
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.

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!
Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

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.

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.

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.

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.

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.

Luxe Pool & Fire Pit | 5 min to Dolphin Mall
Experience sun-soaked luxury in Miami! Dive into the refreshing saltwater pool or unwind on one of the poolside lounge chairs. Newly renovated in 2022, this 4 bed/3.5 bath home comfortably accommodates 10 guests. For endless entertainment, compete in games of ping pong, sing your heart out with the karaoke machine, enjoy board games, or shoot some hoops. Presented by SuCasa Vacay, every detail has been thoughtfully chosen for an unforgettable Miami stay. Property Name: SuCasa Palmas

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!

“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.

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

Private Backyard Oasis • Pool, Jacuzzi & Grill

Lake Of Dreams Miami House - The Paradise Place

KW CanalFront 3BR: Htd Pool, Boat Tie-Up, Pet OK

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

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Waterfront Home 37.5-ft dock, Cabana Club Included

BellaMoon Oasis Miami

State-of-the-art 5-Acre Retreat Pool•Garden•Ponds
Condo rentals with a pool

Gorgeous lagoon-front 2BR Townhouse with 2 pools

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

Tropical Escape at Sunrise

Modern Luxe at Brickell | Pool & Spa Access

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Enjoy sunsets & sunrise in your home away home.

Ocean views at “Sangria Sunrise” 10% off Charters

Beachside Unit 33-Private Tropical Beach Plus Pool
Other vacation rentals with a pool

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Everglades-Homestead. Tropical Retreat. Miami-Keys

Marathon Keys Escape • Pool • Hot Tub • Near Beach

Waterfront Islamorada Pool Heated Home private

Heated* Pool•Hot Tub•Sauna•Games•Prime for Groups*

Cali King 1 BedRoom: Pool Gym Balcony Jacuzzi

Carney's Reef 1B/1B Pool, Large Patio &Living Room

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