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Holiday Rentals with Pools in North Captiva Island

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    Travellers to North Captiva Island are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    22 Matching Rentals in North Captiva IslandView all 33 rentals
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    North Captiva Hidden Beach House with Private Pool 1 Night free July 13-201 / 18
    (8)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    'SEA URCHINS' *****Brand New Beachfront with Beachside Pool & Private Boat Dock1 / 22
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Luxury House 50 yds from beach! Pool, spa, outdoor games area, bikes and kayaks1 / 32
    (21)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Manatee Haven: Upscale Beach View Home with Screened-in Pool, Spa & Elevator!1 / 63
    (16)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Hot Tub
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 February 2017
    North Captiva island is isolated from the mainland and must be reached by boat (unless you can pilot a small plane capable of operating off a grass runway.) There are only a few...
    Reviewed 1 December 2015
    My husband, our four children and I recently stayed a week on North Captiva Island over Thanksgiving week.The island is pretty isolated. You have to take a boat/charter to get...
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    About this property
    Located on the barrier island of North Captiva Island, Manatee Haven is an upscale, non-smoking, beach-view home that offers four bedrooms and three and a half bathrooms with an elevator to all three levels. It is professionally decorated, has a swimming pool and hot tub located in a 3,200 sq. feet...
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    Location Information
    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    NORTH CAPTIVA ISLAND BEACH COTTAGE, BEACH 300FT, POOL,HOT TUB,ROOFTOP GULF VIEWS1 / 50
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Children's Pool
    • Air Conditioning
    • DVD Player
    • Ocean Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 February 2019
    We drove around the island exploring in our golf cart provided for us with our rental and we were convinced The Little Oasis Beach Cottage is the best location on North Captiva...
    Reviewed 26 February 2019
    The owners were excellent to deal with. Very helpful and extremely responsive, which is a valuable thing when you are booking an unknown property online. Check in was easy. The...
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    About this property
    Our calendar is updated in real-time & our competitive rates are accurately displayed. Simply enter your desired dates and click Book Now! ALL bookings are honored INSTANT BOOK TODAY. 2PM EARLY CHECK IN. Home's Open Layout flaunts high ceilings with wood beams & plenty of natural light.2 MASTER...
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    Location Information
    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Ka Hale Kai (The Beach House)1 / 19
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Terrace
    • Private Garden
    • Ocean Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 November 2017
    This house was great. We heard that it had just been acquired by new owners when we arrived (which is good for everything except that I noticed the rental price jumped...
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    About this property
    Escape to a remote tropical island paradise with all the luxuries of home including a large heated private pool,with spacious pool deck. The best views are from the top level observation room with exterior deck that overlooks the Gulf and extraordinary sunsets. This room, with a full bed, also...
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    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Ocean Views
    • Waterfront
    • Patio
    • Washer
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BATMAN's Harbor Hideaway is surrounded by tall Arecas and Mangroves. The views of the harbor from the back lanai and upstairs private screened porch as well as upper crows nest are amazing ! Master bedroom is upstairs with king bed, bathroom with shower, and lounge chairs in screened area with...
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    Location Information
    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Large Island Home w/ Heated Pool Private Beach Access & Tropical Beach Bar/Grill1 / 39
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Washer
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Hot Tub
    • Cable/satellite TV
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 August 2019
    We had the best vacation at Sundancer Beach Retreat! Perfect for our group of 8, tons of space to spread out and our own private beach access! There was so much balcony space on...
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    About this property
    4 Bdrm / 3 Full Bath Tropical Island Retreat with private direct beach access! Brand New Rental, Newly Renovated and Available Now! We are located on the northern tip of North Captiva Island, with tons of privacy away from the crowds! Just a few steps from a pristine white sandy beach overlooking...
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    Location Information
    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Patio
    • Balcony
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is not a rental house we only have 5 guests each year. It is a custom built home located on the preserve and the gulf of mexico. It features a chefs kitchen, elevator, raised golf cart, three wet bars, family rooms on both floors, two laundry centers, beach chairs and umbrella, a grill in the...
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    Location Information
    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Balcony
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blue Macaw is a lovely 3 bedroom home just a block from the beach. The home was recently renovated and refurnished like a new home. This upside down model home has the living area on the second floor to take advantage of lovely nature views. The house is hammocked in in green tropical foliage and...
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    Location Information
    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the Castaway Key subdivision on the island, this charming cottage has everything you need to relax and escape to paradise. Completely renovated with beautiful furnishing and a tropical pool and dining area. This home has a private beach access at the end of Schooner Drive. Each suite...
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    Location Information
    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 6
    Gorgeous Safety Harbor Townhouse with Golf Cart1 / 21
    (1)Terrible
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
    • Patio
    • Grill
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our home, a 3 BR 2 BA townhouse located within Safety Harbor Club on North Captiva Island. Safety Harbor Club is a homeowners association with amenities that include docking, tennis courts, a heated pool, clubhouse, minutes from the beach, and a restaurant. Our unique island is...
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    Location Information
    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful Beach House in a secluded private island1 / 19
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Washer
    • Housekeeping Included
    • Hot Tub
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 July 2016
    Thank you for a wonderful week staying in Viva La Playa. The beds were very comfortable along with the living room furniture and dining area. It is very open and spacious and...
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    About this property
    Located in the exclusive southwest Florida island of North Captiva, just offshore in the Gulf of Mexico. Accessible only by ferry, water taxis or private plane, Viva La Playa is a private getaway without leaving behind the comforts of home. Here, you will find no cars, no crowds nor paved roads....
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    Location Information
    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    043 - Toes In The Sand1 / 36
    (10)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    • Grill
    • Private Outdoor Pool (Heated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2019
    Our vacation was amazing! The house was perfect we couldnt have asked for anything better! Everyone on the island was very nice and helpful.
    Reviewed 31 December 2018
    We just spent an amazing week at Toes in the Sand. The house is beautifully decorated and very comfortable. The owners thought of everything, including a beautiful Christmas...
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    About this property
    Toes In The Sand is a lovely spacious 3 bedroom, 3 bath pool home that has been beautifully designed and furnished by an interior designer. Enjoy 5 screened in porches/decks and over 1500 sq. ft. of outdoor living space. The spacious, well equipped kitchen has a breakfast bar and dining table that...
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    Location Information
    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our townhome in Safety Harbor Club on North Captiva Island! Enjoy a true island vacation at this incredible 3 bedroom, 2 bath townhouse. Accessible only by boat or private plane, North Captiva Island is a premier Southwest Florida beach vacation destination. Renting this Safety Harbor...
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    Location Information
    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    149-Junonia1 / 44
    (11)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 June 2015
    I was initially very anxious scheduling this beach vacation for my growing family. With three children under 5, being on a fairly undeveloped island for the better part of the...
    Reviewed 20 October 2014
    The house was very clean and spacious. We traveled with teenagers and Grandmom and everyone loved it! All of the staff were very friendly and helpful. We enjoyed the...
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    About this property
    Walking distance to the beach. 3 Bedroom 3 Bath. Totally relax in this spacious 3 bedroom home just walking distance to the beach. Beautiful hardwood and tile floors throughout this beach house. Granite counter tops and stainless appliances in the kitchen and a whirlpool tub in the master...
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    Location Information
    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Internet Access
    • Waterfront
    • Balcony
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to The Minnow. This old Florida classic three bedroom home sits directly on the Gulf of Mexico with an expansive private beach and one of the best views on the island. The Minnow is an eco- friendly home. Solar Panels on the roof harness radiant light and heat from the sun and convert it...
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    Location Information
    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Parking
    • Air Conditioning
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    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Old Floridian style sweet and comfortable cottage with mature tropical landscape , 2 minute walk to pristine beach . Cottage has all modern amenities and is filled with natural light Golf cart provided Guest membership in North Captiva Island Club including 2 pools, pool bar, kayaks and bikes...
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    Location Information
    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Wi-Fi
    • Ocean Views
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Captiva Isles on North Captiva Island Book now for best pricing for Summer 2019! Your search for the PERFECT beach vacation house is over with your search for 'Captiva Isles on North Captiva Island, FL'. We look forward to seeing your Face when you decide to Book with us and arrive at our island...
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    Location Information
    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Ocean Views
    • Housekeeping Included
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Not to be missed island gem with new owners! Enjoy Champagne welcome upon arrival at our spacious 4 Bedroom Private Pool Home, which includes North Captiva Island Club Resort Amenities, & 2 Golf Carts, just 400 feet from the beach! Located on the pristine island of North Captiva, 'La Casa Del...
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    Location Information
    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Washer
    • Ocean Views
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Havana Breeze on North Captiva Island Book now for best pricing for Summer 2019 Your search for the PERFECT beach vacation house is over with your search for 'Havana Breeze on North Captiva Island, FL'. We look forward to seeing your Face when you decide to Book with us and arrive at our island...
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    Location Information
    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
    040-Beach House Too1 / 25
    (13)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • DVD Player
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2019
    We had two families with 8 total people - 4 adults and 4 kids ranging from 2 to 15. The house had plenty of space for everyone. There was common space that was large enough to...
    Reviewed 26 March 2016
    Our family has been renting homes on North Captiva Island tow to three times per year for the past 16 year and this is, by far, our favorite island rental home. There is...
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    About this property
    Professionally designed and decorated four bedroom, four and one-half bath home steps from the beach with panoramic water views of both the gulf and the bay, swimming pool and kids’ pool, fantastic sunrises and sunsets. Two golf carts included. As a member of the marina club bring your boat and get...
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    Location Information
    North Captiva Island, Southwest Gulf Coast 33924
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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