Captiva Island Vacation Rentals

Captiva Island is a beautiful island in southwest Florida, nestled right beside the Gulf of Mexico. Accommodation in Captiva Island is luxurious, with lodging ranging from condo rentals and vacation rentals to fully furnished vacation rental homes. Captiva Island is fabled to have gained its name from once being a hot-spot for pirates and conquistadors. The island itself consists of stunning white sand beaches, vibrant blue oceans, and famous sunsets.

Those planning to travel to Captiva Island should be sure to visit Turner Beach --- a quaint beach best known for its highly acclaimed fishing, as well as the ideal spot to find rare and beautiful seashells. Captiva Island is in fact known for its fishing, and is one of the top fishing spots in the country. For those seeking accommodations nearer to the sandy beach, condo rentals and vacation rental homes are highly suggested. For those seeking accommodation closer to the hub of the island, a condo rental is a still a viable option; though, a vacation rental home is considered ideal.

Captiva Island is most renowned for its water activities. From fishing, boating, kayaking and water skiing, to swimming with dolphins and collecting seashells on the sandy beach, Captiva Island has it all. Captiva Island also has a nice central hub which is home to quaint shops and restaurants selling a variety of items and souvenirs.

Accommodations in Captiva Island can be expensive, however, with Owner Directs Last Minute Deals, you may find vacation rentals or other accommodations at a significantly discounted price!

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Captiva Island Vacation Activities

11 Vacation Rentals

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  • Beautifully Renovated Home in

    Beautifully Renovated Home

    Captiva Island: Vacation Rental
    • 5 BDR
    • 5 BA
    • Sleeps 14
    • #232296
    Credit Card Pet Friendly
    Beautifully renovated home in Captiva's Village area with private pool just a short walk to the beach. Stay a week or longer at Tarpon Tales on beautiful Captiva Island, Florida. This four bedroom/four bathroom home has been nicely renovated by the owners and offers a great location in the heart of Captiva's Village area. The master bedroom has a very comfortable king sized bed with en-suite bathroom. The guest bedrooms have a king bed in one with the other two guest bedrooms having queen beds. Step outside onto the expansive deck overlooking the courtyard style heated pool. The entire area is screened in for your maximum enjoyment and comfort. Tarpon Tales also features a separate lower level suite that is only accessible from the outside with a seating area, queen bed and two twin beds, bar and bathroom. It's the perfect spot to lounge while spending the afternoon by the pool. Also included for your stay is free high speed wireless internet, gas bbq grill, beach towels and at least two beach chairs and a beach umbrella.
  • Direct Gulf Front Two

    Direct Gulf Front Two

    Captiva Island: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 6
    • #232291
    Credit Card
    Direct gulf front two bedroom with loft villa located in Captiva Island at the South Seas Island Resort. Experience all that Captiva Island and Southwest Florida's Gulf Coast has to offer at South Seas Beach Villa 2126. This two bedroom/two bathroom with loft direct gulf front condominium has been recently renovated and offers wonderful gulf views from the screened lanai. The master bedroom has a very comfortable king sized bed and en-suite bathroom with the guest bedroom offering two twin beds. There is an additional loft with queen sized sleeper sofa and sleeper sofa in the living room should you have an additional guest or two. We have a fully equipped kitchen including a keurig coffee maker. Enjoy a cup of coffee while gazing out at the Gulf of Mexico in the morning or perhaps a cool beverage during the world famous Captiva Island sunsets in the evening. Our condo is located no the second floor (walk up) and near the community heated pool. There are tennis courts available for a fee, complimentary high speed wireless internet and the location is not far from the shops and restaurants in Captiva's Village Area. Please note that you will not have access to the full South Seas Island Resort amenities.
  • Luxurious Two Bedroom Condo

    Luxurious Two Bedroom

    Captiva Island: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 6
    • #232288
    Credit Card
    Luxurious two bedroom condo at Lands End Village in South Seas Island Resort. Offers beautiful views of the Gulf of Mexico and Redfish Pass.. Enjoy breathtaking sunsets and sweeping views of the Gulf of Mexico from this high-end 2100 sq. Ft. 2 bedroom/2 bathroom Gulf-front condo located within exclusive Lands End Village in South Seas Island Resort. This luxury vacation home is steps away from pristine white-sand beaches and the blue green waters of the Gulf Coast in a serene location bordered by palm trees and tropical flowers. The unit has three outdoor areas - a screened lanai dining area and two open air decks - that provide sweeping views of the Gulf and Redfish Pass. This high-end condominium also offers a fully equipped kitchen, in-unit washer/dryer, dining room and living room area with a plush sectional sleeper sofa (sleeps two) and a flat panel TV. The master bedroom opens to a large deck overlooking the Gulf and has a king-sized bed, flat panel TV and spacious en suite bathroom with a jacuzzi tub, oversize walk-in shower, double sinks and skylights. The second bedroom has two double beds, a flat panel TV, a private deck and a separate full bathroom. Lands End Village amenities provided with this rental are adjacent to the unit and include a resort-style heated pool surrounded by a large sun patio furnished with deck chairs and an outdoor shower, hot tub, gas BBQ grills, tennis courts and underground parking. A beach umbrella, six sand chairs and a beach wagon are also available for your use. The area offers exceptional shelling, biking, fishing, sailing and an opportunity to enjoy all types of water sports (E.G. Kayaking, paddle boarding, water skiing, parasailing, snorkeling/diving). The resort marina and marina store/deli are a five minute walk from the unit. Offshore Sailing School and Captiva Cruises, offering a range of sunset, dolphin & wildlife cruises, are also based at the marina. Chadwick Square shopping mall and Sunny Island Watersports (water sports/bike/beach/golf cart rental equipment) are located at the entrance to South Seas Resort. Captiva's many restaurants and other amenities are within a short distance from there (a list is available upon request). South Seas amenities are not available with this rental. No smoking or pets in this unit. Walk-up - no elevator for this building.
  • Have a Blast at

    Have a Blast at

    Captiva Island: Vacation Rental
    • 5 BDR
    • 4 BA
    • Sleeps 12
    • #232285
    Credit Card Pet Friendly
    Have a blast at Happy Daze on Captiva Island. Private home near the beach in the Village Area of Captiva.. 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 with four attached full baths, two with king beds, one with a queen bed, and one with two sets of bunk beds. There is also a fifth bedroom off the kitchen that is appropriate for children; it has a daybed and a fold-out couch. The house comfortably sleeps twelve people. The property has an elevator and is accessible for those with disabilities, but is not specifically configured for those with disabilities (does not have hand bars in bathrooms, a roll-in shower, etc.) It also has wireless, broadband cable modem access, a laundry room and other amenities. This is a bright, cheerful and very comfortable home that is a wonderful place to bring your children for a vacation. Good fun for all; lots of board games, children’s videos and TV, ping-pong and pool tables by the pool. Come see the dolphins, manatees and river otters swimming nearby. The pool is standard size, sloping to about six feet in depth at the deep end. Pool is kept heated to approximately 90 degrees year round to encourage children to swim and play in the pool, have fun and burn off energy. Please call in advance if you would like the pool temperature lowered.
  • Direct Gulf Front Two

    Direct Gulf Front Two

    Captiva Island: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 6
    • #232283
    Credit Card
    Direct gulf front two bedroom South Seas Island Resort Beach Villa. South Seas Beach Villa 2318 offers direct gulf front views from your private screened lanai. Enjoy your stay on Captiva Island, Florida in our newly redecorated two bedroom/two bathroom condo. Our villa has a king bed in the master bedroom, two twin beds in the guest bedroom as well as a queen sized sleeper sofa in the living room for additional guests. The kitchen in fully stocked and has granite countertops. As our guest, you will have access to the Beach Villa pools (heated), bbq grill areas and tennis courts (additional fee). Being located on the south end of the resort, you would just be a short walk or drive to the many shops and restaurants located in the Village area of Captiva such as The Mucky Duck, Keylime Bistro and R.C. Otters.
  • Beautifully Updated Stilted Home

    Beautifully Updated

    Captiva Island: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 6
    • #230634
    Credit Card
    Beautifully updated stilted home located in the Sunset Captiva community. Walk to the beach, shops and even dock your boat along the bay. Welcome to Sunset Captiva 17. This newly renovated two level stilted, private home, features an updated kitchen, comfortable beds, very nice furniture throughout, flat panel TV's, high speed wireless internet and plenty of seating in our screened lanai. The main level of our home has the comfortable living room with ample seating along with a large flat panel TV and DVD. The main level also has a dining room and open kitchen which has been updated with stainless steel appliances and a keurig coffee maker (standard coffee maker is available as well). There are two sets of sliding doors that open to the screened lanai to feel the nearby Gulf Breezes. There is a laundry room with a full size washer/dryer and a half bath on the main level as well. Walk up the stairway to the second level which has the spacious master suite with a king bed, flat panel TV and en-suite bathroom. The guest bedroom features two twin beds and another full bathroom. Both bedrooms have access to the private sun deck which is perfect for star gazing. Also on the second level is a loft area for additional sleeping in the twin trundle bed. Sunset Captiva 17 offers a great location as it sits just steps to the community pool (heated), tennis courts and bbq grills. You are also about 150 yards to the beach and a short walk across Captiva Drive to the community boat docks should you wish to rent or bring a boat (additional fee applies). Park your car and you can walk everywhere including the shops and restaurants along Andy Rosse Lane as you are in the heart of Captiva's Village Area.
  • Welcome to Sunset Captiva

    Welcome to Sunset Captiva

    Captiva Island: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 8
    • #230617
    Credit Card
    Welcome to Sunset Captiva decor and steps to the beach. Community amenities include a heated pool, tennis court, bbq grills and boat docks!. Experience all Captiva Island has to offer at Sunset Captiva 55. This beautifully renovated three bedroom, two bathroom private, stilted home has sleeping accommodations for up to 8 guests comfortably. Nothing has been overlooked, even down to the Tommy Bahama decor, upgraded lanai furniture and modern kitchen with granite countertops and stainless steel appliances. The main level of the home features a spacious laundry room with full size washer/dryer, kitchen, expansive living room with a large flat panel TV, dining area, queen bedroom and twin bedroom along with a full bath and wrap around screened lanai. There is a desk off the living room should you have to catch up on anything back at the office. Enjoy the high speed wireless internet and Netflix streaming as well. Up the stairs from the main level in the master bedroom suite with a king bed, private deck, loft area off the bedroom with sleeper sofa and en-suite bathroom. Walk down the lane from the home to the community pool, grill steaks at the bbq area, enjoy a game of tennis at the tennis courts, bring your boat and dock at the slips included with the community (must be arranged prior to arrival), visit the many shops and restaurants Captiva has to offer just a block away and, of course, take in the sunshine, sand and waves at the beach just a couple hundred yards from the home. Book your stay today at Sunset Captiva 55. Additional rental items such as bikes, paddle boards or kayaks may be added to your reservation for a nominal fee. Please inquire with our Accommodations Specialists for more information. We look forward to welcoming you to our beautiful islands!
  • Experience Captiva Island in

    Experience Captiva Island

    Captiva Island: Vacation Rental
    • 1 BDR
    • 1 BA
    • Sleeps 4
    • #226358
    Credit Card
    Experience Captiva Island in our one bedroom luxury beach front condo at the South Seas Island Resort. Experience Captiva Island for a few days or a week or longer by staying at South Seas Island Resort and Beach Villa 2313. This one bedroom/one bathroom condominium has been completely renovated and designer decorated and appointed. From the moment you enter, you will notice the custom paint, molding, large floor tile and high end furnishings and finishes. Rest easy on our comfortable king sized bed with new flat panel TV and custom cabinetry providing plenty of space for your belongings. The spa like bathroom has been completely remodeled featuring granite counter tops and a lovely glass shower door. Continue on to the beautifully appointed kitchen with granite counter tops, high end stainless steel appliances and custom wood cabinets. Lounge in the spacious living room with a comfortable sofa that does pull out to a bed if needed and watch a move on the large flat panel TV which has been wall mounted. Have a cocktail and enjoy the world famous Captiva Island sunsets from our screened lanai with high end furniture and some of the best Gulf Views on the Island. You will have access to 3 pools, bbq grills, laundry facilities and of course the sandy Captiva Island beach just steps away from our condo. While full resort access isn't available, there are many shops and restaurants just outside the gates of the resort and in the "Village Area" of Captiva.
  • Private Home on Captiva

    Private Home on Captiva

    Captiva Island: Vacation Rental
    • 4 BDR
    • 4 BA
    • Sleeps 10
    • #225386
    Credit Card
    Private home on Captiva Island with guest suite and pool. 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 and making those special lasting memories. Our guests re-book their vacations year after year as Bird of Paradise Captiva has become their tropical beach home away from home. Bird of Paradise Captiva is located at 11525 Chapin Lane, a three story home nestled within Captiva Island's lush tropical vegetation, it makes you feel secluded within your very own vacation oasis, yet it's just a short walk to the quaint Village Center where you'll find shops, fresh produce, art galleries, restaurants and activities for the entire family. Bird of Paradise's main living level is on the second floor and features all the warmth, comforts and conveniences of home. The home's great room features a 20 foot, exposed beam ceiling as well as a comfortable family gathering and dining area. Adjacent to the fully-equipped and renovated kitchen is a screened lanai to enjoy a quiet morning coffee while listening to the sounds of native wildlife and waves softly crashing on the shore from the Gulf of Mexico, nearby. Two guest bedrooms rooms and two bathrooms complete the second story with the spacious master bedroom suite on the third level overlooking the great room. Bird of Paradise Captiva is just two homes away from the tree covered sandy path leading to the pristine, white sand beach and clear blue waters of the Gulf of Mexico. This child-friendly walk down Palm covered Chapin Lane takes you by Captiva Island's library and just past Chapel by the Sea. When you've had your fill of gulf-side sunbathing and beachcombing, the home's four outside decks, many with screen enclosures, are perfect settings for a refreshing cocktail and conversation before dinner, quiet time, relaxation or reading a good book. Also enjoy the seclusion of the home's large heated swimming pool and its spacious deck; the area is enclosed from the elements and ideal for early evening cat naps or early morning swims.
  • Experience Captiva Island in

    Experience Captiva Island

    Captiva Island: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 8
    • #225383
    Credit Card
    Experience Captiva Island in your own private home with beach access, community pool, tennis and boat dock. 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 Captiva Island beach. Included with this property is free, private boat dockage within walking distance on the bay side—also an amazing location to watch the serene sunrise as the dolphins and manatees frolic. This beautifully furnished home includes 3 bedrooms plus a large loft area with Queen sleeper sofa. The main level features a fully equipped kitchen, spacious and comfortable living area with flat-panel TV and DVD player, dining area, 2 bedrooms, 1.5 bathrooms and a laundry room. Also included on the main level is a spacious wrap-around, screened lanai with dining, lounging furniture and a flat-panel TV. The lanai overlooks the crystal clear pool and tennis areas. The main level bedrooms include a king bedroom with a private screened-in lanai and another guest bedroom with two twin beds. The upper level features the master suite with comfortable king-sized bed, en-suite bathroom and private deck. Also on the upper level is a spacious loft area complete with a sleeper sofa for two additional guests, flat-panel TV and DVD player and additional seating. Accessible from the loft is a sundeck with loungers for catching more rays or relaxing under the starry sky. Sunset Captiva 15 is equipped with high-speed WIFI Internet access, beach towels, casual furnishings and everything you need for the "beach home-away-from-home" you have been dreaming about!
  • Welcome to the Gingerbread

    Welcome to the Gingerbread

    Captiva Island: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 6
    • #225381
    Credit Card Pet Friendly
    Welcome to The Gingerbread House on Captiva Island. Quaint antique style cottage just 300 feet to the beach. Welcome to The Gingerbread House on Captiva Island. This antique style cottage is set just 300 feet from the beautiful Captiva Island beaches. With 2 spacious bedrooms, 2 full bathrooms and a den that closes off to be a third bedroom, there is plenty of space for a family of four. Stay for a week or longer and enjoy the full kitchen and washer/dryer to make your stay that much more accommodating. The Gingerbread House has an expansive screened lanai facing to the west to sit, relax and enjoy a cold beverage or even a meal. The master bedroom has a queen bed with en-suite bath while the guest bedroom has two comfortable twin beds. The den is set up as a family room with a TV and does close off for privacy. High speed wireless internet is included as is beach equipment and beach towels. We look forward to welcoming you to our Captiva Island Cottage that we call The Gingerbread House.

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