Key West Vacation Rentals

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Our top choices for Key West vacation rentals

Houseboat in Stock Island

Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
$355 nightly
The price is $400
Jan 5 - Jan 6, 2026
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
3.0 star property
8.2 out of 10, Very Good, (821)
"The staff goes above and beyond very, very warm and nice people"
United States
erik
Coconut Mallory Resort And Marina By Kees Vacations
8.8 out of 10, Excellent, (205)
"Good stay, everything was comfortable and ready to check in along with the typical amenities you would see at traditional hotels. Only stayed one night but there was a strong odor in the apartment, may have been from previous guests’ cooking but wasn’t unpleasant. Would stay again. "
United States
Juan E.
$478 nightly
The price is $533
Jan 15 - Jan 16, 2026
Total with taxes and fees
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
9.6 out of 10, Exceptional, (414)
"We loved it here! Not very far from Duval street. "
United States
Keghan J.
$337 nightly
The price is $374
Jan 3 - Jan 4, 2026
Total with taxes and fees
Steps from Duval, Pool on Site & Bikes Included!

Vacation Home in Raccoon Key

New Waterfront Home - Dreamside House
2.0 star property
$2,365 nightly
The price is $2,661
Jan 4 - Jan 5, 2026
Total with taxes and fees
New Waterfront Home - Dreamside House

Vacation Home in Raccoon Key

The Seagate Estate at Lunara Bay
10.0 out of 10, Exceptional, (18)
"The perfect House , everything was good "
United States
CARLOS G.
$1,427 nightly
The price is $1,583
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Seagate Estate at Lunara Bay

Vacation Home in Raccoon Key

Capmar House at Lunara Bay
9.8 out of 10, Exceptional, (29)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveler
$1,427 nightly
The price is $1,583
Jan 5 - Jan 6, 2026
Total with taxes and fees
Capmar House at Lunara Bay
7.8 out of 10, Good, (26)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
$454 nightly
The price is $504
Jan 4 - Jan 5, 2026
Total with taxes and fees
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
9.8 out of 10, Exceptional, (17)
"Very clean, kind people, very helpful. "
United States
Anna
$363 nightly
The price is $399
Jan 6 - Jan 7, 2026
Total with taxes and fees
Scott's Cottage - Truman @ Duval | Perfect Location! Ideal for Solos &Couples

Vacation Home in Raccoon Key

Larkshine House at Lunara Bay
2.0 star property
10.0 out of 10, Exceptional, (7)
"well maintained, clean, easy to access"
United States
Raj P.
$2,226 nightly
The price is $2,470
Jan 4 - Jan 5, 2026
Total with taxes and fees
Larkshine House at Lunara Bay

Vacation Home in Raccoon Key

Springtide House at Lunara Bay
9.8 out of 10, Exceptional, (43)
"It was great. House was amazing"
United States
Ernest H.
$1,376 nightly
The price is $1,532
Jan 4 - Jan 5, 2026
Total with taxes and fees
Springtide House at Lunara Bay

Vacation Home in Raccoon Key

Floralee House at Lunara Bay
2.0 star property
9.8 out of 10, Exceptional, (7)
"Amazing house! Spacious, great pool, & good location "
United States
Paige G.
$1,884 nightly
The price is $2,090
Jan 4 - Jan 5, 2026
Total with taxes and fees
Floralee House at Lunara Bay
9.8 out of 10, Exceptional, (18)
"A great price and the best location had a great stay and will be definitely be booking again ! Management and maintenance were very accommodating and friendly.. So glad to have found this place convenient,clean and great price ."
United States
chad b.
$421 nightly
The price is $462
Jan 5 - Jan 6, 2026
Total with taxes and fees
Welcome Matt's - Truman @ Duval | Ideal One-Bedroom Retreat
9.2 out of 10, Wonderful, (31)
"4 nights, was perfect"
United States
Ryan M.
$562 nightly
The price is $624
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Barbados at Sunrise Suites - Balcony & Pool

Vacation Home in Raccoon Key

New Waterfront Home - Sunray House
2.0 star property
$2,549 nightly
The price is $2,867
Jan 5 - Jan 6, 2026
Total with taxes and fees
New Waterfront Home - Sunray House
9.8 out of 10, Exceptional, (33)
"Good place to stay loved it"
United States
Charles I.
$541 nightly
The price is $595
Jan 9 - Jan 10, 2026
Total with taxes and fees
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Vacation Home in Key West

Poolside Cottage #411
9.8 out of 10, Exceptional, (53)
"Perfect for our family! Recommend 10/10!"
United States
Melissa F.
$484 nightly
The price is $537
Jan 3 - Jan 4, 2026
Total with taxes and fees
Poolside Cottage #411
9.8 out of 10, Exceptional, (27)
"The house is perfect for our family. Access to water, pool and close enough to key west!"
United States
John F.
$1,427 nightly
The price is $1,583
Jan 5 - Jan 6, 2026
Total with taxes and fees
Evershore Estate at Lunara Bay | Wellness Home

Vacation Home in Raccoon Key

Suncoast House at Lunara Bay
9.6 out of 10, Exceptional, (41)
"Beautiful House, super clean, perfect location "
United States
carlos s.
$1,900 nightly
The price is $2,110
Jan 20 - Jan 21, 2026
Total with taxes and fees
Suncoast House at Lunara Bay
9.0 out of 10, Wonderful, (29)
"A nice and clean place to come back"
United States
Yudersi S.
$450 nightly
The price is $495
Jan 3 - Jan 4, 2026
Total with taxes and fees
Carey’s Corner | Updated Studio with 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

Price trends for vacation rentals in Key West

Less expensive
More expensive
Next month
September
February
$682
Month
Price
January
$682
February
$923
March
$831
April
$676
May
$613
June
$575
July
$591
August
$550
September
$545
October
$659
November
$666
December
$726
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Key West. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Key West

Everything you need to know about Key West vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Key West vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Key West vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Key West vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Key West. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Key West in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $374 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Key West rentals

At Expedia, we put the best Key West vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Key West rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Key West vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Key West. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 lively festivals and great live music. 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?

SEVENTH HEAVEN~Waterfront 5 BR, 4 Ba Townhome with Pool, Elevator & Dockage!: This Key West vacation home rental is located on the waterfront and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other homes for rent in Key West include Private Parking, Heated Pool - Sweet Caroline and ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking.

How many vacation rentals will I find in Key West?

With 1117 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. Duval Street and Harry S. Truman Little White House are other places to visit while you're in town.

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.