Key West Holiday Rentals

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Check prices for these dates

Tonight
8 Nov - 9 Nov
Tomorrow
9 Nov - 10 Nov
Next weekend
14 Nov - 16 Nov
In two weeks
21 Nov - 23 Nov

Holiday Rentals in Key West

Restaurant
Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
Stock Island
8.8 out of 10, Excellent, (165)
"The stay was beautiful "
United States
Jennifer
The price is HK$866
HK$2,278 total
includes taxes & fees
13 Nov - 14 Nov
Aqua Lodges at Hurricane Hole Marina
Exterior
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
Old Town Key West
8.4 out of 10, Very good, (314)
"Good location "
United States
Paula
The price is HK$1,853
HK$2,348 total
includes taxes & fees
8 Dec - 9 Dec
Hyatt Vacation Club at Sunset Harbor, Key West
Exterior
Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!

Old Town Key West
9.6 out of 10, Exceptional, (408)
"Great place to stay and walk to all the attractions."
United States
Byron Debi L.
The price is HK$693
HK$1,754 total
includes taxes & fees
16 Nov - 17 Nov
Steps from Duval, Pool on Site & Bikes Included!
Meeting facility
Coconut Mallory Resort And Marina By Kees Vacations

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
Key West
8.2 out of 10, Very good, (820)
"Overall a good place to stay and value for money "
United States
Vijay Bhasker
Coconut Mallory Resort And Marina By Kees Vacations
Beach
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Key West
8.6 out of 10, Excellent, (139)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
The price is HK$1,097
HK$2,931 total
includes taxes & fees
17 Nov - 18 Nov
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Outdoor pool, a heated pool
Perfect Location, Private Heated Pool, Pristine Luxury Home!

Perfect Location, Private Heated Pool, Pristine Luxury Home!

Old Town Key West
10.0 out of 10, Exceptional, (192)
"Outstanding place to stay, centrally located!"
United States
Elizabeth Y.
The price is HK$7,388
HK$14,628 total
includes taxes & fees
10 Nov - 11 Nov
Perfect Location, Private Heated Pool, Pristine Luxury Home!
Property grounds
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!

JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!

Old Town Key West
9.6 out of 10, Exceptional, (163)
"Great property right in the middle of everything. Walk to all the sites. Parking is provided and convenient. No condiments - bring your own. Also pack earplugs as roosters and diners at surrounding eateries are loud. Will definitely return!"
United States
Julie P.
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
Marina
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

Stock Island
6.6 out of 10, (12)
"Kevin and Capt. Phil were great hosts. Would definitely stay there again. "
United States
p j.
The price is HK$1,428
HK$2,864 total
includes taxes & fees
11 Nov - 12 Nov
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Outdoor dining
New 4BR/4BA Sleeps 12+ minutes to Beach & Duval St. Private backyard pool oasis

New 4BR/4BA Sleeps 12+ minutes to Beach & Duval St. Private backyard pool oasis

2.0 star property
Beachside
New 4BR/4BA Sleeps 12+ minutes to Beach & Duval St. Private backyard pool oasis
Exterior
Heart of Downtown Key West Cottage With Off-Street Parking

Heart of Downtown Key West Cottage With Off-Street Parking

Key West Historic District
10.0 out of 10, Exceptional, (141)
"Wonderful property. Perfect location. Clean building. Everything you needed for a relaxing stay. Lovely hosts as well. Will stay there again. "
United States
Andrew C.
Heart of Downtown Key West Cottage With Off-Street Parking
A heated pool
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

Stock Island
9.8 out of 10, Exceptional, (140)
"Property manager was attentive and helpful. Beautiful place to stay with a wonderful pool area."
United States
Anonymous traveller
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
1 bedroom, free WiFi, bed sheets
Wahoo Way | Charming Hideaway On Duval Street!

Wahoo Way | Charming Hideaway On Duval Street!

Old Town Key West
9.0 out of 10, Wonderful, (17)
"Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Easy walks to everything!"
United States
Don N.
The price is HK$964
HK$2,462 total
includes taxes & fees
17 Nov - 18 Nov
Wahoo Way | Charming Hideaway On Duval Street!
Exterior
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

Old Town Key West
9.2 out of 10, Wonderful, (186)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location in the middle of everything"
United States
Loyd K.
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
A heated pool
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!

GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!

Beachside
9.8 out of 10, Exceptional, (48)
"Wonderful view, lot's of space, great location "
United States
Valerie
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!
1 bedroom
Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony

2.0 star property
Key West
10.0 out of 10, Exceptional, (1)
"The room was excellent, no complaints at all."
United States
Tonya
The price is HK$2,015
HK$2,929 total
includes taxes & fees
12 Nov - 13 Nov
Island View 1BR Residence With Balcony
Beach nearby
CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!

CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!

Old Town Key West
9.8 out of 10, Exceptional, (128)
"Great location. Nice restaurant next door. Comfortable accommodations"
United States
Anna B.
The price is HK$785
HK$1,975 total
includes taxes & fees
20 Nov - 21 Nov
CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!
Fridge, stovetop, coffee/tea maker, toaster
Super-Cozy boat in Key West!

Super-Cozy boat in Key West!

Key West
8.0 out of 10, Very good, (1)
"Yes, Troy was very welcoming. Met me at the airport and gave me a ride to his boat. Very accomodating. 2 diff.options for sleeping and boat was very comfortable. Plenty of fresh towels.Picked up whatever I needed and brought it out to me. Thx!"
United States
rachael K.
The price is HK$1,936
HK$2,459 total
includes taxes & fees
18 Nov - 19 Nov
Super-Cozy boat in Key West!
Marina
Living the Dream Key West Style

Living the Dream Key West Style

Stock Island
10.0 out of 10, Exceptional, (31)
"Clean rooms pet friendly great view! Exactly as advertised "
United States
Todd
The price is HK$2,093
HK$2,642 total
includes taxes & fees
11 Nov - 12 Nov
Living the Dream Key West Style
Beach nearby
FLOR DE CANA ~ Adults Only, Queen Room w/Pool View at Azul Mansion!

FLOR DE CANA ~ Adults Only, Queen Room w/Pool View at Azul Mansion!

Old Town Key West
9.8 out of 10, Exceptional, (141)
"Rating Details: The property manager was very helpful. The vacation rental was very clean. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Wonderful location, clean, cozy and very private. I will definitely return.."
United States
Teresa K.
The price is HK$817
HK$2,010 total
includes taxes & fees
17 Nov - 18 Nov
FLOR DE CANA ~ Adults Only, Queen Room w/Pool View at Azul Mansion!
Living area
Kingfish Keep | Lively Escape on Duval! Balcony!

Kingfish Keep | Lively Escape on Duval! Balcony!

Old Town Key West
9.8 out of 10, Exceptional, (20)
"Awesome location with excellent communication. "
United States
Gary W.
The price is HK$1,112
HK$3,070 total
includes taxes & fees
16 Nov - 17 Nov
Kingfish Keep | Lively Escape on Duval! Balcony!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Key West Hotel Reviews

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"Beautiful property, courteous and attentive staff, comfortable rooms. Really enjoyed our stay!"
Michael 3-night trip
Posted 4 days ago
Casa Marina Key West, Curio Collection by Hilton

Find out more about Key West

Search for holiday rentals in Key West on Expedia! You can easily find your home rentals, villas, holiday apartments in Key West using one of the methods below:

  • View our selection of featured holiday rentals in Key West
  • Use the map to find apartments and other holiday homes in the Key West neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Key West while they last

Look no further and take a look at our great range of rental properties in Key West!

Frequently asked questions

Can I find holiday rentals in Key West?

Yes, there are holiday rentals in Key West close to Mel Fisher Maritime Museum, or you can select a more secluded option if you're looking for a relaxing stay. Travellers who like culture and the arts give Key West high marks for its great live music and lively festivals. While you're in the area, you can also enjoy the scenic seaside and entertainment choices.

What are some of the best holiday rentals that Key West has to offer?

Perfect Location, Private Heated Pool, Pristine Luxury Home!: This highly rated holiday home rental in Key West is located in the city centre, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Some other homes for rent in Key West include New 4BR/4BA Sleeps 12+ minutes to Beach & Duval St. Private backyard pool oasis and Wahoo Way | Charming Hideaway On Duval Street!.

How many holiday rentals will I find in Key West?

With 1112 Expedia holiday rentals, you're guaranteed to find just the right place for your Key West stay.

What can I see and do in Key West?

Mel Fisher Maritime Museum and Florida Keys Eco - Discovery Center are a couple of the family-friendly sights, whereas cultural attractions include Ernest Hemingway Home and Museum and Key West Lighthouse and Keeper's Quarters Museum. Duval Street and Harry S. Truman Little White House are other places to visit while you're in town.

What are holiday rentals like in Key West?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Key West. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family trips.