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Holiday Rentals in Captiva Island, FL

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    85 Holiday Rentals in Captiva Island
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    $770
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    Overview Reviews (11)
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    $9,750
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    1 / 39
    5 of 5 stars (6) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    $522
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    5 of 5 stars (6) Excellent
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    5 of 5 stars (3) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (3)
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    About this property
    Gorgeous 3 bedroom North Captiva Island home newly decorated, with Gulf view, private pool and a bar making this one of, if not the best home on the Island for entertaining guests. Extra 1/2 bath next to the pool. Starting at the top floor is a Master bedroom suite with a nice sitting area with... View all property information
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    5 of 5 stars (20) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    Overview Reviews (20)
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    • Air Conditioning
    • Balcony
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    • Satellite TV
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    About this property
    Utopia best describes the experience you will feel when you stay at the CINCO DE MAYO beach house. Rest, relaxation and a sense of home will be yours while you enjoy your stay. The Fifth of May is when we found our paradise and thus the name of our home. CINCO DE MAYO is located conveniently... View all property information
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    $439
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    Overview Reviews (17)
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    About this property
    This beautiful island bungelow is the total beach getaway vacation home you have been looking for! With its two luxury bedrooms, two full bathrooms and a queen sleeper sofa, you can comfortably sleep six. The polynesian flair (including a 400 lb solid mahogany tiki head), musical influences and... View all property information
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    $915
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    Overview Reviews (1)
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    • Gym
    • Internet Access
    • Satellite TV
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    • Smoking allowed
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    About this property
    Sea Glass is a spectacular new 4 bedroom North Captiva home with fantastic views of both the Gulf and State Wildlife Preserve. With a short stroll to the beach, about 120 yards, this home is decorated with a Caribbean flair like few others on North Captiva. Two Master Suites and two additional... View all property information
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    $659
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    1 / 21
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Private Outdoor...
    • Satellite TV
    • Washer
    • Water Views
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    About this property
    Serendipity means a 'fortuitous happenstance' or 'pleasant surprise'. It was first coined by Horace Walpole in 1754. In a letter he wrote to a friend Walpole explained an unexpected discovery he had made by reference to a Persian fairy tale, The Three Princes of Serendip. The princes, he told his... View all property information
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    1 / 14
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
    Overview Reviews (1)
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    • Dishwasher
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    About this property
    Luxury living at its best! 4 bedrooms, two living rooms, game room, swimming pool and jacuzzi, snook lights, lovely decks with breathtaking views, and private dock! Solitude is an amazing home with over 3500 square feet of living space and over 5500 square feet of total living. This home is... View all property information
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    $715
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    Overview Reviews (2)
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Wheelchair access
    • Elder access
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    About this property
    Serendipity means a 'fortuitous happenstance' or 'pleasant surprise'. It was first coined by Horace Walpole in 1754. In a letter he wrote to a friend Walpole explained an unexpected discovery he had made by reference to a Persian fairy tale, The Three Princes of Serendip. The princes, he told his... View all property information
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    $1,276
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    Overview Reviews (3)
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    • Satellite TV
    • Washer
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    • Smoking allowed
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    About this property
    Green Flash North Captiva Island is over 2400 square feet of living space under a/c along with 350 square feet of open deck off the top living level and 350 square feet of screen porch area. This designer beach home has outstanding views of the Gulf of Mexico. This is the only home with 180 degree... View all property information
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    $879
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    1 / 42
    5 of 5 stars (2) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
    Overview Reviews (2)
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    About this property
    Large 5 bedroom North Captiva house, literally surrounded by decks. Provides breathtaking views of the Gulf and bay. Rum Point is the perfect home for family vacations. There is plenty of room inside and out. Outside the home is surrounded on 4 floors by decks and has a spacious deck around the... View all property information
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    $5,658
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    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    About this property
    Beautiful vegetation and a variety of single family homes distinguish this subdivision. Easy walk to the beach and a observation tower is available for wildlife viewing. This 3 bedroom 3 bath home with heated pool and wireless internet is just the place for you to enjoy what Sanibel Island is... View all property information
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    $641
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    1 / 33
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
    Overview Reviews (1)
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    • Balcony
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    • Internet Access
    • Satellite TV
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    About this property
    4 BR/5 BA – CAPTIVATION- Relax above the coconut palms. Secluded Preserve home with Ocean to Gulf Views – Screened Pool and Bar/Gaming Area - Resort Privileges, Two golf carts:Remodeled Luxury 4 BR/5 BA – Close to beach, Island Club and Preserve, yet a private, quiet hideaway! Enjoy your Upper... View all property information
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    $507
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    Overview Reviews (1)
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    • Pets allowed
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    • x
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    About this property
    Exquisite time share last two weeks of January. Best location on the resort. Breathtaking Gulf view over golf course, beach 150 feet from bedroom window. Beautiful amenities, pool. hot tub. Our family bought (first choice) timeshares when first built...free golf and tennis 'grandfathered... View all property information
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    $2,514
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    1 / 24
    4 of 5 stars (1) Very good
    Overview Reviews (1)
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    • Balcony
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    • Shared Outdoor Pool...
    • Water Views
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    About this property
    FULL RESORT PRIVILEGES!!!!! Come relax for a week at the islands' only World Class Resort!!! This 2bd/2ba condo has full resort privileges at the luxurious South Seas Island Resort on breathtaking Captiva Island Florida. It has a lovely private pool and hot tub and includes complimentary green fees... View all property information
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    $539
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    Overview Reviews (1)
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    • Air Conditioning
    • Balcony
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    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
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    About this property
    A perfect family vacation with AMENITY ACCESS provided to all resort facilities. Voted #1 of family beach resorts by Parents' Magazine. The resort is on a 330 acre wildlife preserve,maintained as a botanical garden. with a two and a half mile pristine beach Children's water park, H2Whoa, with... View all property information
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    $275
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    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Satellite TV
    • Washer
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    About this property
    The Lazy Lizard is a beautiful and comfortable 3 bedroom, 2 bath private and secluded home nestled in the palm trees on the unique North Captiva Island - just a 500 foot stroll to the pristine beach. The Lazy Lizard is a secluded and romantic home-away-from home located on an island with its... View all property information
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    $1,274
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    1 / 56
    5 of 5 stars (13) Excellent
    Overview Reviews (13)
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    • Air Conditioning
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    About this property
    North Captiva Island dream vacation home with 5 bedrooms, accepting up to 12 guests per rental. Huge private heated pool and large private sun-decks offer the best of both worlds. Just a short walk from the neighborhood's beach and located right at the start of the preserve beach trail, leading to... View all property information
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    $2,559
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    Overview Reviews (35)
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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... View all property information
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    $834
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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... View all property information
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    1 / 24
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Air Conditioning
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    • Grill
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    About this property
    Please Note: Our home is only booked through Royal Shell Property Management on Captiva Island. All payments are made to Royal Shell Property Management. Please be aware that there are multiple internet fishing / email hacking scams that attempt to convince consumers to wire funds offshore. Our... View all property information
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    1 / 25
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    About this property
    Driving up to The Silver Seashell, you will be impressed with the lovely landscaped grounds and the architectural flare. Tucked away are the 28-foot private pool and spa, surrounded by beautiful composite decking – no nails, no screws, no slivers. Enter the front door to find The Silver Seashell... View all property information
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    About this property
    The Turtle Nest is a lovely family friendly home nestled high amongst the tree tops on tranquil North Captiva Island, Florida. This island style home features direct access to the unspoiled beaches of the island and the Gulf of Mexico. The island is accessible only by ferry or private plane. There... View all property information
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    1 / 9
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Situated in the Ibis at the Sanctuary community in beautiful Sanibel Island with views of the 8th fairway at the Sanctuary Golf Club, this third-floor condo is the perfect island getaway! The luxury 2-bedroom, 2-bathroom condo has a master suite, bedroom with a Murphy bed, living area with a 42”... View all property information
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    $1,282
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    1 / 37
    4 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Escape to your own private oceanfront paradise in this 4-bedroom, 5.5-bathroom Captiva Island vacation home named “Beach Destiny.” Just 20 feet via a private path to Captiva Island’s beach famous for its shells, this vacation home is located two houses down from the Mucky Duck restaurant and Andy... View all property information
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    *Brand-new home! New to the All Star Program!* Experience unique touches of luxury in this gorgeous Captiva Island vacation home named “Seaesta.” Situated just a short walk from the beach in the Captiva Village area, this home is nestled close to restaurants, shops, art galleries and more! This... View all property information
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    About this property
    You'll be Captiva-ted by these deluxe villas in Paradise! Options include 2, 3 and 4 bedroom private pool homes, or beach front condos that sleep from 1-10 guests. ~ CAPTIVA BREEZE (4 BR & 4 bath, sleeps 2-10: 2 king, 4 twin, trundle) is our luxury, spacious Old Florida style home. It has a... View all property information
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    About this property
    Location, location, location….this newly constructed eco-friendly beach house has it all. It is situated on one of the best gulf front locations on North Captiva featuring some of the widest beach areas on the island. The breathtaking views from this island gem are jaw dropping and will take your... View all property information
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    $1,153
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Pets allowed
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    About this property
    Enjoy a vacation in paradise just 176 yards from the pristine beach of beautiful Captiva Island! Situated on Andy Rosse Lane among local hot spots for dining, like the famous Mucky Duck, and shopping, this 5-bedroom, 5.5-bathroom Captiva Island vacation home named 'L’atitudes' features 4 king... View all property information
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    A perfect beach house with amazing Gulf-to-Bay views and a private pool! Completely Renovated 2012 – complete with sunset view deck and tiki bar at the pool! Unlike many of the homes on North Captiva Island, a stay at The Conch House will truly let you experience the real beach retreat you... View all property information
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    $898
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    About this property
    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... View all property information
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    $1,461
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    1 / 49
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
    • Fireplace
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    • Water Views
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    About this property
    Experience the beauty of Captiva Island during your vacation with your own private direct bayfront vacation estate. This fabulous, one-of-a-kind mini estate vacation home named “Island Lure,” located in the lovely Captiva Village area, has Gulf access dockage, a private pool with views of the water... View all property information
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