Vacation rentals in Key West

5 out of 5 average rating, 3 reviews

Condo in Marathon

Oceanfront bliss heated pool beach U31

Escape to our oceanfront paradise, where serene ocean views await you! This updated condo offers a cozy king bed, a sofa sleeper, and modern comforts, including two new flat-screen TVs and a Keurig coffee maker. Dive into our large heated pool or explore the beach. Ideal for families and couples seeking a tranquil retreat, this condo combines comfort with the unique charm of the Florida Keys. Experience a slice of beach life, enhanced by our lovingly renovated space and exceptional ocean views.

4.97 out of 5 average rating, 297 reviews

Home in Key West

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.

4.9 out of 5 average rating, 233 reviews

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.

Boat in Key West

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. 🛥️🌴🎣

Condo in Key Colony Beach

A spacious bed is adorned with crisp white linens and a vibrant throw pillow featuring a fish design. Large windows frame the room, allowing natural light to illuminate the interior while offering views of the ocean and nearby palm trees.

4.96 out of 5 average rating, 227 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

Impeccable condo directly on the ocean with water views. Experience a wonderful ocean view from our beachfront condo in Key Colony Beach. Newly renovated studio condo in Key Colony Beach, Florida Keys. Unit #20 offers one king bed, a fully 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.

Home in Upper Sugarloaf Key

The bungalow stands illuminated against a night sky, surrounded by swaying palm trees. Soft reflections shimmer on the water's surface, while the sandy beach extends along the shoreline. The structure features large windows, showcasing a welcoming interior visible from outdoors.

4.93 out of 5 average rating, 117 reviews

The Lighthouse - Beach Houses Key West

If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

A private balcony is shown, featuring colorful patio chairs and vibrant tropical plants. The space is framed by white railings and light blue shutters, creating a fresh and inviting setting for relaxation.

4.89 out of 5 average rating, 279 reviews

Tropical Old Town Bungalow

Great Location, Close to Duval & Beach Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Historic District, which features some of Key West’s most historic homes and properties. Whether you are walking, riding bikes or grabbing a quick cab, no destination is too far from this conveniently located rental.

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.

4.98 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

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.

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, 258 reviews

The Bartlum - Steps to Duval Street

Welcome to the Bartlum, a historic and luxurious studio apartment just steps to Duval Street. This studio, located on Caroline St, has been designed with comfort in mind, offering large windows for natural sunlight and plenty of space to spread out. Enjoy an updated kitchen, spacious bathroom, open concept layout, and all the hot spots of Key west within walking distance!

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.

4.94 out of 5 average rating, 173 reviews

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.

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, 864 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 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, 163 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 modern living area is presented with a comfortable grey sofa and two patterned chairs facing a large sliding door. Natural light fills the space, illuminating a textured wood coffee table and a side table with a lamp. A mounted television displays vibrant sunset imagery.

4.98 out of 5 average rating, 65 reviews

Newly Renovated 2/2 Bath Condo, with shared pool

5 out of 5 average rating, 8 reviews

Apartment in Marathon

New! Waterfront Views | Pool & Tiki Bar

A private deck area features a Jacuzzi in the foreground, surrounded by lush greenery. French doors open to a cozy interior space, showcasing a seating area and warm natural light. Outdoor seating is visible, inviting relaxation.

4.78 out of 5 average rating, 158 reviews

Mango Hideaway @ the Eyebrow House off Duval

A spacious pool area features a large swimming pool surrounded by lounge chairs and vibrant blue umbrellas. Lush palm trees provide shade, and ocean views are visible in the background, enhancing the tranquil atmosphere of the outdoor space.

4.9 out of 5 average rating, 10 reviews

Henry's Penthouse On The Ocean

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, 106 reviews

Waterfront Condo FREE Slip & Pool 2B2B in Key West

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.

4.93 out of 5 average rating, 134 reviews

Duval Street Suites full kitchen, free parking, &

Key West beach vacation rentals

4.88 out of 5 average rating, 118 reviews

A row of townhomes is positioned along the water's edge, surrounded by well-maintained landscaping. Lush green trees provide shade, and the calm water reflects the serene environment. The horizon reveals a glimpse of distant trees and open water.

Condo in Duck Key

Villa 5027 on Duck Key BOAT SLIP available

4.98 out of 5 average rating, 61 reviews

Grouper Getaway @ Ocean Isles Fishing Village

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, 61 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, 309 reviews

Affordable Beachfront Luxury Condo Sleeps 6

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, 80 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, 190 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

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

4.86 out of 5 average rating, 272 reviews

Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock

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, 68 reviews

EYW Getaway

4.97 out of 5 average rating, 37 reviews

Boat in Key West

Houseboat in Key West

4.91 out of 5 average rating, 23 reviews

P31 - 2 bed, 2 bath with Spectacular Open Water on

The outdoor area features a sandy patio surrounded by palm trees, with several blue Adirondack chairs facing a shaded seating area under a white gazebo. The spacious home stands in the background, showcasing multiple balconies and a light-colored exterior.

4.88 out of 5 average rating, 84 reviews

Gorgeous Ocean View Home!

5 out of 5 average rating, 4 reviews

Waterfront Pool Home w/ 30’ Dock, Kayaks & Outdoor