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Key West Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Key West vacation rentals

A wooden signpost with city names and distances in miles.

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 CA $179
CA $390 total
includes taxes & fees
Dec 2 - Dec 3
Steps from Duval, Pool on Site & Bikes Included!
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

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 CA $180
CA $448 total
includes taxes & fees
Nov 20 - Nov 21
Aqua Lodges at Hurricane Hole Marina
A small, private entrance to a house with a brick pathway leading to a door.

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 CA $194
CA $543 total
includes taxes & fees
Nov 28 - Nov 29
Ricky's Retreat - Truman @ Duval | Ideal Getaway!
A pool area with a wooden deck, a two-story building with balconies, and palm trees.

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 CA $161
CA $482 total
includes taxes & fees
Nov 16 - Nov 17
Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
A pathway leading to a covered outdoor seating area with a table and chairs, surrounded by lush greenery and trees.

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 CA $177
CA $582 total
includes taxes & fees
Nov 16 - Nov 17
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
A tropical garden pathway leading to a building with a yellow facade and green shutters.

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, (140 reviews)
"Great place to stay"
United States
walter l.
The price is CA $238
CA $518 total
includes taxes & fees
Nov 29 - Nov 30
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
A narrow brick pathway flanked by white buildings with potted plants and a bench.

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 CA $179
CA $523 total
includes taxes & fees
Nov 16 - Nov 17
Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West
A tropical garden pathway leading to a building with a yellow facade and green shutters.

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.
The price is CA $224
CA $500 total
includes taxes & fees
Dec 1 - Dec 2
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
A brick pathway leading to a white staircase with a covered area above.

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 CA $200
CA $451 total
includes taxes & fees
Dec 1 - Dec 2
SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!
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 CA $346
CA $807 total
includes taxes & fees
Dec 11 - Dec 12
Road's End | Prime Old Town Location! Updated Home w/ Pool
A poolside area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

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 CA $162
CA $484 total
includes taxes & fees
Nov 22 - Nov 23
Chagall's Corner | Newly Remodeled!
A covered porch with white wooden railings, wicker furniture, and hanging lanterns.

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 CA $226
CA $699 total
includes taxes & fees
Nov 17 - Nov 18
Duval Delight | Recently Remodeled Condo on Duval!
A multi-level wooden house with a blue staircase and white railings.

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 CA $228
CA $633 total
includes taxes & fees
Nov 24 - Nov 25
Underwater Cabana at Custom House Inn | On Duval!
A waterfront property with a pool, a thatched-roof structure, and multiple buildings with balconies overlooking the water.

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.
The price is CA $161
CA $470 total
includes taxes & fees
Nov 23 - Nov 24
Pierre's Perch: Discover Charm and Convenience, Perfect Studio Retreat in Key West with Shared Pool
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with bar stools.

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)
"Really enjoyed our stay and the location was convenient to Duval Street and all that it has to offer."
United States
DeEtta H.
The price is CA $277
CA $1,036 total
includes taxes & fees
Nov 16 - Nov 17
Sea Esta Suite | Located On Iconic Duval w/ Pool
A patio with wicker furniture, a hot tub, and a grill.

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 CA $228
CA $701 total
includes taxes & fees
Dec 6 - Dec 7
Duval Hideaway | Dog-Friendly w/ Shared Hot Tub
An outdoor patio area with wooden furniture, a large tree, and lush greenery.

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, (38 reviews)
"Everything was fantastic, great location to the North end of Duval St."
United States
Brett W.
The price is CA $276
CA $684 total
includes taxes & fees
Dec 15 - Dec 16
Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval!
A wooden deck with a large tree, outdoor seating, and a marina in the background.

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 CA $264
CA $450 total
includes taxes & fees
Dec 1 - Dec 2
Poolside Cottage #412
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

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 CA $264
CA $450 total
includes taxes & fees
Dec 1 - Dec 2
Poolside Cottage #411
A narrow stone pathway leading to a yellow building with a white door and a small porch area.

20. Sailor`s Cabin - Old Town - Walk to Duval !

Sailor`s Cabin - Old Town - Walk to Duval !
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 CA $214
CA $431 total
includes taxes & fees
Nov 22 - Nov 23
Sailor`s Cabin - Old Town - Walk to Duval !
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

Ibis Bay Beach Resort

Ibis Bay Beach Resort

10/10 Excellent
"Clean room, Continental breakfast staff was friendly"
david 6-night trip
Posted less than an hour ago
Ibis Bay Beach Resort

Find out more about Key West

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Key West?

Yes, there are vacation rentals in Key West close to Mel Fisher Maritime Museum, or you can select a more secluded option if you want a relaxing stay. Travelers 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 vacation rentals in Key West?

3-bedroom house boat in tranquil Key West with AC: This Key West vacation home rental offers a patio, a barbecue grill, 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 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 vacation rentals will I find in Key West?

With 1025 Expedia vacation rentals, you're sure 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 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 vacation rentals like in Key West?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Key West. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for family gatherings.