180 properties available

Located in Captiva, Florida, United States. The Silverseas Cottage - Charming, Immaculate with Private Pool - 2 Golf Carts Welcome to the Silverseas Cottage, an immaculate and charming 3-bedroom, 2-bathroom vacation home on remote North Captiva Island. Located less than a two minute walk to the gorgeous gulfbeaches, this home was newly remodeled in the spring of 2022. It features over 1,800 square feetof open living space including an expansive new living room with soaring cathedral ceilings, a fullystocked gourmet kitchen, and a beautiful new dining room complete with 180 degree views of theprivate, lushly landscaped pool patio. Our home offers every amenity for our guests, including two golf carts for your use during your stay.Home Amenities & DetailsGround LevelThe lower level and pool deck is the perfect spot for relaxing and entertaining. The heated pooland expansive deck area is a private tropical oasis surrounded by palms, flowering hibiscus, citrustrees, and seagrapes. Here you will find a conversation area, rope hammock

Located in Captiva, Florida, United States. Parrothead's Paradise - 4 BR House - Private Boat Dock & Brand New Heated Pool Welcome to Parrothead's Paradise!Located on the secluded barrier island of Upper Captiva, Parrothead’s Paradise is a large 2300 sqft water view home that comes with an upstairs loft, 360 degree roof top terrace and one golf cart. The generous open floor plan boosts a great room with 13-foot ceilings, a well-stocked and fully-equipped kitchen and plenty of inviting space to entertain two families on three levels. Start your vacation with cocktails on the large outdoor bar that easily accommodates 10 people, offering a Webber barbecue grill surrounded by tropical landscaping with Coconut Palms. Take a stroll to the white sandy private beach (2-minute stroll away), watch turtles and collect shells, or take out the 2-person kayak or Stand up Paddle Boards for a chance to see manatees and dolphins up close. On your way back cool off in the private outdoor shower and relax in a cozy hammock. Enjoy your morning co

Located in Captiva, Florida, United States. Pool Home, Steps from the Beach and Spectacular Sunsets plus StarLink Internet Your search for the PERFECT beach vacation house is over with your search for "Havana Breeze on North Captiva Island, FL" and "HavanaBreezeNCap". We can't wait to see your Face ... after you decide to ... Book and arrive at our island paradise and see our home! North Captiva Island is a truly wonderful and pristine location. And we CALL it the perfect place as our second home and we hope you will CALL it that too! And we list in multiple locations for Florida at less expensive rates for HavanaBreezeNCap. Havana Breeze is a charming Florida style home just 150 feet from the beach with spectacular Gulf of Mexico views. Experience sunset views from both the upper porch and balcony in comfortable rocking chairs and the outdoor dining table. Our fully air conditioned home offers three bedrooms and two and a half baths. Recently painted throughout, everything feels 'fresh' and very comfortable! And our own 15'x34'

Located in Captiva, Florida, United States. 13 Sunset Captiva 2 Bedroom / 2 Bath House / Loft Welcome to beautiful Captiva Island, Florida and paradise! The lovely Sunset Captiva #13 vacation rental home is located in the private, quiet, community of “Sunset Captiva” across from the pool and the beach boardwalk. The community is centrally located on more than 6 miles of spectacular beach on the Gulf of Mexico. There is a pool, dock, two tennis courts, and recreation area complete with gas grills and picnic tables. It’s also conveniently close to The Village and the finest in dining, shopping, and recreation. This is a place that is great to walk and explore.Sunset Captiva #13! The Sunset Captiva community is one of the most popular destinations on Captiva Island, Florida. Sunset Captiva homes enjoy a charming neighborhood of private sandy lanes, with shared use of the large heated pool, tennis courts, and boat dock. Find quiet natural beauty along with convenient proximity to the Captiva Village Center.Sunset Captiva #13 is spe

Located in Captiva, Florida, United States. Life's a Beach: Walk to Private Beach & Village in 5 Minutes Beach Cottage, 3 Bedrooms, 2 Baths, (Sleeps 6)Come visit us on beautiful Captiva Island and stay in our 'Life's a Beach' cottage. Our property is a lovely ground level cottage nestled in beautiful lush and tropical gardens. Located on wonderful Wightman lane a small private beach road in the heart of Captiva Island. Considered one of the best locations on Captiva. From here walk to private beach and village in just 5 minutes. Relax in your private large hot tub, enjoy outdoor dinning and lounging areas in front and back of your vacation home. Relaxation island style is guaranteed. For dinner and sunset drinks walk to Captiva's beautiful and famous shelling beaches and historic village. Enjoy nightly beach front sunsets and award winning dining and shop the many unique stores and galleries.Enjoy the warm gulf waters, restaurants, shops, galleries. Huge variety of activities are available on the island. Fishing, boating, boat c

Located in Captiva, Florida, United States. Stunning Views from a Stunning Condo Goin' Coastal Sunset Captiva Bayside 204. Your eyes will immediately be drawn to the expansive and stunning views of Pine Island Sound as you walk into this luxury Captiva condo. This amazing home is the second floor, corner unit at Sunset Captiva Bayside, central to everything. Along with this stellar location the condo itself has top of the line finishes, beautiful décor, and a deluxe chef’s kitchen. As you walk into the entry you will notice a stunning guest bedroom on the right with a comfy queen bed, twin bed, a wall of windows, custom closet, and a tasteful beach décor. The guest bathroom is stunning with frosted glass countertop, tiled shower with glass enclosure and multiple luxury showerheads.The open and updated kitchen features custom cabinets, solid surface countertops, a 5-burner stove with griddle, wood floors and views of the water. Everything you need to create an amazing meal. The open dining has seating for four and more vie

Located in Captiva, Florida, United States. SOUTH SEAS BEACH VILLA 2126- Two Bedroom Captiva Condo with Gulf Views. INTRODUCING CAPTIVA BEACH VILLA 2126*PHOTOS WERE TAKEN POST HURRICANE IAN, PLEASE JOIN US IN WELCOMING BACK OUR BEAUTIFUL REMODEL ALONG WITH BRAND NEW APPLIANCES, READY FOR THE 2024 SEASON!*Desirable Gulf Beach Villa at South Seas Island Resort is a low density, two-building complex at the northernmost location of the Beach Villas with its own entry. Beach Villa 2126 has been recently renovated and offers direct gulf front views for an outstanding vacation destination. Enjoy miles of Captiva's award-winning beaches. Golf cart and bike rentals are available nearby for all of your island adventures.CONDO FEATURESCaptiva Beach Villa 2126 is direct beachfront offering a soaring living room and dining room adjoining a newly renovated kitchen. In addition to the twin bedroom with its own flat-screen TV and full bath on main living level, this villa offers a large, screened lanai overlooking the beach for Captiva's famous

Located in Captiva, Florida, United States. Family-Friendly Bayside Villa at South Seas Resort Summary:Extensive renovations in October 2023 have created a beautiful, family friendly vacation villa with all the comforts of home. Enjoy the gorgeous waterfront views from the spacious lanai, an updated living room and master bedroom suite with king bed. Featuring 2 full bathrooms and a queen Murphy bed in the living room, this villa comfortably accommodates parties of 4. The well-equipped cook’s kitchen features a stunning island with comfortable seating. The villa offers an array of children’s items including pack-and-play, high-chair, baby beach tent and sand toys. Enjoy the nearby beach with included beach cart, sand chairs, beach umbrella and surf boards. For after beach fun, you will find toys, games and puzzles.The Space:This villa is located on the first floor and boasts 850 square feet of optimized island living space. Enjoy the art from local island artists in the comfortable living room. This villa can sleep a party o

Located in Captiva, Florida, United States. Point of View - luxury Captiva Island Gulf to Bay home Point of View on world famous Captiva Island, Florida. Our five bedroom/four and one half bathroom ulta luxury vacation home has sleeping for up to 16 guests with a private pool/hot tub and dock. Easy beach access a short walk down the driveway and just across Captiva Drive. We call the home Point of View as you can look out the front of the home and see the Gulf of Mexico and behind the home, the Roosevelt Channel. It doesn't get much better than that. The lower level of the home has an expansive room with two queen murphy beds and a king bed with flat panel TV and full bathroom. Upstairs on the main level is the owner suite with king bed, en-suite bathroom and bedroom/TV room just beyond that is accessible from the room or the main area of the home with a sleeper sofa. There is a full kitchen equipped with everything you could imagine to prepare meals for your entire family and friends. The top level has two suites, both with kin

Located in Captiva, Florida, United States. Captiva Island Bayside Villas 1 Bed 2 Bath sleep 4 Beautiful Condo 1 Bed 2 Baths in Captiva Island.Welcome to Bayside Villa located on the beautiful island of Captiva inside the gate of the world-famous South Seas Island Resort. This private unit is within walking distance of the world-famous Captiva beaches, and also the Captiva Village! With stunning views of Pine Island Sound and the South Seas Bayside Marina, this is an exceptional unit condo with lots of natural light. This Captiva Island vacation rental is in the Bayside Villas neighborhood, which has access to app operated washers and dryers, beach access, a hot tub, a community pool, and BBQ grills at the pool. This is a privately owned unit within South Seas Resort. South Seas amenities such as trolley and north pool are NOT available and you do not pay the resort fees for them, but we have the most beautiful beaches and shelling in the world, fabulous salt water fishing, and one of the best places to bike and make family mem

Located in Captiva, Florida, United States. The Beach Nest 2 Bedroom / 2 Bath House Limited-Time Offer: Enjoy a festive feast of savings with a fantastic $500 off on Thanksgiving.Beach Nest is aptly named, perched up among the trees on an upper level with a partial beach view and a short path out to the white sand and the Gulf of Mexico. This is a spacious and modern home with comfortable and complete furnishings, featuring a large screened lanai with views over the Gulf and a separate open sundeck.The kitchen is bright and cheerful, and there is plenty of seating for meals with the large dining table, breakfast bar, and lanai table.The primary suite has a beautiful big bathroom with his and hers basins. There is a big walk-in closet, and a sliding glass door opens onto the screened lanai. The guest bathroom also has a big tile shower.All reservations/cancellations are subject to the terms and conditions (policies) of the American Realty Rental Agreement once the reservation is booked through third-party platforms.Policies incl

Located in Captiva, Florida, United States. Endless Summer 5 Bedroom / 6 Bath House Ultimate Luxury! Endless Summer, located on Wightman Lane in the heart of the eclectic Captiva Village, is a beautiful, well-appointed, and updated home. Rejuvenate yourself in a home that has been splendidly furnished, while just a short stroll to the beach will help the relaxation start immediately upon arrival. While staying in this stunner of a home, you will be also stepping away from popular restaurants, unique shopping, festivals, kayak and boat rentals, and more…This newly constructed home offers 5 bedrooms, 6 bathrooms, and a wonderfully finished lower-level family room with an additional sleeper sofa. The home also features an elevator for convenience and can accommodate up to 12 guests.There is a fully equipped kitchen for family meals, a grand living room, and an extra living area downstairs built for fun. The main level pool and spa are wonderfully situated for optimal access and peaceful privacy. There is a wonderful lanai for outsi

Located in Captiva, Florida, United States. SERENITY - Luxury Captiva Home, 4 Homes From the Beach INTRODUCING SERENITYA Note To Our Guests:With each new sunrise, we’re one day closer to normal on the islands of Sanibel and Captiva. We’re working diligently with our owners to reopen their vacation rentals as quickly and safely as possible. Please be aware that clean up and construction work will continue throughout the islands due to Hurricane Ian.Hurricane Ian Damages to Serenity: -Privacy fence, on right side only, needs to be replaced and pavers need resurfacing. This will not inhibit your stay. -Landscaping is still getting worked on and workers may be there more than once a week. Live the Island life and experience ultimate island living on Wightman Lane, a private shell lined street located just 4 homes from the pristine beaches of Captiva Island. You are just a short walk to all of the islands favorite restaurants, galleries, shops and local marinas plus live music. Relax as you are surrounded by the lush t

Located in Captiva, Florida, United States. One House from the Beach ! New to the rental market ! Literally 30 seconds to the open and stunning Captiva beach.This stunning three-story Captiva beach home is not only one house to the beach it also has side Gulf views from two of its multiple balconies. This spacious home has been thoughtfully designed with the living spaces on the top floor, the bedroom on the middle/second floor and the indoor/outdoor.Walk into the light filled entry that gives you access to the three-car garage, pool and stairs to the upper levels. Your vacation is made easy by unloading items right into the garage and into the elevator that spans all levels of the home. This main level features a beautifully designed bar area with 8 feet sliding glass doors that open to the lush tropical pool, hot tub, outdoor shower, stone patio and gas grill. The perfect spot to relax while listening to the waterfall.The second floor is set up for comfort featuring the first of two living rooms in this home. A large sect

Located in Captiva, Florida, United States. Now Booking ! Luxury Remodel ! Short Stays Welcome Aug until Xmas 2024 All New Beach Front Villa!*Please be aware that there are ongoing construction activities throughout South Seas, leading to the presence of noise, construction materials, and workers on the propertyExperience the allure of stunning water views! This beautiful Gulf Front Villa was just transformed through a comprehensive, high-end renovation. Seize the opportunity to reserve this entirely renovated Gulf Front Villa today.This luxury villa has four bedrooms, three bathrooms, an impressive open-concept kitchen, and completely new high-end furnishings. Upon entering, the meticulous attention to detail in this luxury renovation is immediately apparent. The expansive kitchen features premium appliances and finishes, seamlessly flowing into the large living area that offers unobstructed views of the Gulf. The first bedroom is outfitted with two cozy twin beds and elegant decor, while the first-floor master bedroom offers a

Located in Captiva, Florida, United States. Luxury Gulf Front Villa! 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, 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 which features a King Bed, modern bathroom with glass and ceramic tile, dual head shower, 2 person spa tub, and a private screened veranda. There is also a work desk area to acc

Located in Captiva, Florida, United States. Everything You Need For The Perfect Vacation! Free Parking, Beach and Pool The ultimate vacation spot! Enjoy access to the abundance of resort amenities on this property: from great pools and tennis courts to poolside chairs and towels provided at no extra charge! This property, which boasts a genuine old Florida feel, is surrounded by a 330-acre wildlife preserve, where dolphins and manatees are regular guests. Here you’ll find everything you need to live that dreamy island life. Fill your days with kayaking, sailing, boating, bicycling, golf, and tennis. Enjoy epic fishing, world-famous shelling, or just strolling along the spectacular 2.5-mile stretch of private pristine beach. PLEASE BE ADVISED:- A MANDATORY RESORT FEE of $25 PER EACH PERSON PER NIGHT PLUS TAX WILL BE CHARGED UPON ARRIVAL. - A MANDATORY SERVICE CHARGE OF 12% OF THE NIGHTLY RATE, PLUS TAX, WILL BE COLLECTED UPON ARRIVAL. - The listing is distributed and managed by RoomPicks Accommodations- The resort is still under

Located in Captiva, Florida, United States. Island House 3 Bedroom / 3 Bath House Island House is a private cottage right in the Captiva Village center, across Binder Lane from the bay shore. It’s built in the old Florida style and is registered as a historical cottage. On March 28, 2018, The Captiva Island Historical Society hosted a celebration of the 100-year anniversary of Island House. Built-in 1918 by F.A. Lane and later owned by Pastor Rawls until 1978 when Joe and Nan Baer purchased the Island House and it remains in the Baer/Terrill family today.This is a great location with such easy walking convenience to shops and restaurants. Stroll down Andy Rosse Lane to the beach.Island House has three bedrooms and three baths, plus a day bed in a smaller room. There is a full kitchen, a glassed-in porch, and a nice backyard. It has a laundry with a washer/dryer. For a family requiring less space, you can rent only the downstairs two-bedroom two-bathroom separately for a reduced weekly rate.All reservations/cancellations are su

Located in Captiva, Florida, United States. Making The Best Memories Along The Way! Pools, Beach Access, Restaurant! The ultimate vacation spot! Enjoy access to the abundance of resort amenities on this property: from great pools and tennis courts to poolside chairs and towels provided at no extra charge! This property, which boasts a genuine old Florida feel, is surrounded by a 330-acre wildlife preserve, where dolphins and manatees are regular guests. Here you’ll find everything you need to live that dreamy island life. Fill your days with kayaking, sailing, boating, bicycling, golf, and tennis. Enjoy epic fishing, world-famous shelling, or just strolling along the spectacular 2.5-mile stretch of private pristine beach. PLEASE BE ADVISED:- A MANDATORY RESORT FEE of $25 PER EACH PERSON PER NIGHT PLUS TAX WILL BE CHARGED UPON ARRIVAL. - A MANDATORY SERVICE CHARGE OF 12% OF THE NIGHTLY RATE, PLUS TAX, WILL BE COLLECTED UPON ARRIVAL. - The listing is distributed and managed by RoomPicks Accommodations- The resort is still under re

Located in Captiva, Florida, United States. Life's A Beach 3 Bedroom / 2 Bath House Experience Captiva's FUN in the SUN once more with our NEWLY decorated and refreshed rental, perfect for your family to enjoy!Welcome to Life’s A Beach! This lovely beach cottage has an excellent location along quiet, sandy Wightman Lane, one of the most desirable lanes of the Captiva Village area. From here it’s a quick stroll to the warm Gulf of Mexico sands – beach lovers will find the proximity really convenient. And you’re only a very short walk from shopping, restaurants, activities, and the Island Store.The grounds at Life’s A Beach are carefully landscaped into a beautiful tropical garden. This is a masterwork of natural art, from potted plants and flowering shrubs up to mature palms and massive trees. The garden is enhanced with pergola and trellis structures painted in bright colors. Dense hedges offer luxurious privacy and yet open to spacious outdoor areas where you can enjoy Captiva’s gorgeous weather (when you aren’t out on the beac

Located in Captiva, Florida, United States. South Seas Bayside Villas 5236: Incredible Location, Stunning Bayfront Views! Update following Hurricane Ian: This condo sustained minimal damages from the storm and all items & amenities INSIDE the unit have been repaired and/or replaced and it is ready for rentals! Please note: OUTSIDE construction to the Bayside Villa complex and surrounding South Seas resort may be on-going through 2024. On-site construction & work delays MAY be possible and are out of our control. Certain building amenities such as the elevator, pool heater and more may not be functioning properly. Elevator repairs to this building may be delayed until September 2024 or beyond. There may also be noise associated with on-going construction in complex and surrounding units.Enjoy Captiva Island at its finest in South Seas Bayside Villas #5236, a comfortable 1 bedroom, 2 bathroom with stunning Bay Front views and conveniently nestled within the gates of the South Seas Resort. This cozy & comfortable condo gets rave

Located in Captiva, Florida, United States. Open Breeze - Luxury Near Beach Home on Captiva "Open Breeze" is a luxury home located on beautiful Wightman Lane in the Village of Captiva. The house has 3600 square feet under air, plus over 2000 square feet of screened porches, decks, and lanais. There's five bedrooms and baths, two laundry areas, a full dining area, and a fully-equipped kitchen.You have your own tropical retreat in the pool area with a heated salt-water pool with spa, a bar area with a second refrigerator.The house is within walking distance of all of Captiva's unique restaurants, quaint shops, art galleries, a day spa and the beach is only 300 yards away with direct access off of Wightman Lane.Newly upgraded Kitchen. Upgraded TV's, every room has LED HD Tv, Cable with ALL Channels (Including premium). DVR in 2 rooms + living room. Fastest internet available, 120Mb download speeds. The House is perfect for a large family, a group of friends or even 5 couples! Default pricing is based on a group size of 12 people or

Located in Captiva, Florida, United States. FULL remodel ongoing. 4 bdrm/3 bath. January 2025 rentals. New photos SOON. 'A Shore Thing' is located on beautiful Captiva Island. Our home is only one property away (300ft) from the gorgeous island beach. We are in Captiva Village, therefore within walking distance to all restaurants, shops, McCarthy's Marina, the Captiva Library, and Starbucks. It is also close to the famous and quaint Chapel By The Sea, Captiva's only Chapel which is non-denominational. I think the best attribute our home boasts for your island vacation is the private heated pool nestled among tropical plantings and lush grass, NOT enclosed in a cage. We also have 4 cushy chaise lounges where you can relax the day away. You may also rent a golf cart which is always fun! Come to Captiva Island and fall in love with the beaches, the weather and the people. This is a wonderful place for you and your family to make memories.

Located in Captiva, Florida, United States. Experience once-in-a-lifetime luxury for one-in-a-lifetime prices! Bookings made for Aug, Sept, Oct, Nov, Dec 2024 get a free golfcart!Location! Location! Gulf front with sparkling Captiva beach right out the front door, yet it is a short walk to the village to visit your favorite bar or restaurant. This is the house that has it all -- close to the village, but far enough away to enjoy the quiet and private life on miles of shell strewn beach. This gulf location affords the best of both shores with quick access to the inter-coastal water of pine island sound for fishing and boating.You'll be captivated by beauty, both inside and outside, when you visit this 5 bedroom/4 bath luxurious home on Captiva island. Aloha baby is professionally decorated with a warm, welcoming, casual feel that's accompanied by amazing openness and breath-taking views. This property with developed tropical landscaping and a quiet, secluded heated pool and spa is truly an island paradise.Enjoy unobstructed views