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

Fully renovated 2/2 bath condo w/ shared pool!
**Brand New Listing** Welcome to Captains Choice - The NICEST Unit at Sunrise Suites Key West, unit 302. Tropical winds, sunset views and Key West charm await when you book your stay in this gorgeous completely renovated two bedroom, two bathroom condo "Captain's Choice". Highlights include: Smart TVs in each room Keurig New stainless Kitchen/appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, & Smathers Beach End unit One parking space, free of charge

Oceanfront Lookout Point w/two Kayaks & Deck
Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi
Escape to Northern Key Largo for a relaxing vacation! Discover great restaurants, beautiful state parks, and marine life. This bright, modern studio boasts excellent views of Manatee Bay, free kayaks and paddle boards, and a full kitchen. With access to a swimming pool and docks, there’s always something to do. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

Oasis2 in Key Largo With a million dollar view
Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

Quiet tropical Oasis setting with 1 bed and 1 bath
Tropical oasis centrally located between Miami Beach and Key Largo. Although you may never want to leave. The cozy casita with private bath and balcony is tucked away, surrounded by lush vegetation and sounds of the waterfall. Take a dip in the pool or grotto, relax with an afternoon cocktail under the tiki hut, or snooze in the hammock. During those cooler months soak in the hot tub. Enjoy the miles of nearby walking paths stretching from Coconut Grove to Black Point Marina.

New Aqua Lodge 2Beds 1 Bath with Full Kitchens
This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Kawama N2 Relaxing Lagoon View free bikes & kayaks
Relax and enjoy our family friendly 3 bedroom/3 bathroom Villa Lago in Key Largo! Salt water swimming lagoon, Pools, the Ocean, fishing pier, Marina, Tennis, Bikes, fire pit and playground. Enjoy resort like amenities in the comfort of a home. This beautifully decorated villa sleeps 8 and is conveniently located in a very central location in Key Largo. Close to some great restaurants, diving, fishing, boat tours, State Park. Kawama is fun for all ages.

Beachside Unit 33-Private Tropical Beach Plus Pool
Unit 33 Details: Second Floor, Walk-in shower, Two Queen Beds, Maximum Occupancy 4 Guests, No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

Angler’s Terrace Conde Nast Traveler’s Best Airbnb
As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views

Starr's Suite - 2 person K Suite w/Private Spa!
Starr's Suite features a King Pillow-Top Memory Foam mattress. Renovated in 2010, it features a tumbled marble shower, granite counter-tops in kitchen with dishwasher and vanity. Tommy Bahama bath amenities are provided, as well as coffee, creamer and sugar. 56” Smart TV (bring UN/PW for Netflix, Amazon, etc. to watch your favorite shows). Private Solana spa in your private courtyard. Daily housekeeping is provided. Use of 2 heated pools.

Exquisite Oceanfront Paradise - Key Colony Beach
Experience a wonderful ocean view from our beachfront condo in Key Colony Beach. Newly renovated ground floor with a stunning, clean white interior and just a few steps from our private beach and heated pool. Continental Inn Unit #10 offers one King size bed that sleeps two people. A fully equipped kitchen with essentials (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Reliable WiFi and Smart TV.

“Have Fun at Hacienda Paraíso” Suite 1 | pool |
Welcome to Room 1, the first addition at Hacienda Paraíso. This suite is conveniently located next to another Airbnb suite, providing flexibility for your stay. It features a private entrance, bathroom, kitchenette, and dining table, ensuring a comfortable and self-contained experience. Enjoy the convenience of hotel-like amenities paired with the added bonus of access to our stunning pool and lush yard, creating a truly relaxing retreat.
Popular amenities for Florida Keys rentals with a pool
House rentals with a pool

Cozy 2 br/2 bath home in Cudjoe

Marathon Keys Escape • Pool • Hot Tub • Near Beach

Large Waterfront Home, w/Efficiency, Pool, Kayaks

*New Modern*3/2Duplex/37' Dock/Cabana/Kayaks/Bikes

Waterfront House with 37 ft Dock & Cabana Club

Marathon one-level home on the Marina - with slip!

Tiki Time 2

The Purple Pelican Inn/Private Hot Tub
Condo rentals with a pool

Luxury Top Floor Suite W/ Unobstructed Ocean View

Canal View Condo w/ Pool, Balcony & Bar

Gorgeous lagoon-front 2BR Townhouse with 2 pools

Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath

Tropical Escape at Sunrise

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

🏝 Oceanfront Paradise Awaits You
Other holiday rentals with a pool

Ocean Front Studio private Sandy Beach in Key West

Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s

Twilight #32 Key Largo 4BR Villa | Pool,

Discount - Jan 31! 3 Bed/3 BA Cabana Club Access!

NEW! CASA LARGO -Golf Cart, 2 Kings 3 Bath, Kayaks

Seas the Keys Getaway with plunge pool/spa

Vacation Home Heron Hideaway

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
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- Bayfront Park
- Bayside Marketplace
- Brickell City Centre
- Kaseya Center
- Everglades National Park
- University of Miami
- Sombrero Beach
- LoanDepot Park
- Florida International University
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Dolphin Mall
- Key Biscayne Beach
- Biscayne National Park
- Crandon Beach
- Biltmore Golf Course Miami
- Phillip and Patricia Frost Museum of Science
- Coral Castle
- Fairchild Tropical Botanic Garden
- Sea Oats Beach
- Schnebly Redland's Winery & Brewery
- Miami Seaquarium
- Everglades Alligator Farm
- Matheson Hammock Park
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