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

Key West Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Key West vacation rentals

A row of floating houses with balconies, connected by walkways, on calm water.

1. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (201 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is CA $148
CA $406 total
includes taxes & fees
Oct 31 - Nov 1
Aqua Lodges at Hurricane Hole Marina
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, (461 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 CA $137
CA $333 total
includes taxes & fees
Oct 29 - Oct 30
Steps from Duval, Pool on Site & Bikes Included!
A compact bedroom with a bed, a small kitchenette, and a door leading to a bathroom.

3. 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, (56 reviews)
"Great location "
United States
Joe E.
The price is CA $166
CA $587 total
includes taxes & fees
Oct 27 - Oct 28
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
A narrow brick pathway flanked by white buildings with potted plants and a bench.

4. 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 $166
CA $525 total
includes taxes & fees
Nov 2 - Nov 3
Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West
A swimming pool surrounded by lush greenery, with lounge chairs and a covered seating area.

5. COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!

COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (121 reviews)
"Excellent stay, great location! "
United States
Dr. Christopher S.
The price is CA $186
CA $447 total
includes taxes & fees
Oct 28 - Oct 29
COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!
A small, private entrance to a house with a brick pathway leading to a door.

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

Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Old Town Key West
9.8 out of 10, Exceptional, (40 reviews)
"Fantastic location. Super friendly and helpful host. Everything you need to escape to key west for a long weekend!"
United States
Jamie F.
The price is CA $182
CA $546 total
includes taxes & fees
Oct 26 - Oct 27
Ricky's Retreat - Truman @ Duval | Ideal Getaway!
A covered balcony with wicker chairs, a view of palm trees, and multiple flags.

7. 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
9.8 out of 10, Exceptional, (15 reviews)
"Friendly and clean place, love the look and location will be back"
United States
Amanda G.
The price is CA $169
CA $409 total
includes taxes & fees
Oct 27 - Oct 28
AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
A multi-level wooden house with a blue staircase and white railings.

8. 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)
"Perfect location, spacious room. Our second time staying at this venue."
United States
Colleen L.
The price is CA $213
CA $634 total
includes taxes & fees
Oct 26 - Oct 27
Underwater Cabana at Custom House Inn | On Duval!
A narrow stone pathway leading to a yellow building with a white door and a small porch area.

9. 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, (51 reviews)
"Every detail as stated and parking was better than ever imagined!"
United States
Charles B.
The price is CA $154
CA $371 total
includes taxes & fees
Oct 29 - Oct 30
Sailor`s Cabin - Old Town - Walk to Duval !
A pool area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

10. Leo's Lodge | Newly Updated!

Leo's Lodge | Newly Updated!
Old Town Key West
9.0 out of 10, Wonderful, (37 reviews)
"Very nice place to stay, great pool area and great room. "
United States
Blake
The price is CA $152
CA $483 total
includes taxes & fees
Nov 22 - Nov 23
Leo's Lodge | Newly Updated!
A poolside area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

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, (57 reviews)
"Great crew here. From the airport shuttle to constant communication to make sure we were happy. Would highly recommend for a great getaway! Very convenient to lots of places to have fun."
United States
Jesse M.
The price is CA $290
CA $680 total
includes taxes & fees
Nov 1 - Nov 2
VanGogh Studio | Updated, Old Town, Heated Pool
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, (79 reviews)
"Fantastic location"
United States
Jennifer
The price is CA $214
CA $707 total
includes taxes & fees
Oct 26 - Oct 27
Duval Delight | Recently Remodeled Condo on Duval!
A spacious kitchen with a large island, a dining area with a view, and a balcony with a view.

13. 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.
The price is CA $175
CA $551 total
includes taxes & fees
Oct 26 - Oct 27
Waterfront Dock Pool Key West Near Duval
Exterior

14. Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
Island View 1BR Residence With Balcony
An outdoor patio area with wooden furniture, a large tree, and lush greenery.

15. 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 CA $243
CA $695 total
includes taxes & fees
Oct 29 - Oct 30
Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval!
A white building with a front door, steps, and a mailbox.

16. 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, (54 reviews)
"Great place and very close to the action on Duval St. Would definitely stay again."
United States
Matthew H.
The price is CA $270
CA $784 total
includes taxes & fees
Oct 27 - Oct 28
Holly's Hideaway - Truman @ Duval | Charming Hideaway Near Duval!
A wooden deck with a large tree, outdoor seating, and a marina in the background.

17. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
The price is CA $259
CA $461 total
includes taxes & fees
Nov 9 - Nov 10
Poolside Cottage #412
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, (41 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 CA $203
CA $559 total
includes taxes & fees
Nov 12 - Nov 13
Claude Monet Suite | Cozy Studio with Pool & Patio
A poolside area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

19. Chagall's Corner | Newly Remodeled!

Chagall's Corner | Newly Remodeled!
Old Town Key West
9.0 out of 10, Wonderful, (46 reviews)
"Very nice place to stay, close to many attractions. "
United States
Maria B.
The price is CA $152
CA $483 total
includes taxes & fees
Nov 22 - Nov 23
Chagall's Corner | Newly Remodeled!
A patio with wicker furniture, a hot tub, and a grill.

20. 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)
"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 $220
CA $716 total
includes taxes & fees
Oct 30 - Oct 31
Duval Hideaway | Dog-Friendly w/ Shared Hot Tub
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

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

8/10 Good
"The restaurant and bar were closed. A food truck was onsite but the choices were limited and expensive."
Maureen 4-night trip
Posted less than an hour ago
Parrot Key Hotel & Villas

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.