Vacation rentals in Key West
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Quick stats about vacation rentals in Key West
Total vacation rentals
Explore 2,110 vacation rentals in Key West
Nightly prices starting at
Key West vacation rentals start at $10 per night before taxes and fees
Verified guest reviews
Over 74,900 verified reviews to help you choose
Family-friendly vacation rentals
1,250 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 730 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!
Top-rated vacation rentals in Key West
Guests agree: these stays are highly rated for location, cleanliness, and more.
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.
ATLANTIS...Ocean Front Cottage Retreat!
ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!
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.
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. 🛥️🌴🎣
Historic Cigar House. 3rd floor Suite W/Kitchen
This unit is located in the historic "Cigar House" of the Island City House Hotel. Unit 12 is on the 3rd floor and is one of the most requested units in the entire hotel. Your private balcony overlooks the pool. Only 3 blocks from Duval street so close everything, yet quiet enough for a good nights sleep. You will have your own private entrance and use of all the hotel amenities. The space is a private 1BR with a kitchen and NEW sleeper sofa (12/23). In Old Town, walk to everything.
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.
Hidden Beach unit 1 The Perfect Place to stay
This place is extraordinary. There is nothing like it in Key West. 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.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.
Cudjoe Key Home with a View
We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.
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.
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.
Tropical Heron Hideaway w/ Hot Tub + Pool
Welcome to our charming 1932 Key West retreat in the peaceful Meadows neighborhood. This unique getaway features a private porch, a private hot tub, access to a shared pool and BBQ grill, and all the comforts of home. Blending historic island charm with modern amenities, it’s just minutes from Duval Street, the Historic Seaport, beaches, restaurants, and local attractions—the perfect place to relax and experience authentic Key West.
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!
Popular amenities for Key West vacation rentals
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
Historic fort and park with nature trails, a beach, and scenic views
Summarized by AI
Spend the day between a Civil War–era fort and Key West’s favorite natural beach. Walk the red-brick corridors past cannons and gun ports, visit the small museum, or join a free daily or monthly reenactor tour to learn how soldiers once defended the coastline. Then swim, snorkel right off the beach, paddle, or fish in clear water, with chair and snorkel rentals on site. Finish with lunch or snacks from the concession stand and a shaded picnic or sunset under the trees.
Ernest Hemingway Home & Museum
Historic residence featuring guided tours, lush gardens, and famous six-toed cats
Summarized by AI
Tour Ernest Hemingway’s former home, a National Historic Landmark where many of his most famous works were written, and walk through rooms furnished with original 17th- and 18th-century Spanish pieces. Join a 20–30 minute guided tour or explore on your own to learn about his life, “Wall of Shame,” and Key West history while wandering the lush gardens. Meet the world‑famous polydactyl (six‑toed) cats, whose descendants freely roam the property. Admission is cash only, with a bookstore and gift shop on-site; afterward, you can grab a meal at Moondog Cafe next door.
Southernmost Point
Iconic concrete buoy marking the southernmost point in the continental United States, 90 miles from Cuba
Summarized by AI
At Southernmost Point, you can stand by the giant, candy-striped concrete buoy painted bright red, yellow, and black, marked “90 miles to Cuba,” and grab the classic photo at the southernmost point of the continental United States. Join the line of visitors snapping selfies and family pics with waves crashing, turquoise water, sailboats, and palm trees in the background. Go early to avoid long lines and check the buoy anytime via the southernmost webcam. Afterward, you can pair your visit with nearby Southernmost House and Seaside Café.
Key West Butterfly & Nature Conservatory
Enchanting glass conservatory with diverse butterfly species, exotic birds, and flamingos
Summarized by AI
Step into the glass-enclosed conservatory to stroll among 50–60 species of butterflies from around the world, hundreds of them flying freely around you. Wander past flowering plants, trees, cascading waterfalls, and soothing music while spotting more than 20 species of small, colorful birds and the resident flamingo pair, Rhett and Scarlett. It’s an easy indoor escape for all ages, especially on rainy days. Bring your camera, then finish with their unique photos and gift shop.
Key West apartment rentals
Key West Beachside 1400sf, 2 Bedroom Condo
Duval Balcony - Street Suite
Duval Corner - Pet friendly with Balcony
Duval Street Suites with full kitchen heated pool,
Old Town Key West suite w/ private spa
Sky Suite with Balcony Overlooking Duval Street
Waterfront Condo FREE Slip & Pool 2B2B in Key West
King Bed | Key West *Best Downtown Locations *Cool
Key West beach vacation rentals
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
Houseboat Getaway In Marathon
Affordable Beachfront Luxury Condo Sleeps 6
Lagoona-Matata
Beachfront Villa - Florida Keys
P87 - Modern 4 bedroom, 4 bath home on open water
Vibrant Beachfront Villa
Family Retreat
Private Key West vacation rentals
*August/September specials* off Grid Boat Key West
Cozy Tiny Houseboat: Find Your Peace and Balance
Beach House in Marathon with Amazing Backyard!
3BR In Resort Village, Pools, Free Kayak & Shuttle
b watervibe
Waterfront Dock Pool Condo Near Duval St Pet OK
NEW! Private Pool, 50’ Dock, Kayaks, Waterfront
Sea Glass Cottage in Historic Key West
When is the best time to visit Key West?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $448 | $519 | $482 | $350 | $315 | $286 | $293 | $267 | $246 | $303 | $344 | $384 |
| Avg. temp | 71°F | 72°F | 74°F | 78°F | 81°F | 84°F | 85°F | 86°F | 84°F | 81°F | 77°F | 73°F |
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.
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- Southernmost Point
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