Holiday rentals with a pool in Little Gasparilla Island

Escape to Casa Blu- private pool, minutes to beach

Your next retreat to Florida paradise should be Casa Blu with it's private pool and serene backyard. It's just minutes to area beaches, restaurants and parks. Let the stresses of daily life melt away as you float in the salt water pool, sipping margaritas, listening to Jimmy Buffett singing "It's Five O' Clock Somewhere" The single-floor layout, comfy bedrooms with private baths await. Fast WiFi, Smart TVs, and fully equipped kitchen. Everything's covered, from beach gear to a pack 'n play.

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 your 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

Gulf front romantic cottage in paradise

Gated and surrounded by lush scenery you will feel like you have suddenly escaped to the caribbean! The pressures of the world melt away as you get your first glimpse of the Gulf of Mexico. Eclectic design with mostly Caribbean influences. Marble floors, tile counter tops and a large shower with a sit down bench. Walk the custom pathways which reveal beautiful orchids and exotic plants. Go kayaking, fish off the beach or look for sharks teeth. Take a swim in the pool or work on your tan.

Seaside Boca (Pool + Sauna + Mini Golf + Spa)

Have fun with the whole family at this stylish new Airbnb. With its Key West vibes you’ll be sure to have a great time here! Boca Grande is just minutes away, Publix and shopping center are a short bike ride and boats are welcome as the marina is right next door. House is located in the tranquil area of Cape Haze close to Golf courses where you can stroll or bike to you hearts content. We just added a Game Room, a Pool with jacuzzi, Sauna, plus a multi court and Mini Golf (pics jus refreshed)

Sea La Vie

Escape to 3 acres of tropical bliss on exclusive Palm Island, where luxury meets seclusion. This beautifully updated 5-bedroom, 4-bathroom retreat offers breathtaking views of a serene pond and the Gulf of America. Heated pool & jacuzzi, 50-ft private boat dock, Home theater & game room, Kayaks, bikes, pool table, ping pong, and more, Fire pit, basketball court, volleyball, Steps from a private beach. Accessible only by private ferry, this is more than a getaway; it’s your slice of paradise.

Island Oasis - Boca Grande Club

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.

Sun & Sand Spacious Vacation Canal Pool House

Family friendly, fully-renovated PRIVATE 4br/2 bath pool home near Boca Grande & 2 other beaches. 5 golf courses within community. Screened lanai with HUGE 16x25 pool overlooking canal teaming w/ FL wildlife & amazing sunsets. Nature trails nearby for biking, running, walking, & bird watching. Designed for multi-generational use with the master bedroom separate from the 3 guest bedrooms. Fully furnished--just bring your clothes!! Amazing reviews! ONLY 2 Driveway Parking Spots.

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 100 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!

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.

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.

Island Getaway Pool-Ferry-Grocery Delivery Incl.

*FREE Island Grocery delivery/staging Enjoy our Locally Owned and Operated, Newly 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 Gated Mainland Parking & Ferry to the Island incl. Walk the Uncrowded shelled beach with Birds, Dolphin and Manatee or Venture out for Prime Fishing & Kayaking SWFlorida has to Offer