Key West Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Key West vacation rentals

Front of property

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (186 reviews)
"Beautiful location, quick reply when you contact them. The bar and restaurant were so nice!! We would definitely stay again. "
United States
Stacy
The price is CA $184
CA $438 total
includes taxes & fees
May 28 - May 29
Aqua Lodges at Hurricane Hole Marina
A heated pool

Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool

Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
Old Town Key West
8.6 out of 10, Excellent, (47 reviews)
"Clean room. I wasn’t aware it was a micro hotel but that’s ok."
United States
Michael
The price is CA $133
CA $455 total
includes taxes & fees
May 25 - May 26
Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
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
9.8 out of 10, Exceptional, (33 reviews)
"The property was cozy and a great location for walking."
United States
Elizabeth E.
The price is CA $209
CA $580 total
includes taxes & fees
Jun 1 - Jun 2
Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!
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, (131 reviews)
"Amazing place to stay, excellent experience!!!"
United States
Brad
The price is CA $153
CA $402 total
includes taxes & fees
May 18 - May 19
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
A heated pool

Chagall's Corner | Newly Remodeled!

Chagall's Corner | Newly Remodeled!
Old Town Key West
9.0 out of 10, Wonderful, (41 reviews)
"Very nice place to stay, close to many attractions. "
United States
Maria B.
The price is CA $133
CA $457 total
includes taxes & fees
May 18 - May 19
Chagall's Corner | Newly Remodeled!
TV

The Grand Turk | Spectacular Sunset View, Private

The Grand Turk | Spectacular Sunset View, Private
Key West
8.8 out of 10, Excellent, (14 reviews)
"Great location!"
United States
Sheila
The price is CA $194
CA $621 total
includes taxes & fees
May 24 - May 25
The Grand Turk | Spectacular Sunset View, Private
1 bedroom, free WiFi, 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, (50 reviews)
"Great location, clean space and comfortable beds. Enjoyed our stay!"
United States
Chasity W.
The price is CA $133
CA $535 total
includes taxes & fees
May 28 - May 29
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
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, (36 reviews)
"Great location!!"
United States
Julie
The price is CA $133
CA $474 total
includes taxes & fees
May 27 - May 28
Ricky's Retreat - Truman @ Duval | Ideal Getaway!
A heated pool

VanGogh Studio | Updated, Old Town, Heated Pool

VanGogh Studio | Updated, Old Town, Heated Pool
Old Town Key West
8.6 out of 10, Excellent, (45 reviews)
"Room had everything we needed!Owners and staff were very responsive and offered free shuttle to/from the airport!"
United States
Timothy P.
The price is CA $133
CA $457 total
includes taxes & fees
May 19 - May 20
VanGogh Studio | Updated, Old Town, Heated Pool
Property grounds

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

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Key West
9.8 out of 10, Exceptional, (29 reviews)
"Pleasant stay - had a couple issues that we needed to be fixed that were resolved as quickly as possible. "
United States
Christina M.
The price is CA $209
CA $648 total
includes taxes & fees
May 18 - May 19
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
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, (34 reviews)
"Great place to stay!"
United States
Andrew M.
The price is CA $178
CA $598 total
includes taxes & fees
May 18 - May 19
Kingfish Keep | Lively Escape on Duval! Balcony!
A heated pool

Claude Monet Suite | Cozy Studio with Pool & Patio

Claude Monet Suite | Cozy Studio with Pool & Patio
Old Town Key West
9.6 out of 10, Exceptional, (34 reviews)
"Room was clean and within easy walk to most attractions. Check in and check out was easy. "
United States
Sharon
The price is CA $163
CA $498 total
includes taxes & fees
May 18 - May 19
Claude Monet Suite | Cozy Studio with Pool & Patio
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, (431 reviews)
"Clean room, laundry and great location. Owner/operator was very responsive. "
United States
Ashley
The price is CA $160
CA $360 total
includes taxes & fees
May 18 - May 19
Steps from Duval, Pool on Site & Bikes Included!
Property grounds

The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (45 reviews)
"Every as described, great stay!"
United States
Bryan W.
The price is CA $209
CA $648 total
includes taxes & fees
May 20 - May 21
The Cat Island Suite | Charmingly Renovated w/ Pool
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, (104 reviews)
"Loved it! Quiet, clean, good amenities, close to Duval street. Would 100% go back."
United States
Ian G.
The price is CA $187
CA $445 total
includes taxes & fees
Jun 3 - Jun 4
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
House (1 Bedroom) | Interior

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
3.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (6 reviews)
"Property was clean and quiet nice amenities "
United States
Bradley
The price is CA $343
CA $774 total
includes taxes & fees
May 18 - May 19
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
Terrace/patio

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, (23 reviews)
"Absolutely beautiful and we loved being in the middle of Duval"
United States
Shelley
The price is CA $178
CA $581 total
includes taxes & fees
May 19 - May 20
Underwater Cabana at Custom House Inn | On Duval!
Beach

May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras

May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras
Old Town Key West
9.6 out of 10, Exceptional, (250 reviews)
"The condo/room was very clean and put together, the location is a nice neighborhood."
United States
Bonnie R.
The price is CA $209
CA $484 total
includes taxes & fees
May 18 - May 19
May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras
Marina

Waterfront Condo Dock Pool Near Duval St

Waterfront Condo Dock Pool Near Duval St
Meadows
9.8 out of 10, Exceptional, (26 reviews)
"Great location!Breeze in the balcony while sitting in chairs or taking a nap in the hammock were amazing!Everything was nearby and easily accessible. Views are wonderful!We had a great time spending holidays as a family. "
United States
PARESH J.
The price is CA $237
CA $623 total
includes taxes & fees
May 20 - May 21
Waterfront Condo Dock Pool Near Duval St
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, (59 reviews)
"Nice condo right on Duval St and near beaches. "
United States
Darren B.
The price is CA $209
CA $692 total
includes taxes & fees
May 18 - May 19
Duval Delight | Recently Remodeled Condo on 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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

8/10 Good
"High prices for water in room when you can go to store down Duvall and get it for half the price. Found a roach in my room the last day. Staff great!!!! Resort beautiful!!!"
Lorraine 4-night trip
Posted less than an hour 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 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?

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!: This Key West vacation home rental is located in the city center and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and an oven, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind. Some other homes for rent in Key West include Atlantic Paradise by AvantStay | Great Location w/ & Shared Pool and hot tub! and EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!.

How many vacation rentals will I find in Key West?

With 1016 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.