Vacation rentals in Key West

A serene canal-side view features a spacious sandy area with palm trees. A thatched tiki hut and outdoor seating set the scene for relaxation. The home is positioned in the background, showcasing large windows that reflect the clear blue skies.

4.89 out of 5 average rating, 9 reviews

Twin Dolphin Marathon Deep Water Canal, 100’ Yard!

Don’t miss this one! Dock your boat & relax in the swimspa pool at this deep water, canal home in Marathon’s Boot Key Harbour! Walking distance to ocean front tiki bars, restaurants and attractions! Quiet, residential street at MM 48.5, just off US 1, this one level home is in the heart of the Florida Keys. 2 queen bedrooms plus a sleeper sofa in the living area. With no neighbors on either side of the home, this is the ideal spot for personal space at our 100 foot wide lot. 2 kayaks provided!

4.94 out of 5 average rating, 160 reviews

A serene waterfront view showcases clear turquoise waters under a bright blue sky. A boat can be seen cruising along the horizon, while a patio with seating is visible at the forefront, adjacent to a dock lined with black posts.

Cottage in Cudjoe Key

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

4.92 out of 5 average rating, 131 reviews

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.

Home in Key Colony Beach

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 motorboat is anchored on calm waters, featuring a spacious front deck. Two individuals are seated comfortably, enjoying the view. The boat's sleek design is complemented by a canopy overhead and small steps leading into the water, creating a relaxed atmosphere.

4.9 out of 5 average rating, 230 reviews

Stay on Roxie - free transport & snacks, BYOB.

Read our reviews and relax with last minute weather cancellation! 🌞 Shower, toilet and power to recharge phones, full cellular. Enjoy a peaceful night or two on the water! Free parking and one free round trip transport to/from Roxie per night stay! Roxie is anchored in ~3ft lagoon. We live on a boat a half-mile away if you need anything at all! Roxie has a Keurig, coffee pods, bread, peanut butter-jelly, and bottled waters. No cooking but you may bring to-go food, beer/booze/wine. 🛥️🌴🎣

A decorative wooden sign is mounted on a white post, featuring the text 'Center Court Historic Inn & Cottages' in bold letters. Lush tropical greenery surrounds the area, with palm trees and vibrant plants visible, creating a welcoming entrance to the property.

4.95 out of 5 average rating, 347 reviews

Honeymoon Hideaway, King bed, Private Deck & Spa!

This Historic unit has Pale blue interiors, small efficiency kitchen, platform Pottery Barn King memory foam bed with multiple basket drawers underneath for storage, large shower. Large private deck with 2 person spa, hammock, outdoor sofa and table/chairs. Bose Bluetooth speaker, Alexa. Private gated compound and gated entrance to Honeymoon Hideaway. Renovated August, 2019 with new full bathroom and designer kitchen with dishwasher, 2 burner stove, refrigerator with freezer, microwave!

A wooden deck overlooks the ocean, featuring two light blue lounge chairs positioned under a large umbrella. A sandy area is visible nearby, and a wooden pier extends into the water, with people engaged in activities in the distance.

4.99 out of 5 average rating, 104 reviews

Hidden Beach Duplex, Best Place in Key West

Go to sleep and wake up smiling listening to the waves. Just 3 blocks from Duval Street; this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort. This is an extraordinary condo on an extraordinary property. This is nicest unit of 3 for rent at Hidden Beach. If you are discerning, this really is best place place to stay in Key West.

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.

A light and airy living area features a modern blue sofa adorned with patterned throw pillows. A wooden coffee table sits in front, complemented by a tall indoor plant. A full-length mirror reflects the space, while natural light brightens the room through the patio door.

4.89 out of 5 average rating, 37 reviews

Duval Corner - Pet friendly with Balcony

Welcome to Duval Corner! A beautifully updated one-bedroom condo in the heart of Downtown Key West. This second-floor retreat is perfect for travelers wanting to be steps from it all. Within walking distance to iconic attractions like the Southernmost Point, The Ernest Hemingway Home, and Mallory Square, plus dining hotspots such as Blue Heaven, 7 Fish, and Louie's Backyard; Duval Corner is the ideal base for your Key West adventure.

Condo in Key Colony Beach

4.96 out of 5 average rating, 273 reviews

Amazing Ocean Front Views Key Colony Beach

Newly renovated studio condo in Key Colony Beach, Florida Keys. Unit #40 offers two queen beds, a full equipped kitchen with full-size appliances and essentials, reliable WiFi, and a SmartTV for a comfortable stay. Enjoy the heated pool and private sandy beach just steps away. Sunset Park is next door-perfect for catching a beautiful Florida Keys Sunset.

4.92 out of 5 average rating, 122 reviews

Vacation home Island Suite 16

The Island Suite is part of a historic Key West property built around 1889. Suite #16 is located on the first floor at the rear of the 411 William Street building. The Island Suite has one of the premiere locations in Old Town, Key West with lively Duval Street just 3 blocks away and the neighborhood boasting some of the finest older homes in Key West.

5 out of 5 average rating, 30 reviews

Key West • 2 Cabin • Yacht by Luxury Sea Charters

Skip the hotel room—own the horizon. Step aboard FREE TIME, your 50-foot floating suite in Key West. Two ensuite staterooms, a sun-soaked salon, and a private deck made for sunrise coffee or champagne sunsets. Docked in a premier marina with resort-style perks, this yacht redefines luxury travel—it’s not a stay, it’s a story you’ll tell for years.

A light-filled living space features a teal sleeper sofa and a small dining table with two white chairs. A textured area rug adds warmth to the wood floor. Decorative wall art and a ceiling fan enhance the relaxed atmosphere.

4.92 out of 5 average rating, 133 reviews

Duval Street Suites full kitchen, free parking, &

The Key West Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. In historic Old Town, Key West. Free parking available and the pool is privately located behind the building . Located in the middle of everything yet quiet and away from it all. This space is truly unique and sure to please all ages.

Popular amenities for Key West vacation rentals

Self check-in

Free parking on premises

Monthly stays

Beachfront

Private bathroom

What Airbnb hosts recommend seeing in Key West

Find unforgettable activities and unique points of interest near you. Our hosts share their favorite 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

Summarized 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

Summarized 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

Summarized 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

Summarized 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

Key West apartment rentals

The expansive outdoor pool is framed by palm trees and surrounded by lounge chairs with blue umbrellas. The area is well-lit and features a shaded pavilion. The surrounding building showcases tropical landscaping, providing a relaxing atmosphere for guests.

4.91 out of 5 average rating, 162 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

Apartment in Key Colony Beach

A shaded tiki hut with a thatched roof stands on the sandy shore, overlooking the calm, blue waters of the Atlantic Ocean. Two palm trees frame the structure, creating a serene beach environment, with gentle waves lapping at the rocks in the background.

4.86 out of 5 average rating, 136 reviews

Beachside Unit 22 - Private Beach on Atlantic

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, 863 reviews

Duval Balcony - Street Suite

5 out of 5 average rating, 6 reviews

Apartment in Marathon

Villa 4204 on Duck Key - Boat Slip available

An open concept studio apartment features a modern kitchen with stainless-steel appliances, including a coffee maker and oven. A dining table with black chairs is positioned near the kitchen. In the background, a spacious bed is visible, illuminated by natural light from large windows.

4.86 out of 5 average rating, 256 reviews

The Bartlum - Steps to Duval Street

A shared pool area is showcased overlooking Garrison Bight Marina. Lounge chairs are arranged around the pool, with a thatched gazebo providing shaded seating. The marina is visible in the background, featuring moored boats and palm trees against a clear sky.

4.92 out of 5 average rating, 104 reviews

Waterfront Condo FREE Slip & Pool 2B2B in Key West

5 out of 5 average rating, 7 reviews

Oceanview condo w/pool, jacuzzi

Apartment in Marathon

New place to stay

Complimentary Breakfast & Daily Housekeeping!

Key West beach vacation rentals

5 out of 5 average rating, 21 reviews

An aerial view showcases the resort's central pool surrounded by palm trees and landscaped gardens. The inviting pool area is complemented by a spacious pavilion with a metal roof, providing a gathering space. The background features the resort's accommodations and the lush natural environment.

Condo in Summerland Key

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

The living room features a spacious green sofa complemented by wicker armchairs. A glass dining table sits at the center, with light streaming through open shutters. The backdrop showcases ocean views, enhancing the connection to the balcony and natural surroundings.

4.87 out of 5 average rating, 60 reviews

Ocean front 1BR/1BA Suite w/ kitchen & living rm

4.88 out of 5 average rating, 133 reviews

A cozy living space features a navy blue sofa adorned with nautical-themed throw pillows. A dining area with a glass table and chairs is visible in the background, alongside a decorative display of framed art and a potted plant. Natural light filters through the windows.

Houseboat in Marathon

Houseboat Getaway In Marathon

An Olympic size pool is highlighted in the image, surrounded by palm trees and lounge chairs. The building in the background offers several balconies, and a well-maintained garden area is visible, enhancing the outdoor setting next to the beach.

4.78 out of 5 average rating, 308 reviews

Affordable Beachfront Luxury Condo Sleeps 6

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, 103 reviews

Palm - Beach Houses Key West

A spacious beachfront home is depicted, featuring a large outdoor area with neatly arranged tropical plants. A well-maintained pool is visible in the backyard, alongside a staircase leading to wraparound balconies that provide ample views of the surroundings.

4.9 out of 5 average rating, 79 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

The image captures a sandy beach scene with clear turquoise waters. Sunbathers and beachgoers are seen enjoying the sun on the shore, while lush palm trees line the beach. A beachfront villa is visible in the background, enhancing the coastal setting.

4.92 out of 5 average rating, 189 reviews

Beachfront Villa - Florida Keys

Condo in Key Colony Beach

An expansive view of a private beach is captured, showcasing gentle ocean waves lapping at the shore. Lounge chairs are arranged on a green lawn, offering relaxation options while a solitary figure strolls along the sandy beach. Palm trees frame the scene under a partly cloudy sky.

5 out of 5 average rating, 24 reviews

Private Beach in Marathons Key Colony Beach

Private Key West vacation rentals

A spacious outdoor area is surrounded by tropical landscaping, featuring a BBQ grill and a hot tub. Comfortable lounge chairs are available under umbrellas, with a gravel walkway leading to various seating arrangements. Sunlight filters through the palm fronds, creating a relaxing atmosphere.

4.96 out of 5 average rating, 45 reviews

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys

4.79 out of 5 average rating, 14 reviews

43' Classic Yacht Views, Pools, Duval Shuttle

A spacious balcony overlooks the harbor, featuring a dining table and wooden chairs. Lush palm trees are visible nearby, with the serene water reflecting the blue sky. The scene is perfect for outdoor relaxation and enjoying the coastal ambiance.

4.88 out of 5 average rating, 123 reviews

Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK

4.98 out of 5 average rating, 87 reviews

A busy street scene showcases Duval Street, with clear signage pointing in both directions. Lush palm trees line the sidewalks while pedestrians, enjoying the sunny weather, walk along the path. Colorful storefronts and flags create a vibrant atmosphere typical of Key West.

Home in Key West

Gorgeous Romantic Private Villa, Steps from Duval!

An open-concept living area is featured with light wood flooring and large windows allowing natural light. A modern dining table is set for four, while a cozy seating area includes a sofa and decorative wall art. Nautical elements enhance the coastal ambiance.

5 out of 5 average rating, 22 reviews

Marathon Paradise

A light-filled living area features a comfortable sofa paired with accent tables. Soft blue walls create a calming backdrop, while stylish decor elements, such as framed artwork and lamps, add character. A mirror reflects the space, enhancing its openness and inviting ambiance.

5 out of 5 average rating, 66 reviews

EYW Getaway

A sandy beachfront is framed by palm trees, with the glistening Atlantic ocean in the background. A volleyball net is set up on the sand, along with multiple seating areas for relaxation, inviting guests to enjoy the tranquil environment and scenic views.

4.91 out of 5 average rating, 46 reviews

Viamarhe House-Private beach, Kayak, yard games

A 40-foot catamaran is anchored in clear turquoise waters. Two individuals are enjoying the ocean; one is swimming while another relaxes on the deck. The yacht features a modern design with a spacious deck for sunbathing and enjoying the surrounding scenery.