
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.

King Bed Home by the Bay FAST WI-FI & Coffee
Whether you are visiting the Florida Keys, the beaches of Miami, or looking for a comfortable staycation, discover what South Florida has to offer while feeling at home. You'll be located near Southland Mall, The Falls Shopping Center, Black Point Marina, Miami Metro Zoo, Deering Estates, the Dennis C. Moss Arts Center and more! ❧ 48 minutes from the Florida Keys. ❧ 37 minutes from Miami Beach. ❧ 33 minutes from the Everglades. Message us about long stay, military, & first responder discounts.

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.

Family Oasis Retreat• Heated Pool, Jacuzzi & Grill
Welcome to Forget-me-not Villa, a sanctuary for your family and friends to let loose barefoot and unwind in the private backyard fully fenced, feel the breeze, stargaze at night, and savor the comfort of our exquisite vacation home. The villa features a heated pool and jacuzzi, a grill station, a love seat for romantic moments, a playground for children, an Xbox S for gamers, board games, mini golf, pool volleyball and basketball hoop, Smart TVs& high-speed Wi-Fi & electric car connection.

NEW! "Villa Paradise" ~ Luxury Gem ~ Pool ~ Game Room
Bring your family to the luxurious 3BR 2Bath Villa Paradise in the tranquil and friendly neighborhood in southern Miami, FL. Visit the exciting attractions, natural landmarks, restaurants, shops, and much more, and then retreat to the lavish oasis that will leave you in awe with its stylish design, private backyard, and rich amenity list. ✔ 3 Comfortable BRs ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Heated Pool ✔ Game Room ✔ Smart TVs ✔ Smart House ✔ High-Speed Wi-Fi ✔ Free Parking

One Of A Kind Smart Villa - Pool/Spa/Gym/BBQ/Vibes
🎨 House of Art Miami — where design becomes the experience 🎨 This art-forward smart villa blends resort-style amenities with the comfort, privacy, and freedom of a home. Designed for groups to relax, connect, and enjoy Miami together — without feeling rushed or crowded. 🔥 Heated pool, jacuzzi, fire pit & BBQ 🏀 Mini golf, ping pong & basketball 🖼️ Curated art + immersive sound indoors & out 📍 Minutes from beaches, dining & nightlife More than a stay. An experience. @BeyondTheBNB

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.

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!

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

“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.

*Emerald Seas*-Florida Keys Ocean Front Paradise!
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.
Popular amenities for Monroe County rentals with a pool
House rentals with a pool

Welcome to Waltonhurst

Tropical Retreat Miami 5BR w/Pool | BBQ | GameRoom

Beach House in Marathon with Amazing Backyard!

Everglades-Homestead. Tropical Retreat. Miami-Keys

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

Miami Luxe 4BR | HeatPool • BBQ • Game • Wine Bar

Luxury Oasis in Brickell - Only 3 min to Ocean

Luxury Villa | Spa - Pool |Top Location| Pets |BBQ
Apartment rentals with a pool

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

Oceanfront Breeze, Stunning Views, Beach/Pool

Tropical Escape at Sunrise

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Luxury Condo in Hotel, amenities Downtown/Brickell

Beachside Unit 33-Private Tropical Beach Plus Pool

Old Town Retreat • Pool • Walk to Duval •

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

New Downtown Miami Condo | Pool+Gym+Sauna+Rooftop

Soothing Nest

Tropical Keys Retreat | Pool | Hot Tub | Cinema

Seas the Keys Getaway with plunge pool/spa

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

BellaMoon Oasis Miami

Miami Chic-Heated Pool Near FIU and Coral Gables

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