
Vacation 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.

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. We have bikes available to cruise the miles of nearby paths stretching from Coconut Grove to Black Point Marina.

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.

Feels Like Summer ~ Panoramic Water Views! 2BR
Bluewater Realty Miami welcomes you to The Grand, located in Downtown Miami on Biscayne Bay. Our 2 bedroom Feels Like Summer! is the ultimate retreat. Enjoy incredible panoramic water Biscayne Bay views that will leave you in awe. With South Miami Beach 3 miles away you can take in the sun of Miami Beach, while still feeling the energy of downtown Miami. It's the best of both worlds, giving you the ultimate Miami experience. Your Airbnb Superhosts, Rachel and Mia Bluewater Realty Miami

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.

OCEAN FRONT WITH AMAZING VIEW AND PRIVATE BEACH
ENJOY THE FABULOUS FLORIDA KEYS IN THIS TOP FLOOR NEWLY REMODELED COZY BEACH CONDO Enjoy this updated 1 bedroom condo on the top floor with amazing ocean views! You will enjoy a full kitchen with stainless steel appliances and granite counter tops equipped for your culinary needs. Your living room has a queen pullout couch and small balcony with a fabulous view! Flat screen TVs are in both the living room and bedroom with a King bed. There is also a washer and dryer in your unit!

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!

Key Colony Beach Luxury Condo, New Modern Interior
Luxury private studio condo, ocean front complex, full kitchen, heated pool, private beach in Key Colony Beach, Florida. Enjoy all new furnishings, newly renovated bathroom and a full kitchen stocked with everything you need to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Beautiful ocean front beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use. We provide Amazon Echo for great music during your stay.

2br/1ba w heated pool, 1 mile to robbies marina
Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

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.

Key Largo! Tavernier! Welcome to Paradise!
A perfect tropical getaway! Life is good today! Bright, airy, 500 plus sq ft., canal front studio, close to the bay. From the dock you can KAYAK to mangrove tunnels, fish, or just relax. Cold drink in your hand, life is good today! You are going to have an awesome vacation!! ( NOTE: THE POOL MAY BE SHARED ON OCCASION, WITH OUR FAMILY. A SIGNED LIABILITY RELEASE IS REQUIRED AT CHECK IN )
Popular amenities for Monroe County rentals with a pool
House rentals with a pool

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

The Roseate House at Grassy Key Lic. #VACA-25-222

Waterfront Home 37.5-ft dock, Cabana Club Included

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

NEW! 4-Story Villa, Private Rooftop, Pool, Marina

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Luxury Villa | Spa - Pool |Top Location| Pets |BBQ

Angler’s Terrace Conde Nast Traveler’s Best Airbnb
Condo rentals with a pool

Incredible 49th Flr Bay & Pool Views | Free Spa!

Icon Brickell (W) Huge unit with bay & river views

Front Facing Top Floor Penthouse with Ocean Views

Ocean Views at Ocean Pointe

Fully renovated 2/2 bath condo w/ shared pool!

Ocean views at “Sangria Sunrise” 10% off Charters

Stunning 2 bedroom+17 foot ceilings & heated pool

BEAUTIFULLY DESIGNED OCEANFRONT CONDO
Other vacation rentals with a pool

Tropical Paradise | Best Location, Heated Pool+Spa

Condo de Paradise/Salt Water Pool/Boat Dock

Luxury Villa • Racket Court • Gym • Grand Garden

Waterfront Oasis w/Private Pool-Dockage-Beach

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

Searenity Vacation Rental! Pool, Tiki Hut, Dockage

Oceanfront 3-Story Luxury, Dockage, Gameroom

BellaMoon Oasis Miami
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- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Coral Castle
- Cocoa Plum Beach
- Calusa Beach & Loggerhead Beach
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- Sea Oats Beach
- Far Beach
- Everglades Alligator Farm
- Conch Key
- Theater of the Sea
- Long Key State Park
- Monkey Jungle
- Long Beach
- Horseshoe Beach
- Schnebly Redland's Winery & Brewery
- EAA Air Museum
- Bahia Honda State Park
- Windley Key Fossil Reef Geological State Park
- Sandspur Beach
- Keys' Meads
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