A sunny street lined with historic buildings, a 'ONE WAY' sign, and a flagpole with flags.

Key West Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Key West holiday rentals

Exterior detail

1. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (136 reviews)
"Great place to stay"
United States
walter l.
The price is HK$957
HK$2,402 total
includes taxes & fees
15 Aug - 16 Aug
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Beach towels

2. 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, (449 reviews)
"Great location! Close to everything! We biked everywhere and accommodations had everything we needed. "
United States
Richard A.
The price is HK$699
HK$1,777 total
includes taxes & fees
10 Sept - 11 Sept
Steps from Duval, Pool on Site & Bikes Included!
Exterior detail

3. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (109 reviews)
"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: The property was just as listed. Very clean, quiet, the pool was very refreshing! Great location, walkable to almost anything. Would highly recommend!"
United States
Chris & Sarah F.
The price is HK$942
HK$2,377 total
includes taxes & fees
15 Aug - 16 Aug
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
A heated pool

4. Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool

Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
Old Town Key West
8.8 out of 10, Excellent, (55 reviews)
"It was exactly as presented online. The owners were great with communication and easy to work with throughout the experience. I would stay here again and highly recommend!"
United States
Linda M.
The price is HK$889
HK$2,783 total
includes taxes & fees
15 Aug - 16 Aug
Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
Front of property

5. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (194 reviews)
"The bathroom smelled a bit, but we loved the loft and the vibes of the houseboat. It’s hard to find 3 bedrooms at that reasonable price and we have 3 kids that do not want to sleep together so this was perfect. We ate at the bar and really enjoyed watching the jellyfish. It was a cool!"
United States
Emily
The price is HK$812
HK$2,229 total
includes taxes & fees
16 Aug - 17 Aug
Aqua Lodges at Hurricane Hole Marina
Exterior detail

6. Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Old Town Key West
10.0 out of 10, Exceptional, (122 reviews)
"Very communicative, property was as pictured and bikes were perfect for getting around. We didn’t need a car but had no trouble parking right next to the front door. Sandy’s had the best coffee and food was delicious! Will definitely come again!"
United States
Emily F.
The price is HK$851
HK$2,268 total
includes taxes & fees
25 Aug - 26 Aug
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
1 bedroom, free WiFi, bed sheets

7. Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Old Town Key West
9.6 out of 10, Exceptional, (52 reviews)
"We had a wonderful stay! Alex and Rick were excellent hosts - very accommodating and personable!!! Would definitely stay in this or any other Colocada property in the future!!!"
United States
Michele K.
The price is HK$835
HK$3,113 total
includes taxes & fees
16 Aug - 17 Aug
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Exterior detail

8. Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!

Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!
Old Town Key West
9.6 out of 10, Exceptional, (38 reviews)
"Very clean and comfortable. Great location. I would definitely stay here again. "
United States
Dawn R.
Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!
A heated pool

9. Chagall's Corner | Newly Remodeled!

Chagall's Corner | Newly Remodeled!
Old Town Key West
9.0 out of 10, Wonderful, (45 reviews)
"Great pool. Wonderful location."
United States
Anonymous traveller
The price is HK$889
HK$2,783 total
includes taxes & fees
15 Aug - 16 Aug
Chagall's Corner | Newly Remodeled!
Exterior

10. Ricky's Retreat - Truman @ Duval | Ideal Getaway!

Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Old Town Key West
9.8 out of 10, Exceptional, (39 reviews)
"Fantastic and cozy… and surprisingly right in the middle of Key West fun"
United States
Jay R.
The price is HK$862
HK$2,837 total
includes taxes & fees
16 Aug - 17 Aug
Ricky's Retreat - Truman @ Duval | Ideal Getaway!
A heated pool

11. VanGogh Studio | Updated, Old Town, Heated Pool

VanGogh Studio | Updated, Old Town, Heated Pool
Old Town Key West
8.8 out of 10, Excellent, (56 reviews)
"Nice clean apartment and good walking distance to Old Town restaurants and neighborhood."
United States
Justin R.
The price is HK$837
HK$2,703 total
includes taxes & fees
16 Aug - 17 Aug
VanGogh Studio | Updated, Old Town, Heated Pool
Interior

12. Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30

Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30
Old Town Key West
9.0 out of 10, Wonderful, (198 reviews)
"Fantastic location! Close enough to walk to all the things, but very quiet and relaxing to hang out. Loved the back deck. Owner was very responsive and helpful. Neighbors were nice as well."
United States
Jeanine
The price is HK$1,012
HK$2,465 total
includes taxes & fees
31 Aug - 1 Sept
Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30
A heated pool

13. Claude Monet Suite | Cozy Studio with Pool & Patio

Claude Monet Suite | Cozy Studio with Pool & Patio
Old Town Key West
9.4 out of 10, Exceptional, (38 reviews)
"We had a great stay- The property is exactly as described. Location was convenient and easy to get around by foot or scooter. The neighborhood was quiet and parking was not a problem. We will definitely stay here again!"
United States
Sara F.
The price is HK$958
HK$2,876 total
includes taxes & fees
16 Aug - 17 Aug
Claude Monet Suite | Cozy Studio with Pool & Patio
Property grounds

14. Sea Breeze - One Block from Duval Street

Sea Breeze - One Block from Duval Street
Old Town Key West
9.4 out of 10, Exceptional, (55 reviews)
"Great location. Clean house. Loved my stay here. "
United States
Alan K.
The price is HK$1,279
HK$4,234 total
includes taxes & fees
30 Aug - 31 Aug
Sea Breeze - One Block from Duval Street
TV

15. Kingfish Keep | Lively Escape on Duval! Balcony!

Kingfish Keep | Lively Escape on Duval! Balcony!
Old Town Key West
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay!"
United States
Andrew M.
The price is HK$1,410
HK$3,935 total
includes taxes & fees
14 Sept - 15 Sept
Kingfish Keep | Lively Escape on Duval! Balcony!
Terrace/patio

16. Duval Delight | Recently Remodeled Condo on Duval!

Duval Delight | Recently Remodeled Condo on Duval!
Old Town Key West
9.8 out of 10, Exceptional, (72 reviews)
"Great stay"
United States
Lisa H.
The price is HK$1,382
HK$4,212 total
includes taxes & fees
14 Sept - 15 Sept
Duval Delight | Recently Remodeled Condo on Duval!
Property grounds

17. The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (46 reviews)
"I liked that it was pretty centrally located to everything very nice Thank you we had a great time "
United States
Patti E.
The price is HK$1,450
HK$4,060 total
includes taxes & fees
15 Aug - 16 Aug
The Cat Island Suite | Charmingly Renovated w/ Pool
Outdoor dining

18. Waterfront Condo | Pool, Dock, Parking, Sleeps 8

Waterfront Condo | Pool, Dock, Parking, Sleeps 8
Meadows
9.8 out of 10, Exceptional, (39 reviews)
"The location was geeat, easy to get to everything within minutes. "
United States
Brian G.
The price is HK$914
HK$2,999 total
includes taxes & fees
18 Aug - 19 Aug
Waterfront Condo | Pool, Dock, Parking, Sleeps 8
Exterior detail

19. Holly's Hideaway - Truman @ Duval | Charming Hideaway Near Duval!

Holly's Hideaway - Truman @ Duval | Charming Hideaway Near Duval!
Old Town Key West
9.6 out of 10, Exceptional, (52 reviews)
"Great location close to pretty much everything!!!"
United States
Darryl H.
The price is HK$1,267
HK$3,999 total
includes taxes & fees
16 Aug - 17 Aug
Holly's Hideaway - Truman @ Duval | Charming Hideaway Near Duval!
Property grounds

20. The Andros | Incredible Views w/ Shared Pool

The Andros | Incredible Views w/ Shared Pool
Key West
9.0 out of 10, Wonderful, (45 reviews)
"Stayed 3,nights- would have stayed forever! Rick and staff could not have been more accommodating and friendly- the property was immaculate and maybe the most comfortable bed I’ve ever slept in! Rick was so knowledgeable about the island - had the answers for everything- such a lovely, relaxing stay, we will definitely be back!"
United States
Cynthia R.
The price is HK$1,450
HK$4,060 total
includes taxes & fees
15 Aug - 16 Aug
The Andros | Incredible Views w/ Shared Pool
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

Margaritaville Beach House Key West

Margaritaville Beach House Key West

10/10 Excellent
"The hotal is very comfy, I really appreciated staying in there, for sure I you book more times."
Raphael 2-night trip
Posted less than an hour ago
Margaritaville Beach House Key West

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 entertainment choices and lively festivals. While you're in the area, you can also enjoy the scenic seaside and great live music.

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

3-bedroom house boat in tranquil Key West with AC: This highly rated holiday home rental in Key West offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Some other homes for rent in Key West include Feb 3-10 $245 off the rates close beach full kitchen & patio and TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!.

How many holiday rentals will I find in Key West?

With 1005 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. You can also visit some other popular places in town, such as Duval Street and Florida Keys Beaches.

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.