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Key West vacation rentals

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Top-rated vacation rentals in Key West

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

Rental unit in Key West
Banana Split - Pool, Parking & Private Balcony!
Banana’s Fosters Guest House is a charming complex located in the heart of Key West. In one of the most sought after locations this one-of-a-kind conch home is steps from both the historic seaport and downtown. Relax in the shared pool after a long day out and about or grill out and meet some of the other guests on the shared deck. You cant go wrong with this sweet set up, split into six different units, you can reserve one or all of them to host your next vacation!
G$57,341 GYD per night
Rental unit in Key West
Duval St Apartment w/ Balcony w/parking Adult Only
This large apartment overlooks Duval Street from a private balcony. Perfect location in the heart of Old Town within easy walking distance of restaurants, live music, and historic sites. Guests enjoy daily complimentary continental breakfast in the garden and dips in our heated pool. *Please note you must be 21 or older to make a reservation on this property and all guests must be at least 18 years old.*
G$57,432 GYD per night
SUPERHOST
Rental unit in Key West
At Mine | Lovely Suite steps from Duval Street
Beautifully renovated boutique hotel suite steps from Duval Street. This property is situated on a quiet street and offers a private pool and peaceful accommodation for vacationers and business travelers. The unit features a comfortable Queen-sized bed, hangers, TV, and AC. Indulge in Key West's warm weather year-round. This special place is close to everything, making it easy to plan your visit.
G$34,833 GYD per night

Stay near Key West's top sights

Photo of Southernmost Point of the Continental US
Southernmost Point of the Continental US64 locals recommend
Photo of Mallory Square
Mallory Square100 locals recommend
Photo of The Ernest Hemingway Home and Museum
The Ernest Hemingway Home and Museum103 locals recommend
Photo of Fort Zachary Taylor Historic State Park
Fort Zachary Taylor Historic State Park47 locals recommend
Photo of Key West Butterfly and Nature Conservatory
Key West Butterfly and Nature Conservatory56 locals recommend
Photo of Higgs Beach
Higgs Beach21 locals recommend

Key West house rentals

Home in Key West
Home Away from Home with Free parking
G$47,734 GYD per night
SUPERHOST
Private room in Key West
1-Private room/bbq/patio. 2 full bed 1 couch bed.
G$47,584 GYD per night
SUPERHOST
Home in Key West
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
G$76,918 GYD per night
SUPERHOST
Home in Key West
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
G$79,911 GYD per night
SUPERHOST
Home in Key West
Duval Duplex with free parking
G$47,311 GYD per night
SUPERHOST
Home in Key West
La Casita- Waterfront, Hot Tub & Dock
G$62,901 GYD per night
Home in Key West
Poinciana Treetop ~ Casual Second Floor Duplex
G$40,998 GYD per night
Home in Key West
Private 2BR with Pool in Old Town Key West
G$37,009 GYD per night
SUPERHOST
Home in Key West
Casita de Catherine by AvantStay | Patio + Hot Tub
G$52,659 GYD per night
Home in Key West
Lennon's Lodge, Luxury Accommodations for up to 6!
G$103,808 GYD per night
SUPERHOST
Home in Key West
Charming 1BR Dog Friendly | Deck | W/D
G$24,532 GYD per night
Home in Key West
Relaxing Getaway - Duval Duplex - Free parking
G$47,342 GYD per night
SUPERHOST

Key West condo rentals

Condo in Key West
The Island Suite @ KW vacation
G$60,545 GYD per night
SUPERHOST
Condo in Key West
Duval Corner- Newly Renovated Condo steps to Duval
G$61,307 GYD per night
Condo in Key West
Sky Loft - Penthouse, Shared Pool & Downtown!
G$71,246 GYD per night
Condo in Key West
Duval Street Suite on Duval Free Parking and Pool
G$66,315 GYD per night
SUPERHOST
Condo in Key West
Salt Cay Suite - Pet Friendly, Modern Condo!
G$62,072 GYD per night
Condo in Key West
Sailor's Sanctuary - A Renovated Condo in Key West
G$30,318 GYD per night
SUPERHOST
Condo in Key West
WALK TO BEACH, MALLORY SQUARE, DUVAL STREET
G$38,067 GYD per night
Condo in Key West
Ocean Front Studio private Sandy Beach in Key West
G$18,429 GYD per night
SUPERHOST
Condo in Key West
Condo 2 br, Balcony, Private covered parking
G$63,897 GYD per night
SUPERHOST
Condo in Key West
Spacious Updated Waterfront Condo, 2/2 Pool, Dock
G$32,930 GYD per night
SUPERHOST
Condo in Key West
Sea Breeze- Walking distance & Off-Street Parking!
G$57,475 GYD per night
Condo in Key West
*Come to my Deck for a time you won't Forget!
G$53,873 GYD per night
SUPERHOST

Key West apartment rentals

Rental unit in Key West
Cozy upstairs apartment with pool #3
G$45,228 GYD per night
Private room in Key West
Mallory House Room #1
G$33,987 GYD per night
SUPERHOST
Rental unit in Key West
Studio Blu - Key West, FL - Hip Studio in Old Town
G$40,296 GYD per night
SUPERHOST
Rental unit in Key West
Duval Street Suite full kitchen, parking, & pool
G$59,547 GYD per night
SUPERHOST
Rental unit in Key West
Road's End- Shared Pool, New Furniture & King Bed!
G$60,243 GYD per night
Rental unit in Key West
Honeymoon Hideaway, King bed, Private Deck & Spa!
G$89,307 GYD per night
SUPERHOST
Rental unit in Key West
The Bartlum- Luxurious Studio w/ King Bed!
G$60,545 GYD per night
SUPERHOST
Rental unit in Key West
Historic First Floor Caroline St w/Pool Sleeps 3
G$23,263 GYD per night
SUPERHOST
Rental unit in Key West
Duval Balcony - Street Suite
G$39,668 GYD per night
SUPERHOST
Rental unit in Key West
Key West - Sunrise ❀ The Green House
G$57,656 GYD per night
SUPERHOST
Rental unit in Key West
Key West - Sunset ❀ The Green House
G$56,538 GYD per night
SUPERHOST
Rental unit in Key West
Historic 1st Fl Caroline St - Shared Pool Sleeps 2
G$25,378 GYD per night
SUPERHOST

Stays in Truman Annex

Rental unit in Key West
Creme Brulee Suite- 1 Block To Duval & Shared Pool
G$45,892 GYD per night
Hotel room in Key West
Steps to Duval St - Luxurious King w Balcony
G$72,536 GYD per night
Rental unit in Key West
Poolside Retreat- Tropical Cottage with Parking!
G$62,569 GYD per night
Rental unit in Key West
Honey Bun Hideaway - Pool, Steps to Duval & Grill!
G$44,652 GYD per night

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.


When is 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.


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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