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

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!

Guesthome w/ Heated Pool 5 mins from Miami Airport
This home is located just 5 minutes from the Miami Airport and is central to many attractions here in Miami. Take a walk down Calle Ocho, swim at Miami Beach, enjoy a game at Marlins baseball stadium or American Airlines Arena (home to the Miami Heat), and dine at one of the many popular restaurants such as Versailles. These are all within 15 minutes of this private comfortable home. Come enjoy a location that provides a rich experience into the vibrant hispanic culture that Miami radiates.

Sanctuary Salt water heated pool BBQ Grill Oasis
Come and create unforgettable memories in this modernly designed single-family home with a spacious layout and a range of comfortable bedrooms. It features two king-size beds, one queen-size bed, and a twin fold-up bed, as well as an Italian queen-size sofa bed. The house is bathed in natural light and boasts modern amenities that cater to your convenience. Located in a prime location, this house is close to all the tourist areas!! The pool is salt water with heater, Also a grill area

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.

Luxe Pool & Fire Pit | 5 min to Dolphin Mall
Experience sun-soaked luxury in Miami! Dive into the refreshing saltwater pool or unwind on one of the poolside lounge chairs. Newly renovated in 2022, this 4 bed/3.5 bath home comfortably accommodates 10 guests. For endless entertainment, compete in games of ping pong, sing your heart out with the karaoke machine, enjoy board games, or shoot some hoops. Presented by SuCasa Vacay, every detail has been thoughtfully chosen for an unforgettable Miami stay. Property Name: SuCasa Palmas

Lux apartment in Miami downtown
The best location in Miami Downtown, with a unique view of the bay and the City. Spacious and with high quality details The apartment has large spaces, a living room with a large sofá, a queen bed. It also has smart tv and internet, and coffee in capsules, tea, some bottles of water and other quality details are also offered. Guest access grill and entertainment area pool, online meetings and work sector, different offices and of course a full equipped gym.

The Miracle Cottage & Pool on Acre Miami Florida
Beautiful, brand new PRIVATE cottage on an acre property situated in million dollar neighborhood. Perfect place to relax and enjoy the Miami sun. This is a little piece of heaven in the heart of a magical city. Come & enjoy your best vacation. Charming , peaceful & comfortable . Cottage is a completely separate building from the main house. It’s 900 sf of living area. Cleaning & Decontamination as per CDC guidelines before every check in.

“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.

Eva | 12 ppl HOT Pool |Top Location | Piano | Golf
Renovated family home with 5 bedrooms and 4 full bathrooms. Heated pool year-round, mini golf, BBQ area and swing. Modern design with piano and Smart TVs. Parking for 5 cars. Prime location near airport, beaches and nightlife. Sleeps up to 16: 1 king, 2 queen, 2 full, 2 twin and 2 sofa beds (full & queen). Please confirm total guests. Add pets to reservation. Notify us if traveling with children for pool fence.

Early Bird Deal:Miami Studio w/Marriot Club Access
Welcome to your NEW studio at The Elser — a modern, resort-style tower in the heart of Downtown Miami. Stay steps from Kaseya Center, Bayside, Bayfront Park, and the waterfront. Enjoy the energy of the city outside and a calm, private space inside. ✨ 11+ years hosting · 10K+ 5-star reviews · 50K+ guests — we focus on clean spaces, smooth check-ins, and stays that simply work.

Miami Lux Lake Front Retreat
A destination on its own: 1. Spacious home- over 5500 sqft of living space. 2. Gym with sauna and steam shower. 3. Pool table 4. Gourmet kitchen. 5. Formal dining room. 6. Large TV room with leather sectional, all recliner. 7. Karaoke 8. Kayaks to enjoy the lake 9. Heated Pool 10. Outdoor ping pong 🏓 table 11. Gym 12. Sauna and steam Room

Luxurious house with pool and recreational areas.
Incredible house with 5 bedrooms, 3 bathrooms, large spaces, basketball court, billiards, ping pong, mini golf, heated pool, children's games, barbecue, in one of the best areas of Miami, close to the zoo, beaches, restaurants and recreational and commercial centers.
Popular amenities for Monroe County rentals with a pool
House rentals with a pool

Private Paradise between Miami & the Keys

4BR 3B, Heated Pool & Spa, 60' Dock

| LuxeLanding | Pool+Lounge+Chess+BBQ+Golf+Airport

Heated Pool Oasis • 12 Guests •Midway Keys & Miami

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

The Lux Paradise Miami

Modern Miami Escape | Heated Pool | Games

Marathon one-level home on the Marina - with slip!
Apartment rentals with a pool

Gorgeous lagoon-front 2BR Townhouse with 2 pools

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

Your Happy Place - Oceanfront

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Oceanfront Brickell Miami Condo Pool Free Parking

Cali King 1 BedRoom: Pool Gym Balcony Jacuzzi

Gorgeous Ocean View in Paradise, Close to Key West

Tropical Old Town Bungalow
Other holiday rentals with a pool

Luxury Lakefront Getaway

Beach House in Marathon with Amazing Backyard!

Luxury Boat Stay | Resort Amenities

3BR In Resort Village, Pools, Free Kayak & Shuttle

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

Beach House, Private Pool, Dock, Gulf View Sunsets

Castillo Del Mar- Ocean access from your backyard

Breeze | Family Retreat | Pool & Jacuzzi | 4BR
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- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Long Beach
- Coral Castle
- Homestead-Miami Speedway
- Sea Oats Beach
- Schnebly Redland's Winery & Brewery
- Bahia Honda State Park
- Theater of the Sea
- Everglades Alligator Farm
- Conch Key
- Calusa Campground
- Sunset Park
- Key Largo Kampground And Marina
- Seven Mile Bridge
- The Turtle Hospital
- Dolphin Research Center
- Florida Keys Aquarium Encounters
- Robbies Marina Of Islamorada
- Monkey Jungle
- Homestead Bayfront Park
- Founder's Park
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