Sanibel Island & Captiva Island Vacation Rentals


Properties Available 109 properties available
Sensational views are waiting for you at Pine Cove 403C! Relax and free yourself of stress while overlooking the beautiful waters of the Gulf! Luxury is waiting for you with newly remodeled, updated unit, upgraded appliances, flat screen TVs and views from almost everywhere in the condo! Nestled on West Gulf Drive, you are conveniently located near
Pine Cove 403C
Condominium
$300.00 - $700.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.7 (28)
Welcome home to your very own island oasis with all the luxuries of Gulfside living!! This beautifully appointed 2 bedroom, 2 bath condo is a beach-goers dream come true! Located mid-island in Sanibel Surfside in the heart of Sanibel Island near shell-strewn beaches, miles of bike paths, and nearby shopping and restaurants! Upon entering the condo
Sanibel Surfside 114
Condominium
$275.00 - $650.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.7 (37)
Enjoy this comfortable and convenient 3 bedroom, 2 bath pool home in the heart of Sanibel close to beaches, shopping & bike paths! "The Sand Castle" is sure to brighten your eyes with it\'s updated, island style and brand new decor throughout! The home boasts a large open floor plan with an immaculate outdoor area enclosed by a screened lanai and a
The Sand Castle
House
$240.00 - $611.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (3)
** Please note: Elevators throughout the complex will be serviced in September/October which will cause temporary closures for multiple days. Current scheduled dates for Building E: Monday, October 5th, 2026 to October 8th, 2026 however dates are subject to change due to circumstances beyond our control. Pointe Santo E22 is located in one of San
Pointe Santo E22
Condominium
$250.00 - $625.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.5 (65)
Pointe Santo B25 also known as "Coastal Dream" is your perfect place to be on Sanibel Island. Imagine waking up every morning in the master bedroom with gorgeous views of the Gulf of Mexico! The views from the lanai are even better! You can access the lanai from both the bedroom and living room. The condo features an open concept layout and an imma
Pointe Santo B25
Condominium
$220.00 - $570.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.7 (39)
Kings Crown Update: The community pool is now open! Pickleball courts are expected to be completed by Decemberv 2026. Some elevator repairs are currently ongoing from May - August 2026 to replace door frames and will involve some possible noise disruptions. Updates will be provided when available. Welcome to your Sanibel Island escape in Kings C
Kings Crown 207
Condominium
$325.00 - $795.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
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 beautif
Bayside Villa 5236
Condominium
$257.00 - $465.00 / per night
Bedrooms 1 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.5 (9)
Welcome to "Island Sanctuary", a stunning vacation rental property located on Sanibel\'s east end. This tastefully upgraded home features 3 bedrooms and 2 bathrooms, offering a comfortable, open floor plan and living space adorned with stylish coastal decor. Our guests can enjoy the private pool and a large screened lanai, perfect for outdoor relax
Island Sanctuary
House Pet Friendly
$233.00 - $592.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
Welcome to "Dockside Dream at Ding Darling", an exceptional vacation rental home nestled in a private, oversized setting with direct boating access along the tranquil waters bordering Ding Darling Wildlife Refuge. This architectural beauty offers a perfect blend of elegance and comfort, making it an ideal getaway for families or groups looking for
Dockside Dream at Ding Darling
House Pet Friendly
$285.00 - $666.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 (2)
Welcome to Sanibel Surfside #234, a beautifully updated and thoughtfully appointed 2-bedroom, 2-bath vacation retreat just steps from the sugar-white sands and turquoise waters of the Gulf. Nestled within the highly sought-after Sanibel Surfside community, this inviting condo combines coastal elegance with modern comfort, creating the perfect setti
Sanibel Surfside 234
Condominium
$195.00 - $540.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (3)
Welcome to "Little Beach House Sanibel" — your relaxed island retreat just a short 5 minute stroll from the sandy shores. This charming 3-bedroom, 2-bath home offers the perfect blend of comfort, style, and convenience for your next Sanibel getaway. The spacious open-concept layout features an upgraded kitchen with bright white cabinetry, stainless
Little Beach House Sanibel
House Pet Friendly
$214.00 - $500.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Sanibel Surfside "Sunset" #231 is the most unique and spectacular vacation condominium! Truly the only one of its kind, this magnificent 3,000 square foot condo has some seriously incredible gulf views! This condo boasts 3 bedrooms & 3.5 bathrooms and all the bedrooms offer their own master bedroom suite each with their own large private bathroom f
Sanibel Surfside 231
Condominium
$400.00 - $1,075.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 4.7 (93)

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