
Holiday rentals with a pool in Gasparilla Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Gasparilla Island
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

LAST Minute! NEW Villa-Heated Saltwater Pool & Spa
Experience Cape Coral like never before all from this gorgeous 3bedroom, 3bath villa. This elegant villa boasts a vibrant interior decorated with Italian furniture and fully equipped kitchen. Begin your day with a few laps in the private pool before heading to the Yacht Club Public Beach, Sun Splash Family Waterpark or Pine Island to soak up some sun! After adventurous days, continue making memories back home with a family barbecue and a soak in the hot tub or have a movie night with loved ones!

Boater’s Paradise-Stunning Sunsets! Games Room!
Renovated lanai! This 3 bed/4 bath home is on the nicest canal with 200+ ft of frontage & gorgeous views of the canal & sunset. The pool, tiki hut & docks have full sun all day. Each bedroom has a private bath & there's a 2 pc powder room off the laundry. The primary has a king bed & walkout to pool. The 2nd bedroom has a queen bed & pool access. Bedroom 3 has a queen & private bath. Fully equipped kitchen with everything you need. And a games room! Enjoy stunning sunsets under the tiki hut.

LUX Villa w/ Private Salt Water Pool, Lanai, Canal
Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

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.

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!

Steps to Beach Captiva Includes CLUB & Golfcart
HOST PAYS AIRBNB FEE FALL SPECIALS Golf Cart and Club amenities Included North Captiva Island Cottage! Just steps away from the Gulf's pristine shores, this cozy retreat offers a private hot tub, perfect for families and beach enthusiasts. Enjoy modern amenities, a well-stocked pantry, and a complimentary golf cart to explore the island. Pet-friendly(small fee) accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach STAY WITH US

Green Bamboo - saltwater pool, great backyard.
Welcome to Green Bamboo, the charming and cozy vacation rental located in the beautiful Englewood, Florida! With its prime location, Green Bamboo is the perfect place to explore all that the area has to offer, from the most amazing beaches in the US to world-class golf courses and spectacular sunsets. Home is situated in a peaceful and gorgeous neighborhood. Just a short drive away (5 miles) you will find beautiful beaches, boat rentals and vibrant shopping and dining options.

2 Kings, Pool, Gulf Canal, Game Room and Kayaks
Unwind Cape Coral welcomes you to sunny southwest Florida, close to magnificent beaches, fishing, shelling, Minnesota Twins Spring Training & much more. Come enjoy this new construction home with heated pool, Kayaks, heated and cooled game room (PlayStation 5), gulf access - salt water canal, 4k oled tv's & many more refreshing amenities. You will love this clean & bright home with lovely décor. Located in the highly sought after Pelican neighborhood of Southwest Cape Coral!

Sleeps 10! Coastal Home, Heated Pool, Near Beach!
Follow the sunshine & salty air & arrive at your meticulously maintained home away from home. Whether cooking for one or ten, the chef in the group is certain to appreciate this fully upgraded, open concept kitchen. Start the day brewing coffee in the Keurig & end the day sharing a bottle of chilled Pinot from your wine fridge. Open the sliders & the party extends outdoors. Inflate the raft & spend your days daydreaming afloat in the heated, salt water pool.

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.

BRAND NEW Luxury Villa w/Heated and Chilled Pool
Brand new high-end 3 bedroom 3 bath designer home, elegantly decorated with incredible views and direct no-bridge Gulf access. Come and make your lifetime memories in this elegantly appointed executive villa. Located near Matlacha, Sanibel, Fort Myers, and Naples. Extra wide canal with only trees opposite, a salt water lagoon, and just off the spreader canal means incredible solitude and privacy in your elegant oasis retreat.

Luxury Waterfront Villa• Heated Pool• Dock• Kayaks
Welcome to Sprocket Boathouse, your private, pet-friendly waterfront escape on one of Cape Coral’s widest canals. Watch incredible sunsets from the heated pool, paddle the canals on complimentary kayaks or fish right from your own dock. Start your mornings spotting turtles, iguanas, & herons along the water. Spend the day floating under the sun, then wind down with cocktails & a barbecue as the sky turns pink over the canal.
Popular amenities for Gasparilla Island rentals with a pool
House rentals with a pool

Paradise Found! - 3/2 Pool Home

Tropical Retreat-HeatedPool Tennis PickleBall Golf

Tropical Oasis, pool, pelaton, golf, dog friendly

Luxury Retreat: Oasis with Pool & Putting Green.

Pool Home: Near the Beach

Beautiful Floridian Oasis

Intervillas Florida - Villa Xanadu

Dive into Luxury: Stunning Tropical Home & Pool
Apartment rentals with a pool

One bedroom condo - overlooking harbor!

South Seas Beach Villa 2617: Captiva Island Paradi

Rare walkout condo on Sanibel beach-Fully Restored

Gulf Views & Sunsets | Estero Beach Tennis 206C

Studio, pool, private beach, boat dock shark teeth

Sunshine Swimmers Casita, 206

Cozy studio 1.3 miles to Barefoot Beach

Lovers Key Resort/Ft Myers Beach/Condo/Pool/View
Other holiday rentals with a pool

Luxury Canalfront Pool Retreat w/ Upscale Finishes

Tranquil Pool Spa EsCape Villa

Luxury Home w/ htd Pool/Spa~Gulf Access&Near BEACH

90Degree SaltWater Pool NEW Luxury Spa Gulf Access

Sandy Toes Villa - North Captiva - Water Views

Secluded Paradise,Heated Pool,Beaches and Golf n.

Luxury Beach Retreat w/ Heated Pool

VRCC Villa Mermaid Cove
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- Saint Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Havana Holiday rentals
- Fort Lauderdale Holiday rentals
- Four Corners Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Siesta Beach
- Crescent Beach
- Captiva Island
- Turtle Beach
- Caspersen Beach
- Lido Key Beach
- Manasota Key Beach
- Lovers Key Beach
- Barefoot beach Bonita Springs,FL
- Englewood Beach
- Point Of Rocks
- The Club at The Strand
- Clam Pass Park
- Lakewood National Golf Club
- Marie Selby Botanical Gardens
- Heritage Bay Golf & Country Club
- Myakka River State Park
- Blind Pass Beach
- Bonita National Golf & Country Club
- South Jetty Beach
- LaPlaya Golf Club
- North Jetty Beach
- Worthington Country Club
- Seagate Beach Club
