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

Gumbo Limbo North Captiva
Located on North Captiva, in Safety Harbor Club, this comfortable home is conveniently located near beaches, pools, & boat docks. Nestled among native palms, Gumbo Limbo has a wildlife-friendly, private setting you will love. Beautiful beaches & refreshing pools are a short walk or 2 minutes by golf cart (included). The island has over 5 miles of pristine sandy beaches to explore. 3 large pools, tennis & pickle ball courts, sea kayaks, bicycles & private beach access are available to guests.

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

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.

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!

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.

Steps to Beach Captiva Includes CLUB & Golfcart
BOOKING SUMMER 2026 HOST PAYS AIRBNB FEE ! SPECIAL 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

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!

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!

Amazing Peace River Views
House is a 2 bed, 2 bath layout. The Master bed is a king bed and the guest bedroom is a queen. Both bedrooms have walks in closets with easy and convenient shelving and built in hampers. The laundry is stocked with liquid soap and fragrance free powder with fast efficient machines. There are speakers in the house, lanai and pergola. You will be able to control them via your phone. There is a desk work area with extra monitor for laptops and a printer for your use.

Dolphin beach house 2
ONE OF THE BEST WATERFRONTS IN CAPE CORAL! A short walk to the beach a. This 2,500+sq ft home has stunning sunsets and South Western water views from all main living areas,as well as the Master Suite. Heated pool w/ LED colored lighting, built in Spa,Pool bath, full laundry facility, Lanai,Fireplace ,Wi-fi and TVs in every bedroom, private dock . Boat on lift for rent w/RPM rentals . Large 2-car garage w/5 bicycles,beach wagon & cooler on site.

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.
Popular amenities for Gasparilla Island rentals with a pool
House rentals with a pool

Waterfront Villa•Heated Pool•Dock•Fishing•Kayaks•

Green Bamboo - saltwater pool, great backyard.

Island Pearl | Lake front | Pool | Spa

Modern Villa Heated Saltwater Pool 10 Min to Beach

Tropical Oasis, pool, golf, dog friendly

Waterfront Villa Shellflower with private pool

Water view Villa private Heated Pool golf beach

(Newley Built) Heated Pool/ Golf course Views.
Apartment rentals with a pool

6 Siesta Breakers - Condo, Ocean View, Heated Pool

Rare walkout condo on Sanibel beach

Beachfront fully equipped apartment

Entire Beachside Condo! Don’t worry Beach Happy!

Captiva Beach Villa On The Gulf Beach !

206C Gulf Water Views + 2 bikes + beach gear

Vintage Villa 35 | Steps to Beach | Pool

Comfy Siesta Key Condo
Other holiday rentals with a pool

Waterview & Pool Estate Sleeps 10

Tropical Retreat - Minutes from Boca Grande beach!

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN

Coastal Sanctuary - Pool & Privacy

Saltwater&Sunsets Await You | Beach & Club Pools

Englewood Beach Villa - 3 min Walk to the Beach!

Saltwater Villa/Pool/Jacuzzi/MovieTheater/FishDock

Beach Bliss Retreat on Manasota Key - Ocean View
Destinations to explore
- Seminole Holiday rentals
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- Miami Holiday rentals
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- Rentals with a washing machine and dryer Gasparilla Island
- House rentals Gasparilla Island
- Rentals with beach access Gasparilla Island
- Family-friendly rentals Gasparilla Island
- Rentals with a patio Gasparilla Island
- Rentals with outdoor seating Gasparilla Island
- Rentals with pools Florida
- Rentals with pools United States
- Siesta Beach
- Crescent Beach
- Captiva Island
- Turtle Beach
- Lido Key Beach
- Caspersen Beach
- Manasota Key Beach
- Lovers Key Beach
- Englewood Beach
- Lakewood National Golf Club
- Myakka River State Park
- Stump Pass Beach State Park
- Bonita National Golf & Country Club
- Barefoot beach Bonita Springs,FL
- Heritage Bay Golf & Country Club
- Clam Pass Park
- North Jetty Beach
- Blind Pass Beach
- Marie Selby Botanical Gardens
- Florida Gulf Coast University
- Boca Grande Pass
- Edison & Ford Winter Estates
- South Jetty Beach
- Tara Golf & Country Club




