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
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Key West vacation rentals

Beach towels

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, (446 reviews)
"Great location! Close to everything! We biked everywhere and accommodations had everything we needed. "
United States
Richard A.
The price is CA $126
CA $319 total
includes taxes & fees
Jul 29 - Jul 30
Steps from Duval, Pool on Site & Bikes Included!
Exterior detail

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, (133 reviews)
"Great place to stay"
United States
walter l.
The price is CA $163
CA $420 total
includes taxes & fees
Aug 12 - Aug 13
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Exterior

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

Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Old Town Key West
9.8 out of 10, Exceptional, (38 reviews)
"Fantastic and cozy… and surprisingly right in the middle of Key West fun"
United States
Jay R.
The price is CA $141
CA $493 total
includes taxes & fees
Aug 2 - Aug 3
Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Front of property

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (193 reviews)
"The bathroom smelled a bit, but we loved the loft and the vibes of the houseboat. It’s hard to find 3 bedrooms at that reasonable price and we have 3 kids that do not want to sleep together so this was perfect. We ate at the bar and really enjoyed watching the jellyfish. It was a cool!"
United States
Emily
The price is CA $172
CA $430 total
includes taxes & fees
Jul 27 - Jul 28
Aqua Lodges at Hurricane Hole Marina
Exterior detail

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, (38 reviews)
"Very clean and comfortable. Great location. I would definitely stay here again. "
United States
Dawn R.
The price is CA $141
CA $493 total
includes taxes & fees
Aug 2 - Aug 3
Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!
1 bedroom, WiFi (free), bed sheets

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, (52 reviews)
"Great location "
United States
Joe E.
The price is CA $141
CA $550 total
includes taxes & fees
Aug 16 - Aug 17
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Interior

Summer JULY Special@129 Sun. thru Wed. ngts.lodging Only 129. + extras.

Summer JULY Special@129 Sun. thru Wed. ngts.lodging Only 129. + extras.
Old Town Key West
9.0 out of 10, Wonderful, (198 reviews)
"Fantastic location! Close enough to walk to all the things, but very quiet and relaxing to hang out. Loved the back deck. Owner was very responsive and helpful. Neighbors were nice as well."
United States
Jeanine
The price is CA $176
CA $434 total
includes taxes & fees
Aug 1 - Aug 2
Summer JULY Special@129 Sun. thru Wed. ngts.lodging Only 129. + extras.
Exterior detail

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, (106 reviews)
"Not really close to much but a comfortable bed and clean room. The pool and grounds are lovely. Will stay again but rent a golf cart. "
United States
Laura T.
The price is CA $152
CA $407 total
includes taxes & fees
Aug 3 - Aug 4
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
A heated pool

VanGogh Studio | Updated, Old Town, Heated Pool

VanGogh Studio | Updated, Old Town, Heated Pool
Old Town Key West
8.8 out of 10, Excellent, (54 reviews)
"Good location and value"
United States
Dan W.
The price is CA $158
CA $498 total
includes taxes & fees
Jul 30 - Jul 31
VanGogh Studio | Updated, Old Town, Heated Pool
Exterior detail

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, (51 reviews)
"Great location close to pretty much everything!!!"
United States
Darryl H.
The price is CA $201
CA $691 total
includes taxes & fees
Aug 5 - Aug 6
Holly's Hideaway - Truman @ Duval | Charming Hideaway Near Duval!
TV

Kingfish Keep | Lively Escape on Duval! Balcony!

Kingfish Keep | Lively Escape on Duval! Balcony!
Old Town Key West
9.8 out of 10, Exceptional, (37 reviews)
"Great place to stay!"
United States
Andrew M.
The price is CA $178
CA $606 total
includes taxes & fees
Aug 2 - Aug 3
Kingfish Keep | Lively Escape on Duval! Balcony!
Terrace/patio

Duval Delight | Recently Remodeled Condo on Duval!

Duval Delight | Recently Remodeled Condo on Duval!
Old Town Key West
9.8 out of 10, Exceptional, (69 reviews)
"Great stay"
United States
Lisa H.
The price is CA $201
CA $691 total
includes taxes & fees
Aug 5 - Aug 6
Duval Delight | Recently Remodeled Condo on Duval!
A heated pool

Leo's Lodge | Newly Updated!

Leo's Lodge | Newly Updated!
Old Town Key West
9.0 out of 10, Wonderful, (33 reviews)
"Very nice place to stay, great pool area and great room. "
United States
Blake
The price is CA $167
CA $511 total
includes taxes & fees
Jul 27 - Jul 28
Leo's Lodge | Newly Updated!
A heated pool

Chagall's Corner | Newly Remodeled!

Chagall's Corner | Newly Remodeled!
Old Town Key West
9.0 out of 10, Wonderful, (43 reviews)
"Very nice place to stay, close to many attractions. "
United States
Maria B.
The price is CA $167
CA $511 total
includes taxes & fees
Jul 28 - Jul 29
Chagall's Corner | Newly Remodeled!
Terrace/patio

Duval Hideaway | Dog-Friendly w/ Shared Hot Tub

Duval Hideaway | Dog-Friendly w/ Shared Hot Tub
Old Town Key West
9.8 out of 10, Exceptional, (27 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 CA $201
CA $691 total
includes taxes & fees
Aug 5 - Aug 6
Duval Hideaway | Dog-Friendly w/ Shared Hot Tub
Property grounds

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 CA $309
CA $866 total
includes taxes & fees
Jul 27 - Jul 28
Sea Breeze - One Block from Duval Street
Exterior detail

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Old Town Key West
10.0 out of 10, Exceptional, (122 reviews)
"Very communicative, property was as pictured and bikes were perfect for getting around. We didn’t need a car but had no trouble parking right next to the front door. Sandy’s had the best coffee and food was delicious! Will definitely come again!"
United States
Emily F.
The price is CA $242
CA $521 total
includes taxes & fees
Aug 26 - Aug 27
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
A heated pool

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, (36 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 $183
CA $533 total
includes taxes & fees
Aug 10 - Aug 11
Claude Monet Suite | Cozy Studio with Pool & Patio
Beach towels

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

STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
Old Town Key West
9.8 out of 10, Exceptional, (46 reviews)
"Great location, one block from Duval Street but still quiet, clean and comfortable. "
United States
Jackie H.
The price is CA $270
CA $691 total
includes taxes & fees
Aug 2 - Aug 3
STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
Property grounds

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Key West
10.0 out of 10, Exceptional, (33 reviews)
"Very nice clean place. Had a minor problem with the beds after checking in but property manager was quick to respond and correct issue. Would stay here again. "
United States
Teri K.
The price is CA $276
CA $751 total
includes taxes & fees
Jul 29 - Jul 30
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, 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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Spent only 2 nights there, but the room was clean, staff was welcoming and accommodating. The location was perfect with many great local restaurants within walking distance. We spent most of our day at the biggest pool, which had great bartenders, and even a DJ on one day. All in all, it was short, but memorable trip."
Michele 2-night trip
Posted 5 hours ago
Southernmost Beach Resort and Guesthouses

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 Florida Keys Eco - Discovery Center, 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 lively festivals. While you're in the area, you can also enjoy the scenic seaside and entertainment choices.

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 Luxurious Island Pearl-Private Pool - 2BD/2Bath and Atlantic Paradise by AvantStay | Great Location w/ & Shared Pool and hot tub!.

How many vacation rentals will I find in Key West?

With 1002 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?

Florida Keys Eco - Discovery Center and Key West Shipwreck Museum 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.