partner, Island Essentials Cart Company. Want to book a fishing charter, History Tour, Dolphin Excursion or Sunset Cruise? We’ve got you covered! Contact us to for a one-stop shop experience!  We will text you the entry code and Wi-Fi password on day of arrival once unit is ready. The Daufuskie Rental Group on site team lives on the island and ready to help in any way! Keep in mind that there is no "BRIDGE" to Daufuskie Island, so your adventure begins with your choice of a private boat, ferry, or your very own vessel. Positioned at Marker 40 with 50ft deep water at high tide, it’s just a 20-minute boat ride to Savannah and Hilton Head, offering you endless possibilities for exploration. The fishing in the area is excellent, and you can even catch redfish, speckled trout, and sheepshead right from the backyard dock. If taking a ferry/water taxi, you will need ground transportation from the dock to the rental and book a golf cart as well. Fees apply. DRG is here to help you with all the logistics and more! This property has a cameras on the house only overlooking the front and back yards (not pool) of the property. 4 passenger golf cart included for any reservations created on or after 12/11/25

Harbour Town Luxury w/ Private Pool

Hilton Head Island, SC, US
3 Bedrooms 10 Guests
Sep 9 - 14
$793 night

Experience timeless Hilton Head luxury at 26 Spinnaker Court, just steps from Harbour Town Golf Links and the iconic Yacht Basin. This spacious end unit villa offers light filled living spaces, private ensuite bedrooms, and the largest private pool in Spinnaker Court. Perfectly located in Sea Pines, it is an ideal coastal retreat for unforgettable island stays. Welcome to 26 Spinnaker Court, a newly renovated coastal retreat in the heart of Sea Pines on Hilton Head Island, now proudly part of the Host2Coast collection. Perfectly positioned just moments from Harbour Town Golf Links and the iconic Harbour Town Yacht Basin, this home places you at the center of one of the island’s most sought-after destinations. Guests can easily walk or bike to Harbour Town’s shops, dining, and waterfront views, or hop on nearby Sea Pines Trolley stops for a convenient ride to the beach or South Beach Marina. Surrounded by moss-draped oaks and the charm of Lowcountry living, this property delivers an unforgettable Hilton Head vacation experience. Even better, this home is pet-friendly* for one pup up to 25 lbs, so your furry companion can join in on the getaway. Inside, more than 3,000 square feet of beautifully updated living space welcomes you with natural light, warmth, and a seamless open layout. The fully equipped kitchen features granite countertops, custom cabinetry, stainless steel appliances, and ample prep space, making it ideal for everything from casual breakfasts to elevated dinners. The kitchen flows effortlessly into the dining and living areas, creating a central gathering space designed for connection and comfort. A versatile den adds flexibility with a dedicated workspace and sleeper sofa, perfect for remote work or additional guests. Every detail of this Hilton Head vacation rental has been thoughtfully designed to balance style, function, and relaxation. The bedroom layout offers privacy and comfort for families and groups, with two upper-level bedrooms featuring private en suite bathrooms for a true retreat experience. A unique twin bedroom tucked above a steep, narrow staircase provides a cozy hideaway best suited for agile guests, adding character to the home. The main-level king bedroom offers convenient access to a full adjacent bathroom, ideal for guests seeking single-level living. On the ground level, the entertainment area opens directly to one of the largest private pools and patios in Spinnaker Court, creating a resort-style setting right at home. A full bathroom located just off the pool ensures effortless indoor-outdoor living, making pool days both comfortable and convenient. Step outside and enjoy multiple outdoor living areas designed for soaking in the Hilton Head lifestyle, whether you’re lounging poolside, dining al fresco, or unwinding under the shade of oak trees. With world-class golf, pristine beaches, bike trails, and waterfront dining all within easy reach, every day offers a new way to explore Sea Pines and beyond. The combination of prime Harbour Town proximity, modern renovation, and thoughtful amenities makes this home an exceptional choice for your next island escape. Whether you’re planning a family vacation, golf getaway, or relaxing coastal retreat, this property delivers on every level. Enjoy a vacation reimagined with host2coast, your trusted Hilton Head Island Property Management partner. PROPERTY SPECIFIC DETAILS: * Sea Pines is a gated community in which every vehicle must have a gate pass for entry. One gate pass is included with your reservation at the time of booking. If you require additional passes, please request the exact number needed to ensure they are prepared in advance. Each pass has a fee of $35. All gate passes must be picked up at the host2coast office prior to entry. * Dog Friendly - 1 dog, 25lb max. $250 non-refundable fee. Dog is not permitted on the furniture and must be crated if left alone. Please do not leave furry friends alone outside, as we have wildlife that they should not encounter. * Due to safety concerns, the fireplace is not available for guest use. * Garage is not available for guest use. * Parking available for 2 vehicles. STR Permit # 77160 We want your stay to be all about the memories - not the paperwork. So let’s get the small stuff out of the way early and get back to what matters: your trip! Every reservation is required to complete a quick Guest Portal before check-in. It’s a secure external link we’ll send you shortly after booking, and it’s also where you’ll find all your check-in details - including your all-important door code. The pre-approval process takes just a few minutes and covers three simple steps: 1. Sign the Rental Agreement - a quick electronic signature, no printing required. 2. Guest verification - a fast, standard guest verification. 3. Pick your coverage: Damage Waiver (a small, non-refundable fee covering eligible accidental damage during your stay - our guests’ favorite option, since it takes the stress out of minor mishaps) or Security Deposit (a fully refundable hold, released after checkout as long as everything’s in order). We’ll email your secure portal link before arrival - just a few minutes of your time for a much smoother check-in. Thanks for helping us keep things safe and simple. We can’t wait to host you! Biking is very popular on Hilton Head Island, known for the many award-winning trails. There are recommendations for bike rental companies within your Guest App. You can reserve in advance and they will deliver to you or bring your own! Almost everything you will need is within walking distance, so bring your walking shoes! Sea Pines provides a complimentary seasonal trolley service that helps guests and residents travel around the resort without using a car. The trolley connects major destinations such as Harbour Town, the Sea Pines Beach Club, South Beach Marina, and The Shops at Sea Pines Center, making it easy to access beaches, dining, and shopping throughout the community.

Exceptional 2 BR Vacation Villa with Community Pool and Tennis

Hilton Head, SC, US
2 Bedrooms 6 Guests
Nov 7 - 9
$224 night

Calibogue Club 2604 Escape to sunlit serenity at Calibogue Club 2604, a beautifully appointed 2-bedroom, 2-bath villa nestled in the tranquil Sea Pines community on Hilton Head Island. This inviting retreat features thoughtful design and quality finishes, including gleaming floors, a modern kitchen, and comfortable furnishings that make it easy to feel at home. Enjoy your morning coffee or unwind in the evening in the cozy sunroom, where peaceful lagoon views create the perfect relaxing backdrop. Guests will love the convenience of on-site amenities like a sparkling community pool and well-maintained tennis courts, ideal for a day of recreation and relaxation. When you’re ready to explore, scenic bike trails wind through the area, connecting you to some of Hilton Head’s best attractions, beaches, and nature spots. Whether you’re seeking adventure or a quiet coastal escape, Calibogue Club 2604 delivers an unforgettable Low Country experience. <b>Places to Visit During Your Stay</b><ul> Harbour Town Lighthouse – 1.6 Miles Coligny Beach Park – 4.1 Miles Coastal Discovery Museum – 8.1 Miles Fort Pulaski National Monument – 53.7 Miles Tybee Island Light Station & Museum – 56.3 Miles Harbour Town Golf Links – 1.4 Miles Arts Center Of Coastal Carolina – 5.0 Miles This property’s license number is 29289. <b>Things to Know</b> Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. All guests shall abide by The Good Neighbor Policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m. No smoking is permitted anywhere on the premises. Please note E-bikes are not allowed. Free Wifi Please be aware that the Plantations and Condominium Complexes do not allow trailers, motor homes, motorcycles and/or recreational vehicles and rooftop cargo (i.e. Kayaks, Canoes etc.) other than car top Carriers. Electric bikes are not permitted in the Plantations. License number: 29289,029289

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Vacation Rentals Near Okatie

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