Vacation rentals with a pool in Islamorada

4.95 out of 5 average rating, 105 reviews

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

4.96 out of 5 average rating, 151 reviews

A serene pool area is surrounded by lush tropical landscaping and palm trees. Lounge chairs are positioned around the pool, along with blue umbrellas providing shade. The clear water sparkles under the bright sun, creating an inviting space for relaxation.

Cottage in Islamorada

Charming 2BR cottage in prime keys location w/pool

Your slice of Islamorada awaits at Key Lime Cottage! Step inside this 2-bedroom retreat and you’ll instantly feel at home. Tucked in a quiet neighborhood yet right in the heart of the Florida Keys, it’s the perfect blend of relaxation and convenience. Enjoy a full kitchen, access to a beautiful pool shared with just six homes, outdoor seating with a grill and fire pit and paddle boards. Whether you’re here to unwind, explore, or fish, everything you need for a perfect Keys getaway is right here.

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.

4.86 out of 5 average rating, 271 reviews

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

4.96 out of 5 average rating, 212 reviews

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.

A private beach area is revealed, featuring rows of blue lounge chairs set on soft, sandy ground. Lush greenery borders the beach, while a wooden pier extends into the calm, turquoise water. A thatched gazebo provides shade, and scattered palm trees complete the coastal scene.

4.95 out of 5 average rating, 151 reviews

Your Happy Place - Oceanfront

Experience the ultimate coastal getaway at Ocean Point in the Florida Keys. Nestled along the Atlantic Ocean, our 2 bed/2 bath condo offers unrivaled ocean views from the moment you step inside. Indulge in the array of amenities available at our property including a private beach, pier, marina, snorkeling, family pool and a full service restaurant. Our condo comfortably sleeps 6-7 guests. Equipped with full kitchen and washer/dryer, we provide all the conveniences for a seamless stay.

4.97 out of 5 average rating, 231 reviews

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.

Superhost

Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.

Villa in Marathon

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!

4.86 out of 5 average rating, 609 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

4.96 out of 5 average rating, 79 reviews

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.

5.0 out of 5 average rating, 117 reviews

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.

4.94 out of 5 average rating, 158 reviews

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

Turtle lovers rejoyce! Enjoy this Two Bedroom/Two Bath Condo with the perfect blend of style, comfort and convenience. Featuring a spacious living room and a fully stocked Kitchen. The Master bedroom features a King size bed and ensuite master bathroom. The guest bedroom features a Queen bed with a unattached bathroom. Both bathrooms feature a walk-in shower. The balcony offers views of the nature preserve and peek-a-boo views of the Atlantic Ocean!

5.0 out of 5 average rating, 13 reviews

Townhouse in Islamorada

Fishing Getaway | Dock, Pool & Sunrise

Wake up to breathtaking oceanfront sunrises in the Sportfishing Capital of the World. This luxury 3BR, 3BA townhome in Islamorada features a private dock, waterfront resort-style pool, and a quiet gated community just minutes from the Keys’ best fishing, marinas, restaurants, and attractions. Pet-friendly and fully equipped, it’s the perfect escape for anglers, families, couples, and extended stays.

Popular amenities for Islamorada rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 113 reviews

Casa Solaris | Key Largo home with Private Pool!

A waterfront patio is shown with comfortable seating, overlooking a calm body of water. The sun sets in the distance, casting warm light over the scene. Tropical vegetation can be seen, adding to the serene atmosphere.

4.9 out of 5 average rating, 173 reviews

The Paradise 2

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.

4.91 out of 5 average rating, 205 reviews

Tiny Home on Waterfront | Bay Views | Deck | Pool

A multi-story home is reflected in the calm water, showcasing a spacious deck with dining furniture under palm trees. Lush greenery surrounds the property, enhancing the serene environment. The structure features a staircase leading to a balcony, offering views of the tranquil setting.

4.91 out of 5 average rating, 149 reviews

Paradise Palace 3/3 Waterfront Pool Kayak 60' Dock

4.95 out of 5 average rating, 108 reviews

Home in Marathon

4BR 3B, Heated Pool & Spa, 60' Dock

4.93 out of 5 average rating, 123 reviews

Mariners 212 Great Location with Marina Views

Superhost

Home in Marathon

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

5.0 out of 5 average rating, 4 reviews

5.0 out of 5 average rating, 22 reviews

El Encanto | Private pool & tropical tiki

Condo rentals with a pool

4.97 out of 5 average rating, 232 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

A well-lit living area showcases a comfortable sectional sofa and a wooden dining table with light-colored chairs. A decorative bowl of lemons sits at the center of the table, while large windows offer views of the surrounding landscape and allow natural light to fill the space.

4.93 out of 5 average rating, 171 reviews

BEAUTIFULLY DESIGNED OCEANFRONT CONDO

A spacious living room features a light color palette with a large flat-screen television mounted on the wall. Comfortable seating is arranged around a coffee table, and large windows provide a view of the ocean and natural light. Coastal decor enhances the atmosphere.

4.91 out of 5 average rating, 166 reviews

Lux Suite Open Ocean Views- 2 Balconies+Pool & Bar

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.

4.99 out of 5 average rating, 224 reviews

Ocean Views at Ocean Pointe

4.91 out of 5 average rating, 169 reviews

A modern kitchen features white cabinetry and stainless steel appliances. A wooden cutting board is placed on the counter, complemented by cooking utensils. Soft lighting illuminates the space, enhancing the clean and functional design. A window with shutters allows natural light to enter.

Condo in Key Largo

Gorgeous lagoon-front 2BR Townhouse with 2 pools

A private beach area is visible, featuring soft white sand and arranged lounge chairs facing the calm ocean. Lush greenery lines the shore, with a small tree providing shade. In the background, a wooden pier extends into the water under a partly cloudy sky.

4.9 out of 5 average rating, 337 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

A light-filled living space features a turquoise sofa with yellow accent pillows, paired with a round glass dining table. Rattan chairs complement the decor, which includes a vibrant tropical wall mural and a circular mirror. Modern appliances are visible in the kitchen area.

4.96 out of 5 average rating, 251 reviews

Tiki Time! Ocean Pointe Top Floor King 1 Br/1Ba

An open-concept living area features a comfortable sofa and loveseat, designed for relaxation. A stylish dining table accommodates four. A wall-mounted TV and electric fireplace add modern touches, while large sliding glass doors offer natural light and views of the surrounding landscape.

4.95 out of 5 average rating, 179 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Other vacation rentals with a pool

4.97 out of 5 average rating, 35 reviews

A serene waterfront view captures the modern multi-story building surrounded by lush greenery. The calm water reflects the clear blue sky, while a private wooden dock extends into the water, providing an inviting entrance to the property.

Townhouse in Islamorada

NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom

5.0 out of 5 average rating, 23 reviews

Townhouse in Islamorada

Closest Oceanfront Home - 3 Stories and Boat Dock

4.9 out of 5 average rating, 70 reviews

A houseboat is docked alongside a concrete walkway, with the river water reflecting the sunny blue sky. The boat features a shaded deck on top and a screened-in porch in the front, providing a comfortable outdoor space. Lush greenery is visible along the shore.

Houseboat in Key Largo

Key Largo's Best Kept Secret!

4.96 out of 5 average rating, 53 reviews

4.94 out of 5 average rating, 31 reviews

Aerial view showcasing the charming townhomes surrounded by lush greenery and vibrant palm trees. The turquoise water reflects the clear sky, with boats docked along the canal. The neatly arranged front gardens add to the inviting atmosphere of the neighborhood.

Townhouse in Marathon

Beautiful View! 4BR 3 BA 32FT Dock, Cabana Club!

5.0 out of 5 average rating, 19 reviews

Apartment in Tavernier

Keys Sunset Sanctuary

5.0 out of 5 average rating, 7 reviews

A spacious fishing pier extends into clear turquoise waters under a bright blue sky. The sandy beach surrounding the pier invites relaxation, while lush greenery can be seen in the distance. Minimal benches are positioned along the pier for enjoying the scenery.

Home in Islamorada

Marlin House @ Tarpon Point