
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.

Stunning Studio w/Bay & City View Free Park/Pool
INCREDIBLE VALUE! First, a $30 gift card to our restaurant GreenStreet and a bottle of champagne will be awaiting you in your room! in Coconut Grove, this privately owned & renovated deluxe bright studio on the 15th floor of a luxurious waterfront property offers breathtaking bay & city views, is equipped for 2 guests w/king size bed, full kitchen, full bath & balcony. Enjoy all the luxury amenities we offer, pool & hot-tub w/ incredible bay views, penthouse gym, sauna, business center, squash.

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Enjoy a Top Floor condo with stunning ocean views from your living room and balcony. This condo features a King bed in the bedroom, updated kitchen, a queen pull out sofa and a new washer and dryer. Enjoy the wonderful amenities the property offers to include a Large pool/ spa area or relax on the private beach with lounge chairs provided. There are lighted tennis courts, areas to grill out and a small playground. This property sits on 68 acres and one side is surrounded by a nature preserve.

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

Fun the Keys! Pool, Marina, Clubhouse, Fishing & m
Spend your vacation on the bayside of Key Largo, with the best sunsets to end your day. Steps away from the heated swimming pool and kiddie pool. Walk to a strip of restaurants on the water and enjoy a gorgeous sunset. We have the best fishing, snorkeling, kayaking, paddle boarding and diving the world has to offer. Come enjoy the island life in your comfortable and clean vacation house, on a property with everything you need, just bring your groceries! Two bedrooms with private bathrooms.

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.

Condo in Brickell Business District
Stunning one bedroom condo located in the best area of Brickell just minutes away from Brickell City Centre and Mary Brickell Village with restaurants, bars, shops and entertainment. About this Space -Approx.818 sqft of natural light filled space with gorgeous bay and city views and a large private balcony with dining table and large patio couch -High-speed Wi-Fi -1 free assigned parking spot -Pool, hot tub, jacuzzi, steam room, game room, state of the art gym, and business center

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!

Beachside Unit 37 - Come Relax on the Atlantic!
Unit 37 Details: Second Floor, Walk-in shower, Two Queen Beds, Twin Sofa Sleeper, 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. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.” Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean.

Your Bay View Escape in Coconut Grove, Pool & Gym
- Enjoy breathtaking bay views & sunsets in this fully remodeled Coconut Grove condo - Private balcony perfect for relaxing and taking in the scenic surroundings - Full access to building amenities, including a gym, pool, sauna/steam room and jacuzzi -Onsite restaurant, valet/parking and 24/7 security. - Located just steps from Coconut Grove’s best restaurants, shops, and marinas -Fully equipped kitchen, luxurious oversized shower and cozy bedroom with work desk.

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

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.
Popular amenities for Monroe County rentals with a pool
House rentals with a pool

Sea Ray Cove w/ 80' Dock, Pool, Beach & Tiki Hut

Grouper Getaway @ Ocean Isles Fishing Village

Family retreat oasis, heated pool, jacuzzi & grill

Private Paradise between Miami & the Keys

Key Largo Waterfront: Tiki, Dock, Kayak & Pool

Salt&Seaglass. Key Colony. Screen Porch. Pool Club

Waterview from three sides, Cabana Club, 30' Docks

Tiki Time
Condo rentals with a pool

Feels Like Summer ~ Panoramic Water Views! 2BR

LuxuryPH at Brickell Bay-Amazing MIAMI City VIEWS

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

Stylish designer condo in the heart of Brickell

Stylish Studio Icon, Waterfront Building

Ocean Views at Ocean Pointe

Stunning 2 bedroom+17 foot ceilings & heated pool

Sandy Toes Approved — Studio Beach Escape
Other holiday rentals with a pool

Chiquita Waterfront Canal Home

Salty Mermaid Ocean Pointe 4406

Hyatt Windward Pointe! Great Location!

Modern 1BD Penthouse with Stunning Bay View

P76 - Meticulous 2 bed, 2 bath home with stunning

Boat Dock+King Bed & Cabana Club

Hi-Rise Studio in Brickell

Oceanview condo w/pool, jacuzzi
Destinations to explore
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Calusa Beach & Loggerhead Beach
- Coral Castle
- Sea Oats Beach
- Schnebly Redland's Winery & Brewery
- Long Beach
- Everglades Alligator Farm
- Conch Key
- Bahia Honda State Park
- Theater of the Sea
- Homestead-Miami Speedway
- Monkey Jungle
- Key Largo Kampground And Marina
- Seven Mile Bridge
- Calusa Campground
- Sunset Park
- Robbies Marina Of Islamorada
- Dolphin Research Center
- Florida Keys Aquarium Encounters
- Founder's Park
- The Turtle Hospital
- Things to do Monroe County
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- Things to do Florida
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