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Our top choices for Key West holiday rentals

1. Galleon Resort Efficiency in the old town

Galleon Resort Efficiency in the old town
Key West Historic District
9.6 out of 10, Exceptional, (173 reviews)
"Perfect location!"
United States
Sarah D.
The price is £291
includes taxes & fees
12 Sept - 13 Sept
Galleon Resort Efficiency in the old town

2. Keys Breeze - Walk to Duval, Private Pool

Keys Breeze - Walk to Duval, Private Pool
Old Town Key West
10.0 out of 10, Exceptional, (37 reviews)
"Great place, location, clean and climate controlled. Pool was great and the host was excellent!"
United States
Lisa S.
The price is £847
includes taxes & fees
31 Aug - 1 Sept
Keys Breeze - Walk to Duval, Private Pool

3. Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
The price is £405
includes taxes & fees
30 Aug - 31 Aug
Grand Marina Suite by Brightwild Waterfront

4. Luxurious Island Pearl-Private Pool - 2BD/2Bath

Luxurious Island Pearl-Private Pool - 2BD/2Bath
Key West Historic District
10.0 out of 10, Exceptional, (60 reviews)
"The location was amazing. Easy walk to Duval street, nice grocery store right across the street, your own personal pool, and your own parking space! Definitely made the extra money spent on the rental worth it. Space was clean and perfect for 2 couples on vacation. Would rent again if we came back to Key West!"
United States
Ashley
Luxurious Island Pearl-Private Pool - 2BD/2Bath

5. Rooftop Penthouse

Rooftop Penthouse
Old Town Key West
10.0 out of 10, Exceptional, (55 reviews)
"This was a great stay! Great location house was clean and had several things for us to use! "
United States
Abigail Y.
The price is £645
includes taxes & fees
26 Aug - 27 Aug
Rooftop Penthouse

6. Hollinsed House Studio - Great Location!!

Hollinsed House Studio - Great Location!!
Old Town Key West
9.6 out of 10, Exceptional, (162 reviews)
"Perfect location, nice spot for a long weekend getaway. "
United States
Charlene B.
Hollinsed House Studio - Great Location!!

7. Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!

Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Key West Historic District
9.8 out of 10, Exceptional, (260 reviews)
"Great home in perfect location."
United States
Tim W.
The price is £1,196
includes taxes & fees
30 Aug - 31 Aug
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!

8. 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 place and very close to the action on Duval St. Would definitely stay again."
United States
Matthew H.
The price is £410
includes taxes & fees
23 Sept - 24 Sept
Holly's Hideaway - Truman @ Duval | Charming Hideaway Near Duval!

9. Luxury two floor apartment in prime location of famous Duval Street

Luxury two floor apartment in prime location of famous Duval Street
Old Town Key West
9.6 out of 10, Exceptional, (103 reviews)
"Great stay at a great location. Apartment was very clean. Enjoyed the balcony overlooking Duval St. "
United States
Gregory L.
The price is £432
includes taxes & fees
31 Aug - 1 Sept
Luxury two floor apartment in prime location of famous Duval Street

10. Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!
Old Town Key West
9.2 out of 10, Wonderful, (316 reviews)
"Great stay! Pool was a great amenity. Would definitely book again."
United States
Kayleigh V.
The price is £456
includes taxes & fees
29 Aug - 30 Aug
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

11. Duval Hideaway | Dog-Friendly w/ Shared Hot Tub

Duval Hideaway | Dog-Friendly w/ Shared Hot Tub
Old Town Key West
9.6 out of 10, Exceptional, (29 reviews)
"Great little condo off Duval St. It is close to many places to eat and great coffee next door. I’d stay there again! "
United States
Chrysten V.
The price is £375
includes taxes & fees
7 Sept - 8 Sept
Duval Hideaway | Dog-Friendly w/ Shared Hot Tub

12. 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 £213
includes taxes & fees
26 Aug - 27 Aug
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

13. Two Bedroom Residence With Balcony

Two Bedroom Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (1 review)
"The roosters crowing early morning was irritating "
United States
Catherine
The price is £378
includes taxes & fees
14 Sept - 15 Sept
Two Bedroom Residence With Balcony

14. Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby

Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby
Old Town Key West
9.2 out of 10, Wonderful, (173 reviews)
"Location was excellentt"
United States
Teresa S.
The price is £524
includes taxes & fees
26 Aug - 27 Aug
Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby

15. Old Town Key West suite w/ pool & pet-friendly

Old Town Key West suite w/ pool & pet-friendly
Old Town Key West
9.4 out of 10, Exceptional, (70 reviews)
"Very clean, comfortable beds, many extra pillows, Plenty of towels, everything needed for a weeks stay. Beautiful little courtyard. Great location But still quiet. Would definitely stay again."
United States
Sharon B.
Old Town Key West suite w/ pool & pet-friendly

16. Welcome Matt's - Truman @ Duval | Perfect Hideaway!

Welcome Matt's - Truman @ Duval | Perfect Hideaway!
Old Town Key West
9.8 out of 10, Exceptional, (32 reviews)
"Place was perfect. Great location to visit Key West. "
United States
Kevin C.
The price is £334
includes taxes & fees
13 Sept - 14 Sept
Welcome Matt's - Truman @ Duval | Perfect Hideaway!

17. 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, (215 reviews)
"Perfect spot to enjoy Key West and relax with friends! "
United States
Kim M.
The price is £1,397
includes taxes & fees
9 Sept - 10 Sept
Perfect Location, Private Heated Pool, Pristine Luxury Home!

18. 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, (451 reviews)
"Clean comfortable and close too many attractions."
United States
Mark A.
The price is £170
includes taxes & fees
26 Aug - 27 Aug
Steps from Duval, Pool on Site & Bikes Included!

19. Yellowfin Ledge | Ideal Getaway On Duval! Balcony

Yellowfin Ledge | Ideal Getaway On Duval! Balcony
Old Town Key West
9.4 out of 10, Exceptional, (35 reviews)
"We enjoyed our stay there. It was a very nice little place to have a little getaway in Key West. Thank you"
United States
Shawn W.
The price is £286
includes taxes & fees
30 Aug - 31 Aug
Yellowfin Ledge | Ideal Getaway On Duval! Balcony

20. 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 £382
includes taxes & fees
26 Aug - 27 Aug
Sea Breeze - One Block from Duval Street
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

Find out more about Key West

Everything you need to know about Key West holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Key West holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Key West holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Key West holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Key West. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Key West holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Key West holiday rentals we have selected for you start as low as £170 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Key West rentals

At Expedia, we put the best Key West holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Key West rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Key West holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Key West. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

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 1015 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.