
Vacation rentals with a pool in Gasparilla Island
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Top-rated rentals with a pool in Gasparilla Island
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Beachfront North Captiva | Rooftop Deck | Hot Tub
No bridges. No cars. No crowds. Stella Maris sits directly on the Gulf on North Captiva — a private barrier island reachable only by boat. Step off your deck onto white sand. Watch dolphins from your 360° rooftop deck at sunset. 3 bedrooms, each with private en-suite bath. Cathedral ceilings, gourmet kitchen, formal dining with Gulf views, stone fireplace, hot tub, and included golf cart. Dual club access — Safety Harbor Club included; optional Island Club for pools, kayaks, bikes, and pool bar.
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Blue Laguna - Vacation in paradise!
This bright, fully equipped welcoming three‑story home features a private heated pool and a rooftop observation deck with stunning 360‑degree water views. It offers three comfortable bedrooms and three full bathrooms for up to six guests, plus two screened lanais where you can relax in the island breeze and listen to the birds. A four‑seater golf cart is included, so you can easily explore the beaches and sandy paths of beautiful North Captiva Island. Also full access to Island Club amenities!
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Vacation Paradise in Rotonda
This brand-new home with 3 bedrooms and 3 bathrooms is truly designed for comfort and relaxation. The spacious living room, huge kitchen, and big dining room are an open-layout living area. Our outdoor covered grilling area has outdoor furniture a hot tub, and a heated pool. Walking distance to Long Marsh Golf Club, a short drive to 3 more Gulf Clubs. A Playground for the kids and exercise paths are all here. Amazing 7 beaches to choose to visit with very good restaurants close to the area.
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Luxury Retreats at Boca Grande - Grande Canal
Three bedrooms, two bath retreat located a few blocks from town and the white sandy beaches of Boca Grande. Full kitchen with island and family room. A separate workspace lets you work remotely. Enjoy the deck, porch, pool, and dock. Fish and crab off the dock. Bring your boat or charter one. Stroll the barrier islands and marvel at the tropical palms, flowers, and birds. Recharge and restore yourself in nature, in town. Very walkable, only a few blocks downtown to restaurants and shopping.
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Turtle Bay - minutes to Boca Grande!
Welcome to Turtle Bay Haven – Your Dream Escape on the Gulf Coast! Stay in your own private natural oasis, surrounded by lush greenery and the vibrant tropics of Florida wildlife. - Grocery Stores: just 5-10 min away - Dining Options: A variety of local restaurants are just min away. - Boca Grande: 11 mi (20 min) away, known for stunning beaches. - Manasota Key Beaches : 10 mi (20 min) - Activities: Kayaking, paddleboarding, fishing, hiking, biking, and over 20 golf courses await!
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Beach Getaway + Golf Cart & Club Access
BOOKING FALL 2026 HOST PAYS AIRBNB FEE 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 proximity/ steps to the beach
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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!
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Coastal Sanctuary - Pool & Privacy
Tropical luxury awaits in this 3BR pool home in a quiet residential neighborhood. Relax in a quartz pool (heating available for $25/day) shielded by mature palms for privacy. Enjoy a chef's kitchen, fast Wi-Fi, and a master suite with soaking tub. Two Kings + a family-friendly bunk room. Beach gear included! 15 mins to Englewood/Manasota beaches, 20 mins to Spring Training & Boca Grande, and near world-class golf. Please note - quiet hours (9p - 8a) strictly enforced
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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!
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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.
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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.
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ArtSea Beachfront Remodeled Pool Old Florida
Welcome to ArtSea -- a beautifully remodeled beachfront condo on Gasparilla Island's Gulf shore. where Old Florida lives on in the best possible way. Step outside your door and you're on the sand: a wide shell-strewn beach where the Gulf of America stretches out in front of you and the sky ignites with color every evening at sunset. Tis is Boca Grande--unhurried, authentic, and unlike anything else on Florida's Gulf Coast.
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Popular amenities for Gasparilla Island rentals with a pool
House rentals with a pool

Steps to Beach | Pool + Hot Tub | 2025 Remodeled!
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The Sunfeather - Fun, Sun and Flip Flops
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luxury Brand new villa with pool
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(Newley Built) Heated Pool/ Golf course Views.
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Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN
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Boater’s Paradise in Bokeelia!
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Acogedora, tranquila
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Panoramic Gulf Views | Heated Pool | Beach
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Condo rentals with a pool

Sunset Beach
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100+ 5 Star Reviews and Right on The Beach!
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Studio, pool, private beach, boat dock shark teeth
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View of Gulf, Steps to Beach@The Turquoise Turtle
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Entire Beachside Condo! Don’t worry Beach Happy!
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Captiva Beach Villa On The Gulf Beach !
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Rare walkout condo on Sanibel beach
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Steps to Water! Beach to Bay, Penthouse!
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Other vacation rentals with a pool

Bokeelia Daydreamin' 4 bedroom with Pool!
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The Cottage
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Waterfront Canal Home in Port Charlotte
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Newer 4bd/2ba Canal Pool House, Hot Tub & Game Rm!
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Fun in the Sun
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2/2 SandDollars, CLUB, Boat Slip
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Golden Pond Villa! Minutes from Boca Grande!
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New Home! Heated Pool · Outdoor Bar · 2 Golf Carts
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