Huge 5 bedroom / 6 bathroom estate on bay directly across from Gulf beaches on Captiva's sought after Gold Coast. This family retreat on the Southern end of Captiva provides access to Captiva's world reknown wildlife eco paradise via the Roosevelt Channel to adjacent Blind Pass. A horticultural gem...

Our privately owned MARINA VILLA is much more beautiful and much LESS EXPENSE than the resort condos at South Seas Island Resort. Please note, the rental rate for our privately owned condo is considerably lower than most South Seas Island Resort rates for the same time period, however, our Marina...

Price is usually quoted for just one studio suite, unless otherwise indicated. Each of the two studio suites sleeps no more than 2 adults and 2 Children under 12. Call Now for ON the beach Coquina Cottage!. Coquina Cottage is a unique ~Old Florida~ beachfront cottage sitting on almost an acre...

Welcome to Sunset Captiva 57 – your own little piece of paradise! Sunset Captiva is a small, charming, unique community located in the heart of Captiva Village Center - there is nothing else quite like it on the west coast. Stretching from bay to gulf, it really has it all: a large heated pool –...

THE LITTLE ARK (please note: cleaning fee $125 for 2 people or $150 for 3 or 4 people and club membership fee $75 optional will not appear in booking charges if you book online. These two fees are only payable by check and mailed to owner) The vacation of a lifetime is awaiting those who are will...

Welcome to paradise! Turtle Trax is a 3-bedroom home with sweeping views of the Gulf of Mexico and the most beautiful sunsets! This home has a private screened pool and is situated on an oversized lot to ensure privacy. Swing in the hammock nestled under the trees or lounge by the pool and enjoy...

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...

Once you arrive at The Conch House, the first thing you’ll notice is the spectacular downstairs pool area. Not only is there an oversized pool for everyone’s enjoyment, but there is also an island tiki bar– complete with 4-person bar seating, ice maker, Loungers, Adirondack chairs and a dining...

If you are looking for amazing views, a great pool, great fishing, boating, a place to sleep and value savings, Sea Otter is a great option. It offers a great location but is a no frills lodging experience. Furnishings, décor, fixtures and appliances are dated and meet basic expectations....

Stunning Gulf Front Beauty! Walk out the back door and you’re on the beach! This four bedroom three and ½ bathroom home is the perfect escape for a relaxing beach vacation. The large living room features a flat screen TV, a fireplace, comfortable seating, a desk area and sweeping views of the...

Enjoy the Longboat Pearl for your next vacation getaway. Longboat Pearl is a 3 bedroom 2.5 bath home with a heated pool conveniently located minutes from the beach and just seconds from the North Captiva Island Club. Enjoy every possible amenity when staying at the Longboat Pearl. This gem is...

"The Old Key West House" and some younger folks call it, "The Tree House", but whatever you call it, you will love being nestled in the natural lush vegetation like a tropical rain forest.The house has many special architectural features like an English antique stain glass front door, a bar area...

The name says it all .... Hakuna Matata "No Worries". You will have "No Worries" during your stay at Hakuna Matata on Captiva Island. As you arrive up the winding drive way, you'll see the beautiful home appear just after the private heated pool. On the ground level, there is garage access and an...

Very nice direct bayfront condominium located at Sunset Captiva Bayside. A great location puts you in the Heart of the Captiva Island Village Area. Unit 103 is a very spacious private condo with about 1500 sq ft of space. The master bedroom has a king bed and en-suite bathroom with the guest...

Private street – less than a block to the beach!! Take in the fresh ocean breeze at Island Pearl! Designed to anticipate your every need, Island Pearl is well equipped to entertain up to 8 people and loaded with amenities. You’ll be just steps from the beach or stay home and enjoy your secluded...

Just steps from the gorgeous gulf beaches, Silverseas Cottage is an immaculate and charming three bedroom, two bath home perfect for a single family or small group. Newly renovated, the interior features a fully stocked cook’s kitchen with stainless steel appliances, beautiful labradorite granite...

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...

The "Coral Reef" of North Captiva Island is a 4-bedroom, 4-bath, designer-decorated pool home with views of the Gulf from the Great room/kitchen veranda and the sundeck. There are 2300 sq ft under air with another 1,000 sq ft of Verandas and decks which create a wonderful indoor/outdoor space from...

Best location on the Island!! Directly on the beach with sweeping water front views. 2 Bedroom, 2 Bath.This 2 bedroom, 2 bath home is directly on the beach. The perfect beach cottage. 1000 square feet of living space. The home has a great beachfront bar to hang out and watch the sunsets. On the...

This 3 bedroom townhome with 2 1/2 baths has everything you need for the perfect beach vacation. Relax to bay views from your screened lanai opening off the open floor plan living area-- including a comfortable seating area with a flat screen smart TV and DVD, a large dining room table and galley...

Escape your worries in this Captiva Island beach bungalow. Enjoy the bright and cheery island décor throughout this three bedroom two bath pool home. Surrounded by bright tropical vegetation this home offers a perfect location to the Heart of Captiva as well as ultimate privacy. Equipped with...

Gorgeous views of the Pine Island Sound, watch dolphins, sea otters and osprey from your screened in porch. This two bedroom, two bath home is located in the Gulf to Bay community of Captiva Shores. Walk into the bright open living area with tile floors, tropical furnishings, flat screen TV and...

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...

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...

A dream home for a dream vacation. This 5 bedroom 6 bathroom has everything you would want for an outstanding vacation. Gorgeous views of Pine Island sound, a large screened in pool, u-shaped boat dock in your backyard, a tiled sun deck with great views and a short stroll across the street to the...

Sit right back and watch the waves go by. This delightful 2 bedroom & 2 bath beach house will lift you into the beach vacation of your dreams! Walking through the classic beach entrance gate before a grove of palms, you arrive at the beach house and are immediately welcomed by a chic and...

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...

Directly on the beach! This two bedroom, two bath villa is just about one of the best beach front locations offerred on North Captiva. A truly fabulous location. Just the sand between you and the Gulf of Mexico. Sunsets directly west of your open expanded living area, master suite and Jacuzzi. Just...

LongLook BeachHouse is an amazing 3 bedroom, 3 bath home directly on the Gulf of Mexico. What an experience you will have watching incredible sunsets at LongLook Beachhouse. Just a few steps onto the beach from this lovely home! The level of comfort when staying at LongLook is astounding! There is...

Located in a small beach-to-bay community on the scenic Captiva Island, this fully furnished and fully equipped cottage is just minutes away on foot from the beach. This home is ideally located near all the hot-spots of Captiva. The master bedroom has a queen-size bed, private bathroom and private...

This comfortable 3 bedroom, 2 bath beachfront home is ideal for a family looking for a true island getaway. With its location and feel, it offers a truly memorable vacation! Situated very near the state preserve, this home's location is ideal as a starting point for beachcombing, shelling or...

Sapphire blue water, white sandy beaches, amazing sunsets from your living-room and a luxury four bedroom villa. Everything you need for the perfect friends and family vacation. “Conch” features tropical colors in this remodeled spacious villa. Walk into the living-room with direct Gulf Views...

Stay a week or longer at Tarpon Tales on beautiful Captiva Island, Florida. This five bedroom/five 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...

If you're looking for a perfect tropical vacation home that fits a large family, our stunning Captiva Island Villa is perfect! Our very private and quiet four-bedroom home is located on the Roosevelt Channel of Captiva with its own private dock on the bay. Spend your morning hours looking out of...

Enjoy the breeze of the Gulf of Mexico from this four bedroom home’s rooftop sun deck after walks along the beach, swimming in your private, heated pool, dipping in the hot tub or gazing up at the stars. Every guest will find their own way to unwind whether by the private pool, playing on one of...

Listen to the sounds of the waves from your screened in porch while enjoying world renowned sunsets. This three bedroom two and one half bath Gulf Front Captiva home has everything you want to make this a vacation of a lifetime. Walk into the bright great room featuring direct views of the Gulf of...

Welcome to Sunset Captiva 17! This newly renovated two level stilted, private home, features an updated kitchen, all new 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...

Direct Gulf views, lush tropical landscape, a great location and a charming beach cottage are all the ingredients you need for an amazing Captiva vacation. This is a historical Cape Cod style ground level home with older finishes throughout including the original kitchen. This home features two...

Let your troubles melt away in this luxury three bedroom three bath condo with a den. Relax on the spacious lanai with sweeping direct bay views. The large living room has beautiful views, tile floors, built in cabinets and double tray ceilings with wood accents. The gourmet kitchen features top...

Lollipop, the perfect Captiva vacation home. Central to Captiva village this three bedroom three and ½ bath pool home offers the perfect escape for a relaxing vacation. There are so many great features to this home, cathedral ceilings, screened in porch, updated modern kitchen, pool and spa, two...

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...

The Ultimate Captiva Vacation Home! This stunning seven bedroom six ½ bathroom home overlooks the sparkling waters of Pine Island Sound and Roosevelt Channel. This unique home and its guest house sit on 2.5 acres of stunning, mature tropical landscapes. The entrance of the home features a hand...

Expansive Water Views! This three bedroom three bathroom Captiva Shores townhome features outstanding views of Pine Island Sound and Roosevelt Channel. Watch boats, kayaks, dolphins, manatee and shorebirds from your large private lanai. The large, open living-room features a flat screen...

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...

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...

This cozy two bedroom pool home is like brand new! Fully equipped! Osprey nest is a lovely brand new home with private pool and jacuzzi. This lovely home is interior decorated light contemporary thought through for comfort for a small family up to 6 people. You will enjoy flat screen TV's in every...

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....