
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.

Make It Happen! Brand New with Amazing Water Views
Bluewater Realty Miami welcomes you to The Grand, located in Downtown Miami on Biscayne Bay. Our 2 bedroom Make It Happen! is the ultimate retreat, equipped with everything you could need. Enjoy views of Biscayne Bay and Margaret Pace Park that will leave you in awe. With South Miami Beach 3 miles away you can indulge in the sun of Miami Beach while still feeling the energy of downtown Miami, giving you the ultimate Miami experience. Your Airbnb Superhosts, Rachel and Mia Bluewater Realty Miami

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.

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

Luxury Villa | Spa - Pool |Top Location| Pets |BBQ
Welcome to Jessica and Javier House in Miami! We want to Be your Hosts ! Let us show you why you should book with us: - 2000 ft2 ground floor house - 3BDR Designed for 12 guests - 5 Min to Zoo - 20 Min to Coral Gables and Little Havana - 25 Min to Beach - 30 Min to Miami Airport - Residential Area - Private Pool - Spa - Fast WIFI - Fully equipped kitchen - Dedicated work space - Free Onsite parking - BBQ - Outside dining - Washer & Dryer - Kids and Pet friendly - 2 Sofa beds - Family games

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.

Modern Casa Alegre 2bed/2bath with Pool
Have fun with the whole family and Friends at this stylish Luxury pool Home. Relax under the covered patio or cook all you want on the grill enjoying the view of a nice yard. Parking inside (2) and street. The home is centrally located near popular tourist destinations. Coconut Grove is about 5 min drive, calle ocho (8th street) is 5 min drive, Key Biscayne island (Beaches) is 10 min, Brickell and downtown is 10 min, South beach is about 20 min drive and the airport about 15 min drive.

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.

Lighthouse - Beach Houses Key West
If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. Our amazing Lighthouse is a 2 bed 1 bath Loft Bungalow sitting just a few feet from our private beach. The master bedroom loft is accessed by a spiral stair, and has a beautiful bird’s eye view of the Atlantic Ocean. Our nautical inspired living room leads outside to an exterior deck facing the beach perfect for peaceful mornings.

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!

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

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

Welcome to Waltonhurst

Luxe Super Snapper-Heated Pool, Tiki, Dock, Lanai

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

Luxury Villa • Racket Court • Gym • Grand Garden

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

BellaMoon Oasis Miami

Jan 17-24 Last Minute Cancellation
Apartment rentals with a pool

Canal View Condo w/ Pool, Balcony & Bar

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Front Facing Top Floor Penthouse with Ocean Views

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

Upper Penthouse Corner Unit 2B/2B | Icon Brickell

Stunning 2 bedroom+17 foot ceilings & heated pool

Beachside Unit 33-Private Tropical Beach Plus Pool

Your Bay View Escape in Coconut Grove, Pool & Gym
Other holiday rentals with a pool

Tropical Paradise | Best Location, Heated Pool+Spa

Condo de Paradise/Salt Water Pool/Boat Dock

Discount Available! Pool 100' Dock, Fun Amenities!

A Miami Dream House | Heated Pool | GameRoom | Fun

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

Marathon Keys Escape • Pool • Hot Tub • Near Beach

Waterfront 2-bedroom Home w/Pool and Spa

Chiquita Waterfront Canal Home
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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
- Cannon Beach
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- Sea Oats Beach
- Everglades Alligator Farm
- Conch Key
- Theater of the Sea
- Monkey Jungle
- Long Key State Park
- Horseshoe Beach
- EAA Air Museum
- Schnebly Redland's Winery & Brewery
- Long Beach
- Windley Key Fossil Reef Geological State Park
- Bahia Honda State Park
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