Vacation rentals with a pool in Lower Matecumbe Key

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Lower Matecumbe Key

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

A comfortable living area is highlighted by a light-colored sofa with textured cushions, accompanied by a woven coffee table. Natural light enters through multiple windows, revealing touches of coastal decor and a glimpse of a bedroom in the adjacent space.

Cottage in Islamorada

Islamorada bungalow 2 bed & pool

Welcome to paradise! Completely remodeled and immaculately maintained, Bungalow Blue is nestled away in the quiet quaint Shady Palms community of 7 cottages in Islamorada, MM 76. Ideally situated next to the community heated pool, down the street from private boat ramp. If you're looking to relax and unwind while also being close to all that Islamorada has to offer, this is the place for you. Enjoy the FL Keys lifestyle in your private backyard, take a bike ride to World Famous Robbie's Marina

4.95 out of 5 average rating, 106 reviews

Guest favorite

A collage showcases four images: A serene sunrise over water, a cozy bedroom with a flat-screen TV, an open-concept living area with a kitchen and dining space, and a tranquil view of the evening sun reflected on the bay, complete with a kayak along the shoreline.

Home in Key Largo

Tiny Home on Waterfront | Bay Views | Deck | Pool

Down by the waters of Manatee Bay, you’ll find this idyllic tiny home for 6. With a full kitchen, three comfy beds,and access to a community pool, this is a prime location to enjoy the best of Key Largo. Sit on the deck and dip your toes in the water or explore the bay using the available kayaks and paddle boards. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

4.91 out of 5 average rating, 208 reviews

Guest favorite

A thatched-roof gazebo provides a sheltered seating area with wooden adirondack chairs. The serene ocean glimmers in the distance, while green navigation markers are visible on the water's surface. The structure features a wooden railing surrounding the space, enhancing the coastal atmosphere.

Condo in Tavernier

Toes in the Sand - 2 Bedroom Condo Sleeps 4

Two bedrooms and two full bathrooms on the 4th floor with ocean views. Amenities include a huge heated pool and hot tub with a bar, a beach cafe serving food and drinks, a private Key's beach, viewing pier, rentable boat slips & boat trailer storage, tennis, pickleball courts, basketball, children's swings, and BBQ areas, and gated entry with 24-hour security! Just remember that you're on "Island Time," mon, relax and enjoy! Perfectly located between Key Largo and Islamorada, close to Penneka

4.86 out of 5 average rating, 271 reviews

Guest favorite

A serene waterfront view is framed by palm trees, with two green chaise lounges positioned for relaxation. The setting sun casts warm hues across the sky, reflecting on the water's surface. A Tiki structure adds charm, creating an inviting outdoor space.

Tiny home in Key Largo

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.

4.96 out of 5 average rating, 213 reviews

Guest favorite

Home in Key Largo

Largo Getaway: 3 King Suites + In-Law Space

🔑 Managed by KEYLARGOTRAVELS See our profile for all listings. VIRTUAL TOUR: YouTube @Keylargotravels, go to Shorts it is called Mariners 🛏 SLEEPING Bedroom 1 – First Floor In-Law Suite: King bed, en-suite full bathroom with shower, plus a full-size sleeper sofa in the living area Bedroom 2 – Third Floor Master: King bed, en-suite full bathroom, plus a twin floor mattress available if needed Bedroom 3 – Third Floor Guest Suite: King bed plus twin bunk beds, en-suite full bathroom

4.93 out of 5 average rating, 100 reviews

Top guest favorite

A sunset view is captured from a covered outdoor seating area, showcasing a tranquil waterway. Silhouettes of kayaks and a table are visible, while the setting sun creates a warm glow across the horizon. Natural textures are evident in the thatched roof above.

Tiny home in Key Largo

My Little Oasis2 Waterfront Retreat, Key Largo

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.

4.97 out of 5 average rating, 236 reviews

Superhost

A bright living area features a comfortable gray sofa, decorative chairs, and a coffee table on a patterned rug. Natural light floods the space through large windows, creating a relaxed atmosphere. A wall-mounted TV and a small desk can also be seen, along with coastal decor.

Apartment in Tavernier

When Paradise is Key: Tropical Oceanfront Condo

🚨*PRICE YOU SEE IS ALL IN! Includes Airbnb fees and taxes!*🚨 🚨09.09.26 - 10.14.26 Elevator will be out of service due to installation of a new elevator 🚨 ☀️ Discover the ultimate beachfront getaway in our top floor, two-bedroom, two-bathroom condo, perfectly designed to offer an unforgettable escape. Nestled right on the oceanfront, this retreat comfortably accommodates up to six guests, making it ideal for families, friends, or couples seeking a serene coastal experience. ⛱️

4.88 out of 5 average rating, 102 reviews

Top guest favorite

A clear view of the ocean is captured from the balcony, showcasing the shimmering water beneath a bright blue sky. Lush greenery lines the foreground, while a dock extends into the sea. The scene conveys a serene coastal atmosphere.

Condo in Tavernier

Ocean Views at Ocean Pointe

Conveniently located at MM 92.5, approximately 1 hour drive from Miami, you can enjoy a modern, newly redecorated Keys escape with amazing views of the sunrise right from your oceanside balcony. 2 bed/2 bath with full kitchen and washer/dryer. Pool, beach, pier, BBQ area, and private boat marina within this private community. Kayaks, paddle boards and bikes available for rent. No need to leave, but grocery stores, spas and ample restaurants are close by to fill any need.

4.99 out of 5 average rating, 225 reviews

Superhost

Home in Islamorada

Islamorada Bungalow #5

Bring the whole family to this great place with lots of room for fun.Escape to our charming 2-bedroom, 1-bathroom bungalow in Islamorada, FL, where luxury and convenience await! Relax on the spacious patio and take a refreshing dip in the pool, perfect for unwinding after a day of exploring nearby attractions. You're just moments away from pristine beaches, world-class fishing. Whether you seek adventure or relaxation. Secure your stay now for an unforgettable experience!

4.81 out of 5 average rating, 42 reviews

Guest favorite

A bright bedroom features a spacious bed with a white duvet cover and decorative teal throw. Art depicting fish adorns the walls. Natural light enters through the window, complemented by a stylish lamp. A wooden dresser occupies one corner, enhancing the room's coastal theme.

Bungalow in Islamorada

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

Sleeps 5 adults. 3rd bed is si sofa bed with a queen mattress. Indulge in the ultimate tropical retreat at our captivating bungalow Castaway Island, showcasing over 120 perfect guest reviews across multipl venues. Your hosts' extensive hospitality experience is evident in the restoration and thoughtful amenities, guaranteeing an exceptional vacation experience. Discover your ideal home away from home, where every detail is carefully designed to surpass expectations.

4.96 out of 5 average rating, 79 reviews

Top guest favorite

A private backyard features a heated pool surrounded by tropical landscaping. Lounge chairs are positioned on the wooden deck beside the pool. The two-story home includes large glass doors that open onto the deck, providing easy access to outdoor spaces.

Home in Duck Key

Private Pool Tropical Oasis - Centrally Located

Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool, loungers and outdoor games. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play, bed rails, booster seat, baby gate and kids dishware.

5.0 out of 5 average rating, 120 reviews

Guest favorite

A serene pool area is framed by lush palm leaves, highlighting a sparkling pool with a bubbling spa. Sun loungers are arranged around the pool, complemented by a large blue umbrella providing shade.

Cottage in Islamorada

2BR Island Cottage | Pool • Grill • Near Robbie’s

SEPTEMBER & OCTOBER SPECIAL — SAVE 30%! 🍋 Escape to Key Lime Cottage, a charming 2BR retreat in the heart of the Florida Keys. Enjoy a full kitchen, beautiful pool shared with just 6 neighboring cottages, outdoor seating, grill & fire pit, and paddle boards. Close to Robbie’s Marina and perfectly located for fishing, dining, exploring or simply relaxing. Limited fall dates remain at this special rate — book your Keys getaway while the deal lasts!

4.96 out of 5 average rating, 152 reviews