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Key West Vacation Rentals

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Coconut Mallory Resort And Marina By Kees Vacations

Coconut Mallory Resort And Marina By Kees Vacations

3 out of 5
1445 S Roosevelt Blvd, Key West, FL

Situated by the ocean, this condo building is within 3 mi (5 km) of Fort East Martello Museum and Gallery, Smathers Beach, and Higgs Beach. Key West Harbour ...…

4/5Very Good! (639 reviews)
The building was fantastic The view was decent. The first driveway was hard to get into by the light

"Liked it very much very pretty place to be . The traffic light was pretty hard to get in at the first driveway but the place was very very clean and nice. We sat a coffee cup down on the balcony where everybody walks and the cleaning lady picked it up before we were That's good service"…"

Reviewed on Feb 10, 2021

Coconut Mallory Resort And Marina By Kees Vacations
Pescado Penthouse On Duval

Pescado Penthouse On Duval

3.5 out of 5
1201 Duval St, Key West, FL
The price is $240 per night from Mar 5 to Mar 6

Located in Key West Historic District, this apartment building is steps from Key West Butterfly and Nature Conservatory and Duval Street. South Beach and Southernmost ...…

4.3/5Excellent! (15 reviews)

"I can’t say enough good about our stay! Everything was wonderful! Clean, well stocked, great location ! We will be back!"…"

Reviewed on Jun 30, 2020

Pescado Penthouse On Duval
Yacht in Paradise: 5-Star Marina Resort with pools, bars & restaurants

Yacht in Paradise: 5-Star Marina Resort with pools, bars & restaurants

Key West, FL
The price is $258 per night from Mar 16 to Mar 17

Situated on the waterfront, this houseboat is 0.6 mi (0.9 km) from Robbie's and 1.7 mi (2.8 km) from Key West Harbour. Key West Golf Club and Lower Keys Medical ...…

4.8/5Exceptional! (6 reviews)
Relaxing

"Great getaway for our anniversary. The hotel shuttle transport to Key West was convenient. Unique experience!"…"

Reviewed on Nov 16, 2020

Yacht in Paradise: 5-Star Marina Resort with pools, bars & restaurants
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Hyatt Residence Club Key West, Sunset Harbor

Hyatt Residence Club Key West, Sunset Harbor

3.5 out of 5
200 Sunset Lane, Key West, FL
The price is $429 per night from Mar 2 to Mar 3

Located in Old Town, this condo building is steps from Key West Museum of Art and History and Harry S. Truman Little White House. Duval Street and Mallory Square ...…

4.1/5Very Good! (159 reviews)

"We had a great stay. The property was very clean and comfortable with a great view."…"

Reviewed on Jan 26, 2021

Hyatt Residence Club Key West, Sunset Harbor
Steps From Duval, Pool & Bikes $99-$219 Night!

Steps From Duval, Pool & Bikes $99-$219 Night!

Key West, FL
The price is $129 per night from Mar 11 to Mar 12

Located in Old Town, this apartment building is within a 5-minute walk of Duval Street, Southernmost Point, and Ernest Hemingway Home and Museum. South Beach ...…

4.7/5Exceptional! (140 reviews)

"Everything you need! Even had sunscreen! Perfect little studio!!!"…"

Reviewed on Feb 21, 2021

Steps From Duval, Pool & Bikes $99-$219 Night!
Simonton Court Cottages

Simonton Court Cottages

3.5 out of 5
910 Simonton, Key West, FL
The price is $185 per night from Mar 2 to Mar 3

Located in Key West Historic District, this cottage is within a 5-minute walk of Duval Street and Ernest Hemingway Home and Museum. South Beach and Key West ...…

3.5/5Good! (13 reviews)
So-so

"First of all there was construction on the street so that had an impact on our stay. The courtyard was a lot less than the picture showed. The bed was not very comfortable, soft! And we knew there was no parking but street parking was very difficult which also resulted in our vehicle getting towed. ..."…"

Reviewed on Feb 29, 2020

Simonton Court Cottages
True Paradise: Classic Sailboat in Luxury Marina Resort

True Paradise: Classic Sailboat in Luxury Marina Resort

Key West, FL
The price is $268 per night from Mar 18 to Mar 19

Situated on the waterfront, this historic houseboat is 0.6 mi (1 km) from Robbie's and 1.6 mi (2.7 km) from Key West Harbour. Key West Golf Club and Lower Keys ...…

5/5Exceptional! (1 review)
Great location.

"Enjoyed the marina and facilities"…"

Reviewed on Jan 12, 2021

True Paradise: Classic Sailboat in Luxury Marina Resort
The Hollinsed House

The Hollinsed House

3 out of 5
609 Southard Street, Key West, FL

Located in Key West Historic District, this apartment building is steps from Nancy Forrester's Secret Garden and Duval Street. Mallory Square and Ernest Hemingway ...…

4.5/5Wonderful! (25 reviews)

"Cute property, quiet. Private entrance. Nice courtyard for relaxing. Within walking distance of everything, never had to move our car. Had a Keurig coffee maker. Bed was fairly comfy. Only negative was that the room smelled very musty, but we aired it out when we could and it was manageable and would ..."…"

Reviewed on Dec 14, 2020

The Hollinsed House
"HAVANA VIEJA" ~ Poolside 1 Bedroom, 1 Bathroom with Community Pool!

"HAVANA VIEJA" ~ Poolside 1 Bedroom, 1 Bathroom with Community Pool!

Key West, FL
The price is $279 per night from Mar 10 to Mar 11

Located in Key West Historic District, this historic vacation home is within a 15-minute walk of Duval Street, South Beach, and Higgs Beach. Ernest Hemingway ...…

"HAVANA VIEJA" ~ Poolside 1 Bedroom, 1 Bathroom with Community Pool!
Luxury Waterfront Home With Private Heated Pool and Lush Landscaping!

Luxury Waterfront Home With Private Heated Pool and Lush Landscaping!

Key West, FL

Situated on the waterfront, this vacation home is within 3 mi (5 km) of Higgs Beach, Duval Street, and South Beach. Southernmost Point and Mallory Square are ...…

5/5Exceptional! (5 reviews)
Family Vacation

"We come to KW 2-3 times a year. 1st time to stay on this side of the island. We loved the convenience of everything. House was beautiful. We all had a wonderful time."…"

Reviewed on Aug 5, 2020

Luxury Waterfront Home With Private Heated Pool and Lush Landscaping!
Octopus's Garden @ Coral Hammock Spacious Home & Pool + Last KEY Services..

Octopus's Garden @ Coral Hammock Spacious Home & Pool + Last KEY Services..

Key West, FL

Situated by the ocean, this historic vacation home is within 1 mi (2 km) of Lower Keys Medical Center and Key West Harbour. Key West Golf Club and Robbie's are ...…

4.9/5Exceptional! (36 reviews)
Great place to stay

"Comfortable , easy to access, perfect for our trip"…"

Reviewed on Feb 20, 2021

Octopus's Garden @ Coral Hammock Spacious Home & Pool + Last KEY Services..
Panoramic Ocean Views Now on Sale- Newly Renovated for 2020 !!

Panoramic Ocean Views Now on Sale- Newly Renovated for 2020 !!

Key West, FL

Nestled on the beach, this Key West condo building is within 2 mi (3 km) of Higgs Beach, Duval Street, and South Beach. Southernmost Point and Mallory Square ...…

4.7/5Exceptional! (77 reviews)
Great stay!

"Check in was great, easy to get in and out of the building and just an Uber drive away from Duvall street. Did have a problem with the stove, but property manager was easy to get ahold of!"…"

Reviewed on Feb 11, 2021

Panoramic Ocean Views Now on Sale- Newly Renovated for 2020 !!
The Collins Summary:

The Collins Summary:

Key West, FL
The price is $548 per night from Feb 28 to Mar 1

Located in Key West Historic District, this apartment building is steps from San Carlos Institute - Casa Cuba and Duval Street. Mallory Square and Harry S. Truman ...…

The Collins Summary:
Spa On Duval Summary:

Spa On Duval Summary:

Key West, FL
The price is $513 per night from Feb 28 to Mar 1

Located in Key West Historic District, this condo building is within a 5-minute walk of Duval Street and Key West Butterfly and Nature Conservatory. South Beach ...…

4/5Very Good! (1 review)
great response from management

"very good for the price"…"

Reviewed on Oct 27, 2020

Spa On Duval Summary:
Banyan Resort - 2 Blocks to Sunset Celebration

Banyan Resort - 2 Blocks to Sunset Celebration

Key West, FL

Located in Key West Historic District, this condo building is steps from Key West Film Society, Duval Street, and Harry S. Truman Little White House. Mallory ...…

Banyan Resort - 2 Blocks to Sunset Celebration
Banana's Foster Guesthouse

Banana's Foster Guesthouse

3.5 out of 5
537 Caroline St, Key West, FL
The price is $182 per night from Feb 28 to Mar 1

Located in Key West Historic District, this apartment building is steps from The Oldest House - Key West and Duval Street. Mallory Square and Harry S. Truman ...…

4.1/5Very Good! (37 reviews)

"We enjoyed our stay at Banana's Foster Guesthouse. Our room was very clean and comfortable. Not alot of room, but we were only there pretty much to shower and sleep. Cost was expensive but most all places in Key West are expensive. Plus we booked last minute so were pleased to be able to even get ..."…"

Reviewed on Feb 20, 2021

Banana's Foster Guesthouse
You Wont Find a Better Location for Your Key West Stay

You Wont Find a Better Location for Your Key West Stay

Key West, FL

Located in Key West Historic District, this houseboat is within a 10-minute walk of Schooner Western Union and Duval Street. Mallory Square and Key West Shipwreck ...…

5/5Exceptional! (1 review)
Staying easy in The Keys

"A great way to enjoy Key West. The boats location was excellent for exploring. An easy walk to all of Key West's attractions. We enjoyed sitting on the deck having breakfast and boat drinks. The head was small, typical for a boat. There is easy access to a clean bath house just off the dock. Perfect ..."…"

Reviewed on Feb 24, 2021

You Wont Find a Better Location for Your Key West Stay
PRICES HAVE NEVER BEEN LOWER!

PRICES HAVE NEVER BEEN LOWER!

Key West, FL

Located in Key West Historic District, this historic vacation home is within a 15-minute walk of Duval Street, Higgs Beach, and South Beach. Southernmost Point ...…

4.7/5Exceptional! (52 reviews)
cute and clean!

"I had a wonderful 3-night stay! So pleasant and relaxing to come home to!"…"

Reviewed on Feb 9, 2021

PRICES HAVE NEVER BEEN LOWER!
Southernmost Sanctuary Apartment

Southernmost Sanctuary Apartment

3.5 out of 5
1330 Simonton St, Key West, FL
The price is $193 per night from Feb 28 to Mar 1

Located in Key West Historic District, this apartment building is steps from Simonton Beach, Duval Street, and South Beach. Higgs Beach and Southernmost Point ...…

3.8/5Good! (21 reviews)

"The property was clean. No amenities. No parking. Had to call maintenance 2 times with followups. The pullout couch matress was like sleeping on springs. Entry door had to be fixed twice. A/C ran constantly... Never shut off. And all that during a 1 nite stay."…"

Reviewed on Jan 19, 2021

Southernmost Sanctuary Apartment
Old Town Garden Villas

Old Town Garden Villas

3.5 out of 5
921 Center St, Key West, FL
The price is $278 per night from Mar 2 to Mar 3

Located in Key West Historic District, this villa is within a 5-minute walk of Duval Street and Ernest Hemingway Home and Museum. South Beach and Southernmost ...…

4.6/5Wonderful! (5 reviews)

"Property was very clean, and location was very convenient. Did not like the narrow, steep staircase to the bedroom and bathroom. A/C was very loud, and bed was too soft. It wasn't perfect, but we enjoyed it and it was a quiet stay overall."…"

Reviewed on Nov 1, 2020

Old Town Garden Villas
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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.

Other types of properties in Key West you may be interested in

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue, Key West, FL
Free CancellationReserve now, pay when you stay
The price is $367 per night from Mar 2 to Mar 3
Oceans Edge Key West Resort, Hotel & Marina
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd, Key West, FL
The price is $314 per night from Feb 28 to Mar 1
Ibis Bay Beach Resort
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.

Vacation Rentals in Key West

Search for Vacation Rentals in Key West on Expedia.com! You can easily find your home rentals, villas, short-term apartments for rent in Key West using one of the methods below: 

  • View our selection of featured home rentals in Key West
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  • Enter your travel dates to view the best deals on vacation rentals in Key West while they last

Look no further and take a look at our great range of rental properties in Key West!

Frequently asked questions

Can I find vacation rentals in Key West?
Yes, there are vacation rentals in Key West close to Key West Shipwreck 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 entertainment choices and lively festivals. While you’re in the area, you can also enjoy the scenic seaside and great live music.
What are some of the best vacation rentals in Key West?
Luxury Waterfront Home With Private Heated Pool and Lush Landscaping!: This Key West vacation home rental is located by the ocean and has a balcony, a private yard, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a microwave, and a coffee maker, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a hot tub. Some other homes for rent in Key West include Octopus’s Garden @ Coral Hammock Spacious Home & Pool + Last KEY Services.. and Charming Cottage w/ Private hot tub - 1 Block From Duval, Dogs OK!.
How many vacation rentals will I find in Key West?
With 719 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?
Key West Shipwreck Museum and Mel Fisher Maritime Museum are a couple of family-friendly sights, whereas cultural attractions include Ernest Hemingway Home and Museum and Harry S. Truman Little White House. You can also visit some other popular places in town, such as Duval Street and Mallory Square.
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.