Vacation rentals in Key West
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Top-rated vacation rentals in Key West
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Home in Key West
4.94 out of 5 average rating, 268 reviewsRomantic 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.
Aug 4 – 11
Apartment in Key West
4.98 out of 5 average rating, 441 reviewsBella 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 & BlueTooth stereo system with CD player & radio.
Jan 20 – 27
Vacation home in Key West
4.88 out of 5 average rating, 222 reviewsHistoric 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.
Mar 4 – 11
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Key West vacation rentals
Houses in Key West
Home in Key Largo
4.9 out of 5 average rating, 345 reviewsYour Keys Getaway!
Feb 4 – 11
Home in Marathon
4.96 out of 5 average rating, 118 reviewsOceanfront Tiny Villa in the Heart of the FL Keys
Sep 16 – 23
Home in Marathon
4.9 out of 5 average rating, 155 reviewsBeachfront Villa - Florida Keys
Oct 5 – 12
Home in Cudjoe Key
4.92 out of 5 average rating, 134 reviewsParadise and Cudjoe Bay
Aug 30 – Sep 6
Home in Cudjoe Key
4.97 out of 5 average rating, 115 reviewsCudjoe Key Home with a View
Sep 8 – 15
Home in Cudjoe Key
4.91 out of 5 average rating, 102 reviewsSunrise Beach Escape
Jul 6 – 13
Home in Marathon
4.97 out of 5 average rating, 115 reviewsMarathon one-level home on the Marina - with slip!
May 8 – 15
Home in Marathon
4.99 out of 5 average rating, 103 reviewsSea Ray Cove , 75’ boat dock, 1 block from beach!
Jan 22 – 29
Home in Islamorada
4.97 out of 5 average rating, 162 reviewsFlakey's
Aug 17 – 24
Home in Key Largo
4.98 out of 5 average rating, 114 reviewsWaterfront Sunsets, Great Price, Relaxing Spot!!!
Aug 7 – 14
Home in Marathon
4.97 out of 5 average rating, 31 reviewsThe Gulf Cottage at Marathon Key
Jun 7 – 14
Home in Key Colony Beach
4.98 out of 5 average rating, 44 reviewsCaptain’s Quarters Ahoy Mateys! Florida, Keys
Oct 1 – 8
Condos in Key West
Condo in Key West
4.8 out of 5 average rating, 153 reviewsLarge 2/2 Waterfront Condo Great View Pool & Dock
May 10 – 17
Condo in Key Colony Beach
4.79 out of 5 average rating, 102 reviewsBeachside Unit 28 - Private Beach, Pool & Paradise
Oct 2 – 9
Condo in Key West
4.85 out of 5 average rating, 142 reviewsAnchor Drop modern elegance upgrades throughout vi
Aug 11 – 18
Condo in Key West
4.83 out of 5 average rating, 237 reviewsLa Dolce Vita, Old Town Steps to Duval! 3 blks bch
Mar 21 – 28
Condo in Marathon
4.88 out of 5 average rating, 184 reviewsSombrero Beach Tropical Getaway
Sep 16 – 23
Condo in Tavernier
4.88 out of 5 average rating, 222 reviewsSPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Jul 30 – Aug 6
Condo in Tavernier
4.95 out of 5 average rating, 103 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Jul 20 – 27
Condo in Tavernier
4.95 out of 5 average rating, 154 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
Oct 7 – 14
Condo in Tavernier
4.93 out of 5 average rating, 127 reviewsIt's Tiki Time in the Keys! Mid-Mod 1 Br/1Ba
Apr 24 – May 1
Condo in Key Largo
4.87 out of 5 average rating, 133 reviewsTropical Getaway
Oct 25 – Nov 1
Condo in Key Largo
4.97 out of 5 average rating, 146 reviewsKEYS BEACH RETREAT WITH CAPTIVATING WATERVIEW!
Feb 16 – 23
Condo in Tavernier
4.97 out of 5 average rating, 220 reviewsSea View Oceanfront Condo
Oct 17 – 24
Lake houses in Key West
Home in Key Colony Beach
4.81 out of 5 average rating, 131 reviewsWaterview from three sides, Cabana Club, 30' Docks
Jan 4 – 11
Home in Key Largo
4.89 out of 5 average rating, 157 reviewsOutdoor Paradise - Beach, Boats, Snorkeling & Sun!
Sep 15 – 22
Home in Key Largo
4.89 out of 5 average rating, 101 reviewsNEW CASA PALMA VOTED BEST AIRBNB RENTAL! GOLF CART
Sep 20 – 27
Home in Marathon
5.0 out of 5 average rating, 6 reviewsWaterfront Escape -VACA-23-408
Oct 16 – 23
Home in Cudjoe Key
5.0 out of 5 average rating, 5 reviewsVenture Out -Million Dollar Island Resort
Nov 23 – 30
Home in Key Largo
4.89 out of 5 average rating, 55 reviews5 O'clock Somewhere - Key Largo
Apr 30 – May 7
Home in Marathon
5.0 out of 5 average rating, 14 reviewsWalk to Sombrero Beach, 50’Dock, SPA, Bikes,Kayaks
Sep 8 – 15
Home in Key Largo
4.88 out of 5 average rating, 8 reviewsWaterfront Key Largo Home - Tropical Paradise
Oct 5 – 12
Home in Tavernier
4.96 out of 5 average rating, 50 reviewsSunset Beach Hideaway *Private Beach* *Jacuzzi*
Aug 22 – 29
Home in Marathon
5.0 out of 5 average rating, 4 reviewsMermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!
Feb 2 – 9
Home in Marathon
5.0 out of 5 average rating, 4 reviews5 O'Clock Somewhere Bay House, Drinks on Us!
Sep 14 – 21
Home in Marathon
5.0 out of 5 average rating, 31 reviewsMarathon Beach house w/45’ dock Ocean access
Sep 9 – 16
Quick stats about vacation rentals in Key West
Total rentals | 1.8K properties |
---|---|
Rentals with a pool | 1.2K properties have a pool |
Pet-friendly rentals | 490 properties allow pets |
Family-friendly rentals | 1.1K properties are a good fit for families |
Total number of reviews | 52K reviews |
Nightly prices starting at | $10 before taxes and fees |
Your guide to Key West
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.
The best time to stay in a vacation rental in Key West
Winter is the most popular season in Key West, as the hot weather draws sun-seekers to the beaches, especially around the December holidays. You can also come in spring for sun and fewer crowds — despite Key West’s bustling nightlife scene, it isn’t typically hit by Spring Break crowds like other places in Florida. It’ll be warm enough to get in the water and enjoy beach time, with fewer people than in winter. Despite a September to November hurricane season, autumn is also a good time to check out Key West’s museums or to revel in the hedonistic Fantasy Fest while enjoying cooler air.
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.
Frequently Asked Questions
How is the weather in Key West?
Key West has a tropical climate with warm temperatures year-round. Summers, from June to August, can be hot and humid, often reaching 90°F (32°C). Winters, from December to February, are milder, with temperatures typically around 70°F (21°C), and less rainfall.
What are some of the best things to do in Key West?
Popular activities in Key West include exploring the vibrant coral reefs on a snorkeling trip, discovering local marine life at the Key West Aquarium, or visiting the historic Fort Zachary Taylor State Park. A stroll along Duval Street for shopping and local cuisine is also recommended.
What is the best time of year to visit Key West?
Key West is particularly lively between March and May, with milder temperatures and fewer crowds. During these months, you can enjoy events like the Conch Republic Independence Festival and the Key West Songwriters Festival.
What are the best places to stay in Key West?
Some highly-rated areas to stay in Key West include Old Town, a historic district with classic architecture, Truman Annex for its peaceful atmosphere, and New Town for its modern conveniences. Duval Street is also favored for its proximity to dining and shopping options.
What are the best places to visit in Key West?
Key West is known for diverse attractions such as the Ernest Hemingway Home and Museum, where the renowned author once lived, and the Key West Butterfly and Nature Conservatory. Don't miss the stunning sunsets at Mallory Square, and the view from the historic Key West Lighthouse. The Southernmost Point Buoy is also frequently visited.
What are some hiking trails in Key West?
While Key West is not known for its hiking, you can enjoy a leisurely walk at the Key West Tropical Forest and Botanical Garden. The Island City National Historic District also has interesting paths through the town's picturesque streets.
What are some family activities to do in Key West?
Families can enjoy a visit to the Key West Shipwreck Museum, engage with interactive exhibits at the Florida Keys Eco-Discovery Center, or have fun exploring the Key West Aquarium. A ride on the charming Conch Tour Train is also a delightful way to see the city.
What are some of the best day trip ideas in Key West?
For a memorable day trip, explore the natural beauty of Dry Tortugas National Park, which is accessible by ferry or seaplane. Also, consider a wildlife expedition at the Key West Wildlife Center, or learn more about the region's history with a visit to Fort East Martello Museum.
What types of vacation rentals are available in Key West?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Key West. From over 520 house rentals to over 410 condo rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Are there vacation rentals with a dedicated workspace in Key West?
Yes! Work meets play with ease at over 910 vacation rentals in Key West featuring dedicated workspaces. Stay connected and productive in your home away from home.
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