House holiday rentals in Key West

A sparkling in-ground pool is visible in the foreground, surrounded by a spacious patio. Lounge chairs are positioned along the deck, offering views of the lagoon. Lush palm trees provide shade, while a clear sky enhances the tranquil atmosphere of the waterfront setting.

4.99 out of 5 average rating, 157 reviews

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

2025 - New concrete dock, fenders & fish filet table. This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

A shaded tiki hut is situated on a stone patio beside a tranquil canal. The space is furnished with a table and chairs, surrounded by palm trees. Brightly colored kayaks are neatly arranged on a nearby dock, adding to the outdoor ambiance.

4.9 out of 5 average rating, 105 reviews

*New Modern*3/2Duplex/37' Dock/Cabana/Kayaks/Bikes

Perfectly situated in KCB w/ 37.5' of dockage on a wide and pristine canal that leads easy access to both the Ocean & the Gulf, our newly listed 1/2 duplex is newly renovated w/ brand new AC, appliances, fixtures, furniture, mattresses, & decors. Featuring 3BR 2BA accommodating up to 8 ppl in a large & open living room & backyard, provided w/ multi-game table, bikes, kayaks, 6-burners grill, 2 mins walk to Sunset park, & Cabana Club access, it is the perfect Florida Keys getaway for your family.

A charming entrance is framed by lush tropical landscaping and vibrant foliage. A brick walkway leads through a white arched gate, guiding guests between two pastel-colored cottages. Lush palm trees and colorful plants create a welcoming atmosphere, enhancing the overall serenity of the space.

5 out of 5 average rating, 11 reviews

Robinson Crusoe Cottage~ Delight In Island Vibes

Welcome to your Key West holiday! This newly acquired and improved one-bedroom cottage has all you need to relax and unwind. Whether walking to Duval Street, Mallory Square, or nearby restaurants, you will enjoy a comfortable stay in an ideal location. THE PROPERTY: Enjoy your stay with us at Robinson Crusoe Cottage, part of the quaint Conch Cottages property, which includes 3 separate rentable units: Robinson Crusoe Cottage at the rear, Royal Poinciana Cottage on the right, and Margarita ...

4.97 out of 5 average rating, 285 reviews

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

A covered Tiki Hut is featured at the waterfront, furnished with comfortable seating arrangements. Views of the water and dock are visible beyond the structure, framed by lush greenery and palm trees. The space is designed for relaxation and enjoyment of the serene surroundings.

4.93 out of 5 average rating, 122 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

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.

4.95 out of 5 average rating, 133 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

An aerial view of the waterfront area shows vibrant turquoise waters and lush greenery. The scene includes several residential buildings along the coastline and a nearby marina, with boats visible on the water and the horizon illustrating a scenic expanse.

4.93 out of 5 average rating, 215 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in the beautiful Florida Keys! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

An aerial view captures a vibrant community of stilt homes nestled along the coastline, with clear blue waters stretching in the background. Lush palm trees dot the landscape, while a distinctive red marker indicates a specific location within this scenic setting.

4.84 out of 5 average rating, 114 reviews

Spanish Queen @Venture Out

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

A heated pool is surrounded by a spacious deck, featuring lounge chairs and a dining table with blue chairs. Beyond the pool, a pathway leads to lush greenery and the ocean view under a partly cloudy sky.

4.82 out of 5 average rating, 100 reviews

Palm Breezes! Room for Everyone on the Ocean.

This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.

A modern two-story home with a spacious outdoor area featuring a private pool. Comfortable lounge chairs surround the pool, and a staircase leads to the upper level. The structure is complemented by a rooftop terrace with a sail shade, enhancing the coastal atmosphere.

4.97 out of 5 average rating, 128 reviews

Angler’s Terrace Conde Nast Traveler’s Best Airbnb

As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views

4.92 out of 5 average rating, 106 reviews

Aerial view of a waterfront property featuring a semi-circle dock leading to a small island. Brightly colored chairs in green and turquoise sit on sandy areas, surrounded by clear blue water and lush tropical vegetation. Nearby, additional properties can be seen amidst palm trees.

Home in Summerland Key

Waterfront Haven House with Boat Basin & Ramp!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!

The living area features contemporary furnishings and large windows, allowing for bright natural light and views of the waterways. A dining table is positioned beside the seating area. The spacious lanai showcases an outdoor dining setup with a view of the dock and water.

4.95 out of 5 average rating, 129 reviews

Paradise in Key Colony Beach + Cabana Club

Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

Popular amenities for house rentals in Key West

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The outdoor living area features a private pool surrounded by tropical greenery. Chaise lounges and an umbrella provide shaded seating options, while a porch with colorful cushions offers additional relaxation space. A glimpse of the home's porch and vibrant landscaping enhances the tranquil setting.

4.98 out of 5 average rating, 47 reviews

Casa Serendipity at Old Town

An outdoor seating area features a thatched roof, providing shade over a collection of cushioned seating and a low coffee table. A swimming pool is visible in the background, surrounded by tropical greenery. Large glass doors lead into the interior of the home.

5 out of 5 average rating, 44 reviews

Discount Available! Pool 100' Dock, Fun Amenities!

A spacious wooden dock extends over calm waters, featuring a thatched tiki hut and several lounge chairs in a soft blue hue. Lush greenery surrounds the area, complemented by a serene sky at sunset, providing a peaceful atmosphere for relaxation.

5 out of 5 average rating, 35 reviews

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

5 out of 5 average rating, 12 reviews

P52 - Canal front, 2 bedroom, 3 bath with private

A well-lit dining area features a round wooden table surrounded by six woven chairs. A decorative centerpiece is placed on the table. Adjacent, a cozy living space is visible, showcasing a sectional sofa, a ceiling fan, and large windows allowing natural light.

4.86 out of 5 average rating, 71 reviews

Cozy 2 br/2 bath home in Cudjoe

A serene pool area is framed by palm trees and lush greenery, offering views of the ocean. Comfortable lounge chairs are positioned around the pool, which features a spa. The scene includes bright umbrellas, enhancing a relaxing outdoor space under a clear blue sky.

4.98 out of 5 average rating, 55 reviews

Oceanfront with Pool near Sombrero Beach

An aerial view showcases a private dock with a boat alongside a heated pool. Lounge chairs are positioned near the pool, complemented by vibrant palm trees and neatly arranged outdoor furniture. The tranquil waters reflect the bright surroundings, enhancing the overall relaxing atmosphere.

4.95 out of 5 average rating, 22 reviews

Paradise Cove! 50ft Dock Pool BBQ

Home in Upper Sugarloaf Key

A sandy beach area is framed by swaying palm trees, leading to a two-story bungalow elevated on stilts. Lounge chairs are arranged on the shore, providing a relaxing spot, while kayaks are visible in the background, enhancing the inviting beach setting.

4.75 out of 5 average rating, 99 reviews

Palm - Beach Houses Key West

Weekly house rentals

5 out of 5 average rating, 5 reviews

Oceanfront 2BR in Venture Out - 35’ Dock + Pool

An outdoor seating area features a sectional sofa and high-top bar stools with a view of the water. A peaceful ambiance is created by the surrounding palm trees and the gentle waves of Vaca Cut. Laundry facilities are visible on the left side of the image.

4.91 out of 5 average rating, 47 reviews

Florida Keys Oceanside Utopia

4.98 out of 5 average rating, 54 reviews

Grouper Getaway @ Ocean Isles Fishing Village

A serene waterfront scene features a pier with thatched roof structures surrounded by calm blue waters. The sky is partly cloudy, showcasing a blend of whites and blues. Buoys are placed in the water, adding a touch of color to the landscape.

4.86 out of 5 average rating, 49 reviews

Relaxing Home in the Keys

A serene outdoor space features a clear swimming pool surrounded by palm trees. A covered lounge area provides shade, while lounge chairs offer spots for relaxation. The tranquil waters are visible in the background, enhancing the overall atmosphere of the private retreat.

5 out of 5 average rating, 15 reviews

Waterfront Oasis w/Private Pool-Dockage-Beach

4.78 out of 5 average rating, 9 reviews

An inviting living area features a cozy sectional sofa adorned with patterned pillows. Large windows provide ample natural light, while a TV stands on a wooden console. A dining area with a light fixture and a view of the balcony is visible in the background.

Home in Summerland Key

Sailfish Dream on Cudjoe Key-28 day minimum

The exterior of a charming two-story conch-style home showcases a light yellow facade with white trim. Surrounded by lush greenery, the property features a sandy pathway leading to a covered porch with bright red accents, and a staircase leading to the upper level.

4.86 out of 5 average rating, 21 reviews

Tropical Hideaway @ Tropical Village

5 out of 5 average rating, 90 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

Private house rentals

A spacious Tiki Hut offers shade with palm fronds overhead, surrounded by a paved area. A light blue table with matching chairs is arranged under the hut, providing an inviting spot for relaxation beside the canal.

4.96 out of 5 average rating, 77 reviews

Updated Key Colony Tiki Hut-37.5 Dock-Cabana Club

A view from the balcony reveals tranquil waters of the Atlantic Ocean stretching towards the horizon. A thatched-roof structure is visible nearby, with a dock extending into the water, surrounded by lush greenery.

5 out of 5 average rating, 20 reviews

Casita Mar Canal, Direct Ocean 2/2 You'll Love It!

A large resort-style pool is framed by tropical landscaping and palm trees, providing a serene atmosphere. The crystal-clear water reflects the blue sky, and a spacious deck is lined with lounge chairs for relaxation. A shaded cabana area is visible in the background.

4.93 out of 5 average rating, 14 reviews

Mermaid's Retreat at Coral Hammock Key West Islan

A spacious outdoor area features a tiki hut with a thatched roof, a swimming pool surrounded by lounge chairs, and a boat docked beside a canal. Lush palm trees provide shade, enhancing the tropical ambiance of the property. The home is visible in the background.

4.96 out of 5 average rating, 80 reviews

Searenity Vacation Rental! Pool, Tiki Hut, Dockage

A private pool with crystal-clear water reflects sunlight, featuring a large inflatable flamingo floating serenely. The surrounding area is bright and spacious, with a view of a light-colored house and tropical greenery in the background.

4.99 out of 5 average rating, 70 reviews

Casa Blue Flamingo

4.94 out of 5 average rating, 31 reviews

2BR/2BA Retreat in the heart of Marathon! 3 beds

5 out of 5 average rating, 9 reviews

Wahoo Way | Charming Hideaway On Duval Street!

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.