
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.

Beach House, Private Pool, Dock, Gulf View Sunsets
You don’t come to the islands to stay in a town—you come to slow down. Welcome to our tropical keys beach home, tucked away from the traffic and noise of US Hwy #1. Sway with the palms on the wraparound deck, soak in wide-open panoramic bay views, and catch fiery sunsets right off your dock. Fire up the BBQ, brew a Keurig, float in the private pool, or cast a line from the 300’ private pier/dock. Easy going island living with ocean / gulf breezes, comfy beds, quality linens, Wi-Fi, and cable TV.

*NEW!*Paradise Point~VIEWS!~Open Water~Dock~Pool!
✨ Welcome to Paradise Point! 🌊⛵ Indescribable Views! This stunning sanctuary offers Water Frontage on 3 sides giving over 180° of unparalleled Atlantic Ocean Views, Direct Ocean Access from your Private Dock, perfect for boating or fishing right from the backyard🎣🐟 After a day on the water, unwind in your Heated Pool, take in the breathtaking views, & fire up the grill for a sunset BBQ to remember! 🌅 Whether you're looking for relaxation, luxury, or adventure, Paradise Point has it all! 🌴☀️

Tiny Home on Waterfront | Bay Views | Deck | Pool
Down by the waters of Manatee Bay, you’ll find this idyllic tiny home for 6. With a full kitchen, three comfy beds,and access to a community pool, this is a prime location to enjoy the best of Key Largo. Sit on the deck and dip your toes in the water or explore the bay using the available kayaks and paddle boards. 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!

Castillo Del Mar- Ocean access from your backyard
Welcome to PARADISE! — perfect for salty families, fishing lovers and beach goers • Prime Location – In Key Colony Beach with access to Cabana Club pool & private beach • Walk to Dining – Steps from Sparky’s Landing & Island Company • Boater’s Paradise – Backyard dockage for boats up to 30 ft • Spacious Kitchen – Family-style layout with 4-person bar top • Boho Dining Room – Perfect for cozy dinners and entertaining • Amenities include washer + dryer, fully stocked kitchen, Cozy Tv Room

Amazing Oceanfront Home
Mesmerizing views, directly on the Atlantic Ocean! Sleeps 10 with 4 bedrooms and 3 bathrooms. We have a 28 foot pool (heat, for an extra charge) with a view you will not forget. We have Paddle boards, Kayaks, bikes, snorkel gear, etc. We also have a game room with a ping pong table, big screen TV, card table, and a piano. We have a very nice Kid's Park (just down the street). I do Last Minute Deals, just contact me! We require a standard signed rental agreement in order to rent the house.

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.

The Lighthouse - Beach Houses Key West
If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

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!

Islamorada Bungalow # 5
Bring the whole family to this great place with lots of room for fun.Escape to our charming 2-bedroom, 1-bathroom bungalow in Islamorada, FL, where luxury and convenience await! Relax on the spacious patio and take a refreshing dip in the pool, perfect for unwinding after a day of exploring nearby attractions. You're just moments away from pristine beaches, world-class fishing. Whether you seek adventure or relaxation. Secure your stay now for an unforgettable experience!

Great key Largo home with water front and pool
we have a dog clean fee , always ask the before booking Fantastic canal front home located in Key Largo. Bring your own boat and enjoy it all! The home is minutes away from Gilbert resort, best seafood in the world at any number of local restaurants, Souvenir stores and the best fishing and diving spots. The home has 2 bedrooms and 2 bathrooms, fully furnished, spacious living room with large TV, Full kitchen with all appliances and amenities and a beautiful deck

Private Pool Tropical Oasis - Centrally Located
Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool, loungers and outdoor games. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play, bed rails, booster seat, baby gate and kids dishware.

“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

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

Lake Of Dreams Miami House - The Perfect Place

Blue House Marine in Key Largo

White House - Receive $400 towards a Boat Rental!

P87 - Modern 4 bedroom, 4 bath home on open water

⭐ Rare Waterfront Western Exposure Vacation Home

Luxury Glow Villa | 4K Cinema | Heated Pool & Spa

FL Keys Ocean Front Escape
Condo rentals with a pool

Gorgeous lagoon-front 2BR Townhouse with 2 pools

Your Happy Place - Oceanfront

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

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Ocean Shores Villa 2 with pool and boat slip

Ocean views at “Sangria Sunrise” 10% off Charters

Beachside Unit 33-Private Tropical Beach Plus Pool

Tiki Time! Ocean Pointe Top Floor King 1 Br/1Ba
Other holiday rentals with a pool

Soothing Nest

Sol Island ~ Waterfront Oasis ~ Pool ~ Dock ~ Kayaks

Renovated Anglers Reef 2BR + Sleeper + Ocean Views

Waterfront 2-bedroom Home w/Pool and Spa

Seas the Keys Getaway with plunge pool/spa

Premium Waterfront Marco Island Condo

NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom

Tequila Sunrise
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Havana Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Rentals with a fire pit Florida Keys
- Townhouse rentals Florida Keys
- Condo rentals Florida Keys
- Ski-in/ski-out rentals Florida Keys
- Guesthouse rentals Florida Keys
- Mansion rentals Florida Keys
- Beach house rentals Florida Keys
- Rentals with a fireplace Florida Keys
- House rentals Florida Keys
- Cottage rentals Florida Keys
- Tiny house rentals Florida Keys
- Bed and breakfasts Florida Keys
- Resort rentals Florida Keys
- Luxury rentals Florida Keys
- Rentals with a washing machine and dryer Florida Keys
- Apartment rentals Florida Keys
- Private suite rentals Florida Keys
- Holiday home rentals Florida Keys
- Rentals with a kayak Florida Keys
- Rentals with breakfast Florida Keys
- Serviced apartment rentals Florida Keys
- Rentals with beach access Florida Keys
- Rentals with an EV charger Florida Keys
- Hotel rooms Florida Keys
- Rentals with outdoor seating Florida Keys
- Pet-friendly rentals Florida Keys
- Rentals with a patio Florida Keys
- Beach condo rentals Florida Keys
- Rentals with an accessible height bed Florida Keys
- Smoking-friendly rentals Florida Keys
- Rentals with a home theatre Florida Keys
- Boat rentals Florida Keys
- Villa rentals Florida Keys
- Rentals with lake access Florida Keys
- Fitness-friendly rentals Florida Keys
- Family-friendly rentals Florida Keys
- Boutique hotels Florida Keys
- Beachfront rentals Florida Keys
- Rentals with a hot tub Florida Keys
- Rentals with an accessible height toilet Florida Keys
- RV rentals Florida Keys
- Bungalow rentals Florida Keys
- Houseboat rentals Florida Keys
- Rentals with a sauna Florida Keys
- Campsite rentals Florida Keys
- Waterfront rentals Florida Keys
- Rentals with pools Florida
- Rentals with pools United States
- Bayfront Park
- Bayside Marketplace
- Kaseya Center
- Brickell City Centre
- Everglades National Park
- University of Miami
- Calle Ocho Plaza
- Sombrero Beach
- LoanDepot Park
- Dolphin Mall
- Zoo Miami
- John Pennekamp Coral Reef State Park
- CG Cosmetic Surgery
- Crandon Beach
- Biscayne National Park
- Key Biscayne Beach
- Biltmore Golf Course Miami
- Florida International University
- Avana Plastic Surgery
- Phillip and Patricia Frost Museum of Science
- Coral Castle
- Fairchild Tropical Botanic Garden
- Mia Aesthetics Miami
- Schnebly Redland's Winery & Brewery
- Things to do Florida Keys
- Sports activities Florida Keys
- Sightseeing Florida Keys
- Nature and outdoors Florida Keys
- Art and culture Florida Keys
- Tours Florida Keys
- Food and drink Florida Keys
- Things to do Florida
- Entertainment Florida
- Sports activities Florida
- Wellness Florida
- Food and drink Florida
- Tours Florida
- Art and culture Florida
- Nature and outdoors Florida
- Sightseeing Florida
- Things to do United States
- Entertainment United States
- Wellness United States
- Sports activities United States
- Art and culture United States
- Sightseeing United States
- Tours United States
- Food and drink United States
- Nature and outdoors United States




