Some info has been automatically translated. Show original language

Vacation rentals in Key West

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Key West

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Home in Key West

4.94 out of 5 average rating, 268 reviews

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.

Aug 4 – 11

G$105,090 GYD per night
Guest favorite

Apartment in Key West

4.98 out of 5 average rating, 441 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 & BlueTooth stereo system with CD player & radio.

Jan 20 – 27

G$71,088 GYD per night
Superhost

Vacation home in Key West

4.88 out of 5 average rating, 222 reviews

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.

Mar 4 – 11

G$84,826 GYD per night

Stay near Key West's top sights

Duval Street62 locals recommend
Mallory Square100 locals recommend
Key West Butterfly and Nature Conservatory56 locals recommend
Fort Zachary Taylor Historic State Park47 locals recommend
Higgs Beach21 locals recommend
Sebago Watersports6 locals recommend

Houses in Key West

Guest favorite

Home in Key Largo

4.9 out of 5 average rating, 345 reviews

Your Keys Getaway!

Feb 4 – 11

G$37,378 GYD per night
Guest favorite

Home in Marathon

4.96 out of 5 average rating, 118 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Sep 16 – 23

G$83,441 GYD per night
Guest favorite

Home in Marathon

4.9 out of 5 average rating, 155 reviews

Beachfront Villa - Florida Keys

Oct 5 – 12

G$84,902 GYD per night
Guest favorite

Home in Cudjoe Key

4.92 out of 5 average rating, 134 reviews

Paradise and Cudjoe Bay

Aug 30 – Sep 6

G$76,346 GYD per night
Guest favorite

Home in Cudjoe Key

4.97 out of 5 average rating, 115 reviews

Cudjoe Key Home with a View

Sep 8 – 15

G$60,285 GYD per night
Superhost

Home in Cudjoe Key

4.91 out of 5 average rating, 102 reviews

Sunrise Beach Escape

Jul 6 – 13

G$83,656 GYD per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 115 reviews

Marathon one-level home on the Marina - with slip!

May 8 – 15

G$124,750 GYD per night
Guest favorite

Home in Marathon

4.99 out of 5 average rating, 103 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

Jan 22 – 29

G$139,230 GYD per night
Guest favorite

Home in Islamorada

4.97 out of 5 average rating, 162 reviews

Flakey's

Aug 17 – 24

G$55,129 GYD per night
Guest favorite

Home in Key Largo

4.98 out of 5 average rating, 114 reviews

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Aug 7 – 14

G$54,720 GYD per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

The Gulf Cottage at Marathon Key

Jun 7 – 14

G$31,405 GYD per night
Guest favorite

Home in Key Colony Beach

4.98 out of 5 average rating, 44 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

Oct 1 – 8

G$51,909 GYD per night

Condos in Key West

Superhost

Condo in Key West

4.8 out of 5 average rating, 153 reviews

Large 2/2 Waterfront Condo Great View Pool & Dock

May 10 – 17

G$127,288 GYD per night
Superhost

Condo in Key Colony Beach

4.79 out of 5 average rating, 102 reviews

Beachside Unit 28 - Private Beach, Pool & Paradise

Oct 2 – 9

G$48,675 GYD per night
Guest favorite

Condo in Key West

4.85 out of 5 average rating, 142 reviews

Anchor Drop modern elegance upgrades throughout vi

Aug 11 – 18

G$108,562 GYD per night
Guest favorite

Condo in Key West

4.83 out of 5 average rating, 237 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

Mar 21 – 28

G$105,715 GYD per night
Guest favorite

Condo in Marathon

4.88 out of 5 average rating, 184 reviews

Sombrero Beach Tropical Getaway

Sep 16 – 23

G$49,154 GYD per night
Superhost

Condo in Tavernier

4.88 out of 5 average rating, 222 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Jul 30 – Aug 6

G$56,348 GYD per night
Guest favorite

Condo in Tavernier

4.95 out of 5 average rating, 103 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Jul 20 – 27

G$56,355 GYD per night
Guest favorite

Condo in Tavernier

4.95 out of 5 average rating, 154 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

Oct 7 – 14

G$87,470 GYD per night
Guest favorite

Condo in Tavernier

4.93 out of 5 average rating, 127 reviews

It's Tiki Time in the Keys! Mid-Mod 1 Br/1Ba

Apr 24 – May 1

G$57,444 GYD per night
Guest favorite

Condo in Key Largo

4.87 out of 5 average rating, 133 reviews

Tropical Getaway

Oct 25 – Nov 1

G$49,359 GYD per night
Guest favorite

Condo in Key Largo

4.97 out of 5 average rating, 146 reviews

KEYS BEACH RETREAT WITH CAPTIVATING WATERVIEW!

Feb 16 – 23

G$141,281 GYD per night
Guest favorite

Condo in Tavernier

4.97 out of 5 average rating, 220 reviews

Sea View Oceanfront Condo

Oct 17 – 24

G$56,563 GYD per night

Lake houses in Key West

Superhost

Home in Key Colony Beach

4.81 out of 5 average rating, 131 reviews

Waterview from three sides, Cabana Club, 30' Docks

Jan 4 – 11

G$81,560 GYD per night
Guest favorite

Home in Key Largo

4.89 out of 5 average rating, 157 reviews

Outdoor Paradise - Beach, Boats, Snorkeling & Sun!

Sep 15 – 22

G$44,760 GYD per night
Superhost

Home in Key Largo

4.89 out of 5 average rating, 101 reviews

NEW CASA PALMA VOTED BEST AIRBNB RENTAL! GOLF CART

Sep 20 – 27

G$84,468 GYD per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 6 reviews

Waterfront Escape -VACA-23-408

Oct 16 – 23

G$127,173 GYD per night
Superhost

Home in Cudjoe Key

5.0 out of 5 average rating, 5 reviews

Venture Out -Million Dollar Island Resort

Nov 23 – 30

G$65,667 GYD per night
Guest favorite

Home in Key Largo

4.89 out of 5 average rating, 55 reviews

5 O'clock Somewhere - Key Largo

Apr 30 – May 7

G$69,725 GYD per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 14 reviews

Walk to Sombrero Beach, 50’Dock, SPA, Bikes,Kayaks

Sep 8 – 15

G$91,655 GYD per night
Guest favorite

Home in Key Largo

4.88 out of 5 average rating, 8 reviews

Waterfront Key Largo Home - Tropical Paradise

Oct 5 – 12

G$123,035 GYD per night
Guest favorite

Home in Tavernier

4.96 out of 5 average rating, 50 reviews

Sunset Beach Hideaway *Private Beach* *Jacuzzi*

Aug 22 – 29

G$212,536 GYD per night
Superhost

Home in Marathon

5.0 out of 5 average rating, 4 reviews

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

Feb 2 – 9

G$167,965 GYD per night
Superhost

Home in Marathon

5.0 out of 5 average rating, 4 reviews

5 O'Clock Somewhere Bay House, Drinks on Us!

Sep 14 – 21

G$169,423 GYD per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 31 reviews

Marathon Beach house w/45’ dock Ocean access

Sep 9 – 16

G$84,712 GYD per night

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

G$2,094 GYD 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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West