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Rentals with Pool in Captiva Island, FL

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    Travelers to Captiva Island are booking December dates now. Secure your vacation rental today, and have the perfect trip.
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    $1,800
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    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    5 of 5 stars (4) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    5 of 5 stars (14) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    9 Bedrooms / 9 Bathrooms / Sleeps 30
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    • Satellite TV
    • Ping Pong Table
    • Private Outdoor...
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    • Watersports Nearby
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    About this property
    Sea Oats Captiva Island is a Luxury Estate featuring 9 bedrooms and accommodating up to 30 guests. At almost 10,000 square feet, and on over 3 acres of waterfront property, privacy and nature abound. An ideal site for gatherings, family and corporate, one can choose to never leave the property. A... View all property information
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    Captiva Island, Southwest Gulf Coast 33924
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    5 of 5 stars (4) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • DVD Player
    • Deck
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    • Private Outdoor...
    • Washer
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    • Pet-friendly
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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... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed January 27, 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 attractions...
    5 of 5 stars Reviewed June 18, 2014
    I just wanted to thank you for making our stay on Captiva so enjoyable. We really enjoyed staying at Captiva Cottage. Captiva Cottage was the perfect size, and had everything we...
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Linens Provided
    • Parking
    • Grill
    • Children's Pool
    • Ocean Views
    • Terrace
    • Balcony
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    • Pet-friendly
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    • Child-friendly
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    About this property
    timeshare week available w/b 7 august, right on beach Amenities 2 bedroom condos with screened balconies Fully equipped kitchens Cable TV/DVD player Laundry facilities on property Air conditioning Covered parking Heated pool Tennis court Picnic areas with... View all property information
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    Captiva Island, Southwest Gulf Coast 33924
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    1 / 24
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Water Views
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Playground
    • Waterfront
    • Air Conditioning
    • Private Outdoor...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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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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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed August 4, 2013
    We returned to one of our favorite places on the planet - the Land's End Villas on Captiva Island - part of the South Seas Resort. Villa #1625 offered us spectacular views of...
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Waterfront
    • TV
    • Water Views
    • Wi-Fi
    • Air Conditioning
    • Housekeeping...
    • Ocean Views
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
    • x
    • x
    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... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
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    5 of 5 stars (55) Excellent
    4 Bedrooms / 5 Bathrooms / Sleeps 12
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    Amenities & Details
    • Satellite TV
    • Watersports Nearby
    • Waterfront
    • Hot Tub
    • Air Conditioning
    • Shared Tennis Court
    • Private Outdoor...
    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Bluefin Beach House, on North Captiva, is a luxurious 4 bedroom, 4 1/2 bath beach front home with private heated pool & spa. Completed the end of 2009. This professionally designed & decorated beach home was 3 years in the making and is situated on the preferred Gulf of Mexico side of the island.... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed November 3, 2014
    I have stayed at the Blue Fin Beach house yearly for several years now and oh what an experience. The interiors are beautiful, just out of architectural digest . The home is well...
    5 of 5 stars Reviewed June 1, 2014
    Bluefin Beach House was the perfect location for our annual "Camp MamiePapaWana" week with our children and their families. The home was clean, luxurious, and well appointed for...
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    5 of 5 stars (1) Excellent
    6 Bedrooms / 6 Bathrooms / Sleeps 24
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    Amenities & Details
    • Waterfront
    • Playground
    • Ocean Views
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Private Outdoor...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our elegant Bali Hi Estate is a three-acre property, located in the heart of Captiva Island right on the beach of the Gulf of Mexico. Lush, award winning landscaping and over 400 feet of depth from Captiva Drive make this secluded estate the perfect venue for family vacations and private events.... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed May 1, 2014
    I cannot recommend Bali Hi enough, we have been coming here for several years with our young children. They love the private playground, swimming pool and collecting sea shells on...
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    1 / 27
    4.5 of 5 stars (3) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Satellite TV
    • Washer
    • Dryer
    • Waterfront
    • Water Views
    • Stereo System
    • Air Conditioning
    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    About this property
    Our privately owned MARINA VILLA is much more beautiful and much LESS EXPENSE than the resort condos at South Seas Island Resort. Amenities can be purchased at the South Seas front desk (239) 472-7696 or 1-800-669-0508. You pick the days and how many people. Please make sure to COMPARE our rates... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed September 10, 2014
    My husband and I traveled to South Seas resort with our 2 little ones. This rental didn't offer the amenities of the resort, because of that we got a great rate, more than HALF...
    4 of 5 stars Reviewed September 13, 2013
    We stayed at The Marina Villas, went with young kids as well as the grandparents, everyone had a wonderful time. The villas have a small private pool, which was great when the...
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    4.5 of 5 stars (17) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Shared Outdoor Pool...
    • Hot Tub
    • Dryer
    • Internet Access
    • Washer
    • Satellite TV
    • Air Conditioning
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed July 7, 2014
    I had the pleasure of staying at Rockstar for the July 4th weekend. The most impressive part(s) for me was the overall cleanliness of the home, the amazing beaches, and wildlife...
    4 of 5 stars Reviewed April 17, 2014
    My family really enjoyed our stay at the Rockstar Beach House. A few minor snags with lining things up, but the stay was perfect. The house was clean and comfortable with...
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    5 of 5 stars (11) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Reviews (11) Make Inquiry
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    • Private Outdoor...
    • Stereo System
    • Hot Tub
    • DVD Player
    • Water Views
    • Internet Access
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    You'll Be Captivated! This Old Florida style Captiva Island rental will captivate you! A fantastic Captiva Island rental that is just a short stroll from Captiva's beautiful white sand beach and offers the ambiance of a true island paradise! Be Captivated is a spacious Florida beach home... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
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    1 / 25
    5 of 5 stars (52) Excellent
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Reviews (52) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Private Outdoor...
    • Stereo System
    • Water Views
    • Hot Tub
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed March 19, 2015
    This is a great rental house. It has absolutely everything you need for a super time on North Captiva. This was our third stay here and we are already reserved for next year. The...
    5 of 5 stars Reviewed February 2, 2015
    Amazing home with everything you will need to truely getaway. We couldn't be more happy with our stay at Los Olas. The owners are wonderful, and we hope to get a chance to go back...
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    $1,995
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    1 / 33
    5 of 5 stars (35) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • TV
    • Washer
    • Stereo System
    • Air Conditioning
    • DVD Player
    • Private Outdoor...
    • Wi-Fi
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed November 27, 2014
    Just back from a week at the Mermaid House. This was the 2nd time we rented from Larry. The first being April 2013, we rented the Sun & Moon House. The Mermaid House was great for...
    5 of 5 stars Reviewed November 3, 2014
    My husband and I loved our stay at the Mermaid House. The house is extremely clean and very well stocked with everything you could possibly need during your stay. The private...
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    1 / 21
    5 of 5 stars (11) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (11) Make Inquiry
    Amenities & Details
    • Water Views
    • DVD Player
    • Washer
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    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 heated... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed April 5, 2015
    We had excellent service. Marie sent us a comprehensive welcome packet that provided all the guidance we needed to prepare for the trip. The rental property was perfect for our...
    4 of 5 stars Reviewed March 2, 2015
    My husband and I joined our friends and their toddler for a weekend in The Little Oasis on North Captiva Island. The house was perfect for two couples. The layout was private...
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    5 of 5 stars (26) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (26) Make Inquiry
    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Stereo System
    • Private Outdoor...
    • Washer
    • Air Conditioning
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Experience the laid back Captiva Island lifestyle in this beautifully decorated Key West inspired 3 bedroom and 3 bath beach home on the beachside of Captiva's village center. It's located on very popular Wightman Lane, a short, 3 minute stroll on our private, sandy lane to the beach. Captiva's... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed July 10, 2015
    We've stayed on Captiva many times and this was one of our favorite houses. The house looks brand new and is well maintained. It is stocked with everything you would need...
    5 of 5 stars Reviewed April 4, 2015
    We had the best week at the Sun and Moon over thanksgiving. Two adults and our 2 girls loved every minute. The house was perfect. Close to everything. We never used our car the...
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    1 / 15
    5 of 5 stars (7) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (7) Make Inquiry
    Amenities & Details
    • Shared Tennis Court
    • Internet Access
    • Air Conditioning
    • Water Views
    • DVD Player
    • Satellite TV
    • Deck
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Only a one block walk to Captiva Village shops and restaurants, this property is in top condition and equipped with everything you need to enjoy a romantic or family vacation to the fullest. You do not need to pack beach towels (7 are provided), nor do you even need to buy aluminum foil or ZipLock... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed August 17, 2014
    We loved our stay at #48. It had everything we could ever need for our family of five (5 yr-11yr olds) and it was a perfect location to the town center of Captiva, pool, beach...
    5 of 5 stars Reviewed December 13, 2011
    My family has been blessed with three different stays with Sunset Captiva 48. We are a middle aged hard working couple with two small children...but when we are on Captiva it is...
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    4.5 of 5 stars (3) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Waterfront
    • Washer
    • Internet Access
    • Children's Pool
    • Stereo System
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Marvel at the stunning views of the Gulf from this beautiful newly (2014) renovated three bedroom, two and one half bath Townhome. Walk into the expanded living room enclosed with floor to ceiling windows overlooking the Gulf of Mexico providing very wide ocean/sunset views. Open the sliders to... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed May 13, 2015
    We have stayed here twice, both for spring break. The location of the rental is pretty perfect: across the street from a beautiful beach, within a short driving distance to fun...
    4 of 5 stars Reviewed April 3, 2015
    We were very pleased with the unit. Excellent setup for two couples and a couple of kids, and well appointed. We particularly appreciated all of the beach gear that came with the...
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    5 of 5 stars (12) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (12) Make Inquiry
    Amenities & Details
    • Hot Tub
    • Waterfront
    • Water Views
    • Private Fishing...
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Beach Villa Sunset Dreams is a richly remodeled and appointed townhome with tropical beach décor for an unforgettable family vacation. The Villa is unique with awe inspiring direct gulf views and sensational sunsets, as well as sunrise views over the bay. The property is only 30 steps to the beach... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 01450
    5 of 5 stars Reviewed March 24, 2015
    The decor was fresh and newly done. Wonderful colours and attention to detail. Kitchen well supplied and dishes matched decor. Bedrooms clean, pretty and comfortable. Sunsets...
    5 of 5 stars Reviewed January 26, 2015
    This was our second stay at Sunset Dreams, and we love it. The owner has equipped this house with everything you need for a few days or a few weeks. We've stayed many places on...
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    1 / 18
    5 of 5 stars (4) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • Deck
    • Washer
    • DVD Player
    • Shared Outdoor Pool...
    • Air Conditioning
    • Satellite TV
    • Stereo System
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
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    1 / 28
    5 of 5 stars (10) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Reviews (10) Make Inquiry
    Amenities & Details
    • Water Views
    • DVD Player
    • Shared Tennis Court
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Exotic and lavish furnishings from faraway places await you at this professionally-decorated and landscaped luxury home located just off the beach. Pamper yourself with the finest amenities in this 4000 sq. ft. (2500 under air), 3 bedroom dream beach house spread out over 5 levels. You can indulge... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed July 8, 2015
    Our vacation stay at the Compass Rose was awesome! We loved everything about it! The beach and water views from the decks are beautiful. The furnishings in the house are better...
    5 of 5 stars Reviewed July 7, 2015
    Once again, the Compass Rose exceeded expectations – and that’s saying something because this was our second stay at the Compass Rose. The first is summarized in my June 25, 2014...
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    1 / 20
    5 of 5 stars (7) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (7) Make Inquiry
    Amenities & Details
    • Private Outdoor...
    • Water Views
    • DVD Player
    • Watersports Nearby
    • Satellite TV
    • Stereo System
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Millertime Villa is a relaxing home with a lovely private pool, lots of amenities and a perfect location on beatiful Captiva Island. This is our tenth year renting our home with the goal of providing memorable Captiva Island vacations. With 3 bedrooms and 2 full baths, this home comfortably... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed January 26, 2015
    The house is extremely comfortable and welcoming. We made great use of the pool and adjoining screened porch. All three generations of our family were able to feel right at home...
    5 of 5 stars Reviewed October 16, 2014
    We travel to Captiva every year to relax, and Miller Time is the perfect vacation rental. It is well kept, very clean, close to the amazing beach, on a quiet street, walking...
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    5 of 5 stars (11) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveler have booked this property
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    Amenities & Details
    • Watersports Nearby
    • Private Outdoor...
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • DVD Player
    • Water Views
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    THE LITTLE ARK The vacation of a lifetime is awaiting those who are will to journey to paradise and beyond. The pace of the island is slow and relaxing, a great romantic getaway for couples or a chance to spend quality time with your family with memories that will last a lifetime. This... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed July 1, 2015
    Just completed a week stay at The Little Ark and could not have had a better time. The house was great. Had everything we needed and having the pool right at the bottom of the...
    5 of 5 stars Reviewed March 9, 2015
    We have previously stayed on Sanibel and Captiva but decided to venture out of our comfort zone to North Captiva. We stayed for a long weekend and wish we would have stayed...
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    $2,600
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    1 / 10
    5 of 5 stars (1) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Private Outdoor...
    • Hot Tub
    • Satellite TV
    • Waterfront
    • DVD Player
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Welcome to Grande Casa, a private estate situated on Captiva Island, Florida. Enjoy the mild gulf breeze while sipping cold drinks in our open floor plan, island style house. This home is situated privately on a manicured lot overlooking the bay, on the Gulf of Mexico. Sunny days can be spent... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    From
    $4,550
    / Week
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    1 / 53
    5 of 5 stars (17) Excellent
    5 Bedrooms / 2 Bathrooms / Sleeps 12
    Overview Reviews (17) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Private Outdoor...
    • Watersports Nearby
    • DVD Player
    • Hot Tub
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed May 29, 2014
    Where do I begin! Thank you, Thank you, Thank you to a wonderful place of peace, tranquility, relaxation, and adventure to celebrate the renewing of my parents Wedding vows of 50...
    5 of 5 stars Reviewed April 13, 2014
    This was our fourth visit to North Captiva and our first to Windswept. It was the perfect house for our group of 8: 6 adults and 2 teens. We found the opportunity to stay in such...
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    $2,600
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    4.5 of 5 stars (3) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Ocean Views
    • Air Conditioning
    • Watersports Nearby
    • Private Outdoor...
    • Private Fishing...
    • Wi-Fi
    • Water Views
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Welcome to Grande Casa, a private estate situated on Captiva Island, Florida. Enjoy the mild gulf breeze while sipping cold drinks in our open floor-plan, island style house. This home is situated privately on a manicured lot overlooking the bay, on the Gulf of Mexico. Sunny days can be spent... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed January 14, 2015
    We loved this home. It was lovely being on the Bayfront and watching all the boats and wildlife. We saw manatees and dolphins right off the dock almost each day. The beach is a...
    4 of 5 stars Reviewed January 19, 2013
    My husband and I rented this home the week after Thanksgiving for a quiet, much needed vacation. Overall, this home was everything as described and the photos were an accurate...
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    $1,000
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    5 of 5 stars (2) Excellent
    6 Bedrooms / 6 Bathrooms / Sleeps 14
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • DVD Player
    • Private Outdoor...
    • Internet Access
    • Washer
    • Dryer
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Incredible newly built Mediterranean style home located in the Heart of the Village on Andy Rosse Lane. Bella Bellini is a professionally Robb & Stuckey decorated, luxurious 6 bedroom/6.5 bathroom private home with a quiet, secluded heated pool and spa. A courtyard style design located on a... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed March 13, 2015
    We just returned from a week at Bella Bellini and it was the perfect place for 4 couples and 22, & 24 year old grandchildren. The golf carts we rented were perfect to tool around...
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    $400
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    1 / 27
    4.5 of 5 stars (5) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Shared Tennis Court
    • Water Views
    • Stereo System
    • Satellite TV
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Come enjoy our spacious 4 bedroom, 3 bath luxury beach home, on a very private island! It will be a completely unique experience, and 'Shore to Please'! North Captiva Island presents guests with the ultimate in private island experiences. The island is located 5 miles off the coast of Florida and... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    2 of 5 stars Reviewed August 4, 2013
    We stayed in different home three years ago and decided to return but wanted to stay in a different home this time.We chose this one and we were less than pleased after the first...
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    $5,600
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    5 Bedrooms / 8 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Water Views
    • Air Conditioning
    • Waterfront
    • Private Outdoor...
    • Wi-Fi
    • Satellite TV
    • Ping Pong Table
    • Ocean Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    From
    $450
    / Night
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    1 / 26
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Water Views
    • DVD Player
    • Boat Available
    • Internet Access
    • Satellite TV
    • Stereo System
    • Deck
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    From
    $1,139
    / Night
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    1 / 49
    4 Bedrooms / 6 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Private Outdoor...
    • Water Views
    • Stereo System
    • Grill
    • Hot Tub
    • Balcony
    • DVD Player
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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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    Location Information
    Captiva Island, Southwest Gulf Coast
    From
    $1,575
    / Week
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    1 / 18
    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Water Views
    • DVD Player
    • Shared Tennis Court
    • TV
    • Stereo System
    • Watersports Nearby
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This is is a great beach vacation home 75 steps from beach, tennis and pool, a short walk to restaurants and shopping. It has 2 bedrooms, 2.5 baths, and beautiful views. Spend the day at the beach, watch a memorable sunset, and dine overlooking the Gulf. Enjoy the best possible location on... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed February 24, 2013
    We have enjoyed two visits to #10 Sunset Captiva and thoroughly enjoyed both trips. Perfect location offers a private road, reserved parking and easy acces to both beach and...
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    $1,960
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    1 / 24
    4 of 5 stars (1) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool...
    • Water Views
    • Patio
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Gym
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    4 of 5 stars Reviewed January 8, 2015
    Location is great and the food was even better. The rooms are nice but a little dated but you won't want to be in the room anyway.
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    $700
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    1 / 52
    4 of 5 stars (1) Very good
    5 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Waterfront
    • DVD Player
    • Water Views
    • Private Outdoor...
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    4 of 5 stars Reviewed June 21, 2015
    Beautiful house and location but the pool water was cloudy and full of sand. It appears it was not cleaned in months. I will definitely stay again but will call ahead to make sure...
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    $4,480
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    1 / 14
    5 of 5 stars (1) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Water Views
    • Private Outdoor...
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Deck
    • Boat Available
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    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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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    From
    $771
    / Night
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    1 / 49
    5 of 5 stars (11) Excellent
    4 Bedrooms / 5 Bathrooms / Sleeps 8
    Overview Reviews (11) Make Inquiry
    Amenities & Details
    • Grill
    • Patio
    • Refrigerator
    • Air Conditioning
    • Internet Access
    • Washer
    • Gym
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Inquire about our JUNE SPECIAL!! New , new , new !! Fish in your back yard off the dock, Play in your private heated pool, Entertain on your cabana / pool deck, Watch sun rises, and sun sets from your observation deck or find your private nook away from it all. There are four bedrooms including... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed June 28, 2015
    As SWFL residents, our family of four makes frequent visits to N. Cap. This was our first stay at Rum Cove, but it won't be our last. The house and property are well-kept and...
    5 of 5 stars Reviewed May 27, 2014
    Location, location, location! We have stayed on North Captiva Island for over 15 years and this is one of the few rental locations with private boat dockage. Even with the...
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    $1,925
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    5 of 5 stars (2) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Stereo System
    • Water Views
    • Hot Tub
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This stunning multi-level, multi-deck home is located just yards from the pristine North Captiva beaches of the Gulf of Mexico. This island beach rental is designed with comfort and luxury in mind, and with the utmost attention to capturing the beauty of the creation all around. Enjoy the Crews... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    5 of 5 stars Reviewed June 12, 2011
    We just returned from 7 days on North Captiva, and we are still talking about what a great time we had. If I had to summarize our week, I would say that it was just a week of...
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    $600
    / Night
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    1 / 14
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Waterfront
    • Hot Tub
    • Water Views
    • Stereo System
    • Internet Access
    • Air Conditioning
    • Private Outdoor...
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    From
    $286
    / Night
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    1 / 24
    5 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Private Outdoor...
    • Satellite TV
    • Air Conditioning
    • Stereo System
    • Internet Access
    • Hot Tub
    • DVD Player
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    From
    $514
    / Night
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    1 / 16
    5 Bedrooms / 5 Bathrooms / Sleeps 14
    Overview Make Inquiry
    Amenities & Details
    • Water Views
    • Deck
    • Private Outdoor...
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Location Information
    Captiva Island, Southwest Gulf Coast 33924
    From
    $514
    / Night
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    1 / 21
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Private Outdoor...
    • Washer
    • DVD Player
    • Satellite TV
    • Deck
    • Air Conditioning
    • Water Views
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Location Information
    Captiva Island, Southwest Gulf Coast
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    1 / 22
    5 Bedrooms / 6 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Watersports Nearby
    • Air Conditioning
    • Wi-Fi
    • Stereo System
    • DVD Player
    • Satellite TV
    • Private Outdoor...
    • Private Fishing...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This unique luxury 5300 sq.ft. home 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 leads you on the left to... View all property information
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    Location Information
    Captiva Island, Southwest Gulf Coast 33924