Captiva, FL Vacation Rentals

Step into island living just a short stroll from the sandy shores of the Gulf of Mexico. Ventura Captiva 2B is a beautifully updated 3-bedroom, 3-bath townhome offering peaceful bay views, stylish interiors, and a prime location in the heart of Captiva Island. This elevated, two-story retreat features a remodeled coastal kitchen with granite countertops, a spacious island, and top-of-the-line appliances. The kitchen flows effortlessly into the dining area and living room, both tastefully decorated in an elegant coastal style that sets the tone for a relaxed and refined vacation. On the main floor, you’ll find two bedrooms: a guest room with two twin beds and a hallway bathroom with a tub/shower combo, as well as a spacious primary suite with a king bed, dedicated desk area, serene bay views, and a private bath with a tiled walk-in shower. Upstairs, a quiet loft-style den offers a cozy spot to read or unwind, along with a third bedroom featuring another king bed and a full bathroom with a tub/shower combo--perfect for extra privacy and comfort. Step outside to enjoy the screened lanai overlooking the tropical grounds and the bay. Ventura Captiva is a small, tranquil complex of just ten homes, offering resort-style amenities including a heated pool, grilling area, fishing pier, and complimentary boat dockage (first-come, first-served). Just two blocks from the heart of Captiva Village, you’ll be within easy walking distance of the island’s best dining, shops, music venues, marinas, dolphin cruises, and, of course, stunning Gulf sunsets. Whether you’re here for the beach, the boating, or simply to relax and reconnect, Ventura Captiva 2B offers the perfect blend of comfort, bay views, boat access, and island charm.

Holley House is one of the southernmost houses on Captiva. This is the “Gold Coast” section of Captiva Island, famous for its secluded luxury estates and fantastic tropical surroundings. Down here the island is narrow: you live right on the water near Blind Pass (the bridge from Sanibel onto Captiva), and beach access is directly across the street. Your view encompasses a broad sweep of small, uninhabited keys as well as the northern tip of Sanibel Island. The Roosevelt Channel leads out to Pine Island Sound and the Intracoastal Waterway. There are very few visual clues that you haven’t landed on your very own tropical island! Your visit begins with the blue and white Holley House sign on Captiva Drive, guiding you into the landscaped grounds (more than an acre). The gently curving driveway — just long enough for seclusion — leads you past palms and sea grapes to a circular drive with plenty of parking including shaded areas. Another area of the driveway is handy for additional parking or for storing your boat trailer(s). The warm-hued house just glows in the tropical sunlight. Step inside to the spacious and beautifully decorated main level. You’re drawn immediately to the large rear windows and the unique “round tower” screened lanai, both overlooking the water. Then gaze down at your large, private pool, with a stunning patio and shell-lined path onto the private boat dock. Guests love taking advantage of the Holley House waterfront location! Enjoy the ever-changing tides, and fish from the dock. Rent some kayaks by the day or by the week (or bring your own), and explore the ever-fascinating keys and mangrove-lined creeks right across the channel. It’s like having your own Ding Darling National Wildlife Refuge only a few paddle-strokes from your vacation estate. Or use the dock as your home base for fishing and motor boating Captiva, Sanibel, and the many other nearby islands. Plan on spending plenty of time on the awesome white-sand beach, sunning or swimming in the warm waters of the Gulf of Mexico, hunting shells, or taking long walks and enjoying this part of paradise. Holley House has deeded beach access directly across Captiva Drive. The living room is bright and spacious, with plenty of windows to let in the natural light. Comfortable seating enjoys views over the water, as well as the 55-inch HDTV (with HD DVR and DVD). Board games and puzzles can involve the whole family together – fun when retreating from the blazing sunshine or a tropical rain shower. A corner of the living room has been set up as a nice little office, with a writing desk, phone, and chairs. Holley House features an amazing screened lanai, capitalizing well on the lovely waterfront location. Just off the living room, this unique octagonal porch has a peaked roof and resembles a castle round tower. With a dining table, two side tables, and ten chairs, there is plenty of space for enjoying the Captiva environment within the shelter. The dining table is spacious for six, and there are two additional chairs that can be pulled up. A side cupboard holds interesting decorations. But the best part is enjoying the big views over the water! The remodeled, kitchen is bright and modern. New cabinets, floors, and all new (2016) appliances make it a pleasure to use. Also remodeled on the main level is the powder room (half bath) off the entrance foyer. Rounding out the main level is a utility room with a full-size clothes washer and dryer. The four ample-sized bedrooms are on the upper level at Holley House. The master is on the southeast, with a king bed and en-suite bathroom (step-in shower with seat). An HDTV is ceiling-mounted for comfortable viewing from the bed. The queen bedroom (in the northwest) has a flatscreen TV, a large dresser, and a closet. The twin’s bedroom (in the northeast) has a flatscreen TV, lots of closet space, and wicker furniture including a dresser and two bedside tables. A cozy chair is perfect for relaxing in the nook, gazing over the water, or reading a book borrowed from the shelf on the upstairs landing. The twin’s bedroom (in the southwest) has a glider seat as well as a wicker chair and dresser, plus a closet. These bedrooms share the full bathroom, with a tub and shower. Property Manager will only book reservations up to 51 weeks in advance. All our properties have contact-free check-in, no need to stop at the office (or a stop light none of those here)!

All new furnishings in this bright, beautifully decorated three-bedroom, three-bathroom Captiva village home. This home has partial Bay views at the end of a quiet lane near the bay. Turtle Cottage is centrally located to everything Captiva has to offer. Walk into the bright and charming second floor with soaring ceilings, an open living room, and an open large kitchen. The screen-enclosed lanai has comfortable furnishings with partial Bay views. The floor also features the master bathroom suite with attractive coastal décor, a king bedroom, and an attached full bathroom. Relax in the sunroom with comfy chairs to sit, relax, read a book, and enjoy the tropical sights and sounds. This floor also has a full guest bathroom. The first-floor lower level is accessed from the outside and has two bedrooms with a full bathroom. The first guest bedroom has two adorable twin beds with a nautical theme. The second bedroom has a king-size bed with a small patio to enjoy the island atmosphere. A large bathroom, large laundry room, and small kitchenette make this lower level perfect for extended family or friends. At the end of Old Lodge Lane, this charming and open home is the perfect location to relax after a day on the beach. A short walk to Andy Rosse Lane, where you can shop, dine, or listen to live music. Access the beach from Andy Rosse Lane or Laika Lane, a short walk from Turtle Cottage. Property Manager will only book reservations up to 51 weeks in advance. All our properties have contact-free check-in; no need to stop at the office (or a stop light, none of those here)!

While you won’t have access to resort amenities, this villa comes with plenty of its own perks! Your property condo amenities include a large heated pool, pickleball and tennis courts, high-speed Wi-Fi, outdoor grills, community washer/dryers (coin operated), beach chairs and towels, and—of course—the beach just steps away. It’s everything you need for the perfect getaway! Golf Cart rentals are close by, but please note that only electric carts are allowed within the gates of the resort. Enjoy picturesque sunsets year-round from the screened lanai overlooking the blue Gulf of Mexico and long walks on the uncrowded beach of Captiva Island. Don’t miss out on this Gulf-front, bedroom one bathroom updated condo! Located in the highly desirable Beach Villas at the south end of the Island Resort, this property has a wonderful view of the Gulf of Mexico and the stunning sunsets. This specific unit was chosen pre-construction so as not have any pool area directly in front of the unit, where the surrounding plantings could obscure the view. The view is superior to many of the higher- up units. The condo is conveniently located within walking distance of Captiva Village, where you will find dining and shopping. It’s nice not to have to worry about parking at the restaurants or where your car keys are. This updated one-bedroom condo is very well equipped, and you will find most of the accommodations of home. Some of the amenities included are; fully equipped kitchen, full size refrigerator with ice maker, dishwasher, separate bedroom with king size bed and ceiling fan (queen sofa sleeper out in living room), coin laundry (down stairs), stereo with ipod and mp3 attachment, 2 smart Roku flat panel TVs (55" living room & 43" bedroom), where guests can log into their favorite channels and they are automatically logged out upon departure, resort), hair dryer, Iron, Ironing Board, free WI-Fi internet connection, plantation shutters, and porcelain tile flooring throughout. There is an elevator, but you may not need it since the condo is on the first level, up only one flight of steps. This particular unit was chosen for the prime ocean view without having to go up and down additional steps every time you go somewhere. Captiva does beckon you to get out and go. Enjoy the graceful wildlife. Property Manager will only book reservations up to 51 weeks in advance. All our properties have contact-free check-in; no need to stop at the office (or a stop light, none of those here)!

Heads up! You might hear some construction sounds or see a bit of cleanup happening, but it’s all part of the adventure. So grab your shades, relax, and enjoy the vibes! Welcome to Your Dream Beachfront Getaway! This is THE place to be! Step into your very own Gulf Front Villa, where breathtaking water views meet luxury living. This villa has just undergone a jaw-dropping renovation, and it’s ready for you to call it your home away from home. With three spacious bedrooms, three bathrooms, and a fabulous open loft, there’s plenty of room for everyone. And did we mention the views? You’ll have the stunning Gulf of Mexico right outside your window! Cooking? Relaxing? Entertaining? This villa has you covered! The open kitchen is perfect for whipping up your favorite meals, while the dining and living areas are perfect for chilling out and soaking in those amazing views. The large lanai is your go-to spot for sunrises, sunsets, and everything in between, with the soothing sounds of the Gulf to complete the experience. Master king suite on the first floor. A guest bedroom with two twins on the main floor. Upstairs is a bedroom with a queen bed and an open loft with twin trundle beds on the upper level. This space is perfect for families or groups looking for a relaxed, beachy vibe. It’s the ultimate home base for your dream vacation! When you’re not lounging on the lanai, head outside for a beach day! Swim, sunbathe, and search for unique shells along Captiva Island’s pristine shores. Prefer a heated pool dip? You’ve got it! Or, explore the island’s charming boutiques, art galleries, and fresh seafood spots. Don’t forget to fire up the outdoor grills for a BBQ, rent bikes or golf carts, or embark on an unforgettable dolphin-sighting cruise with Captiva Cruises. Feeling adventurous? Try parasailing or jet skiing, or rent a kayak for more thrills! Planning ahead is a breeze with Property Manager! You can book up to 51 weeks in advance—no office check-in required! Just show up, settle in, and start your vacation stress-free. While you won’t have access to resort amenities, this villa comes with plenty of its own perks! Your property condo amenities include a large heated pool, pickleball and tennis courts, high-speed Wi-Fi, outdoor grills, community washer/dryers (coin operated), and—of course—the beach just steps away. It’s everything you need for the perfect getaway! Golf Cart rentals are close by, but please note that only electric carts are allowed within the gates of the resort. Extended patio for year-round use; please note that the patio is not screened in

Bird of Paradise is located in the heart of Captiva Island, yet it offers privacy and comfort. Central to the beach, shops, restaurants, marinas, live music, bars, and watersports. This tranquil four-bedroom home sleeps ten comfortably. Walk into the main living room with soaring white-washed ceilings that give the home a comfortable beach feel. Relax in the spacious living room with plenty of seating for family and friends, a flat-screen television, and an open concept into the dining room. Enjoy the gorgeous dining room table with seating for eight. The large updated kitchen is off the dining room, has beautifully painted cabinets, and is perfect for creating amazing meals or heating up takeout from the delicious Captiva restaurants. On this level, there are two guest bedrooms and two bathrooms. The first bedroom has a comfortable queen bedroom, and the second bedroom has two comfy bunk beds with a full on the bottom and twins at the top. The master suite on this third floor features a comfortable king bed, a private deck, and a large master bathroom with granite countertops and a walk-in shower. The fourth bedroom is on the lower level with a king bed, a television, and a chair that folds out to a twin. This area is very private with its own entrance. The large heated pool is the perfect area with tropical landscaping and a pool cage. It is the perfect spot to relax and enjoy the amazing weather. The game area underneath the house features a ping pong table and a pool table. Just two homes down from the beach path, which takes you past the charming Chapel by the Sea to stunning white beaches. Bird of Paradise has everything you need for an amazing family beach vacation. Book this home today, and you will be thrilled with your choice! Property Manager will only book reservations up to 51 weeks in advance. All our properties have contact-free check-in, no need to stop at the office (or a stop light, none of those here)!

Your dream tropical escape awaits at Summer Breeze, a stunning 7-bedroom, 6-bathroom home just three houses from the sandy shores of Captiva Beach on the iconic Andy Rosse Lane. With room to sleep up to 15 guests, it’s the ideal retreat for large families and groups. Location, Location, Location Captiva Island is pure paradise—spend your days shell-seeking along the Gulf, setting out on a dolphin cruise, casting a line on a fishing charter, or exploring charming shops and restaurants just steps from your door. By evening, stroll to the beach to witness one of Captiva’s world-famous sunsets or enjoy live music and cocktails at one of the many restaurants on your street. The Home Inside, Summer Breeze is bright, spacious, and beautifully updated, blending coastal décor with all the comforts of home. Soaring living room with cathedral ceilings, built-in bookshelf wall, plush sectional sofa, flat-screen TV, and Sonos sound system perfect for movie nights. Open-concept gourmet kitchen with new stainless steel appliances, large island (seats 4), a cozy sunlit seating area, and everything you need to make entertaining a breeze. The expansive dining table seats 8+ with additional seating at the bar and in the adjacent sitting area and screened lanai overlooking the custom pool. Outdoor living area where you can step onto the screened-in porch, complete with comfortable seating and overhead string lights, or lounge by the pool just steps away. The palm tree surrounds and tropical landscaping complete the picture-perfect island atmosphere. Second ground floor-living area walks out to the pool featuring sectional seating, flat-screen TV, soundbar with subwoofer, and a kitchenette offering a full-sized fridge, microwave, and spacious counter bar area—perfect for those poolside snacks and drinks. A dozen classic board games fill the shelves for nighttime fun. Bedrooms This home was designed for groups and families of all sizes, offering seven comfortable retreats each named after a classic beach song—a playful and memorable detail that brings the island spirit indoors. Primary Suite 1 (Main, King): “Kokomo.” Spacious, offering an ensuite bath with jacuzzi tub, dual sinks and shower, private screen porch access, a desk area, and king bed—the perfect tropical escape. Guest Suite 2 (Main, King): “Walking on Sunshine.” Bright, cheerful, and designed to lift your spirits with a King bed, TV, and dedicated adjacent full bath with walk-in shower. Guest Suite 3 (Upstairs, King): “Island in the Sun.” This relaxed and breezy king bedroom with private en-suite bathroom has private rooftop deck access overlooking the pool with views of the gulf. Guest Suite 4 (Upstairs, 2 Queens): “Surfer Girl.” This spacious suite provides two queen beds and tropical charm alongside a private en-suite bathroom and shared access to the rooftop deck. Guest Suite 5 (Lower, King): “Under the Boardwalk.” This king bedroom brings cool coastal vibes featuring a retro record player, private en-suite bath with shower and steps out to the spacious poolside sitting area with couches, perfect for laid-back lounging and easy indoor-outdoor living. Guest Suite 6 (Lower, 2 Twins): “Wipeout!” The kid-friendly and fun surfer décor features two twin beds—perfect for younger guests. Guest Suite 7 (Lower, 2 Doubles): “Surfin’ USA.” Brings a West Coast vibe to this room, perfect for teens with two double beds in a spacious layout. All bedrooms feature high-quality mattresses, fresh linens, and plenty of storage space. Outdoor Paradise Step outside and enjoy: Sparkling pool and hot tub surrounded by lush tropical landscaping with palm trees Pool basketball hoop for fun and games in the sun Plenty of loungers and seating for relaxation Grill station for family barbecues Relaxing couch and sitting area under the covered porch Tables for outdoor meals and plenty of umbrellas to shade you from the sun An expansive front porch with comfortable seating provides a perfect setting for morning coffee, cocktails, people-watching, and soaking in Captiva’s breezes ** Limited Parking available, two mid-size vehicles only! Arrangements for additional parking at Sanibel Office can be made in advance. Please plan accordantly ** Why Summer Breeze? Steps to the beach and village dining, entertainment, and live music 7 spacious bedrooms and beautifully updated bathrooms Multiple living spaces and kitchens Private pool, hot tub, and outdoor setting Easy access to water sports, shelling, and fishing charters Sleeps up to 18 guests Ideal for large families and groups Summer Breeze isn’t just a home—it’s a Captiva Island experience. With 7 bedrooms, multiple living spaces, rooftop decks with ocean views, a poolside lounge, and playful song-themed décor, it’s perfect for family reunions, groups of friends, or multi-generational getaways. Guests love the music-inspired personality and the unbeatable location just steps from the beach and Captiva’s vibrant village.

This five-bedroom channel-front estate home is the perfect place for a memorable friends and family vacation. This stunning pool home is located on the Roosevelt Channel. Watch dolphins, manatees, and sea birds from one of the many decks. A short stroll across the street to the left to Blind Pass/Turner Beach, where you can view world-renowned sunsets! * This property does not have deeded beach access. This estate home has everything you need for an amazing vacation. Walk into the large living room with an open ceiling to the 2nd level. The huge dining room features updated furnishings and seating for 10. The large kitchen has plenty of cabinet space, large countertops, and updated appliances. Lounge in one of the two expansive living rooms with views over the tropical grounds and Roosevelt channel. The second living room has a new 85-inch flat screen television with surround sound, a large sectional sofa, and a pool table. It also opens to views of the channel and lanai. There are also two King bedrooms on this floor. Both have flat-screen televisions and private full bathrooms. The 2nd floor features another king bedroom with a private bathroom and views of the channel. Two more bedrooms complete the 2nd floor. The first bedroom has a king bed and a day bed, the second bedroom has a queen bed. Both bedrooms have flat-screen televisions and share a full bathroom with an updated shower. There are multiple decks to view the water, watch the wildlife, or just relax. *Smart televisions with streaming services only* The lower level features a large heated pool, hot tub, seating area, grill, kayaks, one paddleboard, and two life jackets. There is also a pack and play and a high chair. Everything you need to make lasting memories! *The dock cannot accommodate a boat but is great for fishing* Property Manager will only book reservations up to 51 weeks in advance. All our properties have contact-free check-in; no need to stop at the office (or a stop light, none of those here)!

Introducing Sunset Captiva Bayside 103, Sea to Sea, a beautifully remodeled bayfront retreat in the heart of Captiva Island Village. This first-floor condominium offers the rare combination of peaceful waterfront living and walkable access to Captiva’s restaurants, shops, and sandy Gulf beaches. Set directly on Pine Island Sound, this spacious two-bedroom, two-bath residence invites you to slow down and soak in the views. Watch boats drift by from your living room, enjoy soft morning light over the bay, and unwind in the evenings as the water reflects the changing sky. With 1,500 square feet of living space, the condo feels open and relaxed, perfect for families or couples traveling together. Remodeled in 2023, the interior is fresh and thoughtfully designed with coastal elegance throughout. The open-concept layout includes a comfortable living area with a smart TV, free WiFi, cable, and a queen sleeper sofa for additional guests. The fully equipped kitchen features stainless steel appliances and everything you need to prepare meals at home, whether it’s a casual breakfast or a sunset dinner. A dining area sits just off the kitchen, and a washer and dryer are conveniently located inside the unit. The primary bedroom offers a restful king bed and a private en-suite bathroom, creating a peaceful retreat at the end of the day. The guest bedroom includes one queen bed and one double bed, making it ideal for additional family members or friends. The dock is usable for boating needs, and it does have electricity. If you’re traveling with a larger group or need additional space, Sunset Captiva Bayside 104 is also available nearby. Captiva and Sanibel offer some of the most treasured natural beauty in Southwest Florida. Blind Pass and Redfish Pass are close by for world-famous shelling, boating, and fishing. Spend your days exploring island waters, enjoying watersports, or simply relaxing on island time. Sanibel Island is less than ten miles away and offers easy access to beloved attractions including the J.N. Ding Darling National Wildlife Refuge, the CROW Wildlife Clinic, the Bailey-Matthews National Shell Museum, and the historic Sanibel Lighthouse and Fishing Pier. Sunset Captiva Bayside 103 is the perfect blend of waterfront serenity, island charm, and resort-style

Conch is ready to Welcome Guests! Sapphire blue water, white sandy beaches, amazing sunsets from your living room, and a luxury four-bedroom villa. Everything you need for the perfect friends and family vacation. “Conch” features tropical colors in this remodeled spacious villa. Walk into the living room with direct Gulf Views including sunset views nightly. The open floor plan flows into the large dining area with seating for six. Continue into the TV area with a large flat-screen TV, DVD player, and iPod docking station. The large gourmet kitchen has all you need to make the perfect meal or just heat leftovers. Have your morning coffee at the breakfast nook featuring sliding doors overlooking the beach. The first floor features two spacious bedrooms and doors to the screened lanai overlooking tropical grounds. The first bedroom has a comfy king bed and flat-screen TV. The second bedroom has a queen bed also with a flat-screen TV. They share the spacious guest bathroom with a shower. The second floor also has two bedrooms. The Gulf-facing bedroom has amazing views from the corner window a king bed and a flat-screen TV. The Bay-facing bedroom has bunk beds with a comfortable queen on the bottom, and twin on the top, a Wii and a flat-screen TV, and its own private lanai with tropical views. Both bedrooms share a large guest bath with a shower and tub. Conch is the perfect vacation getaway. Captiva Beach Villas is a four-unit Gulf to Bay Complex. Complete with a heated pool, hot tub, gas grill, picnic area, and boat dock. The dock has electricity, and water and can accommodate a 26-foot boat. Please contact our office for the dock fee. Property Manager will only book reservations up to 51 weeks in advance. All our properties have contact-free check-in, no need to stop at the office (or a stop light none of those here)!

Donax is ready to Welcome Guests! The beautiful townhome sustained very little damage from hurricane Ian. The small damage has been repaired and this Gulf Front townhome is ready for guests to enjoy the beautiful and open beaches of Captiva. Sapphire blue water, white sandy beaches just steps from your front door and a luxury villa. Everything you need for the perfect friends and family vacation. Donax Beach Villa offers spacious rooms, rich colorful décor and comfortable living. Walk into the professionally decorated living room featuring expansive views of the Gulf of Mexico where you can relax to the waves while watching a spectacular sunset. The open floor plan easily flows into the dining area with seating for six. Beyond the dining area is a comfortable family room with large flat screen television and DVD player where you can lounge your nights away watching your favorite movie. The large gourmet kitchen has all you need to make the perfect meal or just heat up left overs. Have your morning coffee at the breakfast nook featuring sliding doors overlooking the beach. Get a full night’s sleep in the spacious master with king bed, flat screen TV and screened lanai with tropical views. Relax in the master bathroom spa tub, separate shower, double sinks and make-up area. The two large guest rooms on the second floor share a large bathroom and office area. The Gulf facing bedroom features windows with amazing views, a king sized bed and flat screened TV. The second guest room features a double bed, a twin bed, a WII and a private lanai with tropical views. Donax is the perfect vacation home. Captiva Beach Villas is a four unit Gulf to Bay Complex. Complete with heated pool, hot-tub, gas grill, picnic area and boat dock. The dock has electricity, water and can accommodate a 26 foot boat. Please contact our office for dock fee. Property Manager will only book reservations up to 51 weeks in advance. All our properties have contact free check-in, no need to stop at the office (or a stop light none of those here)!

Tucked away on picturesque, shell-lined Laika Lane, Sunkissed Cottage is a beautifully updated three-bedroom, three-bathroom home perfectly positioned in the heart of Captiva Village. A short stroll beneath the natural canopy of the lane brings you to Captiva’s breathtaking beaches—ideal for unforgettable sunsets, lazy beach days, and world-class shelling. Designed with comfort and coastal style in mind, the home features a fully updated kitchen with glass tile accents and everything you need to prepare a fabulous meal. Whether you’re cooking for two or a full house, you’ll find it all in a space that’s both functional and beautiful. The open living room invites everyone to relax together with a sectional sofa and flat-screen TV—perfect for movie nights or catching up after a day in the sun. Sunkissed Cottage offers a spacious layout with a king bed in the primary suite, twin beds in one guest room, and a queen bed in the other. A dedicated game room with a pool table and ping pong table keeps the fun going indoors, rain or shine. Outdoors, enjoy your private, screened-in heated pool surrounded by an impressive two-story pool cage. The expansive outdoor space is ideal for lounging, dining al fresco, or simply soaking up the island breeze. From your front door, you’re within easy walking distance to Captiva’s best shops, restaurants, marinas, live music, and ice cream. Sunkissed Cottage is the ultimate Captiva escape—charming, comfortable, and close to everything.

**Lollipop is considered a value property which means great location, and a good interior but some worn fixtures and some worn exterior** Lollipop is the perfect Captiva vacation home. Central to Captiva Village this three-bedroom three and ½ bath pool home offers the perfect escape for a relaxing vacation. There are so many great features to this home, cathedral ceilings, a screened-in porch, an updated modern kitchen, a pool and spa, and multiple decks. A short three-minute stroll down sandy Laika Lane and you will be on the world-renowned beaches of Captiva. The master suite features a comfortable king-size bed and a large shower in the master bathroom. The first large guest room features ample space a comfortable queen bed and ba athroom in the hallway. The second guest room has a double bed and ample closet space. A day bed off of the living room with a trundle is a comfortable space for your guests. The third full bathroom is located off of the dining area on this main floor. Relax by the pool, walk to the beach, walk to restaurants and marinas. The perfect location for the perfect vacation. Property Manager will only book reservations up to 51 weeks in advance. All our properties have contact-free check-in, no need to stop at the office (or a stop light none of those here)!

NEW TO THE RENTAL MARKET — Be one of the first to experience Captiva’s finest beachfront living! Wake up to breathtaking 180-degree views of both the Gulf of Mexico and the Bay in this extraordinary beachfront home, ideally positioned between two spectacular shorelines. Designed with relaxed coastal elegance in mind, this spacious and luxurious retreat offers seamless indoor-outdoor living—perfect for entertaining, unwinding, and creating unforgettable memories. An open-concept layout with a thoughtful split floor plan offers both privacy and connection. Natural light pours through expansive windows, showcasing sweeping water views from nearly every room. Outdoor Living Highlights: Step outside to enjoy multiple decks, a screened lanai, a large fenced backyard with pavers, and a private pool and spa—all nestled in lush tropical landscaping. For those who enjoy time on the water, the property includes access to a shared dock (ideal for fishing only). Bedroom Layout: Main Floor Gulf-Front Guest Suite: Enjoy a beautiful Gulf view in this serene guest room with a queen bed and direct access to the screened lanai. Wake up to stunning Gulf views and the peaceful rhythms of coastal life. Main Floor Guest Suite with Pool and Bay Views: This inviting queen bedroom offers tranquil vistas of the pool and Bay, making it a restful retreat for guests. Top Floor Master Suite: The ultimate sanctuary—this spacious suite features a king bed, panoramic Gulf views, a luxurious spa-style bath, walk-in closet, and front-row seats to dolphins by day and stars by night. Entertainment Den: Enjoy your favorite shows and movies with the large flat-screen television. Lower-Level Family Suite: Ideal for families or larger groups, this level includes a full living area, a bedroom with a king bed and two twin beds, a full bathroom, and direct access to the pool and beach. Additional Features: Private pool and spa Gourmet kitchen with Gulf views, stone countertops, and access to an alfresco dining deck Additional ice maker for guest convenience—perfect for beach days and entertaining Multiple outdoor spaces for relaxing or entertaining Galvalume roof, composite decking, and impact-rated windows and doors for peace of mind One Bay garage access available for loading/unloading only (no vehicle parking) Security camera monitoring of outdoor areas only Dock access is for fishing use only Location Perks: Centrally located near Tween Waters and Captiva Village—walk to dining, shopping, and island activities. Whether you’re watching the sunset from one of the many decks, swimming under the sun, or enjoying an evening breeze, this home offers the ultimate in coastal comfort and luxury living.

Beach, Shops, Restaurants, Music, Boat Cruises and Galleries all WALKING DISTANCE from Villa Del Mar. Experience the ultimate vacation home in this beautiful five bedroom, media room, game room and heated pool! Villa Del Mar (Formerly known as Breathless) is a stunning five-bedroom home on the best street on Captiva Island! Located five houses from the world- famous stunning white beaches of Captiva Island but also in the heart of Captiva Village. This home and location are the best of both worlds! Hidden behind the double wood doors is an amazing courtyard with a large, heated pool, a hot tub, pool games, and multiple lounge chairs. Walking into the home on this first level means walking into a large game room with a ping pong table, flat-screened TV, and foosball. The theater room with a large pit couch that can be made into an extra queen bed is also on this level, as well as a large bedroom with two queen beds, a flat screen television, and a bathroom. The main level of the home has a huge kitchen with custom cabinets, top-of- the-line appliances, and granite counters. The open living room features two loveseats and one couch, built-ins, and a flat-screen television. The open dining has seating for eight with additional seating for eight at the breakfast bar and breakfast nook. This floor also features a desk, half bath, and laundry room. Also on this level are additional balconies and walkways leading to the separate bedroom suite with a microwave, wet bar, small fridge, and coffee maker. This area has a king bed, flat screen television, and an attached bathroom with shower/tub combination. The third floor features the stunning master bedroom suite with a king bed, tropical furnishings, wet bar, coffee maker, balcony, and attached master bathroom with jet tub and separate shower. There are two additional bedrooms on this floor. The first has a king bed, a flat-screen television, and an attached bathroom featuring a shower/tub combo. The other bedroom features two twin beds, a flat-screen television, and an attached bathroom with a shower. The two-car garage has all the beach chairs, toys, and beach carts to easily take items to the beach. It is within walking distance to everything! Restaurants, the beach, shopping, live music, marinas, and water sports. The ultimate beach home for the ultimate beach vacation. Property Manager will only book reservations up to 51 weeks in advance. All our properties have contact-free check-in; no need to stop at the office (or a stop light, none of those here)!

Welcome to Dancing Dolphin – A Colorful Captiva Vacation Rental in the Heart of the Village Beautiful pool just installed! Dancing Dolphin is your perfect Captiva Island vacation rental, nestled in the heart of Captiva Village. As you pull into the driveway, you’re greeted by the home’s namesake—a fun-loving dolphin in sunglasses that sets the tone for your laid-back island getaway. Just a short stroll to the beach, bay, restaurants, shops, and marinas, this colorful beach house has everything you need for an unforgettable escape. With a private outdoor elevator and stairs for easy access to the second-floor living space, getting in and out is a breeze. Punch in your code, turn the knob, and step into a spacious, sunny open-concept living area with soaring ceilings and two cozy sitting zones. One is anchored by a wall of bookshelves, and the other by a comfy L-shaped section—ideal for movie nights or lazy afternoons. Off the main space, the Sea Turtle Bedroom features a king-size bed and charming coastal touches. Directly across is the Manatee Bedroom, decorated in soothing blue stripes with two low-profile twin beds—great for kids but worth noting for guests with mobility concerns. This bedroom opens up to the screened lanai, outfitted with seating for six, an outdoor table, a wall-mounted TV, and two swinging hammock chairs—your new favorite place for morning coffee or evening wine. The hallway bath is bright and cheerful with a playful “fishy” theme, and a nearby closet holds basic cleaning supplies (though we hope you won’t need them). The fully equipped kitchen makes dining a breeze. Everything is labeled and ready for you: a four-slot toaster, airfryer, blender, Keurig, and drip coffee makers, and all the cookware you need. Gather around the dining table, which seats eight, for family meals, game nights, or fresh-caught seafood feasts. Seashell, the Master Suite offers a king-size bed, access to the lanai, and a private en- suite bath with everything you need to unwind after a day in the sun. Downstairs, the fun continues. The game room features a foosball table, pool/ping pong table, flat-screen TV, futon, and walls lined with vintage movie posters—a total hit with teens and nostalgic adults alike. A full bathroom with a shower is conveniently located just off this space. An adjacent office offers a quiet getaway space with a desk, a stationary bike, and hand weights. The laundry room includes a stackable washer/dryer, plenty of beach towels, and an air mattress for any extra guests. You’ll also find a gear room stocked with outdoor games, and all your Captiva beach essentials: two beach carts, umbrellas, beach chairs, two paddle boards, boogie boards, sand toys, and more. The Sunset Bedroom downstairs features a queen bed and dresser—cozy, quiet, and the perfect place to recharge. Outside, a gas grill is ready for your catch of the day, and the home is just a quick walk to the beach down Laika Lane. Whether you’re shelling at sunrise, dining at the Mucky Duck or Bubble Room, or just soaking in the Gulf breeze, you’re never far from what makes Captiva so magical. Sleeps 9 comfortably, which makes it perfect for families, couples, or a friends’ getaway. Highlights: Prime location in Captiva Village Sleeps 9 | 4 bedrooms | 3 full baths Screened lanai with TV, seating, and hammock chairs Game room with pool table, foosball, and movie-themed decor Fully stocked kitchen + gas grill on outdoors piazza Beach carts, chairs, umbrellas, boogie boards, paddle boards, toys Outdoor games and an air mattress included Walk to the beach, bay, restaurants, shops, and marinas Book your stay at Dancing Dolphin today—where the beach is steps away, the vibes are always chill, and memories are made under the sun. Property Manager will only book reservations up to 51 weeks in advance. All our properties have contact-free check-in, no need to stop at the office (or a stop light, none of those here)!

2 Minute Walk to the Beach Escape your worries in this Captiva Island beach bungalow. Enjoy the bright and cheery island décor throughout this three-bedroom, two-bath pool home. Surrounded by bright tropical vegetation, this home offers a perfect location in the Heart of Captiva as well as ultimate privacy. Equipped with everything you need to enjoy your vacation this bungalow features vaulted ceilings, tile floors in the living areas, a 47 inch flat screen TV in the great room, two DVD players, televisions for each bedroom, Wi-Fi, a fully equipped kitchen with a large refrigerator, dishwasher, range, washer, dryer and dining table for six. The relaxing master bedroom has a king-sized bed, ma aster bathroom with a shower, and its own private patio. The first guest room has two closets and two comfy twin beds. The 2nd guest room has a queen bed and sliding doors that look out over the tropical pool. Spend your days relaxing by the large screened-in pool, reading a book on the screened-in patio, or walking on the beautiful beaches. Spend your nights enjoying the delicious island restaurants, watching amazing sunsets, or listening to a local musician play tropical tunes. A truly perfect location, “Wait N’ Sea” is just minutes to the beach, the bay, the local marinas, and restaurants yet offers the seclusion of a private home. Reme Halo air disinfection system installed in the central AC Property Manager will only book reservations up to 51 weeks in advance. All our properties have contact free check-in; no need to stop at the office (or a stop light, none of those here)!

Step into your very own Gulf Front Villa, where breathtaking water views meet relaxed luxury. This two-bedroom, two-bath villa has just undergone a stylish renovation and is ready to be your home away from home. With plenty of space, updated coastal design, and the sparkling Gulf of Mexico right outside your window, this is the vacation spot you’ve been dreaming of. Whether you’re cooking, lounging, or entertaining, this villa is designed for comfort and ease. The open kitchen is thoughtfully stocked for all your culinary needs, while the dining and living spaces flow seamlessly to the large screened lanai. Morning coffee, evening sunsets, or simply listening to the waves—you’ll want to spend all day out there. The primary suite offers a plush king bed and serene Gulf views, creating the perfect retreat. The guest bedroom is thoughtfully designed for flexibility featuring two twin beds, making it an ideal space for families or friends traveling together. From the lanai, step right into island life! Collect seashells along Captiva’s pristine shores, lounge on the sand, or take a refreshing dip in the heated pool. Beyond the beach, explore boutique shops, art galleries, and incredible seafood restaurants. Fire up the outdoor grills, rent bikes or golf carts, or head out with Captiva Cruises for dolphin sightings. Adventurers can try parasailing, jet skiing, or kayaking to see the island from a new perspective. With Property Manager, planning ahead is easy—you can book up to 51 weeks in advance, and there’s no office check-in required. Just arrive, settle in, and start your stress-free getaway. While resort amenities are not included, your villa has plenty of its own. Enjoy a large heated pool, pickleball and tennis courts, high-speed Wi-Fi, outdoor grills, community washer/dryers (coin-operated), and—best of all—the beach just steps away. Golf cart rentals are nearby, but remember, only electric carts are permitted within the gates of the resort. This villa has it all: Gulf-front views, a stylish interior, and the perfect layout for a relaxed island escape. Your dream Captiva vacation starts here!

Beach Villa Sunset Dreams is a recently richly remodeled and appointed townhome with tropical beach décor for an unforgettable family vacation. The Villa is unique, with awe-inspiring direct gulf views and amazing sunsets, as well as sunrise views over the bay. The property includes exclusive access to over 380 feet of Gulf beach frontage, deep-water direct access boating, lush landscaping, and a large tropical pool with spa, all shared by only 4 other Villas. Luxury awaits you in this 2400 sq. ft. three bedroom, two and a half bath home. Upgrades include granite, marble and glass tile, an elevator, five flat screen televisions, four DVD players, two Wii play stations, high-speed wireless internet, iPod docking stations, and all high-end appliances. The upper level has a large master bedroom that features a King Bed, a modern bathroom with glass and ceramic tile, dual head shower, two-person spa tubs, and a private screened veranda. There is also a work desk area to accommodate your laptop equipped with two monitors and a printer. The first level includes two guest bedrooms, one with a King Bed and the other with four bunk beds (one with a lower double bed), both with a screened veranda. The Villa contains many book selections to read and several children’s games for enjoying your vacation. Guests also enjoy a BBQ grill area and a boat dock complete with power and water. Sunset Dreams is a part of the five-unit Captiva Beach Villas on the highly desired "Tween Waters" stretch, which is walking distance to Captiva Village, and can accommodate up to 8 people. • Sleeps 8 • Luxury Villa • Direct Gulf Views • Deep Water Direct Access • 380 ft of Gulf beach frontage Property Manager will only book reservations up to 51 weeks in advance. All our properties have contact-free check-in; no need to stop at the office (or a stop light, none of those here)!

Enjoy Captiva Island at its finest in Bayside Villa #5236, a comfortable 1 bedroom, 2 bathroom with stunning Bay Front views and conveniently nestled within the gates of a renowned island resort. This cozy & comfortable condo gets rave reviews from guests lucky enough to vacation in this unit while staying at the renowned island resort on beautiful Captiva Island. Light, bright and tastefully decorated this 1 bedroom, 2 bathroom condo which can accommodate 4 adults has lovely views of the amazing views of Roosevelt Channel and Pine Island Sound from the screened lanai and offers spectacular sunrises. The Gulf and the gorgeous Captiva beaches are a short stroll from the building and the condo. Condo amenities include: 1 bedroom/2 bathrooms -- 1 King bed & pull-out sleeper sofa (sleeps 4), Smart TVs (streaming only), WIFI available, fully equipped kitchen, coin operated laundry facilities on-site, community pool, elevators. Bed linens and bath towels included. No Pets allowed. This unit comes stocked with beach chairs, beach towels and an umbrella. Bayside Villas amenities that are available with this rental include: heated community pool & hot tub, BBQ grills, tennis courts (fee may apply), parking and direct access to award winning Captiva Island beaches! ** This condo is privately owned and is NOT associated with the SS Resort rental program. Full resort amenities are NOT available with the rental of this unit including resort pool, golf course access, trolley use, select stores & restaurants, beach rentals, resort appointed parking and any on-site shops within SS Resort. Resort guests pay a premium for these amenities. Incidental Damage Benefit - We understand accidents happen! Every booking with Property Manager includes protection for those incidental accidents causing damage to the property. Applies to incidental damage only with limits. Details in rental agreement. 3 night minimum rental available. This unit is non-smoking with a maximum occupancy of 4 people. Property Manager, or "Property Manager" provides a variety of high quality, meticulously attended vacation rental homes and condos on Sanibel & Captiva Islands. We are a boutique vacation rental company who strive to make your next island adventure to be the most relaxing and memorable experience possible. We look forward to seeing you soon!!

Welcome to your perfect Island escape! This beautifully updated 3-bedroom, 3-bath Bayside Villa penthouse, located near South Seas, offers everything you need for a relaxing and memorable getaway. With the largest floor plan in Bayside Villas, this spacious two-story condo provides plenty of room for your family to unwind and reconnect—all while enjoying stunning views of the Roosevelt Channel and Pine Island Sound. Step onto your private screened lanai and watch boats drift by, dolphins play, and seabirds glide across the water. Inside, you’ll find a full kitchen, comfortable living area, and three inviting bedrooms—each with its own private bath. The master suite features a king bed and breathtaking bay views, the second bedroom offers a bright setting with another king bed, and the third bedroom includes two double beds perfect for families or friends. The beach is just a short walk away, and you’re ideally located near the entrance of South Seas for easy access to Captiva’s shops, restaurants, live music, art galleries, and all the fun of island life. While you won’t have access to resort amenities, your Bayside Villa comes with plenty of its own perks: a large heated pool, high-speed Wi-Fi, outdoor grills, community washer/dryers (coin-operated), beach chairs and towels, and—of course—the beach just steps away. Golf cart rentals are available nearby (electric carts only within the gates). *Please be aware that there is ongoing construction throughout the resort* Property Manager will only book reservations up to 51 weeks in advance. All our properties offer contact-free check-in—no office stops and no stoplights on Captiva!

Stunning Gulf Front Beauty! Walk out the back door, and you’re on the beach! This four-bedroom, three ½ bathroom home is the perfect escape for a relaxing beach vacation. The large living room features a flat-screen TV, a fireplace, comfortable seating, a desk area, and sweeping views of the beach and sparkling blue waters of the Gulf. Dine in the open dining room with seating for eight or dine el fresco on the screened-in porch overlooking the Gulf. Create a fabulous meal in the large open kitchen with updated appliances, hard surface counters, and tile backsplash. Relax in the first-floor master suite with a king-sized bed, flat screen TV, and a private screened-in patio overlooking the gulf. The beautiful master bathroom has dual sinks and a tiled glass shower. Your guest and family will be more than comfortable in the first-floor guest bedroom suite with an attached powder room, a queen bed, a flat-screen TV, and relaxing beach and Gulf Views. The second guest bedroom features two twin beds, a flat-screen TV, and tropical views. Share the master bathroom or use the hall bathroom with a walk-in shower. The second master suite upstairs has more amazing views of the beach and the Gulf of Mexico, a king-size bed, and a flat-screen TV. The large master bathroom has a walk-in closet, a bath and shower combination, and plenty of counter space. Relax your days away in the private large heated pool. Spend your nights watching the stars from the hot tub. Stroll along the pristine white beaches of Captiva and watch world-famous sunsets from your backyard. A truly special beach home for an amazing vacation. The Winshall home also features wheel chair accessible ramps to the home. Property Manager will only book reservations up to 51 weeks in advance. All our properties have contact-free check-in; no need to stop at the office (or a stop light, none of those here)!

Direct Gulf Front Views! This three bedroom two and one half bath townhome is centrally located on Captiva Island. Amazing views from the living room and front porch! Walk into the bright, open living room that overlooks the Gulf of Mexico. The large kitchen features a beautiful mosaic backsplash, tall modern cabinets, a small table with great views and everything you need to make an amazing meal. The large living room opens up to a dining area with seating for six. Enjoy the sectional sofa off of the dining area and large flat screen TV. The first master bedroom features a king bed, flat screen TV and a screened lanai overlooking the pool. The second guest room has two comfortable twin beds and two trundles, a flat screen TV and also opens to the screened lanai overlooking the pool. The large shared bathroom has dual sinks, a separate shower and tub. The master retreat on the top floor features stunning views, a comfy king bed, a large sitting area and screened lanai overlooking the pool. The master bathroom features dual sinks, a separate bathtub and shower. Everything you need for a once in a lifetime beach vacation. Property Manager will only book reservations up to 51 weeks in advance. All our properties have contact free check-in, no need to stop at the office (or a stop light none of those here)! *** Four unique, luxury villas comprise Captiva Beach Villas. Enjoy the Gulf to Bay locale which offers spectacular beaches and bay fishing. Other features include a swimming pool with a spa and boat docks.

Discover the perfect blend of Gulf-front tranquility and bayfront adventure in this stunning Key West-style estate nestled within the exclusive, gated Tarpon Bay community of Captiva Island. With deeded private beach access for shell seekers and direct Gulf access via Pine Island Sound, this home offers the best of island living for beach lovers and boating enthusiasts alike. Set on a sprawling one-acre estate, this resort-style retreat features a private elevator, a whole-home generator system, and an attached guest house, providing both convenience and luxury. The outdoor living space is an entertainer’s paradise, with a heated resort-style pool, cascading spa, and a fully equipped outdoor kitchen--perfect for al fresco dining under the stars. Inside, the home boasts high-end finishes and modern comforts, including a chef’s kitchen, multiple private balconies, and spacious living areas designed for relaxation. Each of the three elegantly appointed bedrooms offers a plush king-size bed, ensuring a peaceful night’s sleep. Whether you’re kayaking along the Roosevelt Channel, fishing in world-class waters, or simply unwinding by the pool, this breathtaking estate provides an unforgettable Captiva Island escape. # Property Details Size: 3 Bedrooms | 5 Bathrooms (4 full, 1 half) | Sleeps 6 Setting: Gulf & Bayfront | Private Beach Access | Waterfront # Amenities \- Private beach and bay access - Perfect for shelling, kayaking, and boating \- Resort-style heated pool and spa - Featuring a sun shelf and cascading waterfall \- Outdoor kitchen and entertaining area - Includes a built-in grill, lounge seating, and dining space \- Private dock and boat slip - Easy Gulf access for fishing, sailing, and water excursions \- Smart home features and high-speed WiFi - Seamless connectivity and convenience \- Chef’s kitchen - Fully stocked with premium appliances and cookware \- Pet-friendly - Bring your furry companion for an island getaway \- Pool Bar # Additional Features \- Entertainment: Smart TVs, board games, stereo system \- Outdoor activities: Kayaks, bicycles, beach essentials, hammocks \- Parking: Private garage and free on-site parking \- Check-in: Smart lock for easy, contactless entry Indulge in the ultimate island escape, where luxury meets adventure in one of Captiva’s most exclusive enclaves. **Front Door Outdoor Camera Present** Book now for an unforgettable stay!