Vacation rentals in Cudjoe Key, FL with a pool

Explore 76 vacation rentals, homes, and villas with pools in Cudjoe Key, FL 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 $104 per night and homes offering up to 8 bedrooms and 8 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.

76 Homes with Pools in Cudjoe Key

Villa Jekjak

Summerland Key, FL, US
4 Bedrooms 8 Guests
Oct 31 - Nov 28
$746 night

Villa Jekjak- 4 BDR, luxury residence with pool & beach Enjoy the unobstructed 270-degree ocean view in this newly renovated beachfront residence. Located in the most exclusive part of Cudjoe Gardens this 2- story house is surrounded by the water on 3 sides. Three bedrooms and two bathrooms are impressively decorated in a soft coastal palette and are located on the second main living floor. Amble of natural light emphasizes the open and easy-flowing design of the main floor. Well-equipped chefs kitchen has top-of-the-line appliances and is a perfect retreat for culinary-inspired guests. Highlighted by the walls of glass doors, Family Friendly floorplan combines the living room, dining room and opens to the oceanfront terrace.  The vaulted ceiling adds great drama to the space. Light & Airy Master Suite features King Bed, a private Master Bathroom with a stand-up shower, and a large walk-in closet. The guest wing offers generously scaled 2 bedrooms and a shared bathroom. The downstairs Guest Quarter enclosure has an additional private queen bedroom, rec room, TV area, and a wet bar and full bathroom. The private pool is nestled on a sandy beach and surrounded by meticulously maintained grounds. Deep access to world class fishing and free dockage makes this house a boaters paradise! This house is truly Paradise Found! The property is PET-friendly with a non-refundable PET fee. Additional features: Washer & Dryer Central AC & ceiling fans throughout Starter supply paper products Starter set cleaning products Linens, bath, and pool towels Kitchen cookware, dishes, flatware, glassware Wireless high-speed internet Fully fenced private residence Housekeeping services available Original Art Private dock Private Beach and a hammock Outdoor Shower BEDROOMS>>Master- King Bed Guest Bedroom #1- Queen Bed Kids Room- Bunk Bed Downstairs Guest Quarter- 1 Queen Bed

Foster’s Folly | Gorgeous canalfront pool home

Summerland Key, FL, US
3 Bedrooms 6 Guests
Sep 3 - Oct 1
$310 night

Gorgeous canalfront pool home close to open water on Cudjoe Key Escape to a slice of paradise on Cudjoe Key, where luxury meets tranquility in this stunning 3-bedroom, 2-bathroom stilted home with pool on a boating canal. This monthly rental offers a perfect blend of upscale comfort and coastal charm, providing an idyllic retreat for your Key West getaway. Step inside to discover a beautifully appointed interior, where every detail exudes warmth and sophistication. The spacious living area invites you to unwind with plush furnishings and stylish accents, while large windows bathe the space in natural light and offer enchanting views of the surrounding waterfront paradise. Prepare delicious meals in the gourmet kitchen, equipped with modern appliances, sleek countertops, and ample cabinet space. Adjacent to the kitchen, the dining area sets the stage for memorable gatherings with loved ones, while sliding glass doors seamlessly connect the indoor and outdoor living spaces. Venture outside to experience the ultimate in outdoor living, where a waterfront pool beckons you to soak up the Florida sunshine and cool off with a refreshing swim. Lounge on the expansive pool deck, furnished with comfortable seating and dining areas, as you savor the gentle sea breeze. For a truly unforgettable experience, ascend to the rooftop deck and witness the spectacle of the sun rising and setting over the horizon, casting a mesmerizing palette of colors across the sky. Boating enthusiasts will delight in the convenience of the 40 feet of dock space, just steps from your door. Launch your own vessel or explore the surrounding waters by kayak or paddleboard, immersing yourself in the natural beauty and serenity of the Florida Keys. Whether you’re seeking adventure on the water or simply seeking solace amidst the beauty of the outdoors, this exquisite vacation rental offers the perfect blend of luxury, comfort, and coastal living for your Florida Keys escape. Indulge in the ultimate vacation experience at this stunning waterfront oasis on Cudjoe Key. Please note that during your stay, the owner’s boat will be stored on the lift and his vehicle will be parked under the house, but there’s still plenty of room for you to park your vehicles and trailer. The primary guest must sign a rental agreement. This home requires a minimum 28-day stay per county ordinance. Proper county and state taxes are collected regardless of booking platform. Renter must be 25 or older. Overnight occupancy is limited to a maximum of 6 people, and all guests need to be registered with the property manager. No smoking. Small dog permitted with manager approval and nonrefundable fee. There’s a cap on electric ($300) and water/sewer ($150). Pool heat is an additional $15 per day. Guests have the house to themselves. A car is recommended. A car is recommended. There is a city bus that runs from Key West to Marathon several times a day. The Lower Keys have limited taxi service and Uber/Lyft.

Sirena Key | Luxury Oceanfront Estate, Pool, Guest Cottage, Dock, 30min to Key West

Summerland Key, FL, US
5 Bedrooms 14 Guests
Sep 9 - Oct 7
$413 night

🏡 Amenities: Dock, Guest Cottage, Pool, Spa, Outdoor Kitchen, Firepit 🌊 Kayaks, and Paddle Boards 📍 30 Minutes to Key West and Marathon 🐶 Dog Friendly 🤝 24/7 Guest Support Welcome to Sirena Key, a luxury oceanfront gated estate in the exclusive island community of Summerland Key in the Florida Keys. This private vacation rental is designed for families and groups seeking the perfect blend of resort-style amenities and the comforts of home. Step through the gates and you’re greeted by a charming garden with bistro seating, a tranquil spot to relax while children enjoy the open grassy lawn. The estate includes a spacious main house with 4 bedrooms and 3.5 bathrooms, as well as a private guest cottage with a living room, pullout sofa, full kitchen, dining area, bed and bathroom. Together they create the ideal setup for multi-family getaways, offering both elegant gathering spaces and private areas. Outdoors, unwind beside the sparkling pool and spa, complete with hotel-style loungers, a cabana bed, hammock, and umbrellas. A full outdoor kitchen with seating makes alfresco dining effortless, while kayaks and paddleboards invite adventure on the water. Evenings can be spent gathered around the firepit or at the private oceanfront lounge, perched at the edge of the ocean with shaded loungers and breathtaking views. With space for up to 14 guests, Sirena Key offers the ultimate Florida Keys experience, just 30 minutes from both Key West and Marathon. 🍽️ INDOOR MODERN KITCHEN + DINING -Chef’s kitchen with induction cooktop, stainless steel appliances, and beverage fridge -Counter seating for 3, and formal dining table for 6 -Open-concept living room with large sectional, Smart TV, and motorized blackout blinds ✨ ENTERTAINMENT + LOUNGING SPACES -Movie theater with projector, oversized sectional, motorized blackout blinds, and pool + ocean views. -Game room with pool table, shuffleboard, Smart TV, motorized blinds, and direct patio access with chic outdoor dining table. -Secret garden entry with lounge seating and dining table. 🛏️ MAIN HOUSE BEDROOMS All bedrooms feature the following amenities: ✔ Premium beds, pillows, linens, and sheets ✔ Ceiling fans ✔ Tv’s ♛ Primary Suite (2nd Floor): King bed, spa-style ensuite, walk-in closet, desk, seating area, Smart TV, water views, coffee nook, motorized blackout blinds. Ensuite includes double vanity, spa tub, dual shower-heads, and private toilet room. -First-Floor Bunk Room: Four twin bunks, sectional, Smart TV, blackout blinds, private porch with dining table for 4, ensuite bathroom with shower and vanity. -First-Floor Queen Bedroom #1: Queen bed, Smart TV, access to Jack-and-Jill bathroom with shower and vanity. -First-Floor Queen Bedroom #2: Queen bed, desk, Smart TV, Jack-and-Jill bathroom access. 🏡 PRIVATE GUEST COTTAGE The separate guest cottage is a fully equipped retreat of its own, perfect for families traveling together or guests who want more privacy. -Studio layout; Queen bed -Living room with pull-out sofa -Kitchen + dining area -Private bathroom with shower and vanity 🛁 BATHROOMS All full bathrooms are generously stocked with: ✔ Shampoo & conditioner ✔ Body soap ✔ Fluffy towels ✔ Toilet tissue -Primary Ensuite: Spa tub, dual shower heads, double vanity, motorized blackout blinds, private toilet room -Bunk Room Ensuite: Shower and vanity -Jack-and-Jill Bath: Shared by two queen rooms, shower and vanity -Half Bath: Vanity, sink, toilet, washer/dryer and storage -Cottage Bathroom: Shower and vanity 🌴RESORT-STYLE OUTDOOR SPACES Sirena Key’s outdoor spaces are designed like a private resort. -Automatic front gate for secure entry, expansive driveway with space for multiple vehicles. -Pool and spa with cabana-style bed, hotel-style loungers, umbrellas, and hammock -Pergola with large sectional lounge sofa -Full outdoor kitchen with seating, Lynx propane grill, Asado grill, and prep space -Kayaks and paddleboards available for guest use -Garden patio and shaded dining areas 🌊 OCEANFRONT EXPERIENCES ​​​​​​​ This home takes oceanfront living to the next level! -Private dock with fish-cleaning station, running water, and hose -Bait fridge -Separate oceanfront lounge right with firepit, chairs, and 3 loungers featuring built-in personal shade canopies -Boat lifts are for owner use only and not available to guests ⚠️ OCEANFRONT SAFETY NOTE Sirena Key is situated directly on the ocean with a private dock and open water access. Due to the home’s oceanfront setting and pool design, extra care and supervision are required when children are present. Children must be fully supervised at all times when outdoors or near the pool, dock, or water. Parents or guardians are responsible for ensuring the safety of all members of their party during their stay. This home is best suited for guests who are comfortable managing an oceanfront environment. 📍POINTS OF INTEREST + LOCATION HIGHLIGHTS Sirena Key is located in Summerland Key, one of the most desirable islands in the Florida Keys, just 30 minutes from Key West & Marathon. Guests enjoy easy access to marinas, fishing, snorkeling, and world-class attractions. -Big Pine Key & National Key Deer Refuge – 15 minutes -Bahia Honda State Park – 25 minutes -Marathon – 35 minutes -Key West – 30 minutes -Islamorada – 1 hour 15 minutes -Key Largo – 2 hours EXTRA DETAILS -High-speed WiFi throughout the property -Motorized blackout blinds in primary bedroom, primary bathroom, game room, living room, bunk room, and theater -Washer and dryer -EV charger available (requires an adapter for Teslas) -Responsive 24/7 guest support team Book your stay at Sirena Key and enjoy the ultimate Summerland Key vacation rental. A private Florida Keys estate with luxury amenities, a separate guest cottage, and unforgettable waterfront living. Other Things to Note: -Guests are welcome to use the boat dock during their stay. It can accommodate boats up to 40 ft in length. Please note that boats with more than a 3 ft draft may not be suitable. -Boat lifts are for owner use only and not available to guests HOUSE RULES: Check-in time: 4:00 PM Check-out time: 10:00 AM All guests must sign our rental agreement as mandated by Florida Law. -The minimum rental age is 25. A picture ID must be provided to the company no less than 72 hours (about 3 days) before arrival. -If you would like the pool heated during your stay, there is a $40 fee per day or $1,000 per month. Please coordinate with us prior to your arrival so that we can arrange for the heater to be on. -Please provide an accurate guest count. -No smoking or vaping. If evidence is discovered of either smoking or vaping, the guest will be subject to a fine of up to $1,000 -No parties or events. If unauthorized persons are discovered on the premises, guests will be subject to additional fees and/or immediate eviction. -Quiet time is from 10:00 PM - 8:00 AM -This property is equipped with security cameras on the outside of the property at the entrance and pointing at the dock. These cameras are used during the check-in process to verify identity and guest count. If there is an incident, we will review the footage. There are no cameras inside the property or pointing toward the pool area. Starter Supplies: We provide trash bags, paper towels, toilet paper, detergent, and bathroom amenities to accommodate this home’s maximum occupancy for the first three days of your stay. Same-Day Bookings: Same-day bookings require approval from the company. We will ask you to provide information on your group and the purpose of your stay. If your stay is approved, we require a government-issued ID for identity verification. Your phone number must match the phone number on your account, or we will not be able to honor your reservation. Same-day reservations will not be accepted after 2:00 PM. All same-day reservations require at least 3 hours before check-in. We may have to extend check-in time to later than 4:00 PM. Pet Policy: This property is dog-friendly, with an additional $750 per month, per pet. For stays of two months or longer, the fee is $2,000 per month, per pet. While staying with us, you are responsible for the actions of your pet. Please keep your dog(s) off the furniture and pick up all waste. All waste should be bagged and disposed of in the outside trash bin. Failure to comply with our pet policy may result in an additional $100 fee. Please let us know if you will be bringing your dog (only dogs under 25 lbs are permitted, sorry). Baby Bundle: If you have little ones, we offer: Pack-n-play with a thicker mattress & a high chair for $65 per stay. Please make your request at the time of booking or 24 hrs prior to your arrival. Property Care Instructions: Treat this home like your own. -Any/all outdoor umbrella(s) must be placed in the closed position when not in use and at the time of check-out. This must be done in order to prevent breakage due to weather conditions. Failure to comply may result in an additional charge. -Please ensure that the grill is covered when not in use. This helps to maintain the grill’s condition for future guests. Failure to comply may result in a cleaning or maintenance fee. Mid-Stay Cleaning Requirement: For all extended stays of 30 nights or longer, a mandatory mid-stay cleaning is required every 30 days. If your reservation is 60 days, two mid-stay cleanings will be required, and so on. This helps keep the home maintained during longer stays and ensures everything stays in great condition. Mid-Stay Cleaning Fee: $750 (Main House + Cottage) We’ll reach out after booking to schedule the mid-stay cleaning(s) and send the payment link.

Fishermen’s Paradise | Pool, 220’ Dock & Open-Water Views

Big Pine Key, FL, US
3 Bedrooms 8 Guests
Aug 31 - Sep 2
$638 night

Welcome to Fishermen’s Paradise, a beautifully appointed open-water retreat on Big Pine Key. Enjoy a private heated pool, 220 feet of dockage for one guest boat, outstanding access to the backcountry, Gulf and Atlantic, and frequent visits from the island’s famous Key Deer. This Lower Keys escape is designed for unforgettable days on and off the water. Welcome to your perfect island retreat on Big Pine Key. Freshly remodeled and thoughtfully designed, this three-bedroom, four-bath waterfront home combines modern comfort with the natural beauty of the Lower Florida Keys. With 2,000 square feet of elevated living space, a private resort-style pool, private dockage for one guest boat and sweeping open-water views, this is the ideal place to relax, explore and enjoy life on the water. Boaters and anglers will appreciate the exceptional waterfront setup. Guests are welcome to dock one boat at the property during their stay, in accordance with Monroe County regulations. The 220-foot dock offers some of the best boating access in the Lower Keys, with approximately 5 feet of water depth at the end of the dock. Amenities include a step-down platform, swim ladder, power, water and an outdoor shower for rinsing off after a day on the water. From here, you’ll enjoy quick access to the backcountry flats, Gulf waters and the Atlantic, making it easy to spend your days fishing, diving, snorkeling or exploring the countless islands and sandbars that make the Lower Keys so special. Anglers will appreciate the dedicated bait freezer located in the downstairs storage, along with a selection of fishing rods available for guest use. After a day on the water, enjoy a game of cornhole while taking in the waterfront setting. Want to explore beyond the boat? A local outfitter can deliver bikes, kayaks and paddleboards directly to the property. Your property manager can also provide recommendations for fishing charters, boat rentals and other local adventures. Inside, you’ll find a beautifully updated kitchen equipped for everything from quick breakfasts to fresh-catch dinners. A wine cooler and small ice maker make entertaining easy. To make your arrival even more relaxing, guests may arrange grocery delivery through their preferred delivery service before check-in, and we’ll gladly place everything inside the home so your vacation can begin the moment you walk through the door. Each bedroom serves as a private retreat with its own en-suite bathroom, generous storage space and smart TV with DirecTV Stream. Outside, unwind by the resort-style pool and take in the open-water views. The pool is heated from mid-October through mid-April, making it comfortable to enjoy during the cooler months. A selection of pool toys adds to the fun for guests of all ages. Keep an eye out for the island’s famous Key Deer, which are frequently spotted passing through the property. Found only in the Lower Florida Keys, these endangered miniature deer provide a unique wildlife-viewing opportunity that many guests remember long after their stay. **Sleeping Accommodations** • Primary Suite: King bed and large tub/shower combination • Guest Suite 1: Queen bed plus oversized twin chair/sleeper and tub/shower combination • Guest Suite 2: Queen bed with private shower • Living Room: Queen sleeper sofa Big Pine Key is home to the National Key Deer Refuge, miles of scenic bike paths, excellent kayaking trails and some of the most pristine natural landscapes in the Florida Keys. Conveniently located near local restaurants, shops and marinas, the home is just 20 miles from Marathon, 31 miles from Key West and only 5 miles from Bahia Honda State Park, widely regarded as one of the most beautiful beaches in the Florida Keys. Spend your days boating, fishing, snorkeling, kayaking, wildlife watching or simply relaxing poolside with water views. Whether you’re planning a fishing trip, a family getaway or a relaxing escape by the water, this exceptional waterfront home offers the perfect setting for an unforgettable Keys vacation. **Good to Know** • Primary renter must be at least 25 years old and sign a rental agreement. • Maximum overnight occupancy is 8 guests. • All guests must be registered with the property manager. • No smoking or pets permitted. • Guests may bring and dock one boat and trailer during their stay, in accordance with Monroe County regulations. • The home is fully licensed for short-term vacation rentals, and all required county and state taxes are collected regardless of booking platform. • Shorter stays may be available when calendar openings permit.

Manatee Watch | 5 bedrooms, pool, ocean access

Big Pine Key, FL, US
5 Bedrooms 12 Guests
Sep 13 - Oct 11
$415 night

Gorgeous pool, big dock & easy ocean access from this 5 bed/4 bath home on Big Pine Key Discover your dream waterfront getaway on Big Pine Key! This impeccably updated 5-bedroom, 4-bathroom boating home offers unparalleled luxury and convenience, just seconds away from Pine Channel on the oceanside of Big Pine Key. Nestled just four houses in from Pine Channel, this stunning property features a breathtaking custom pool and spa, perfect for unwinding after a day of exploring the pristine waters. With a 60-foot concrete dock equipped with large piles with fenders, accommodating your big boat has never been easier. Convenient steps lead down into the deep water 70-foot wide canal, providing effortless access for swimming, kayaking, or paddleboarding. And keep your eyes peeled for endangered manatees, frequent visitors to the clear, deep canal. Boasting 2,400 square feet of meticulously designed living space, this isn’t your average Keys rental! The main floor features a king en suite with walk-in closet and a second king bedroom, plus a full bath off the hall. Upstairs, discover three additional bedrooms, including a king en suite with sleeper sofa, desk, large TV with game console and balcony with panoramic open water views. With two queen beds in the 2nd upstairs bedroom, another queen bed in the third and a full bath and seating area off the hall, there’s ample space for everyone to relax in comfort. Indulge your culinary aspirations in the fully equipped kitchen, complete with modern appliances including an instant pot, sous vide, and KitchenAid stand-alone mixer. Enjoy meals at the breakfast bar for three or gather around the dining room table that comfortably seats six. For outdoor dining, head to the poolside area. Unwind on one of the two covered porches, each offering peekaboo views of the open water. The waterfront custom pool and spa, featuring a waterfall and tanning ledge, provide the ultimate relaxation spot. Completed in March 2023, the pool measures 14 by 30 feet and boasts a stunning finish with pebble tech and custom tile. The spa backs up to a custom bar with a quartzite countertop, offering the perfect vantage point for soaking in the views of the pool and canal. There’s lockable storage downstairs for all of your gear, plus parking for three vehicles and a boat trailer. Experience luxury living on Big Pine Key – book your stay at this spectacular vacation rental today! The primary guest must sign a rental agreement. This is a minimum 28-day rental per county ordinance. Proper county and state taxes are collected regardless of booking platform. Renter must be 25 or older. Overnight occupancy is limited to a maximum of 12 people, and all overnight guests need to be registered with the property manager. Well-behaved dog permitted with manager’s approval and payment of nonrefundable $250 fee. No smoking. There’s a cap on electricity ($300) and water/sewer ($200). Pool heat available upon request for an additional charge.

The Dreamside House at Lunara Bay

Key West, FL, US
8 Bedrooms 16 Guests
Aug 30 - Sep 1
$1,439 night

Discover a luxurious new waterfront home, 8 spacious bedrooms and a private pool at Lunara Bay - a collection of 26 Luxury homes in a gated community! . This stunning home offers exceptional amenities, including free gym access and ample living space perfect for relaxation and entertainment. Dock boats up to 40’ at private slips, relax in your private pool, access the FYT gym, and enjoy itineraries from our local guest experience team. Extend your stay 7+ nights for 10% off your entire stay! Experience luxury with our private boat excursions and chauffeur services. Enjoy customized aquatic adventures or arrive in style with our premium transportation options. Expect excellence tailored to your stay. For more information, please reach out! The open-concept floor plan, both indoors and outdoors, creates a warm atmosphere ideal for entertaining and quality time with loved ones. Whether you’re relaxing by the pool, playing games, grilling, or dining in various areas, there’s something for everyone. The fully equipped kitchen is perfect for home-cooked meals or for a private chef to elevate your culinary experience. With high-speed internet and keyless entry, your vacation will be seamless and convenient. Outside, the spacious fenced yard provides a safe play area for children and a perfect space for your pets. This property features eight bedrooms, each with a king bed and ensuite bathroom. Our self check-in makes the process seamless. Guests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay. Boating & Private Dock Slip: We encourage boating. Here’s what you need to know in order to do so safely: - Dock accommodates a boats up to 50’ in length. Travel by car, boat, or plane to Modern Keys, The driveway allows parking for up to 4 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations! - Private washer/dryer - Located in a gated community - Free gym access at FYT - Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximum

Evershore House | Pool, Parking, Dock!

Key West, FL, US
4 Bedrooms 12 Guests
Aug 30 - Sep 1
$959 night

Evershore Estate is a waterfront 4-bedroom, 4-bath home at Lunara Bay - a collection of 26 luxury homes in a gated community. Perfect for activity and relaxation, it features a private pool and dock, parking, a pet-friendly gated yard, and fitness amenities including a Peloton, free weights, and yoga mats. Tailored itineraries help you uncover hidden gems and local favorites for an unforgettable Lunara Bay experience. Indulge in luxury with our private boat excursions and chauffeur services. Sail away on tailored aquatic adventures or arrive in style with our elite transportation solutions. Experience excellence, tailored just for your stay. Please reach out for more information! The open concept floor plan makes entertaining a breeze and encourages family time around the dining room table. A fully equipped kitchen awaits your home cooked meals or private chef experience. With high speed internet access and keyless entry vacation has never been more convenient and easy. The spacious fenced in yard and gated dock access are perfect for children and your furry friends. Or enjoy an outdoor workout with at-home gym equipment. Evershore House is a four-bedroom, four-bath home sleeping up to 12 guests with stunning decor. Bedroom 1: King Bed Bedroom 2: King Bed Bedroom 3: King Bed Bedroom 4: King bed & twin over twin trundle bed Extra Sleeping: Queen pull-out couch in the living room Our contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival. Boating: We encourage boating. Here’s what you need to know in order to do so safely: - Private dock can accommodate boats up to 50’ in length. Maximum one boat per dock. - There is no power or pump out service to the slips. - The Florida Keys are a notoriously difficult place to navigate. How to Access: Stair access only the home is elevated above sea level Travel by car, boat, or plane to Evershore House, The driveway allows parking for up to 4 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations! - Extend your stay 7+ nights for 10% off your entire stay! - Elevate your stay and ask us about our Private Chauffeur services. - Private washer/dryer - Located in gated community. - Comes with free gym access to FYT. - Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximum

Waterlane House at Lunara Bay

Key West, FL, US
4 Bedrooms 10 Guests
Aug 31 - Sep 2
$959 night

Waterlane House is an inviting waterfront 4-bedroom, 4.5-bath home at Lunara Bay - a collection of 26 luxury homes in a gated community! Enjoy a private pool and dock, parking, and a pet-friendly gated yard for the perfect Key West retreat. Your stay includes complimentary FYT gym access and custom itineraries to uncover hidden gems and local favorites for an unforgettable experience. Indulge in luxury with our private boat excursions and chauffeur services. Sail away on tailored aquatic adventures or arrive in style with our elite transportation solutions. Experience excellence, tailored just for your stay. Please reach out for more information! The open concept floor plan makes entertaining a breeze and encourages family time around the dining room table. A fully equipped kitchen awaits your home cooked meals or private chef experience. With an oven, stove top, toaster oven, grill, microwave and water dispensing fridge, cooking is a breeze. The high speed internet access and keyless entry vacation has never been more convenient and easy. Sleeping up to 10 guest this home features two king beds, four twin beds, and a queen-sized sleeper sofa. The spacious fenced in yard and gated dock access are perfect for children and your furry friends. Our dock is equipped with a fish fillet station and hose for an easy clean up after a day at sea! Our contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival. Boating: We encourage boating. Here’s what you need to know in order to do so safely: - Private dock can accommodate boats up to 50’ in length. Maximum one boat per dock. - There is no power or pump out service to the slips. - The Florida Keys are a notoriously difficult place to navigate. How to Access: Stair access only the home is elevated above sea level Travel by car, boat, or plane to Waterlane House. The driveway allows parking for up to 4 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations! - Extend your stay 7+ nights for 10% off your entire stay! - Elevate your stay and ask us about our Private Chauffeur services. - Private washer/dryer - Located in gated community. - Comes with free gym access to FYT. - Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximum

Palmgale Estate at Lunara Bay

Key West, FL, US
6 Bedrooms 16 Guests
Aug 30 - Sep 1
$959 night

Palmgale Estate is a luxurious 6-bedroom, 6.5-bath home at Lunara Bay - a collection of 26 luxury homes in a gated community! Located just minutes from Key West’s vibrant center, it offers a private slip at our exclusive marina for boats up to 40’. Enjoy the convenience of docking steps from your door, plus free access to FYT gym. Our guest experience managers can craft a customized itinerary for your group. Contact us for more info and elevate your vacation experience! Step into a realm where contemporary elegance meets island charm. The expansive living areas invite you to unwind or host gatherings, filled with natural light from generous windows. Each bedroom offers a serene escape, featuring plush bedding and private en-suite bathrooms for ultimate comfort and seclusion. The bed layout is as follows: Bedroom 1: King Bed Bedroom 2: Two Bunk Beds with two queen and two twin sized Mattresses Bedroom 3: King Bed Bedroom 4: King Bed Bedroom 5: King Bed Bedroom 6: King Bed All bedrooms have an ensuite bathroom Our self check-in makes the process seamless. Guests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay. Boating & Private Dock Slip: We encourage boating. Here’s what you need to know in order to do so safely: - Dock in our exclusive marina which accommodate boats up to 40’ in length. Maximum one boat per slip. - There is no power or pump out service to the slips. - The Florida Keys are a notoriously difficult place to navigate. Travel by car, boat, or plane to Palmgale House. The driveway allows parking for up to 2 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations! - Extend your stay 7+ nights for 10% off your entire stay! - Elevate your stay and ask us about our Private Chauffeur services. - Private washer/dryer - Located in gated community - Free gym access at FYT - Fans inside bedrooms only operate with the light on. - Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximum

The Starboard House at Solaire Lunara Bay

Key West, FL, US
8 Bedrooms 20 Guests
Aug 31 - Sep 2
$1,458 night

Explore a stunning new build at Lunara Bay—a collection of 26 luxury homes in a gated community. This exceptional eight-bedroom home features a private pool, top-tier amenities including complimentary gym access, and expansive living areas perfect for unwinding and entertaining. With modern design and upscale finishes, Starboard House blends comfort, elegance, and convenience for an elevated stay. Indulge in opulence with our exclusive boat trips and chauffeur services. Experience tailor-made aquatic adventures or travel in elegance with our premium transport options, designed just for you! The spacious open-concept layout, both inside and out, creates a warm setting perfect for entertaining and connecting with loved ones. Relax by the pool, enjoy games, grill, or dine in various charming spots—there’s something for everyone. The fully stocked kitchen is ideal for cooking or hiring a private chef. With high-speed internet and keyless entry, your retreat is seamless. The enclosed yard ensures a safe space for kids and pets. Located right in your backyard, kayaks and paddle boards offer effortless access to water adventures. Bedroom Configuration: This property includes seven king bedrooms and one room with two bunk beds, each featuring ensuite bathrooms. Our self check-in ensures a seamless arrival. Guests will receive a personalized access code before arrival and direct contact with a local guest experience manager for any questions, needs, or recommendations during their stay. Boating & Private Dock Slip: We encourage boating. Here’s what you need to know for a safe experience: - There is shore power available at the dock should you need it. - Dock is private for boats up to 50’ and a limit of one boat per dock. - Navigating the Florida Keys can be challenging, so please proceed with caution. Travel by car, boat, or plane to Modern Keys, The driveway allows parking for up to 4 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations! - Extend your stay 7+ nights for 10% off your entire stay! - Elevate your stay and ask us about our Private Chauffeur services. - Private washer/dryer - Located in a gated community - Free gym access at FYT - Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximum. - We’re excited to provide you with access to the kayaks and paddleboards located on the side of the house. You’ll find the paddles and life jackets in the bin to the left of the kayaks. If they seem low, you will also find an air pump in that bin as well. For your safety, please be sure to wear a life jacket while using the equipment.

Capmar House | Huge Home & Pool

Key West, FL, US
4 Bedrooms 10 Guests
Aug 31 - Sep 2
$959 night

Capmar House is a beautiful waterfront 4-bedroom, 4-bath home at Lunara Bay - a collection of 26 luxury homes in a gated community! Enjoy a private pool and dock, parking, and a pet-friendly gated yard for a relaxing getaway. Your stay includes complimentary FYT gym access, plus personalized itineraries to uncover hidden gems and local favorites for an unforgettable Key West experience. Indulge in luxury with our private boat excursions and chauffeur services. Sail away on tailored aquatic adventures or arrive in style with our elite transportation solutions. Experience excellence, tailored just for your stay. Please reach out for more information! The open concept floor plan makes entertaining a breeze and encourages family time around the dining room table. A fully equipped kitchen awaits your home cooked meals or private chef experience. With high speed internet access and keyless entry vacation has never been more convenient and easy. The spacious fenced in yard and gated dock access are perfect for children and your furry friends. Capmar House is a four-bedroom, four and a half-bath waterfront estate sleeping up to 10 guests. Bedroom 1 - King bed Bedroom 2 - King bed Bedroom 3 - King bed Bedroom 4 - King bed Extra Sleeping - Queen pull-out couch in living area Our contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival. Boating: We encourage boating. Here’s what you need to know in order to do so safely: - Private dock can accommodate boats up to 50’ in length. Maximum one boat per dock. - There is no power or pump out service to the slips. - The Florida Keys are a notoriously difficult place to navigate. How to Access: Stair access only the home is elevated above sea level Travel by car, boat, or plane to Capmar House. The driveway allows parking for up to 4 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations! - Extend your stay 7+ nights for 10% off your entire stay! - Elevate your stay and ask us about our Private Chauffeur services. - Private washer/dryer - Located in gated community. - Comes with free gym access to FYT. - Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximum

Aquaria House | Pool & Boat Dock

Key West, FL, US
4 Bedrooms 10 Guests
Aug 30 - Sep 1
$959 night

Experience the Aquaria House at Lunara Bay - a collection of 26 luxury homes in a gated community! This stunning waterfront 4 bedroom, 4.5 bath home is perfect for those looking to embrace all that Key West has to offer. Enjoy a private pool & dock, convenient parking, and a pet-friendly gated yard for a truly relaxing getaway. We provide personalized itineraries to help you and your party make the most of your Lunara Bay experience. Indulge in luxury with our private boat excursions and chauffeur services. Sail away on tailored aquatic adventures or arrive in style with our elite transportation solutions. Experience excellence, tailored just for your stay. Please reach out for more information! The open concept floor plan makes entertaining a breeze and encourages family time around the dining room table. A fully equipped kitchen awaits your home cooked meals or private chef experience. With high speed internet access and keyless entry vacation has never been more convenient and easy. The spacious fenced in yard and gated dock access are perfect for children and your furry friends. Aquaria House is a four-bedroom, four and a half-bath home sleeping up to 10 guests with breathtaking decor. Bedroom 1 - King Bedroom 2 - King Bedroom 3 - King Bedroom 4 - King Extra Sleeping - Queen pull-out couch in the living area Our contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival. Boating: We encourage boating. Here’s what you need to know in order to do so safely: - Private dock can accommodate boats up to 50’ in length. Maximum one boat per dock. - There is no power or pump out service to the slips. - The Florida Keys are a notoriously difficult place to navigate. How to Access: Stair access only the home is elevated above sea level Travel by car, boat, or plane to Aquaria House, The driveway allows parking for up to 4 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations! - Extend your stay 7+ nights for 10% off your entire stay! - Elevate your stay and ask us about our Private Chauffeur services. - Private washer/dryer - Located in gated community. - Comes with free gym access to FYT. - Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximum

Seagate House | Waterfront w/Dock

Key West, FL, US
4 Bedrooms 10 Guests
Aug 30 - Sep 1
$959 night

Discover your dream Key West getaway at Lunara Bay - a collection of 26 Luxury homes in a gated community! Seagate Estate is a 4BR, 4.5BA luxury waterfront home blending island charm with modern elegance, just minutes from downtown. Dock your boat right in the backyard, unwind in your pool, enjoy gym access, and enjoy curated itineraries from our local guest experience team. Elevate your visit with our Private Chauffeur Service for effortless transportation. Indulge in luxury with our private boat excursions and chauffeur services. Sail away on tailored aquatic adventures or arrive in style with our elite transportation solutions. Experience excellence, tailored just for your stay. Please reach out for more information! The open concept floor plan makes entertaining a breeze and encourages family time around the dining room table. A fully equipped kitchen awaits your home cooked meals or private chef experience. With high speed internet access and keyless entry vacation has never been more convenient and easy. The spacious fenced in yard and gated dock access are perfect for children and your furry friends. Our dock is equipped with a fish fillet station and hose for an easy clean up after a day at sea! Seagate House is a 4 bedroom, 4.5 bath home sleeping up to 10 guests with sleek contemporary decor. Bedroom 1: King bed with en suite bathroom Bedroom 2: King bed with en suite bathroom Bedroom 3: King bed with en suite bathroom Bedroom 4: King bed with en suite bathroom Extra Sleeping: Queen pull-out couch in living area Our self check-in makes the process seamless. Guests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay. Boating: We encourage boating. Here’s what you need to know in order to do so safely: - Private dock can accommodate boats up to 50’ in length. Maximum one boat per dock. - There is no power or pump out service to the slips. - The Florida Keys are a notoriously difficult place to navigate. How to Access: Stair access only the home is elevated above sea level Travel by car, boat, or plane to Seagate House, the driveway allows parking for up to 4 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations! - Private washer/dryer - Located in gated community. - Comes with free gym access to FYT.

Coastal Compoun d

Key West, FL, US
8 Bedrooms 16 Guests
Aug 30 - Sep 1
$2,176 night

This compound is comprised of two homes in exclusive Key Cove Landings, by combining Coastal Comfort and 3/4 Time, two 4-bedroom homes! The perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. This home includes plenty of off-street parking in the private garages, as well as on the driveways in front of the homes. Key Feature: 6 en’suite bedrooms in addition to a bedroom in each home off the living room, each with two twin beds. The homes have the same large open floorplan with spacious seating areas. The master bedrooms have King-sized beds, large flat-screen HD TVs, and en-suite bathrooms complete with a glass showers, large Jacuzzi tubs and separate room for the facilities. Second bedrooms have King-sized bed, flat-screen HD TVs, large walk-in closets, and glass sliding doors providing access to the waterfront balcony. The bathrooms are en-suite. The third bedrooms are also on the 2nd floor with en-suite bathroom. We suggest looking at each individual listing for more specific information on each of the homes that comprise this Key Cove Landings compound. AMENITIES: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. Pets Considered. This property will accommodate 16. This compound does not include dockage. RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).

Coastal Comfort

Key West, FL, US
4 Bedrooms 8 Guests
Aug 30 - Sep 1
$670 night

Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be in Coastal Comfort. This home is located in the private community of Key Cove Landings, on an exclusive lane of waterfront residential homes. The perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. This home includes plenty of off-street parking in the private garages, as well as on the driveways in front of the house. Key Feature: 3 en’suite bedrooms This home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with plush couches around a large HD flat screen Smart TV. One of the couches also pulls out to a Queen-sized sleeper sofa for additional guests. There is a dining table with seating for up to 6 diners, with additional seating for 4 at the kitchen bar. The master bedroom has a King-sized bed, a large flat-screen HD TV, and an en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony. The second bedroom has a King-sized bed, a flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The bathroom is en-suite. The third bedroom is also on the 2nd floor with a Queen bed, flat screen TV, balcony access and en-suite bathroom. On the main floor there is a fourth bedroom with trundle bed. There is a half bath down the hall. Out back is one of the highlights of this home: the covered lanai and pool area. The covered outdoor dining area comfortably seats six for a poolside meal. The pool is heavenly, with views of the open water and visiting heron on the tropical greenery that surrounds the back yard. There is also a pool lounge area with comfortable chaises in a piece of deck that gets equal sunshine and shade. The backyard is complete with a large propane grill for a poolside BBQ. AMENITIES: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. Pets Considered. This property will accommodate 8. Dockage is not available at this home’s development. RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates). DOG FRIENDLY. Please contact us to confirm specific pet policies.

New! Altair House | Pool, Pets!

Key West, FL, US
6 Bedrooms 14 Guests
Aug 30 - Sep 1
$959 night

Discover your dream Key West vacation at Lunara Bay - a collection of 26 Luxury homes in a gated community!! Altair House is a 6BR, 6.5BA pet-friendly estate blending island charm with modern elegance, just minutes from downtown. Dock boats up to 40’ at private slips, relax in your private pool, enjoy free access to FYT gym, and curated itineraries from our local guest experience team. Extend your stay 7+ nights for 10% off your entire stay! Indulge in luxury with our private boat excursions and chauffeur services. Sail away on tailored aquatic adventures or arrive in style with our elite transportation solutions. Experience excellence, tailored just for your stay. Please reach out for more information! The Altair House is everything you’re looking for, both modern and laid-back. This residence fully embraces its oceanic surroundings, inviting you to experience complete tranquility. The sleeping arrangements of the home are as follows: Bedroom 1: King bed with a walk-in closet, double vanity en-suite bathroom & balcony access Bedroom 2: King bed with a walk-in closet, double vanity en-suite bathroom & balcony access Bedroom 3: King bed with en-suite bathroom Bedroom 4: King bed with en-suite bathroom and balcony Bedroom 5: Two twin over twin bunk beds, this room does not have a door Bedroom 6: Double bed with en-suite bathroom The open-concept floor plan seamlessly connects the indoor and outdoor areas, making it perfect for entertaining and spending quality family time. Whether you’re relaxing by the pool, playing a game of pool, grilling delicious meals, or simply relaxing in one of the multiple dining and seating areas, this home has everything you need to create lasting memories. The fully equipped kitchen is ready to cater to your culinary desires, whether you prefer to cook your own meals or hire a private chef. Stay connected with high-speed internet access and enjoy the convenience of keyless entry, making your vacation experience even more seamless and hassle-free. Outside, the spacious fenced-in turf yard provides a safe space for children to play, as well as a perfect area for your furry friends to roam around. Guests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay. Boating & Private Dock Slip: We encourage boating. Here’s what you need to know in order to do so safely: - Dock in our exclusive marina which accommodate boats up to 40’ in length. Maximum one boat per slip. - There is no power or pump out service to the slips. - The Florida Keys are a notoriously difficult place to navigate. How to Access: Stair access only the home is elevated above sea level. Travel by car, boat, or plane to our luxury estate. The driveway allows parking for up to 3 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter, moke or bike for the day to explore the area. Feel free to ask us for recommendations! - Elevate your visit with our Private Chauffeur Service for effortless luxury transportation. - Private washer/dryer - Located in gated community - Free gym access at FYT - Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximum

Floralee House at Lunara Bay

Key West, FL, US
6 Bedrooms 16 Guests
Aug 30 - Sep 1
$959 night

Discover your dream Key West getaway at Lunara Bay - a collection of 26 Luxury homes in a gated community! Floralee House is a 6BR, 6.5BA luxury waterfront estate that seamlessly blends high-end finishes with modern elegance, just minutes from downtown. Dock your boat right in the backyard, unwind in your pool, enjoy complimentary gym access, and enjoy curated itineraries from our local guest experience team. Elevate your visit with our Private Chauffeur Service for effortless transportation. Enter a space where modern sophistication blends seamlessly with tropical style. The spacious living areas are perfect for relaxation or entertaining, illuminated by large windows that let in plenty of natural light. Every bedroom serves as a peaceful retreat, complete with luxurious bedding and private en-suite bathrooms for extra comfort and privacy. The bed layout is as follows: Bedroom 1: King Bed Bedroom 2: Two Bunk Beds with two queen and two twin sized Mattresses Bedroom 3: King Bed Bedroom 4: King Bed Bedroom 5: King Bed Bedroom 6: King Bed All bedrooms have an ensuite bathroom Our self check-in makes the process seamless. Guests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay. Boating & Private Dock Slip: We encourage boating. Here’s what you need to know in order to do so safely: - Dock in our exclusive marina which accommodate boats up to 40’ in length. Maximum one boat per slip. - There is no power or pump out service to the slips. - The Florida Keys are a notoriously difficult place to navigate. Travel by car, boat, or plane to Floralee House. The driveway allows parking for up to 2 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations! - Private washer/dryer - Located in gated community. - Free gym access at FYT - Fans inside bedrooms only operate with the light on. - Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximum

Suncoast House | Pool & Boat Dock

Key West, FL, US
5 Bedrooms 14 Guests
Aug 30 - Sep 1
$959 night

Discover your dream Key West vacation at Lunara Bay - a collection of 26 luxury homes in a gated community! Suncoast House is a 5BR, 5.5BA waterfront, pet-friendly home blending island charm with modern elegance, just minutes from downtown. Dock boats up to 40’ at private slips, relax in your private pool, access the FYT gym, and enjoy curated itineraries from our local guest experience team. Extend your stay 7+ nights for 10% off your entire stay! Indulge in luxury with our private boat excursions and chauffeur services. Sail away on tailored aquatic adventures or arrive in style with our elite transportation solutions. Experience excellence, tailored just for your stay. Please reach out for more information! The open concept floor plan makes entertaining a breeze and encourages family time around the dining room table. A fully equipped kitchen awaits your home cooked meals or private chef experience. With high speed internet access and keyless entry, vacation has never been more convenient and easy. The spacious fenced in yard and gated dock access are perfect for children and your furry friends. The Suncoast House is a five-bedroom, five-and-a-half-bath home with breathtaking decor. Sleeping up to 14 guests: Bedroom 1: King Bedroom 2: King Bedroom 3: Two Twins Bedroom 4: King Bedroom 5: King & Two Day Beds Extra Sleeping: Queen pull out couch Our contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival. Boating: We encourage boating. Here’s what you need to know in order to do so safely: - Private dock can accommodate boats up to 50’ in length. Maximum one boat per dock. - There is no power or pump out service to the slips. - The Florida Keys are a notoriously difficult place to navigate. How to Access: Stair access only the home is elevated above sea level Travel by car, boat, or plane to Suncoast House, The driveway allows parking for up to 4 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations! - Private washer/dryer - Located in gated community. - Comes with free gym access to FYT. - Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximum - Elevate your visit with our Private Chauffeur Service for effortless luxury transportation.

The Greenmoor House at Lunara Bay

Key West, FL, US
6 Bedrooms 14 Guests
Aug 30 - Sep 1
$1,199 night

Discover your dream Key West vacation at Lunara Bay - a collection of 26 luxury homes in a gated community! The Greenmoor House is a 6BR, 6.BA luxurious new build offering exceptional amenities, including: free gym access and ample living space perfect for relaxation and entertainment. With modern design and high-end finishes, this property is ideal for those seeking comfort and style. Experience a new level of living that combines elegance and convenience in this remarkable home. Experience luxury with our private boat excursions and chauffeur services. Enjoy customized aquatic adventures or arrive in style with our premium transportation options. Expect excellence tailored to your stay. For more information, please reach out! The open-concept floor plan, both indoors and outdoors, creates a warm atmosphere ideal for entertaining and quality time with loved ones. Whether you’re relaxing by the pool, playing games, grilling, or dining in various areas, there’s something for everyone. The fully equipped kitchen is perfect for home-cooked meals or for a private chef to elevate your culinary experience. With high-speed internet and keyless entry, your vacation will be seamless and convenient. Outside, the spacious fenced yard provides a safe play area for children and a perfect space for your pets. Bed layout: Bedroom 1: King Bed Bedroom 2: Two bunk beds Bedroom 3: King Bed Bedroom 4: King Bed Bedroom 5: King Bed Bedroom 6: King Bed All bedrooms feature ensuite bathrooms. Our self check-in makes the process seamless. Guests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay. Boating & Private Dock Slip: We encourage boating. Here’s what you need to know in order to do so safely: - Dock accommodates a boats up to 40’ in length. - There is no power or pump out service to the slips. - The Florida Keys are a notoriously difficult place to navigate. Travel by car, boat, or plane to Modern Keys, The driveway allows parking for up to 4 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations! - Private washer/dryer - Located in a gated community - Free gym access at FYT - Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximum

Catchlight House at Lunara Bay

Key West, FL, US
6 Bedrooms 16 Guests
Aug 30 - Sep 1
$959 night

Catchlight House is a stunning 6-bedroom, 6.5-bath home at Lunara Bay—a collection of 26 luxury homes in a gated community. Just minutes from Key West’s vibrant center, it offers spacious living areas, beautiful outdoor spaces, and a private marina slip for boats up to 40’. Guests also enjoy complimentary FYT gym access and personalized itineraries curated by our guest experience team for an unforgettable stay. Step inside and be greeted by a beautifully appointed interior featuring modern furnishings and island-inspired décor. The expansive living areas provide ample space for relaxation and entertainment, while large windows flood the rooms with natural light. Each bedroom is a tranquil oasis, complete with plush bedding and en-suite bathrooms for privacy and convenience. The bed layout is as follows: Bedroom 1: King Bed Bedroom 2: Two Bunk Beds with two queen and two twin sized Mattresses Bedroom 3: King Bed Bedroom 4: King Bed Bedroom 5: King Bed Bedroom 6: King Bed All bedrooms have an ensuite bathroom Our self check-in makes the process seamless. Guests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay. Boating & Private Dock Slip: We encourage boating. Here’s what you need to know in order to do so safely: - Dock in our exclusive marina which accommodate boats up to 50’ in length. Maximum one boat per slip. - There is no power or pump out service to the slips. - The waters of the Florida Keys are notoriously difficult to navigate, so please use extra caution when traveling to and from the property. Travel by car, boat, or plane to Catchlight House. The driveway allows parking for up to 2 vehicles and your boat trailer. Rent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations! - Extend your stay 7+ nights for 10% off your entire stay! - Elevate your stay and ask us about our Private Chauffeur services. - Private washer/dryer - Located in gated community - Free gym access at FYT - Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximum

NEW! Ebberly House | Amazing Pool

Key West, FL, US
6 Bedrooms 14 Guests
Aug 31 - Sep 2
$959 night

Discover your dream Key West getaway at Lunara Bay - a collection of 26 Luxury homes in a gated community! Ebberly Estate is a 6BR, 6.5BA pet-friendly home blending island charm with modern elegance, just minutes from downtown. Dock boats up to 40’ at private slips, relax in your private pool, access the FYT gym, and enjoy curated itineraries from our local guest experience team. Experience seamless indoor-outdoor living here! Ideal for entertaining with the open-concept layout, fully equipped kitchen,the poolside lounging, ping pong games, grilling, and multiple dining areas – ensuring unforgettable moments. Outside, a spacious fenced grass yard offers safe play for children and freedom for furry friends to roam. Sleeping arrangements include: Bedroom 1: King bed, walk-in closet, double vanity en-suite, balcony access Bedroom 2: King bed, walk-in closet, double vanity en-suite, balcony access Bedroom 3: King bed, en-suite bathroom Bedroom 4: King bed, en-suite bathroom, balcony Bedroom 5: Two twin bunk beds (no door) Bedroom 6: Double bed, en-suite bathroom Our self check-in makes the process seamless. Guests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay. Boating & Private Dock Slip: We encourage boating. Here’s what you need to know in order to do so safely: - Dock in our exclusive marina which accommodate boats up to 40’ in length. Maximum one boat per slip. - There is no power or pump out service to the slips. - The Florida Keys are a notoriously difficult place to navigate. Travel by car, boat, or plane to our luxury estate. The driveway allows parking for up to 4 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter, moke or bikes for the day to explore the area. Feel free to ask us for recommendations! - Extend your stay 7+ nights for 10% off your entire stay! - Elevate your stay and ask us about our Private Chauffeur services. - Private washer/dryer - Located in gated community - Free gym access at FYT - Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximum

New! Windrose House | Pool

Key West, FL, US
6 Bedrooms 14 Guests
Aug 30 - Sep 1
$959 night

Windrose House is a newly designed 6-bedroom, 6-bath home at Lunara Bay - a collection of 26 luxury homes in a gated community! Enjoy a private pool, fire pit, parking, and a pet-friendly gated yard. Dock your boat at the exclusive marina for boats up to 40’ just steps from the house. Stay active with complimentary FYT gym access, and use personalized itineraries to uncover hidden gems for an unforgettable Key West experience. Indulge in luxury with our private boat excursions and chauffeur services. Sail away on tailored aquatic adventures or arrive in style with our elite transportation solutions. Experience excellence, tailored just for your stay. Please reach out for more information! The open-concept floor plan, both indoor and outdoor, creates a welcoming atmosphere for entertaining and spending quality time with family and friends. Whether it’s relaxing by the pool, playing pool, grilling, or dining and lounging in various areas, there are options for everyone. You’ll find a fully equipped kitchen ready for preparing home-cooked meals or even for a private chef to enhance your culinary experience. With high-speed internet access and keyless entry, your vacation will be convenient and hassle-free. Outside, the spacious fenced-in yard provides a safe space for children to play, as well as a perfect area for your furry friends to roam around. The sleeping arrangements of the home are as follows: Bedroom 1: King bed with a walk-in closet, double vanity en-suite bathroom & balcony access Bedroom 2: King bed with a walk-in closet, double vanity en-suite bathroom & balcony access Bedroom 3: King bed with en-suite bathroom Bedroom 4: King bed with en-suite bathroom and balcony Bedroom 5: Two twin over twin bunk beds, this room does not have a door Bedroom 6: Double bed with en-suite bathroom Our self check-in makes the process seamless. Guests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay. Boating & Private Dock Slip: We encourage boating. Here’s what you need to know in order to do so safely: - Dock in our exclusive marina which accommodate boats up to 40’ in length. Maximum one boat per slip. - There is no power or pump out service to the slips. - The Florida Keys are a notoriously difficult place to navigate. Travel by car, boat, or plane to Modern Keys, The driveway allows parking for up to 4 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations! - Extend your stay 7+ nights for 10% off your entire stay! - Elevate your stay and ask us about our Private Chauffeur services. - Private washer/dryer - Located in gated community - Free gym access at FYT - Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximum

The Joyrise House at Solaire Lunara Bay

Key West, FL, US
6 Bedrooms 12 Guests
Aug 31 - Sep 2
$1,439 night

Discover elevated island living at Joyrise House at Lunara Bay, an exclusive collection of 26 luxury residences within a private gated waterfront community. This newly built six-bedroom retreat offers the perfect blend of sophistication and relaxation, featuring a private pool, a private boat dock accommodating vessels up to 50 feet, and expansive indoor and outdoor living spaces designed for effortless entertaining. Enjoy complimentary gym access and personalized itineraries curated by our local Guest Experience Team, ensuring a seamless and unforgettable Florida Keys escape. Extend your stay 7+ nights for 10% off your entire stay! The home’s open-concept indoor and outdoor living spaces create an inviting atmosphere perfect for entertaining and spending quality time with family and friends. Whether you’re relaxing by the pool, grilling the day’s catch, enjoying meals together, or gathering for games and conversation, there’s ample space for everyone to connect and unwind. The fully equipped kitchen is ideal for everything from casual breakfasts to gourmet dinners and can easily accommodate private chef experiences for an elevated culinary experience. Modern conveniences, including high-speed Wi-Fi and keyless entry, ensure a seamless stay from arrival to departure. Outside, the spacious fenced yard provides plenty of room for children to play, pets to roam, and families to enjoy the outdoors together. Sleeping Arrangements Bedroom 1: King Bed with Ensuite Bathroom Bedroom 2: King Bed with Ensuite Bathroom Bedroom 3: King Bed with Ensuite Bathroom Bedroom 4: King Bed with Ensuite Bathroom Bedroom 5: King Bed with Ensuite Bathroom Bedroom 6: King Bed with Ensuite Bathroom Each of the six bedrooms features a king bed and private ensuite bathroom, offering comfort, privacy, and a relaxing retreat for every guest. Our self check-in process is designed to be seamless and convenient. Guests will receive a personalized access code prior to arrival, along with direct contact information for a dedicated local Guest Experience Manager who is available to assist with questions, recommendations, and special requests throughout your stay. Whether you’re arriving by car, boat, or plane, getting around is easy. The driveway accommodates up to four vehicles, with additional space for a boat trailer. Looking to explore the area at a slower pace? Golf carts, scooters, and bicycles are available for rent and offer a fun way to experience the Lower Keys. Want us to handle the booking? Your Guest Experience Manager is happy to assist with transportation arrangements and local rental providers. - Private washer and dryer - Located within the exclusive gated community of Lunara Bay. - Complimentary fitness center access at FYT. - Pets are welcome! Maximum of two pets per stay, with a 40-pound weight limit per pet and a $250 pet fee per stay. - Enhance your stay with our Private Chauffeur Service, offering convenient transportation throughout the Lower Keys and Key West.

Triple Crown Villa- Boaters paradise with Pool

Key West, FL, US
4 Bedrooms 8 Guests
Aug 26 - Sep 23
$348 night

Luxury 4bdr/4ba house with pool&dock If you’re looking for a luxurious and unforgettable waterfront vacation experience, look no further than this stunning vacation rental property on the Key Haven Peninsula. Surrounded by water on three sides, this property boasts an impressive 245 feet of canal frontage with two boat lifts, a double car garage, and a beautiful pool for your enjoyment. The 15000 square foot lot is surrounded by magnificent tropical gardens, creating a breathtaking and tranquil setting for your stay. Inside, you’ll find over 3000 square feet of living space, with fine interior design and amenities that exude comfort and luxury. The large kitchen is fully equipped with modern appliances and ample counter space, making it easy to prepare meals for your family and friends. The spacious living and dining areas provide plenty of room for entertaining guests and hosting dinner parties. This property features 4 perfectly scaled bedrooms, each with its own private bathroom. The bedrooms are designed with luxury and comfort in mind, providing a peaceful retreat for guests after a long day spent on the water. The high-quality amenities and attention to detail throughout the property ensure that your stay is comfortable, enjoyable, and unforgettable. Whether you’re a seasoned boater or just looking for a waterfront getaway, this vacation rental property is the perfect choice for your next vacation. You’ll have everything you need for the ultimate waterfront vacation experience, from the beautiful pool to the stunning tropical gardens. This spacious and high-quality home is perfect for families, groups of friends, or anyone looking for a luxurious and relaxing getaway. Book your stay now at this stunning vacation rental property and experience the ultimate waterfront Key West vacation.

Vacation Rentals in Cudjoe Key by Amenities & Features

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Vacation Rentals Near Cudjoe Key

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