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Vacation rentals in Key West

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Top-rated vacation rentals in Key West

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Guest favorite
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
4.92 out of 5 average rating, 131 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.

Guest favorite
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
4.9 out of 5 average rating, 234 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. 🛥️🌴🎣

Guest favorite
A wooden sign with the name 'Center Court' is prominently displayed, surrounded by lush tropical foliage. The sign features a decorative design and is mounted on a white post, indicating the location of the historic inn and cottages.
Home in Key West
4.91 out of 5 average rating, 239 reviews

McCartney's Manor - Deluxe K Suite W/Pvt. Spa!

Beautifully decorated, step inside with cool pastel colors. The amenities include a blue tooth speaker, Alexa Echo, and a full kitchen with dishwasher. End your day by relaxing in front of the 65" Smart TV (bring your login information for Netflix/Amazon). The tumbled marble shower adds a luxurious touch to your stay. Located in a gated compound with 3 other units, you'll have privacy during your stay. The heated family pool is next door, while the adult heated pool is across the lane.

Guest favorite
A tranquil outdoor pool is surrounded by palm trees, with lounge chairs and tables positioned for relaxation. Umbrellas provide shade near the water, while a charming cottage can be seen in the background under a clear blue sky.
Townhouse in Key West
4.86 out of 5 average rating, 234 reviews

Poolside Cottage #412

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of KW. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the seaport and world famous Duval Street! Bikes, golf carts, kayaks, stand-up paddleboards and other watercraft can all be rented locally!

Top guest favorite
Apartment 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.

Guest favorite
Condo in Key West
4.9 out of 5 average rating, 136 reviews

Walk to Duval ! Cozy Key West Cottage

Welcome to The Cozy Little Cottage! A REAL ISLAND GETAWAY IN KEY WEST!!! Nestled in the heart of Key West, The Cozy Little Cottage, welcomes you to a sanctuary of comfort and convenience. Stay in the heart of Old Town Key West—just steps from Duval Street, yet tucked away for a peaceful retreat. 🚫 As typical in Old Town Key West, there is no dedicated on-site parking. Street parking is available nearby on a first-come, first-serve

Superhost
A comfortable outdoor seating area is showcased, with bright blue cushions arranged around a dark table. The view overlooks crystal-clear waters, and decorative lanterns provide soft lighting. A potted flower adds a touch of color beside the seating, enhancing the peaceful ambiance by the water.
Home in Cudjoe Key
4.88 out of 5 average rating, 130 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Guest favorite
The houseboat is anchored in the Cow Key Channel, featuring a sunlit exterior with a white finish. A deck extends from the entrance, complemented by a hammock and kayaks nearby. Clear blue skies and calm waters create a peaceful setting.
Houseboat in Key West
4.93 out of 5 average rating, 223 reviews

Beautiful Houseboat in Key West

Enjoy a unique and peaceful stay on our cozy houseboat in Key West. Perfect for couples or small families who want a relaxing water experience close to town. Comfortable sleeping area, deck space, and beautiful sunset views. Check-in is by appointment with personal captain meet-and-greet and boat transfer from the marina. A memorable island stay surrounded by nature and ocean air.

Guest favorite
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.
Apartment in Key West
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!

Top guest favorite
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
4.91 out of 5 average rating, 526 reviews

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.

Guest favorite
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.
Apartment in Key West
4.92 out of 5 average rating, 106 reviews

Waterfront Condo FREE Slip & Pool 2B2B in Key West

🌴 Key West Waterfront Paradise – FREE Dockage Included! Wake up to breathtaking marina views, unwind in the heated pool, and walk or bike to Duval Street in minutes. Enjoy a spacious condo with a private balcony, exclusive boat slip, and all the comforts you need for an unforgettable stay in the heart of Key West.

Guest favorite
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
4.94 out of 5 average rating, 169 reviews

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Spencer’s 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

Popular amenities for Key West vacation rentals

Self check-inFree parking on premisesMonthly staysBeachfrontPrivate bathroom

Stay near Key West's top sights

Smathers Beach

57 locals recommend

Key West

392 locals recommend

Key West Lighthouse Museum

55 locals recommend

Southernmost Point

104 locals recommend

Ernest Hemingway Home & Museum

268 locals recommend

Mallory Square

61 locals recommend

Key West apartment rentals

Guest favorite
A private balcony is adorned with festive garland, offering a view of a serene pool area surrounded by lush greenery. Two wicker chairs provide a comfortable spot to relax and enjoy the outdoors, with sun loungers visible beside the pool.
Apartment in Key West
4.96 out of 5 average rating, 24 reviews

Casa Caribe 2bed2bath sleeps 6 beautiful decorated

Top guest favorite
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.
Apartment in Key West
4.91 out of 5 average rating, 163 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

Top guest favorite
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.
Apartment in Key Colony Beach
4.86 out of 5 average rating, 136 reviews

Beachside Unit 22 - Private Beach on Atlantic

Guest favorite
Apartment in Marathon
5 out of 5 average rating, 9 reviews

Villa 4204 on Duck Key - Boat Slip available

Top guest favorite
The entrance to a charming village is marked by an archway adorned with colorful lettering and a distinctive emblem. Lush palm trees line the quiet street, which is paved with bricks, and features colorful buildings along either side.
Apartment in Key West
4.92 out of 5 average rating, 167 reviews

Duval Street Suites with full kitchen heated pool,

Top guest favorite
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.
Apartment in Key West
4.99 out of 5 average rating, 67 reviews

Newly Renovated 2/2 Bath Condo, with shared pool

Superhost
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.
Apartment in Key West
4.79 out of 5 average rating, 159 reviews

Mango Hideaway @ the Eyebrow House off Duval

Superhost
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.
Apartment in Key West
4.9 out of 5 average rating, 10 reviews

Henry's Penthouse On The Ocean

Key West beach vacation rentals

Guest favorite
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
5 out of 5 average rating, 21 reviews

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Superhost
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
4.88 out of 5 average rating, 134 reviews

Houseboat Getaway In Marathon

Guest favorite
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.
Condo in Key West
4.78 out of 5 average rating, 312 reviews

Affordable Beachfront Luxury Condo Sleeps 6

Superhost
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.
Home in Upper Sugarloaf Key
4.75 out of 5 average rating, 103 reviews

Palm - Beach Houses Key West

Top guest favorite
An aerial view showcases a serene beach setting with a clear blue pool at the center, surrounded by lush green lawns and palm trees. The gentle waves of the ocean are visible in the background, with two white, two-story buildings framing the scene.
Home in Key Colony Beach
4.94 out of 5 average rating, 48 reviews

Island Breeze

Top guest favorite
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.
Home in Marathon
4.92 out of 5 average rating, 190 reviews

Beachfront Villa - Florida Keys

Top guest favorite
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.
Condo in Key Colony Beach
5 out of 5 average rating, 24 reviews

Private Beach in Marathons Key Colony Beach

Superhost
An airy dining area features a white stone-topped table positioned beneath a stylish light fixture. Large glass doors allow natural light to flood the space, connecting indoor and outdoor seating areas. The wooden floor adds warmth to the contemporary design.
Home in Marathon
4.83 out of 5 average rating, 12 reviews

SeaEsta! Bring your boat & 1 block to the beach!

Private Key West vacation rentals

Guest favorite
A spacious outdoor dining area features a glass-top table with several red chairs, set against a vibrant backdrop of greenery and water. The view of the calm sea and fluffy clouds can be seen in the distance, enhancing the tranquil setting.
Home in Cudjoe Key
4.86 out of 5 average rating, 35 reviews

Yellow Home - Receive $400 towards a Boat Rental!

Guest favorite
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
4.94 out of 5 average rating, 163 reviews

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

Guest favorite
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
4.92 out of 5 average rating, 112 reviews

Waterfront Haven House with Boat Basin & Ramp!

Guest favorite
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.
Condo in Key West
5 out of 5 average rating, 70 reviews

EYW Getaway

Guest favorite
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.
Home in Marathon
4.92 out of 5 average rating, 48 reviews

Viamarhe House-Private beach, Kayak, yard games

Top guest favorite
An outdoor theater area is outlined by a modular seating arrangement with blue cushions and dark wicker. A large projection screen is mounted on a wooden wall, creating an inviting space for movie nights. Soft lighting from overhead strands completes the ambiance.
Home in Marathon
4.93 out of 5 average rating, 41 reviews

Oceanview Marathon - Screened Porch, Theater & Bar

Superhost
Home in Cudjoe Key
4.86 out of 5 average rating, 7 reviews

Tropical Paradise

Top guest favorite
A vibrant sunset casts a warm glow over the outdoor area featuring a sheltered gazebo, surrounded by lush greenery and reflective water. Nearby, a modern living room is furnished with comfortable seating and a large screen, creating an inviting space for relaxation.
Home in Marathon
4.95 out of 5 average rating, 113 reviews

Coco Plum Waterfront Hideaway Home in Marathon

When is the best time to visit Key West?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$80,827 GYDG$90,226 GYDG$85,631 GYDG$73,100 GYDG$65,790 GYDG$59,733 GYDG$61,195 GYDG$55,765 GYDG$51,379 GYDG$63,284 GYDG$71,847 GYDG$80,201 GYD
Avg. temp21°C22°C24°C25°C27°C29°C30°C30°C29°C27°C25°C23°C

Frequently Asked Questions

  • What are the best places to stay in Key West?

    Key West has inviting neighborhoods like Old Town, known for historic homes, and Mallory Square, which is close to lively waterfront activities. Staying near Duval Street places you close to dining and entertainment, while quieter areas like Truman Annex often attract those seeking a relaxed atmosphere.

  • What are the best things to do in Key West with kids?

    Families often explore the Key West Butterfly and Nature Conservatory, visit the Key West Aquarium, and play on sandy beaches. Interactive museums, pirate-themed tours, and dolphin-watching excursions are frequently suggested for children.

  • What are some of the best things to do in Key West?

    You can explore Ernest Hemingway Home and Museum, stroll lively Duval Street, or watch the sunset at Mallory Square. Visitors frequently snorkel in clear waters, discover art galleries, and tour historic sites around the island.

  • How is the weather in Key West?

    Key West has warm weather year-round, with winter temperatures around 65–76°F (19–24°C) and summer highs reaching 91°F (33°C). Rainfall tends to be higher from June through October, while breezes help make coastal areas pleasant.

  • What are the best places to visit in Key West?

    Mallory Square draws crowds for daily sunset gatherings, and the Southernmost Point is popular for photos. The Ernest Hemingway Home and Museum and Key West Lighthouse highlight the island’s historic character.

  • What are some hiking trails in Key West?

    Key West has shorter walking paths, like the nature trails at Key West Tropical Forest & Botanical Garden and scenic shoreline walks around Fort Zachary Taylor Historic State Park. These areas combine greenery with views of the water.

  • What are some family activities we can do in Key West?

    Families can explore interactive exhibits at the Key West Shipwreck Museum, watch sea life at the Key West Aquarium, or join mangrove kayak tours. Sandy beaches and creative workshops are frequently suggested, especially for children.

  • What are some of the best day trip ideas from Key West?

    Day trips often include exploring the islands and marine life in Dry Tortugas National Park, visiting nearby wildlife refuges, or snorkeling from local boat tours. Historic landmarks and island nature preserves are also frequently suggested.

  • Are there any pet friendly accommodations available in Key West?

    Key West has pet-friendly vacation rentals in several neighborhoods, including Old Town and New Town. Many hosts welcome pets, and local parks make it easy to enjoy island walks with your dog.

  • What are some local tips for visiting Key West?

    Locals recommend wearing reef-safe sunscreen, exploring by bike or foot, and trying fresh seafood at casual spots. Sunset gatherings in Mallory Square and early morning walks along quiet streets offer unique island perspectives.

  • What is Key West known for?

    Key West is known for its lively Duval Street, colorful sunsets, and waterfront celebrations in Mallory Square. The city has a rich literary history, historic architecture, and active arts and water sports communities.

  • What are the best hidden gems to explore in Key West?

    Smaller museums like the Key West Firehouse Museum and Secret Garden, tucked-away art studios, and secluded beaches are frequently suggested by locals. Exploring side streets often reveals tucked-away architecture and murals.

  • What are the best foods to try in Key West?

    Key lime pie is frequently suggested, alongside fresh grouper sandwiches, conch fritters, and tropical fruit salads. Coastal restaurants highlight Caribbean-influenced seafood and Cuban flavors in many dishes.

  • What should I bring for a trip to Key West?

    Pack light clothing, sun protection, swimwear, sturdy sandals, and a reusable water bottle for outdoor activities. A wide-brimmed hat and rain jacket can be useful, especially from late spring through early fall.

  • What is the nightlife in Key West like?

    Duval Street is known for lively bars, music venues, and late-night gatherings, while waterfront lounges around Mallory Square attract sunset crowds. Explore dance floors, drag shows, and laid-back patios throughout the area for varied experiences.

  • What are the most popular events or festivals in Key West?

    Fantasy Fest draws creative costumes and parades each fall, and Hemingway Days celebrates the author's legacy in summer. The Conch Republic Days highlight local history, while waterfront sunset celebrations are daily traditions.

  • Are there family friendly vacation rentals in Key West?

    Key West has family-friendly vacation rentals in neighborhoods such as Old Town, Truman Annex, and Bahama Village. Many hosts provide amenities suitable for children, with easy access to beaches and parks.

  • When is the best time to visit Key West?

    Late winter through spring is often recommended for milder temperatures, less rainfall, and lively events. The island buzzes with festivals, water activities, and vibrant sunsets during these months.

All about Key West

Key West is a town that overflows with zest: turquoise waters and sandy beaches, dive bars that never seem to close, stunning sunsets, pastel-hued homes, great American literary legacies, and a sordid haunted past. Chow down on key lime pie and conch fritters, snap a pic at the southernmost point of the continental United States, and take in as much sea and sun as your eyes can handle.

Key West sits right across the Florida Strait from Cuba, and the influence can be felt in many of the island’s favorite haunts, where you can learn to dance the salsa, sample locally distilled rum, and pile your breakfast plate high with sweet fried plantains and savory beans. However you spend your days, make sure that you’re back in Mallory Square before sunset, when live music from restaurant patios and vendors’ stalls fills the pedestrian-only square and people celebrate the show-stopping sunset with all the fanfare it deserves.

What are the top things to do in Key West?

Snorkeling

Home to the only living Barrier Reef in the continental United States, Key West has some of the most incredible snorkeling in the world. Head out to the cluster of tiny islands known as the Dry Tortugas National Park for the best of the best: this area is home to unspoilt coral reefs, hundreds of species of tropical fish, starfish, and conch.

Ghost tours

Key West is rumored to be one of the most haunted cities in America, in juxtaposition with its sunny, good-time appearance. For fans of classic horror, be sure to ask about a famous local doll and the film franchise he inspired. Listen to ghost stories on board a spooky train tour, go on a guided walk around town, or check out the quirky inscriptions on the local graves at the cemetery.

Key lime pie

Key lime pie can be found on just about any menu here, from dive bars to high-end bistros, and with good reason — the island’s eponymous pie is zesty, creamy, and delicious. Traditionally made from tangy key lime juice and a rich, sweet custard of egg yolk and condensed milk atop a crust, everybody from home cooks to renowned chefs has their own take on how it should be made. Try as many versions as you can while you’re here, and join in on the debate of cooked versus uncooked filling, graham cracker versus pie crust, and whipped cream versus meringue topping.

Quick stats about vacation rentals in Key West

  • Total vacation rentals

    Explore 2,130 vacation rentals in Key West

  • Nightly prices starting at

    Key West vacation rentals start at G$2,089 GYD per night before taxes and fees

  • Verified guest reviews

    Over 69,260 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,280 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 680 rentals that welcome pets

  • Vacation rentals with a pool

    1,650 properties feature pools

  • Rentals with dedicated workspaces

    1,010 properties have a dedicated workspace

  • Wi-Fi availability

    2,050 of Key West vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Free parking on premises, and Monthly stays across Key West rentals

  • 4.8 Average rating

    Key West stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore

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