
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.

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

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.

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.

Gorgeous Ocean View in Paradise, Close to Key West
This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.

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.

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!

Casa Cascada in Coral Gables Area
Welcome to Casa Cascada - in the heart of Coral Gables. Where you are 3 miles from Miami International Airport, close to Miracle Mile, Little Havana, South Beach and some of the best restaurants and shopping in Miami. Come and stay a while where the vibe is eclectic and inspiring, yet the most relaxing. Enjoy any one of our four open concept bedrooms — or relax in our personal favorite space, the backyard. Where the sound of the waterfall soothes your soul.

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

Tiny Home on Waterfront | Bay Views | Deck | Pool

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

Cudjoe Key Home with a View

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

Dec. 60% off! Oceanfront 4 Bikes/2Kayaks. KING bed

Lux 4BR Retreat w/ Heated Pool, BBQ, and Bikes

Anglers Terrace, Condé Nast Traveler's Best Airbnb

3 Bedroom Home - Perfect Location & Private Pool
Condo rentals with a pool

Affordable Beachfront Luxury Condo Sleeps 6

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

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

Stunning 2 bedroom+17 foot ceilings & heated pool

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

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

BEAUTIFUL 2BD ★ OVERLOOKING THE OCEAN ★BRICKELL
Other vacation rentals with a pool

Waterfront, Dock, Pool, Pickleball, near Key West!

Coastal Oasis #44 Key Largo 4BR Villa | Partial

Discount Available! Pool 100' Dock, Fun Amenities!

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

Luxury Villa • Racket Court • Gym • Grand Garden

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

Marathon Keys Escape • Pool • Hot Tub • Near Beach

Searenity Vacation Rental! Pool, Tiki Hut, Dockage
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- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Coral Castle
- Cocoa Plum Beach
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- Cannon Beach
- Far Beach
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- Conch Key
- Theater of the Sea
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- Long Key State Park
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