Holiday Rentals in Key West

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Check prices for these dates

Our top choices for Key West holiday rentals

1. 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, (464 reviews)
"We liked sitting by the pool and visiting with other guests. The air conditioner struggled to keep the room cool; it ran all night long to maintain 72 degrees."
United States
Karen
The price is €241
includes taxes & fees
2 Dec - 3 Dec
Steps from Duval, Pool on Site & Bikes Included!

2. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (202 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is €310
includes taxes & fees
16 Nov - 17 Nov
Aqua Lodges at Hurricane Hole Marina

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

Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Old Town Key West
10.0 out of 10, Exceptional, (41 reviews)
"Ricky’s Retreat is in a fantastic location. The room was all you need in Key West. Highly recommend it and will definitely stay there again."
United States
Brian R.
The price is €345
includes taxes & fees
16 Nov - 17 Nov
Ricky's Retreat - Truman @ Duval | Ideal Getaway!

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, (58 reviews)
"The room was functional. We loved the location and ease of getting everywhere. The pool was really nice. The only complaint is that the entire bathroom floods when you take a shower. We ended up using our flip flops to squeegee the water to the drain, because the drain is higher than the rest of the floor. Highly recommend providing a squeegee to help with flooding."
United States
Shawn
The price is €307
includes taxes & fees
15 Nov - 16 Nov
Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool

5. Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Old Town Key West
9.6 out of 10, Exceptional, (45 reviews)
"Great stay! "
United States
Victoria T.
The price is €372
includes taxes & fees
16 Nov - 17 Nov
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

6. 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, (139 reviews)
"Great place to stay"
United States
walter l.
The price is €327
includes taxes & fees
24 Nov - 25 Nov
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

7. Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West

Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West
Old Town Key West
9.8 out of 10, Exceptional, (27 reviews)
"Awesome location & very helpful host!"
United States
Jay M.
The price is €331
includes taxes & fees
16 Nov - 17 Nov
Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West

8. 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, (115 reviews)
"Absolutely perfect! Great location, great property and great unit. Beautiful pool area with ice machine and filtered water dispenser was a highlight for the very hot and humid time we visited. Would return immediately and stay in the same spot. Thank you for a very enjoyable time in Key West!"
United States
Justin D.
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

9. SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!

SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!
Old Town Key West
10.0 out of 10, Exceptional, (20 reviews)
"Great location, super nice room......"
United States
Russell B.
The price is €303
includes taxes & fees
1 Dec - 2 Dec
SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!

10. Road's End | Prime Old Town Location! Updated Home w/ Pool

Road's End | Prime Old Town Location! Updated Home w/ Pool
Old Town Key West
9.6 out of 10, Exceptional, (28 reviews)
"Excellent property and the communication with the hosts was excellent. Love that they offered complimentary pickup from the airport to the property too."
United States
Mike C.
Road's End | Prime Old Town Location! Updated Home w/ Pool

11. Chagall's Corner | Newly Remodeled!

Chagall's Corner | Newly Remodeled!
Old Town Key West
9.0 out of 10, Wonderful, (47 reviews)
"Very nice place to stay, close to many attractions. "
United States
Maria B.
The price is €309
includes taxes & fees
22 Nov - 23 Nov
Chagall's Corner | Newly Remodeled!

12. Duval Delight | Recently Remodeled Condo on Duval!

Duval Delight | Recently Remodeled Condo on Duval!
Old Town Key West
9.8 out of 10, Exceptional, (81 reviews)
"Fantastic location"
United States
Jennifer
The price is €439
includes taxes & fees
15 Nov - 16 Nov
Duval Delight | Recently Remodeled Condo on Duval!

13. Underwater Cabana at Custom House Inn | On Duval!

Underwater Cabana at Custom House Inn | On Duval!
Key West Historic District
9.8 out of 10, Exceptional, (28 reviews)
"We had a great comunication with the host. They were very responsive to all my questions and concerns. The check in process was very easy. They helped me with my car and shuttled me to the unit. The place was right on Duval Street. Although like that not very noisy as it was at the back. You could be in your room and at the bar for music and drinks in a minute. The room was comfortable and clean. If I go back to Key West again, I will not look for any other place to stay than Custom House."
United States
EMIN
The price is €398
includes taxes & fees
24 Nov - 25 Nov
Underwater Cabana at Custom House Inn | On Duval!

14. Pierre's Perch: Discover Charm and Convenience, Perfect Studio Retreat in Key West with Shared Pool

Pierre's Perch: Discover Charm and Convenience, Perfect Studio Retreat in Key West with Shared Pool
Old Town Key West
9.0 out of 10, Wonderful, (25 reviews)
"Super cute place. "
United States
Amanda M.
Pierre's Perch: Discover Charm and Convenience, Perfect Studio Retreat in Key West with Shared Pool

15. Sea Esta Suite | Located On Iconic Duval w/ Pool

Sea Esta Suite | Located On Iconic Duval w/ Pool
Old Town Key West
9.6 out of 10, Exceptional, (59 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is €653
includes taxes & fees
16 Nov - 17 Nov
Sea Esta Suite | Located On Iconic Duval w/ Pool

16. 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, (30 reviews)
"Close to everything ! It was a perfect location and we loved the hot tub. Amazing that it came with a parking spot. Would stay again."
United States
Jenn O.
The price is €440
includes taxes & fees
6 Dec - 7 Dec
Duval Hideaway | Dog-Friendly w/ Shared Hot Tub

17. Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval!

Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval!
Key West Historic District
9.6 out of 10, Exceptional, (37 reviews)
"Everything was fantastic, great location to the North end of Duval St."
United States
Brett W.
The price is €701
includes taxes & fees
13 Dec - 14 Dec
Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval!

18. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (38 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
The price is €281
includes taxes & fees
1 Dec - 2 Dec
Poolside Cottage #412

19. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (72 reviews)
"Excellent cottage in a quiet location. Our family of 4 enjoyed the stay & plan to return in the future!"
United States
Jennifer W.
The price is €281
includes taxes & fees
1 Dec - 2 Dec
Poolside Cottage #411

20. Prime Downtown Key West Spot - The Cozy Little Cottage!

Prime Downtown Key West Spot - The Cozy Little Cottage!
Old Town Key West
9.6 out of 10, Exceptional, (52 reviews)
"Every detail as stated and parking was better than ever imagined!"
United States
Charles B.
The price is €305
includes taxes & fees
2 Dec - 3 Dec
Prime Downtown Key West Spot - The Cozy Little Cottage!
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.

Find holiday rentals that suit your style

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 €241 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.

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

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 ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking and Hemingway Caribbean Townhome/Private Pool by Beach,Key West charm,free parking.

How many holiday rentals will I find in Key West?

With 1025 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.

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