Holiday houses in Key West

5 out of 5 average rating, 4 reviews

Sunset Harbor 2 bed Ocean views!

This is a great unit with large balcony. Sunset Harbor is perfectly located in downtown Key West. Walk along the boardwalk/head to Duval Street only a couple blocks away. The resort has pool, hot tub, grills for use during your stay. There are laundry facilities free of charge. There are NO daily resort fees, parking is extra. Each unit has a King sized bed , Queen sized bed, and sofa bed. Specific units are assigned by front desk. No guarantee about floor but all 2 bedrooms have ocean views.

4.92 out of 5 average rating, 72 reviews

A beach home with a turquoise roof is nestled among palm trees and tropical landscaping. Two sets of chairs in yellow and blue are positioned on the sandy area in the foreground, inviting relaxation. A private pool and lush greenery are visible in the background.

Home in Marathon

Beach House, Private Pool, Dock, Gulf View Sunsets

You don’t come to the islands to stay in a town—you come to slow down. Welcome to our tropical keys beach home, tucked away from the traffic and noise of US Hwy #1. Sway with the palms on the wraparound deck, soak in wide-open panoramic bay views, and catch fiery sunsets right off your dock. Fire up the BBQ, brew a Keurig, float in the private pool, or cast a line from the 300’ private pier/dock. Easy going island living with ocean / gulf breezes, comfy beds, quality linens, Wi-Fi, and cable TV.

Superhost

Home in Key West

5 out of 5 average rating, 3 reviews

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

Your own private Key West hideaway awaits. Surrounded by lush tropical landscaping, this peaceful home offers a large pool, outdoor shower, grill, and fire pit — perfect for relaxing days and starlit evenings. Enjoy complete privacy indoors and out, with three comfortable bedrooms, a fully equipped kitchen, washer/dryer, and 66' of canal frontage- bring your own boat or ask one of our favorite captains to pick you up! Whether out on the town or relaxing in your own home, you will love it here!

5 out of 5 average rating, 15 reviews

Boat in Key West

Luxury Boat Stay | Resort Amenities

A Whim isn’t just a place to sleep - it’s permission to unplug and let vacation unfold naturally. Docked at the exclusive Perry Hotel & marina, this 40 ft 2-bed luxury boat with island bright touches is tucked away from the crowds in a resort style marina while being just minutes from downtown Key West. Featuring indoor and outdoor spaces for living, dining, and relaxing, as well as hotel amenities such as a pool, 3 bars and restaurants, and a gym. Vacation differently on A Whim.

4.94 out of 5 average rating, 168 reviews

A spacious living area features a comfortable futon adorned with a decorative pillow. Large windows provide views of the tranquil water, allowing natural light to brighten the space. The walls are designed in a soft, neutral tone, enhancing the overall welcoming feel.

Houseboat in Key West

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Soencers boat yard Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

4.87 out of 5 average rating, 108 reviews

A private outdoor area features a hot tub surrounded by tropical foliage. A dining table with chairs is situated nearby on a wooden deck, offering shade from the overhead structure and a relaxing atmosphere for outdoor meals.

Home in Key West

Near Duval: Hot Tub, Sleeps 6, Top Location

Just 30 seconds from vibrant Duval Street, this iconic conch home is your perfect Key West escape! With two bedrooms, one bathroom, a full kitchen, and private outdoor perks—like a hot tub, second-story sundeck, and outdoor shower—you’ll have everything you need to relax in paradise. Ideal for up to 6 guests, it’s a tropical haven steps from world-class dining, shopping, and beaches. Book now and soak up the island life! Don’t forget to click the ♥ to save it for later.

4.94 out of 5 average rating, 53 reviews

A cozy sleeping area featuring a quilted bedspread in various patterns. A kitchenette with modern appliances is visible, complemented by cabinetry. Two refrigerators are nestled in the corner, and a large mirror reflects the space. Ambient lighting and decorative touches add character.

Houseboat in Marathon

b watervibe

Disfruta de los sonidos de la naturaleza cuando te quedes en este lugar único. Es algo diferente para disfrutar con tu pareja de un momento romántico y divertido y así relajarse y olvidarse de la vida cotidiana. Puedes disfrutar de la pesca ,de paseos en kayak ,vivir una aventura y disfrutar de otras actividades locales.Prueba de la expericiensa y ya ustedes diran.Esta casa flotante ofrece un espacio para 2 adultos. Está Esta es una experiencia de Acampada

4.98 out of 5 average rating, 542 reviews

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs & DVD players.

4.92 out of 5 average rating, 123 reviews

Condo in Key West

Old Town Retreat • Pool • Walk to Duval •

Stay in the heart of Old Town Key West—just 3 blocks from Duval—while enjoying a peaceful retreat with a pool and historic island charm. Start your mornings with coffee in a quiet tropical setting, then explore nearby shops, restaurants, and nightlife. After a day out, unwind by the pool or relax in your private suite. Perfect for couples or small groups who want to be close to everything without the noise.

4.91 out of 5 average rating, 523 reviews

The Tiki Suite is presented on a wooden platform, showcasing thatched roofing and an inviting porch area. Two stand-up paddleboards are placed alongside the structure, with calm waters reflecting the clear sky.

Houseboat in Key West

Tiki Suites ~ Original Tiki ~ Private Water Stay

Stay on the water in this one-of-a-kind Tiki Suite in Key West. This private floating bungalow blends boat life with comfort, featuring a custom bed, panoramic views, and direct access to the ocean. Swim, paddle, or relax in a hammock surrounded by nature. A peaceful, off-grid glamping experience you won’t find anywhere else. Accessible by boat only.

4.94 out of 5 average rating, 173 reviews

A serene pool area is visible in the foreground, bordered by lush greenery and ocean views. Tall palm trees sway gently along the shoreline, where the calm water reflects the sky. A distant pier can be seen, enhancing the coastal atmosphere.

Condo in Key West

Beach Club Ocean Front 2BR Condo

Come fall in love with Key West in our luxurious ocean front condo. The Key West Beach Club is located directly on the Atlantic in a quiet residential secured building. It is a 2BR, 2 1/2 Bath located in Mid-Town.

Superhost

A warm-toned room features wood-paneled walls accented by natural light from two windows. A spacious bed with an orange bedspread is positioned alongside a cozy seating area comprising two cream-colored couches facing a small round table.

4.84 out of 5 average rating, 865 reviews

Duval Balcony - Street Suite

Located in the heart of Duval St, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a balcony overlooking Duval St.

Popular amenities for Key West holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

What Airbnb hosts recommend seeing in Key West

Find unforgettable activities and unique points of interest near you. Our hosts share their favourite things to do and must-visit places to see in Key West.

Fort Zachary Taylor Historic State Park Beach

Historic fort and park with nature trails, a beach, and scenic views

Summarised by AI

Swim, snorkel, and fish at the only natural beach in Key West, then refuel at the on-site snack shack or concession stand for an easy lunch between dips. Rent lounge chairs and snorkel gear, bring water shoes for the coral, and use the park grills for a simple cookout by the water. Explore the Civil War–era fort, see the largest collection of Civil War seacoast guns and cannons, and visit the small museum. Stay for sunset over the Gulf of Mexico, a local favorite view.

Mentioned by 1,522 local hosts

The Hemingway Home and Museum

Historic residence featuring guided tours, lush gardens, and famous six-toed cats

Summarised by AI

Tour this National Historic Landmark to see the rooms and writing studio where Hemingway penned some of his most famous works, furnished with much of his original 17th- and 18th-century Spanish furniture. Stroll the lush gardens, visit the Wall of Shame, and browse the on-site bookstore and gift shop. Meet the world‑famous six‑toed cats, whose descendants still freely roam the property and are cared for by a perpetual trust. Bring cash for the entrance fee, then grab a bite at Moondog Cafe next door.

Mentioned by 268 local hosts

The Key West Butterfly and Nature Conservatory

Enchanting glass conservatory with diverse butterfly species, exotic birds, and flamingos

Summarised by AI

Step into the glass-enclosed conservatory and walk among 50–60 species of butterflies from around the world, all flying freely through lush plants, trees, and cascading waterfalls. Watch for more than 20 species of small, colorful birds and meet the resident flamingos, Rhett and Scarlett, who have become local celebrities. It’s peaceful, fully covered, and great for kids or a rainy-day activity. After exploring, browse the on-site photos and unique gifts, or use your same-day pass to return.

Mentioned by 91 local hosts

Southernmost Point of the Continental U.S.A.

Iconic concrete buoy marking the southernmost point in the continental United States, 90 miles from Cuba

Summarised by AI

At the Southernmost Point Buoy, you stand at the southernmost point of the continental United States, just 90 miles from Cuba, marked by the big candy-striped concrete buoy and nonstop photo ops. Snap your must-have shot with the bright red, yellow, and black “90 miles to Cuba” marker, turquoise ocean and palm trees behind you, and watch boats drift past. Expect a line, especially after 9am, so go early. Afterward, pair it with nearby “southernmost” spots or the Seaside Café by the Southernmost House.

Mentioned by 103 local hosts

Other great holiday rentals in Key West

4.88 out of 5 average rating, 667 reviews

Hotel room in Key West

The Sanchez House Room #3

A comfortable room features a spacious bed with crisp white linens, positioned against a coral-themed accent wall. Natural light streams through a window with white shutters. A small dining table and chairs complement a kitchenette area, while a large mirror enhances the sense of space.

4.86 out of 5 average rating, 1,666 reviews

At Mine | Lovely Suite steps from Duval Street

4.93 out of 5 average rating, 15 reviews

Home in Summerland Key

Starlight Serenity - Hideaway with Stunning Views

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 out of 5 average rating, 10 reviews

Castillo Del Mar- Ocean access from your backyard

Home in Key Colony Beach

5 out of 5 average rating, 4 reviews

Waterfront Retreat w/ Dock + Cabana Club

A view from a private balcony showcases the resort pool, surrounded by palm trees and a sun terrace. Lounge chairs are arranged neatly around the pool, while shaded seating areas provide options for relaxation. The bright blue sky enhances the atmosphere of leisure.

Condo in Key West

4.77 out of 5 average rating, 259 reviews

Pool View Suite | Beachside Resort