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Holiday Rentals with Pools in Captiva Island

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    Travellers to Captiva Island are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    98 Matching Rentals in Captiva IslandView all 141 rentals
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    SAND ANCHOR in Sunset Captiva #191 / 26
    (2)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    • Satellite TV
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One Bedroom Bayside Villa - One King Bed plus Sleeper Sofa: From a large screened balcony, guests can revel in tranquil views of the Bayside Marina of Pine Island Sound and the mangrove forest. Located in the South Village area of the resort, they are a short walking distance to the beach,...
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    Captiva Island, Southwest Gulf Coast 33924
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Harbourside Guest Room 2 Queen Beds at the South Seas Island Resort: These guestrooms are located at the prestigious North Pointe, the center of many of the Resorts activities. From the open balcony guests may watch yachts and sailboats in South Seas Marina, or they may watch dolphins and manatees...
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    Captiva Island, Southwest Gulf Coast 33924
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Charming Captiva Cottage1 / 16
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Patio
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Washer
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 January 2015
    Captiva Cottage is cozy enough for two yet can easily accommodate a family or group of friends. Wonderfully located, it is private, quiet but within easy reach of the...
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    About this property
    You are just 300 steps from the beach in this private and secluded 3bedroom/3bath vacation home. The Captiva Cottage is the only home on this over one acre property nestled among other estate zoned properties in this stretch of Captiva Island, also referred to as the Gold Coast. The private beach...
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    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Balcony
    • Grill
    • Satellite TV
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One Bedroom Beach Villa with One Queen Bed plus Sleeper Sofa: From a screen balcony, guests enjoy views of the Gulf of Mexico, pristine white-sand beaches and stunning Captiva sunsets. These villas are situated in the South End of the resort and are aproximately 100 yards from the sandy beaches,...
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    Captiva Island, Southwest Gulf Coast 33924
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Air Conditioning
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    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Harbourside Guestroom One King at South Sea Island Resort: These guestrooms are located at the prestigious North Pointe, the center of many of the Resorts activities. From the open balcony guests may watch yachts and sailboats in South Seas Marina, or they may watch dolphins and manatees as they...
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    Captiva Island, Southwest Gulf Coast 33924
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Balcony
    • Porch
    • Patio
    • Grill
    • Outdoor Dining Area
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in a small beach-to-bay community on the scenic Captiva Island, this fully furnished and fully equipped cottage is just minutes away on foot from the beach. This home is ideally located near all the hot-spots of Captiva. The master bedroom has a queen-size bed, private bathroom and private...
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    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Captiva Villa- What a Place!1 / 23
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Washer
    • Patio
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2016
    Our family with two teenage daughters and our friends with teenagers stayed here immediately following graduation. We had an absolutely wonderful vacation. This house is...
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    About this property
    The Captiva Villa is located on a charming private lane in the heart of Captiva, a few minutes stroll from the Gulf beach. This spacious vacation home has 4 bedrooms, 3 baths, and sleeps 8-10 comfortably. The Master Suite has a king bed, TV with VCR & DVD, i pod docking, tray ceiling with ceiling...
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    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Satellite TV
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront Artist Retreat on the water with private dockage. Very unique, totally renovated, State protected home. 3 bedrooms, 2.5 baths. Sleeps 7. High end, commercial appliances. Private swimming pool. Beach access less than a mile. Floating dock for easy access in and out of water via...
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    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    THE LITTLE OASIS VERY PRIVATE & ROMANTIC LOCATION1 / 21
    (16)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 days ago
    Very quiet and relaxing. My wife and I stayed here for our honeymoon. Great place to sit back and relax.
    Reviewed 27 January 2017
    Nice home with many amenities. Great location stunning setting.Beautiful beaches, a walkers paradise.
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    About this property
    VERY PRIVATE AND ROMANTIC ONLY 300 STEPS TO BEACH - 2 BED/2BATH HOUSE W/PRIVATE POOL/HOT TUB W/GULF VIEWS. Newly furnished lovely 2bed/2bath house QUEEN bed in master bedroom and a Queen bed and Daybed in the other bedroom w/kitchen w/stainless steel appliances, LR,DR, with own private...
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    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Romantic Beach House w/ private pool & rooftop spa1 / 30
    (16)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Patio
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 February 2017
    Our trip to North Captiva was one of our favorites to date! We originally were looking for beach houses in Sanibel or Captiva, but without realizing we booked on North Captiva...
    Reviewed 17 November 2016
    What a totally awesome vacation. So much more than we ever expected. We would love to go back there again sometime. So peaceful, so quiet, so relaxing. We loved just spending...
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    About this property
    THE LITTLE ARK (please note: cleaning fee $125 for 2 people or $150 for 3 or 4 people and club membership fee $75 optional will not appear in booking charges if you book online. These two fees are only payable by check and mailed to owner) The vacation of a lifetime is awaiting those who are will...
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    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Windswept North Captiva 5 Bedrooms, Heated Pool1 / 53
    (19)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Hot Tub
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 March 2017
    Everything you read about Windswept is absolutely as advertised - fantastic well kept house full of all amenities imagined, great private heated pool, short walk to what feels...
    Reviewed 23 February 2017
    Wendy and Mark are FANTASTIC. Their home is beautiful, full of character, and equipped with everything (and far more) to make for a perfect vacation - books, kids movies...
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    About this property
    Windswept vacation home offers luxurious accommodations, heated private pool, and a truly one-of-a-kind vacation retreat. A vacation at Windswept, on North Captiva, is the perfect place to reconnect with nature, your family, and your friends. Vacation stays at Windswept available with a 7 night...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
    • Satellite TV
    • Balcony
    • Hot Tub
    • Wi-Fi
    • Parking
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One Bedroom Beach Villa with One King Bed plus Sleeper Sofa: From a screen balcony, guests enjoy views of the Gulf of Mexico, pristine white-sand beaches and stunning Captiva sunsets. These villas are situated in the South End of the resort and are aproximately 100 yards from the sandy beaches,...
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    Captiva Island, Southwest Gulf Coast 33924
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Captiva Island. “Happy Daze” - beautiful, child-friendly home with a very private, well heated pool. The home is a very short walk to the beach (the island is only about 600 yards wide, at its widest point) and shops and restaurants in the village. Our single family home has five bedrooms, four...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the breeze of the Gulf of Mexico from this four bedroom home’s rooftop sun deck after walks along the beach, swimming in your private, heated pool, dipping in the hot tub or gazing up at the stars. Every guest will find their own way to unwind whether by the private pool, playing on one of...
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    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Captiva Retreat at 47 Sunset Captiva1 / 18
    (5)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Porch
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Satellite TV
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2016
    Rented bikes and came to the pool before we got the keys to our house at the realtor. Property manager was very rude and chastised us. He even followed us off the property down...
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    About this property
    Captiva Retreat (47 Sunset Captiva) is a 2,200 Sq.Ft. detached free-standing home with 2 private bedrooms (2 queens, bunk beds), private den with queen-size wall bed, loft with single bed, and three full bathrooms. It comfortably accommodates 8 guests. If you can't get by without checking...
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    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    242 - Beach Daze1 / 25
    (19)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Satellite TV
    • Waterfront
    • DVD Player
    • Hot Tub
    • Washer
    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 August 2016
    My husband & I took our 2 kids to this island over spring break & had a great time! Each morning we woke up, made breakfast & took it down to the beach to enjoy...
    Reviewed 9 May 2016
    Very nice condo on the beach and what a beach. Condo was very clean and comfortable.Kitchen nicely equipped and all appliance's worked. Hot tub was great for night star...
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    About this property
    Directly on the beach! This two bedroom, two bath villa is just about one of the best beach front locations offerred on North Captiva. A truly fabulous location. Just the sand between you and the Gulf of Mexico. Sunsets directly west of your open expanded living area, master suite and Jacuzzi. Just...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Patio
    • Washer
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Captiva Island condo at the Hideway. Third floor unit with breathtaking sunrise views overlooking the Bay/ ICW. Just a short 5 min walk to the Beach for sunset, shopping, dinner, and dolphin wayching. 2 bedroom unit. Master has king bed and separate bathroom. Second guest room has two twin beds...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    6 Bedroom Luxury Beach Front Estate/breath taking sunset views!1 / 53
    (1)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Private Outdoor Pool (Heated)
    • Washer
    • Satellite TV
    • Internet Access
    • Balcony
    • Air Conditioning
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2017
    We have been vacationing on Captiva island for 20 years and we can not believe the owners of New Latitude are renting this home. My wife and I were amazed by the quality of the...
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    About this property
    Welcome to New Latitude, located at 16500 Captiva Drive on the Gold Coast of world famous Captiva Island, Florida. Renown for some of the best sunset views found on the Island ... New Latitude is quite befitting. Be mesmerized by the soft, serene, sunrise from your roof top porch and experience an...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Waterfront
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely beachfront home has a private beach and two large open porches overlooking the water. Watch the dolphin go by and see the tarpon jumping in the sun. If you like to fish, this beach is the premier spot on the island near Captiva Pass. Head down to the North Captiva Island Club, included...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bird of Paradise on Captiva Island offers a luxurious escape from the non stop hustle and bustle of everyday life. Whether you're looking for a quick, quiet romantic or family getaway or a more extended vacation adventure, this modern near beach home is the perfect vacation destination for relaxing...
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    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    LAS OLAS, N. CAPTIVA 4 Bedroom  2.5 Bath Pool Home1 / 25
    (57)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Patio
    • DVD Player
    • Hot Tub
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2017
    Las Olas continues to be a prime rental on North Captiva. It has everything you need for a great vacation away from it all. This was our fifth stay here and each one has been...
    Reviewed 9 August 2016
    Our family and our 4 legged two labs loved this house. Very comfortable, spacious, great location.. Nothing was left out.. Total privacy, the home in set back from road with...
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    About this property
    Newer construction 4 bedroom 2 1/2 Bath Large 3 story home with Private heated Pool. 5 Story Observation tower with 360 degree views. OPEN floor plan with large great room kitchen area on 3rd floor with large screened in Lanai offering Alfresco dining. 10 foot ceilings and 8 foot doors and...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Wi-Fi
    • Washer
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Patio
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Listen to the sounds of the waves from your screened in porch while enjoying world renowned sunsets. This three bedroom two and one half bath Gulf Front Captiva home has everything you want to make this a vacation of a lifetime. Walk into the bright great room featuring direct views of the Gulf of...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    082 - Sunset Cove1 / 7
    (4)Average
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunset Cove is a "Rustic", 2 star, 3 bedroom 2 bath Gulf view home. Hidden in lush tropical foliage with no nearby neighbors, this home offers a feel of delicious privacy. And to top it all off, a private pool. This house is in need of updating but the price makes it a great deal on the island.
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    234B-Beach's Edge1 / 24
    (29)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Satellite TV
    • Balcony
    • Waterfront
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 May 2016
    Our family thoroughly enjoyed our time at Beach's Edge! we had three adults and 4 children ages 2-7 years old, there was something for all of us. The house had everything we...
    Reviewed 18 May 2015
    While this may not be the fanciest house on the island, it is by far the best location! Truly right on the beach. The pictures are very accurate, it was clean, very comfortable...
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    About this property
    Sit right back and watch the waves go by. This delightful 2 bedroom & 2 bath beach house will lift you into the beach vacation of your dreams! Walking through the classic beach entrance gate before a grove of palms, you arrive at the beach house and are immediately welcomed by a chic and...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are looking for amazing views, a great pool, great fishing, boating, a place to sleep and value savings, Sea Otter is a great option. It offers a great location but is a no frills lodging experience. Furnishings, décor, fixtures and appliances are dated and meet basic expectations....
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    075 - Isle Be There1 / 24
    (19)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Terrace
    • Washer
    • Satellite TV
    • Balcony
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2016
    We stayed here 14th-21st Feb. Group of 8 - 4 adults and 4 children age range 4 to 18. The house was in an excellent position. Very well maintained and the decor was lovely...
    Reviewed 5 December 2014
    We had a great time. Once we figured out logistics of food, transportation everything was great. Kids were looking at property to nuy. House was good. We were comfortable and...
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    About this property
    This spacious 4 bedroom home is by far one of the best values on North Captiva Island.This wonderful property has brand new owners, a new name, Isle Be There, (formerly called Snail’s Pace), and a number of upgrades, both inside and out, to make your stay most relaxing and comfortable. The grounds...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Anchors Aweigh on world famous Captiva Island. Our vacation rental home is set on nearly 1.5 acres of tropical landscaping and directly on the Roosevelt Channel. Our home is a fisherman's dream as you have access to a private dock with direct access to Pine Island Sound and Blind Pass...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    073C - Island Time I1 / 23
    (17)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    • Washer
    • Waterfront
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fabulous 2 bedroom 2 bath Bayfront home with private dock. Just steps to your own private beach! Best fishing spot on the island. Fabulous beachfront home has a private dock, private beach, manicured grounds and screened-in porch overlooking the water. Watch the dolphin go by and see the tarpon...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunset Captiva #15 is a 3 bedroom/2.5 bathroom with loft deluxe, private, stilted home in the quaint village of Captiva Island. Its highly desirable beachside location is within a quiet community directly across from the expansive heated pool, tennis courts and within a minute’s walk to the sandy...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    106-Longboat Pearl1 / 24
    (6)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Hot Tub
    • Satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the Longboat Pearl for your next vacation getaway. Longboat Pearl is a 3 bedroom 2.5 bath home with a heated pool conveniently located minutes from the beach and just seconds from the North Captiva Island Club. Enjoy every possible amenity when staying at the Longboat Pearl. This gem is...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Gorgeous, relaxing, and newly decorated 4 bedroom home with private dock. Sunsets on the beach!1 / 46
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Grill
    • Washer
    • Wi-Fi
    • Satellite TV
    • Patio
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Loved the Pink House! Well stocked home with everything you need! Family friendly home equipped with bikes, sand toys, fishing poles, kayaks and paddle board. Relaxing pool in...
    Reviewed 22 December 2016
    This was my second time staying at the house. Our family has been staying at various homes on Captiva for 15+ years. This house is a joy; the interior space is very usable for...
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    About this property
    If you're looking for a perfect tropical vacation home that fits a large family, our stunning Captiva Island Villa is perfect! Our very private and quiet four-bedroom home is located on the Roosevelt Channel of Captiva with its own private dock on the bay. Spend your morning hours looking out of...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    210-Sunset Beach1 / 24
    (17)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Satellite TV
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2012
    I thoroughly enjoyed my stay at North Captiva Island. It was our first family vacation in years, and it couldn't have been any more perfect! The Sunset Beach House (so...
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    About this property
    This comfortable 3 bedroom, 2 bath beachfront home is ideal for a family looking for a true island getaway. With its location and feel, it offers a truly memorable vacation! Situated very near the state preserve, this home's location is ideal as a starting point for beachcombing, shelling or...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Private Outdoor Pool (Heated)
    • Grill
    • Air Conditioning
    • Terrace
    • Satellite TV
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just steps from the gorgeous gulf beaches, Silverseas Cottage is an immaculate and charming three bedroom, two bath home perfect for a single family or small group. Newly renovated, the interior features a fully stocked cook’s kitchen with stainless steel appliances, beautiful labradorite granite...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Captiva Beach Villas-Conch1 / 26
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Satellite TV
    • Washer
    • Waterfront
    • Hot Tub
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 January 2017
    We've rented from Kingfisher several times. Great experience. This particular townhouse couldn't be any better!
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    About this property
    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...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    258-Turtle Trax1 / 20
    (13)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Air Conditioning
    • Internet Access
    • Balcony
    • Washer
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 January 2016
    We lo ved this place , very clean and in perfect condition , Only one Word That said It all about this place, SPECTACULAR.
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    About this property
    Turtle Trax is a lovely three bedroom beach view pool home. This cozy home is professionally decorated and has sweeping views of the Gulf of Mexico and sunsets. Turtle Trax is a lovely quaint cottage just steps away from the Gulf Beaches. Situated on a nice over sized lot, this home affords extra...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Balcony
    • Washer
    • DVD Player
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let your troubles melt away in this luxury three bedroom three bath condo with a den. Relax on the spacious lanai with sweeping direct bay views. The large living room has beautiful views, tile floors, built in cabinets and double tray ceilings with wood accents. The gourmet kitchen features top...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Satellite TV
    • DVD Player
    • Washer
    • Air Conditioning
    • Internet Access
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine a beach vacation at a house that's like your very own luxury beach resort called Gulf Dreams on-the-beach. The deed to this luxury beach house states that the property's west boundary is the Gulf of Mexico. The house has 75 feet of private, white sand Gulf beach for your pleasure, easily...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lollipop, 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, screened in porch, updated modern kitchen, pool and spa, two...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    16879 Captiva Drive1 / 25
    (6)Very good
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Patio
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 March 2011
    We were a family group of eight, that included four 18 year olds. Having the separate downstairs unit was great to give them (and us) space. Great location (if you prefer, as...
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    About this property
    A dream home for a dream vacation. This 5 bedroom 6 bathroom has everything you would want for an outstanding vacation. Gorgeous views of Pine Island sound, a large screened in pool, u-shaped boat dock in your backyard, a tiled sun deck with great views and a short stroll across the street to the...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    085-Gulf Breeze Cottage1 / 24
    (29)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • Washer
    • Balcony
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 March 2016
    We have stayed in North Captiva before but have never rented through the club. What a great experience!!!! Luggage service!!! Are you kidding me!!!! Priceless!!!! Great staff on...
    Reviewed 25 January 2015
    I gave a average review based on all the problems we had the first 2 days. The unit is nice inside. The hot tub outside on the deck had nasty slimy stuff around the intake...
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    About this property
    Just like new 1000 square foot gulf Breeze cottage with vaulted ceilings, sunken spa, large wrap around screened porch, great water views and tasteful furnishings. Gulf Breeze Cottage is truly the perfect name for this like new beach cottage. Just 100 yards to the Beach with direct beach access...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Captiva Mermaid Pool House  -  Aug 12th & 19th Weeks Open!1 / 32
    (41)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Porch
    • Washer
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 April 2017
    Best vacation rental experience ever from the minute we walked in the door at the mermaid house we knew we were in for a week of perfection. The house has everything you need to...
    Reviewed 1 April 2017
    My sister and I have a lovely tradition of vacationing in Florida with my now 86-yr-old mother, 83-yr-old aunt and my cousin. This year was our 8th trip, after missing a couple...
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    About this property
    Experience the laid back Captiva Island lifestyle with this classic 2 br, 2 full bath cottage, just 150 yards off the beach. Sleeping 6, its private, secluded, screened and large 26 x 14 foot heated pool (with Mermaid mosaic on the pool floor) is off the double French doors of the living room. The...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Wi-Fi
    • Washer
    • DVD Player
    • Grill
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gorgeous views of the Pine Island Sound, watch dolphins, sea otters and osprey from your screened in porch. This two bedroom, two bath home is located in the Gulf to Bay community of Captiva Shores. Walk into the bright open living area with tile floors, tropical furnishings, flat screen TV and...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    163-Pelican Pointe1 / 25
    (9)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Grill
    • Internet Access
    • Hot Tub
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 December 2012
    We stayed at Pelican Pointe over the Thanksgiving holidays. This property offers the best location, the best views, hot tub with views and elevator. The owners/management...
    Reviewed 2 July 2012
    This is a pretty well equipped home. However, we arrived during Tropical Storm Debby and the entire island was flooded. The golf cart would not go through the roads that were...
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    About this property
    This 4 bedroom home has the best views on the island! Walk out your door onto the beach. Pelican point, brand new (Dec 2007) 4 bedroom luxury home only 12 steps to the Gulf of Mexico waters. Only a sugar white sand beach seperate you and the Gulf of Mexico. Enjoy some of the most incredible views...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    MANATEE COVE1 / 36
    (2)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Grill
    • DVD Player
    • Washer
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 April 2017
    Had a fantastic holiday at Manatee Cove April 2017. The house feels very homely and is tastefully and comfortably furnished and equipped - including beach wagon and cooler...
    Reviewed 7 March 2017
    This is a remarkable rental property...spacious, elegant comfortable, secluded, well-managed, consumer-friendly and it even allows you to bring Bowser! The distance from Captiva...
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    About this property
    This unique luxury 5300 sq.ft. home ( recently remodeled ) is nestled on an acre of tropical charm with a 450 foot sandy driveway.There is deeded beach access directly across the road . Secluded on the pool side of the house is a tiny private beach and a private dock on Roosevelt Channel which...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 8
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    031-Fish Tales1 / 24
    (10)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Satellite TV
    • DVD Player
    • Internet Access
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 March 2017
    We rented this home to get ready for our wedding and then to stay for our honeymoon! Perfect water and sunset view. Only complaints we had was that some of the lights did not...
    Reviewed 9 January 2014
    We stayed at Fish Tales in North Captiva Island for five nights in December with a family of 8. The house was bright and spacious. It has large principal rooms and many...
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    About this property
    Rent this spacious home full of light and color with magnificent views of Captiva Pass, Cayo Costa and the Gulf.Fish Tales beckons through a colorful front entrance door to the bedroom level. To your right find the den/fourth bedroom which offers a daybed and hideaway cot. Adjacent is the third...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Waterfront
    • Washer
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The name says it all .... Hakuna Matata "No Worries". You will have "No Worries" during your stay at Hakuna Matata on Captiva Island. As you arrive up the winding drive way, you'll see the beautiful home appear just after the private heated pool. On the ground level, there is garage access and an...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    241 Surfside1 / 23
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Grill
    • Balcony
    • Air Conditioning
    • Internet Access
    • Terrace
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 July 2016
    Where to begin with this lovely vacation house.....First of all, it's a home and not just a house. This rental is beautifully decorated with vibrant colors and thoughtful...
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    About this property
    Enjoy Surfside, a lovely 3 bedroom home just steps to the beach. The home is 2000 square feet under a/c with living space on the upper floor and bedrooms on the lower level. The living space is spacious combining the kitchen, dining, a large screen porch and spacious living room. The living room...
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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