Vacation rentals with a pool in Little Gasparilla Island

Paradise Cottage Island Oasis

An enchanting, GROUND LEVEL tropical Palm Island paradise that delivers the epitome of off the grid, private island living. 7 minute walk to sugar sand beaches offering buckets of seashells, shark’s teeth & award winning sunsets! Return home to your private, swimming pool surrounded by mature, tropical foliage that has the look and feel of a Caribbean resort. Follow the winding path that leads to the harbor with dock: toss a line, boat to no bridges out to GOM, launch kayaks, take in nature!

Island home w/POOL, Private DOCK & BEACH access!

Forget the crowds, if you're dreaming of a private beach escape, this spot has you covered! Located on the private Palm Island-ONLY accessible by 5 minute car ferry or private boat. Relax in this 3BR/3BA private retreat with a PRIVATE POOL & PRIVATE DOCK w/power&water in the backyard. Private BEACH access across the street, ultra comfortable premium mattresses, beach chairs/toys, kayaks, plus a fully equipped kitchen, outdoor dining space with grills easy for coastal living. No bridges to gulf!

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN

Luxury beach house with pool in a charming old-FL beach town, one of FL’s best kept secrets! New kitchen, 2 covered balconies & a walled backyard oasis. Spend sunny days by turquoise waters of the Gulf & host a cookout on the covered patio & pool. Enjoy the sea breeze while sipping your favorite beverage on the covered balcony off the living area. Lounge in style in the patio or go for a swim in the 6’ deep heated pool. You're walking distance to restaurants/bars and 57 seconds to the beach!

Island Getaway Pool-Ferry-Grocery Delivery Incl.

10-minute passenger ferry ride to this boat-access-only, car-free island Locally Owned & Operated Updated LGI Condo with Magnificent Views 2 private SW facing decks offer a.m Sun, Gulf, Palm & Pool Views. Beautifully furnished with everything to enjoy your Island time Uncrowded shelled beach with Birds, Dolphin and Manatee -Venture out for Prime Fishing & Kayaking SWFlorida has to Offer There are no grocery stores or restaurants on the island, plan to bring everything you’ll need with you

3BR Resort Home · Pool, Gym + Beach Club Access

We beat Milton and are ready to host you. The Village Houses in the Boca Grande Club possess a distinct charm that sets them apart. The village houses offer an intimate connection to nature. Our homes is surrounded by lush tropical foliage, providing a serene backdrop of swaying palms and vibrant flowers. Our guests enjoy access to a range of exclusive amenities. Whether lounging by the pool, or indulging in gourmet dining, out home provides a wealth of experiences for our guests.

Cape Haze Cottage

2023 Cape Haze Cottage , 3 bedroom 2.5 bath elevated canal front pool home. Quiet waterfront neighborhood with easy access to everything this amazing area has to offer. Screened lanai provides sunset views, private pool, outside shower, steps away from canal front for Kayaking and fishing or just watching the endless variety of nature. Situated just six minutes from stump pass by boat, access to the gulf , beaches and fishing both inshore and offshore. This is a piece of heaven.

AMAZING Cape Haze Location -community kayak launch

Ready for warm sunshine, tropical breezes and lush landscaping? Spaniard's Retreat is the ideal location for your get away. This home is set in the charming Old Florida neighborhood of Cape Haze. Old banyan and pin-oak trees line the picturesque streets where homes are spaciously placed. Upon entering you will be greeted by the panoramic sliding doors overlooking the heated pool and spa. This truly feels like a private oasis. 3 bedrooms and 2.5 baths offer generous accommodations.

Lux Home on Gulf w/Private POOL & 50ft Dock

Rest your feet & your soul as you getaway from it all! This luxurious little piece of paradise is tucked away on a quiet Gulf Coast waterway. 10min from Englewood Beach and 5 min from stores. Tie your boat up in the back yard to the private 50 ft dock. Spend your days fishing, catching sunsets or in the pool every evening! Easy access to Don Pedro Island, local sandbars, inlet and several restaurants, all at your fingertips! Pack your bags, kick back- paradise is waiting!

Island Home & Casita, Pool, Golf Cart, Beach

Complimentary golf cart INCLUDED. With a short stroll to warm sand and crystal waters of Englewood Beach. With all the the modern comforts in place all you have to do is relax on your short stay or extended visit. Updated 2/2 main house and 1/1 Casita with a private entrance. Walk right out the front door to the new expansive pool patio featuring a saltwater heated pool, outdoor kitchen and plenty of furniture for spending time soaking in the warm Florida sun!

The Cottage

Coastal paradise with direct Gulf access! Located in historic Cape Haze, this beautiful retreat is just minutes from Boca Grande’s world-famous beaches, fishing, and island charm. Enjoy easy access to boating, three full-service marinas, waterfront dining, golf courses, shopping, and miles of pristine coastline. Whether you're fishing, beachcombing, or simply relaxing, this is the perfect base for experiencing the very best of Florida’s Gulf Coast.

Paradise on the Bay

Waterfront pool home just a short drive to Boca Grande with all the amenities that you would expect. Enjoy spectacular sunsets over Lemon Bay. With more than 250 ft of seawall for deepwater dockage, this home can accomodate even the largest boats. Fantastic fishing from your front yard! Three bedrooms and two baths make this the perfect vacation destination for family and friends. 3 Kayaks and a canoe are available for your enjoyment.

Manasota Key

Direct Ocean Front Unit. Imagine having a glass of wine at sunset overlooking world class views of the Gulf of Mexico. Steps to the beach and unsurpassed views. Excellent restaurants and Tiki Bars within walking distance. This unit is a 1 bedroom 1 bath spacious unit that can comfortably sleep 4. It includes a King bed & Full size sleeper sofa. It also has a beautiful kitchen with granite countertops and tile floors throughout. No Pets.