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
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Key West holiday rentals

A pathway leading to a covered outdoor seating area with a table and chairs, surrounded by lush greenery and trees.

1. 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, (44 reviews)
"Great stay! "
United States
Victoria T.
The price is NZ$738
includes taxes & fees
16 Nov - 17 Nov
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
A white building with a covered porch and a palm tree.

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, (463 reviews)
"This studio is in a wonderful location and comes with bikes and a pool spa. It is a fabulous place to stay for a relaxing get-away island-style."
United States
Laura D.
The price is NZ$469
includes taxes & fees
2 Dec - 3 Dec
Steps from Duval, Pool on Site & Bikes Included!
A row of floating houses with balconies, connected by walkways, on calm water.

3. 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 NZ$515
includes taxes & fees
10 Nov - 11 Nov
Aqua Lodges at Hurricane Hole Marina
A narrow alleyway with white buildings, a stone pathway, and various plants.

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

Welcome Matt's - Truman @ Duval | Perfect Hideaway!
Old Town Key West
9.8 out of 10, Exceptional, (35 reviews)
"Great place to stay, near everything."
United States
Tony R.
Welcome Matt's - Truman @ Duval | Perfect Hideaway!
A tropical garden pathway leading to a building with a yellow facade and green shutters.

5. 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 NZ$613
includes taxes & fees
10 Nov - 11 Nov
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
A covered balcony with wicker chairs, a view of palm trees, and multiple flags.

6. AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
Old Town Key West
9.6 out of 10, Exceptional, (18 reviews)
"Friendly and clean place, love the look and location will be back"
United States
Amanda G.
AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
A tropical garden pathway leading to a building with a yellow facade and green shutters.

7. 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.
The price is NZ$654
includes taxes & fees
1 Dec - 2 Dec
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
A wooden deck with a large tree, outdoor seating, and a marina in the background.

8. 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 NZ$562
includes taxes & fees
1 Dec - 2 Dec
Poolside Cottage #412
A narrow pathway flanked by white picket fences and a tree with pink flowers.

9. OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST

OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
Old Town Key West
9.6 out of 10, Exceptional, (158 reviews)
"Excellent location for a week in the Keys. Was able to walk to all the Duval Street attractions. "
United States
Michael R.
OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
A building with a red door, a covered porch, and a bamboo plant in the foreground.

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.
The price is NZ$761
includes taxes & fees
15 Nov - 16 Nov
Road's End | Prime Old Town Location! Updated Home w/ Pool
A narrow alleyway with white buildings, a stone pathway, and various plants.

11. 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, (43 reviews)
"This place is FANTASTIC! The service was great. I 10/10 recommend staying here. The space was clean and ready for our arrival."
United States
Megan
The price is NZ$689
includes taxes & fees
9 Dec - 10 Dec
Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!
A pool area with a wooden deck, a two-story building with balconies, and palm trees.

12. 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 NZ$608
includes taxes & fees
11 Nov - 12 Nov
Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
A covered porch with white wooden railings, wicker furniture, and hanging lanterns.

13. 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 NZ$883
includes taxes & fees
10 Nov - 11 Nov
Duval Delight | Recently Remodeled Condo on Duval!
A multi-level wooden house with a blue staircase and white railings.

14. 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, (27 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 NZ$786
includes taxes & fees
10 Nov - 11 Nov
Underwater Cabana at Custom House Inn | On Duval!
A poolside area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

15. 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 NZ$604
includes taxes & fees
1 Dec - 2 Dec
Chagall's Corner | Newly Remodeled!
A modern living room with a sofa, coffee table, and a dining area with a table and chairs. There is a kitchen area with cabinets and appliances.

16. The Grand Cayman | Beautifully Remodeled Key West!

The Grand Cayman | Beautifully Remodeled Key West!
Key West
9.8 out of 10, Exceptional, (22 reviews)
"Great facility and loved the location! "
United States
Matt R.
The price is NZ$851
includes taxes & fees
29 Nov - 30 Nov
The Grand Cayman | Beautifully Remodeled Key West!
A spacious kitchen with a large island, a dining area with a view, and a balcony with a view.

17. Waterfront Dock Pool Key West Near Duval

Waterfront Dock Pool Key West Near Duval
Meadows
10.0 out of 10, Exceptional, (41 reviews)
"Clean, comfy and had everything we expected."
United States
Chrystalbelle R.
Waterfront Dock Pool Key West Near Duval
A poolside area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

18. 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, (43 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 NZ$684
includes taxes & fees
12 Nov - 13 Nov
Claude Monet Suite | Cozy Studio with Pool & Patio
A narrow stone pathway leading to a yellow building with a white door and a small porch area.

19. 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 NZ$584
includes taxes & fees
2 Dec - 3 Dec
Prime Downtown Key West Spot - The Cozy Little Cottage!
A poolside area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

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

VanGogh Studio | Updated, Old Town, Heated Pool
Old Town Key West
8.8 out of 10, Excellent, (58 reviews)
"Great location! Easy walk to everything! Comfortable bed, easy checking in, and beautiful property."
United States
Lynn S.
The price is NZ$842
includes taxes & fees
10 Nov - 11 Nov
VanGogh Studio | Updated, Old Town, Heated 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

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"This is a very comfortable place to stay"
Wendi 1-night trip
Posted 1 hour ago
DoubleTree Resort by Hilton Grand Key - Key West

Find out more about Key West

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Key West holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Key West. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Key West. Seeing all the best attractions is bound to make you fall in love with Key West. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Key West short-term rentals, that won’t be hard to do.

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 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.