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

Xanadu|Fishing/ Pool/Dock|Kayaks|Bar/Gazebo/ Kids
Welcome to XANADU Luxury Villa 🌊 your canalfront paradise with a private BOAT DOCK ☀TOP LOCATION📍, close to: beautiful beaches 🏖️ Gasparilla Island, Siesta Key, Englewood! ☀Dock Ideal to FISH 🎣| Deck🎴 ☀BAR🍷 ROOM Dancing Light 🪩 ☀DEDICATED WORKSPACE 💻 ☀GAME🎮 Room /Roblox/Arcades🕹️ ☀Smart TVs in every room📺 ☀HEATED Pool 🏊♀️ ☀Fast WIFI📶 ☀Ping Pong Area in Sand 🏓 ☀Fully equipped kitchen🍽️ ☀Pool Table and Games🎱♟️ ☀ Outside dining table😋/Fireplace ☀BBQ🍖Ice Maker🧊 ☀Self check in 🔐 Smart Lock
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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!
LocationFamilyBeach

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.
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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)
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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
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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.
LocationFamilyBiking

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.
LocationFamilyDecor

*New Listing* ☀️TheAquaOasis🌴Pool-6 miles to beach
Welcome to the Aqua Oasis! This home was built in 2020 and located just 6 miles to multiple beaches in sunny Englewood, FL! The home consists of 3 bedrooms & 2 full baths, an option to heat the outdoor pool, relaxing outdoor chairs around a gas fire pit, fenced in back yard to let your pets roam, and a gas grill to whip up your favorite meals! If your family desires your own, private space and private pool, but you want close proximity to local beaches- THIS IS FOR YOU!
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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!
ValueFamilyPool

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.
ValueLocationHospitality

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.
ValueFamilyBarbecue
Popular amenities for Don Pedro Island rentals with a pool
House rentals with a pool

Waterfront| Pool & Spa | Near Beach| No Extra Fees
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Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN
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10 mins to Beach, Heated Pool, Beach Gear & Games
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Turtle Bay - minutes to Boca Grande!
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luxury Brand new villa with pool
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Water view Villa private Heated Pool golf beach
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Lemon Bay Getaway
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(Newley Built) Heated Pool/ Golf course Views.
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Condo rentals with a pool

Sunset Beach
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Beach Studio 55
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Entire Beachside Condo! Don’t worry Beach Happy!
LocationValueCleanliness

Ocean Oasis on Manasota Key - Ocean View
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Vintage Villa 35 | Steps to Beach | Pool
LocationValueBathroom

Bay Life @ManasotaKeyCondos
LocationFamilyCondition

Studio, pool, private beach, boat dock shark teeth
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Boardwalk Beachfront Getaway
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Other holiday rentals with a pool

Incredible Water View! Heated/Salt/Sun filled pool
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Sunset Dreams Awaits 36TV
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Island Pool Home, Beach, Dock, Bay, Boating & Fish
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Brand New modern home in Sunny FL with pool/spa
BeachConditionOutdoor spaces

Hidden Gem in Punta Gorda
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Spa, Heated Pool, Tropical Waterfront Near Beach
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Cozy beach house with pool
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Saltwater Pool & Spa Villa on a Gulf-Access Canal
LocationPoolGetting around
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