Vacation rentals with a pool in Duck Key

4.89 out of 5 average rating, 118 reviews

A bright and spacious living area features a large dining table with wooden chairs and a central coffee table. Soft seating is arranged around a sliding glass door that opens to the outdoor patio. Decorative curtains frame the windows, enhancing natural light.

Villa in Duck Key

Waterfront Island Escape with Private Plunge Pool

Come and relax in your own private plunge pool that overlooks a turquoise canal on the beautiful Duck Key. The outdoor living space is quiet and serene, making it a perfect place to unwind. Families and honeymooners alike can enjoy this island oasis. Centrally located at Mile Marker 61, Duck Key is just a short drive to Key West. Explore everything the Florida Keys have to offer or stay locally to enjoy world-renowned restaurants, fishing, snorkeling, and diving. The opportunities are endless.

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4.87 out of 5 average rating, 181 reviews

A serene sunset view showcases a circle of white Adirondack chairs positioned around a fire pit. The calm waters reflect vibrant hues of orange and purple from the sky, creating a peaceful atmosphere.

Townhouse in Key Largo

Sunrise Escape - Ocean Front Villa - Sleeps 10

Wake up to the sunrise over the ocean and unwind with sunset views from your private jetty. This marina-front, ocean-view townhouse in Kawama Yacht Club puts you steps from kayaking, snorkeling, and the best of the Keys. Spacious, stylish, and designed for unforgettable family and friend getaways. Breathtaking sunrises from one of two private terraces, coffee in hand, overlooking the marina and the Atlantic Ocean. Located in an exclusive, quiet section of Kawama Yacht Club, this beautifully po

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4.83 out of 5 average rating, 78 reviews

A bright and airy living area features a comfortable sofa and armchair, with large glass doors offering access to a private patio. A ceiling fan hangs above, and a TV sits on a light-colored entertainment unit, enhancing the space's open feel.

Townhouse in Marathon

Beachy Townhome Perfect For A Relaxing Getaway!

Beautiful and spacious 2B/2.5 Ba townhouse in Duck Key, FL. Enjoy the crystal clear waters and amazing wildlife that calls this island home, while staying in a comfortable home of your very own! High speed internet (273 download/10 upload Mbps), and large 4k smart tv's provide great indoor entertainment, while the private plunge pool provides that calming outdoor experience for all. Enjoy a morning cup of coffee or an evening glass of wine on the back patio while watching the sun paint the sky.

ValueFamilySleep quality

A serene view of a canal populated by several pelicans floating on the water's surface. Palm trees line the shore, and colorful houses are visible in the background. A boat is docked nearby, enhancing the peaceful coastal scene.

4.98 out of 5 average rating, 129 reviews

Waterfront House with 37 ft Dock & Cabana Club

Right in the middle of the action between Miami and Key West. This 2/2 house has been nicely renovated and furnished with new stainless kitchen appliances and a gorgeous granite countertop. Comfortable outside/inside living space perfect for a getaway in paradise. Walk out to the porch and backyard, and you will be engulfed by the beauty of the sunset views while lying on the cozy hammock. It features lots of outdoor entertaining: fishing, paddling, BBQ or just plain hanging out in the shade.

LocationFamilyBiking

5.0 out of 5 average rating, 91 reviews

A private patio area features a plunge pool surrounded by lush tropical landscaping. Two lounge chairs are positioned nearby, offering a relaxing space. A light blue sky with scattered clouds creates an inviting ambiance, while palm trees add a touch of the tropics.

Townhouse in Duck Key

Duck Key *Delight* private plunge pool

This beautiful townhouse was remodeled in late 2021 with a modern tropical inspired scheme. High speed internet-1,000 mbps, and 4K Smart TV's provide great entertainment. The patio's lush landscape with torches create a cozy setting at night and during the day the water sounds over the plunge pool allow for relaxation and fun. Take a break, lounge, have a morning cup of coffee and observe nature wake up. Explore close by fun tropical activities and great restaurants. Delve into Conch life!

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Palm trees are seen swaying gently in the breeze, framing the entrance to the cottage, which features a welcoming front porch with two wooden chairs. The interior showcases a modern dining area, complete with a chandelier and decorative plants. A plunge pool is visible in the outdoor space, surrounded by tropical greenery.

4.93 out of 5 average rating, 132 reviews

Villa with Pool - Hawks Cay - Duck Key

Welcome to our tropical Conch Cottage, a lovely place to create memories on your idyllic Florida Keys vacation in paradise. Our stylish waterfront villa sits alongside a clear turquoise canal on picturesque Duck Key, inside the Hawk's Cay resort, and just 10 minutes from busy Marathon. Get involved in on-site activities like snorkeling, scuba diving, fishing, boating and dolphin encounters—or simply lay out on the coral stone patio, soak up the sun, and slide into your private plunge pool.

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4.94 out of 5 average rating, 31 reviews

Townhouse in Marathon

Beautiful View! 3BR 3 BA, Cabana Club Membership!

Sun Kissed Tails in Hawks Cay on Duck Key is a 3 bedroom 3 bath townhome with a fully stocked kitchen in the Hawks Cay resort on Duck Key, MM61. This property does not have a boat slip, but you can possibly rent one based on availability. Enjoy the local beaches a short drive away (Coco Plum Beach and Sombrero Beach) and ENJOY THE POOL AND BEACH AT THE OCEAN FRONT CABANA CLUB, just a 15 drive to Key Colony Beach. The Cabana Club has a pool, Tiki Bar and restaurant, ocean front sandy beach!

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5.0 out of 5 average rating, 116 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.

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4.95 out of 5 average rating, 108 reviews

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

Enjoy breathtaking views of the Gulf and Ocean from the screened in patio of this beautiful 4 BEDROOM/3 BATH canal front home. Bring your boat to the 60' dock on a 200' wide canal just 10' away from the Ocean. Relax by the pool/spa area after a day of fishing. A pool heater is offered as an option for your convenience. Please inquire about water heater fee and operating instructions before booking. (VR Lic # PLR2020-00104)

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4.84 out of 5 average rating, 144 reviews

An outdoor lounge area features a private spa pool surrounded by tropical plants and seating. Soft lighting creates a welcoming atmosphere, while the vibrant sunset sky adds a colorful backdrop. Sliding doors connect the space to the interior of the villa.

Villa in Marathon

Villa in Paradise. Plunge pool. Middle of the Keys

Baja Breeze 🏝, a freshly updated, family-friendly, resort-style villa in the ♥ of the Keys. ♥ Please save Baja Breeze by clicking on the heart in the top right hand corner, this will help you find it again and share with others! 🛶 Waterfront canal view 🌴 Gated Resort Area 👙 Private spa pool 📍 Halfway between Key Largo and Key West ☀️ Outdoor dining/lounge area 🍳 Fully stocked Kitchen 📶 300Mbps+ Wifi

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4.98 out of 5 average rating, 42 reviews

A spacious outdoor area features a private pool surrounded by a wooden deck. Loungers invite relaxation under the shade of palm trees. The home, with two stories, showcases a covered patio equipped with dining furniture, complemented by lush greenery for added privacy.

Villa in Duck Key

Florida Keys Sanctuary

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 and loungers. 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 and kids dishware.

LocationFamilyNearby

4.91 out of 5 average rating, 77 reviews

A charming two-story villa is framed by swaying palm trees against a bright blue sky. Lush greenery borders the pathway leading to the entrance, which features a porch with round windows and white railings, emphasizing the inviting exterior of the residence.

Villa in Marathon

Seas the Keys Getaway with plunge pool/spa

Waterfront Spa Villa with Private Plunge Pool/spa, located in beautiful Hawks Cay situated conveniently between Marathon and Islamorada in the Florida Keys. Enjoy world-class fishing, diving & snorkeling, boating adventures and more. Swim with Dolphins, visit the Dolphin Research Center or spend the day at a tropical adventure park, all just minutes from your front door!

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Popular amenities for Duck Key rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A paved outdoor patio features two lounge chairs and a small round table, surrounded by tropical plants and palms. The tranquil canal is visible in the background, offering a serene waterfront view.

4.94 out of 5 average rating, 144 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

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A tropical backyard features a private saltwater pool surrounded by seating areas. A thatched-roof Tiki Hut is adorned with string lights. A gas fire pit sits centrally, while walls are embellished with colorful fish murals. Lush greenery completes this inviting outdoor space.

4.91 out of 5 average rating, 116 reviews

Tiki Time! Private Pool~Tiki Hut~Kayak~Grill!

FamilyValueLong stay

4.96 out of 5 average rating, 27 reviews

A private pool is framed by lush tropical foliage and wooden decking, offering a serene outdoor space. Lounge chairs are positioned beside the pool, while a dining area with a large table is visible under the covered porch, providing shaded seating options.

Home in Duck Key

Villa 7201 - 4 Bedroom 3 Bath with Boat Slip

LocationFamilyParking

4.93 out of 5 average rating, 81 reviews

Beach House, Private Pool, Dock, Gulf View Sunsets

ValueFamilyAccess

5.0 out of 5 average rating, 12 reviews

Lux Waterfront: Dock, Volleyball, Putt Putt, More

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5.0 out of 5 average rating, 4 reviews

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

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5.0 out of 5 average rating, 5 reviews

Entire private two family water front home.

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A wooden dock extends over calm water leading to a circular stone embankment. Lush greenery and palm trees surround the scene, alongside a distant white building with green roofing. The clear blue sky and gentle water highlight the serene waterfront setting.

4.92 out of 5 average rating, 12 reviews

3/2 Home w Dock, lagoon, kayaks!

LocationFamilyView

Condo rentals with a pool

4.93 out of 5 average rating, 119 reviews

The image showcases a vibrant living space within the Dapper Dolphin condo, featuring a stylish kitchen with granite countertops, a cozy dining area, and a comfortable bedroom with a king-sized bed. The outdoor area displays a large pool surrounded by lounge chairs, highlighting the resort's inviting atmosphere.

Condo in Marathon

Dapper Dolphin | Canal View + Breakfast + Pool

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Condo in Key Colony Beach

4.97 out of 5 average rating, 334 reviews

Bright Cheery Condo, Ocean Views in Key Colony

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A light-filled living room reveals ocean views through sliding glass doors. A spacious white couch and armchair offer comfort, while a wooden coffee table rests on a patterned rug. Decorative elements include natural wall art and a bright indoor plant, enhancing the coastal ambiance.

4.99 out of 5 average rating, 112 reviews

Tequila Sunrise

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4.97 out of 5 average rating, 231 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

ValueFamilyHot tub

4.91 out of 5 average rating, 140 reviews

Turtle Nest 1 Private beach,Pool, 2bed 2bath

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Condo in Key Colony Beach

The image captures a view of the Atlantic Ocean framed by lush palm trees. A pathway meanders alongside the vibrant green lawn, leading toward the beach. The clear blue sky is visible above, enhancing the calm and serene coastal atmosphere.

4.88 out of 5 average rating, 168 reviews

Beachside Unit 33-Private Tropical Beach Plus Pool

FamilyValueIndoor spaces

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, 250 reviews

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

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A spacious living area features light blue walls and coastal decor. A comfortable sofa is positioned against the wall, accompanied by a patterned throw pillow. A coffee table is centrally placed, while a bar seating area with stools offers additional gathering space. Natural light fills the room.

4.93 out of 5 average rating, 121 reviews

Light, Bright & Nautical Condo at Ocean Pointe

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Other vacation rentals with a pool

Townhouse in Key Colony Beach

A serene outdoor space features two wooden lounge chairs positioned on a grassy area beside calm waters. A small table is placed nearby, and a private dock extends towards the water, flanked by lush greenery in the background under a bright blue sky.

5.0 out of 5 average rating, 15 reviews

Castillo Del Mar- Ocean access from your backyard

FamilyLocationParks

4.8 out of 5 average rating, 41 reviews

Home in Islamorada

Islamorada Bungalow #5

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A resort-style pool is surrounded by lounge chairs, set on a brick patio with a view of palm trees and the ocean. The scene is bright and open, showing a clear sky with scattered clouds, enhancing the outdoor leisure space.

4.8 out of 5 average rating, 15 reviews

Oceanview Rooftop Retreat 3BR 3BA in Marathon FL

LocationValueComfort

5.0 out of 5 average rating, 16 reviews

Townhouse in Islamorada

Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio

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A clear view of a swimming pool framed by lush greenery and manicured grass, extending toward the Atlantic Ocean. The tranquil water reflects the blue sky above, enhancing the serene setting.

4.89 out of 5 average rating, 19 reviews

SAY'S BY THE SEA

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A private pool is bordered by lush palm trees and a thatched Tiki Hut. Lounge chairs are arranged around the pool area, and colorful outdoor decor adds a cheerful touch. Clear blue skies and sunshine illuminate the space, creating an inviting outdoor retreat.

4.94 out of 5 average rating, 32 reviews

Private Pool! Luxury Paradise Pointe, Pet Friendly

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A light-filled living area features a comfortable seating arrangement with leather sofas and a large area rug. A television is housed within a white entertainment unit, flanked by decorative glass vases. Expansive sliding glass doors open to the outside, providing an airy ambiance.

4.95 out of 5 average rating, 79 reviews

Sea Glass Beach Bungalow in Key Colony Beach!

ValueLocationHot tub

An outdoor area features a fenced pool surrounded by colorful chairs. Palm trees provide shade, and the spacious deck above is visible. The setting reflects a relaxed atmosphere with nearby greenery enhancing the tranquil environment.