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Key West Vacation Rentals

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Vacation Rentals in Key West

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 CA $280 per night from Nov 30 to Dec 1

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

4/5Very Good! (143 reviews)

"Beautiful property. Excellent location within walking distance to everything. Will be staying here again!"…"

Reviewed on Oct. 20, 2020

Hyatt Residence Club Key West, Sunset Harbor
NEW Listing! Luxury 44' Catamaran Yacht Sleeps 6!

NEW Listing! Luxury 44' Catamaran Yacht Sleeps 6!

7025 Shrimp Rd, Key West, FL

Situated by the ocean, this houseboat is 0.6 mi (1 km) from Robbie's and 1.8 mi (2.9 km) from Key West Harbour. Key West Golf Club and Lower Keys Medical Center ...

5/5Exceptional! (10 reviews)
Great accommodations

"Scott and his team were great! The boat was very functional for 4 adults and had all the amenities we needed. We didn’t have great weather everyday so we only took the boat out 1 day, but Jack our captain made the trip relaxing and enjoyable! I would defiantly recommend Jack for your trips. Hannah ..."…"

Reviewed on Apr. 4, 2020

NEW Listing! Luxury 44' Catamaran Yacht Sleeps 6!
Kimpton Ella's Cottages

Kimpton Ella's Cottages

3.5 out of 5
811 Simonton Street, Key West, FL
The price is CA $221 per night from Dec 6 to Dec 7

Located in Key West Historic District, this cottage is within a 10-minute walk of Duval Street, South Beach and Ernest Hemingway Home and Museum. Southernmost ...

4.9/5Exceptional! (8 reviews)

"Amazing Key West styled cottages. Very clean and appears to be a newer place."…"

Reviewed on Aug. 10, 2020

Kimpton Ella's Cottages
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Brand New! Waterfront 4 Bedroom Condo at Bayfront Suites & Marina

Brand New! Waterfront 4 Bedroom Condo at Bayfront Suites & Marina

801 Eisenhower Drive, Unit 10, Key West, FL

Located in Meadows, this condo is within 1 mile (2 km) of Nancy Forrester's Secret Garden, Duval Street and Ernest Hemingway Home and Museum. South Beach and ...

5/5Exceptional! (3 reviews)
Lobster Mini Season

"Awesome accommodations and location"…"

Reviewed on Aug. 16, 2020

Brand New! Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
Casa Marina Home With Spacious Backyard, Private Pool and Mature Landscaping for Privacy

Casa Marina Home With Spacious Backyard, Private Pool and Mature Landscaping for Privacy

908 Flagler St, Key West, FL

Located in Old Town, this holiday home is within a 10-minute walk of Higgs Beach and Duval Street. South Beach and Key West Butterfly and Nature Conservatory ...

5/5Exceptional! (1 review)
Quaint and comfortable mid century modern home located in the Casa Marina area.

"We love Key West and have traveled there many times. This home was perfect for our stay. It is four blocks from South Duval Street giving us easy walking access to many of the restaurants and bars. The backyard is a lush tropical paradise with plenty of privacy. The heated pool was fabulous. There ..."…"

Reviewed on Dec. 24, 2018

Casa Marina Home With Spacious Backyard, Private Pool and Mature Landscaping for Privacy
Simonton Court Cottages

Simonton Court Cottages

3.5 out of 5
910 Simonton, Key West, FL
The price is CA $169 per night from Dec 2 to Dec 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)

"Great location. Clean and easy to find cozy setting."…"

Reviewed on Dec. 4, 2019

Simonton Court Cottages
KEY West Livin' Beautiful 50' Yacht With 3 Bed, 2 Bath Sleeps 6

KEY West Livin' Beautiful 50' Yacht With 3 Bed, 2 Bath Sleeps 6

6810 Front street, Key West, FL

Situated on the waterfront, this historic houseboat is within 2 miles (3 km) of Key West Harbour, Robbie's and Lower Keys Medical Center. Key West Golf Club ...

4.1/5Very Good! (17 reviews)
Unsatisfied

"I just thought from the pictures, I was disappointed in the condition of the boat from -- after I agreed to rent from owner, he sent a list of his requirements that made my stay very inconvenient."…"

Reviewed on Feb. 15, 2020

KEY West Livin' Beautiful 50' Yacht With 3 Bed, 2 Bath Sleeps 6
Beautiful Boat With Wonderful Deck Anchored off of Fleming Key in Key West

Beautiful Boat With Wonderful Deck Anchored off of Fleming Key in Key West

0 Simonton street, Key West, FL
The price is CA $391 per night from Dec 8 to Dec 9

Situated in Key West, this houseboat is within 1 mi (2 km) of Schooner Western Union, Duval Street, and Mallory Square. Key West Aquarium and Key West Shipwreck ...

4.8/5Exceptional! (5 reviews)
Great Get Away!

"My husband and I were looking for some peaceful time together and we accomplished that!"…"

Reviewed on Aug. 15, 2020

Beautiful Boat With Wonderful Deck Anchored off of Fleming Key in Key West
Sunrise Suites Resort

Sunrise Suites Resort

3 out of 5
3685 Seaside Drive, Key West, FL

Situated near the airport, this condo is 1.2 mi (1.9 km) from Fort East Martello Museum and Gallery and within 3 miles (5 km) of Smathers Beach and Key West ...

4/5Very Good! (976 reviews)

"I like the fact that I just went to my room and opened with the key code and that avoid the time that usually spent in the lobby doing the check in."…"

Reviewed on Jun. 15, 2020

Sunrise Suites Resort
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 is within 3 miles (5 km) of Fort East Martello Museum and Gallery, Smathers Beach and Higgs Beach. Key West Harbour is 2.5 ...

4/5Very Good! (634 reviews)
All in all good place to stay

"All in all was a great place to stay. The manager was a little bit rude when we arrived, which gave a bad first impression. The place is beautiful and clean, the room was very nice. The other draw back is they advertise as having slips for boats, once booked we called and were told they only have ..."…"

Reviewed on Aug. 24, 2020

Coconut Mallory Resort And Marina By Kees Vacations
Steps From Duval, Pool & Bikes $99-$219 Night!

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

1016 Howe St., Key West, FL
The price is CA $129 per night from Dec 6 to Dec 7

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! (125 reviews)
Great Location & Pool

"We really enjoyed our stay at this property and Key West. We were able to walk to just about everything. We really liked being close to Duval Street, but being in a residential area without the noise. Check-in was easy and street parking readily available. The owner communicated with us as required ..."…"

Reviewed on Nov. 16, 2020

Steps From Duval, Pool & Bikes $99-$219 Night!
Island Pearl - Cozy Nightly Rental in the Heart of Key West NEW Listing

Island Pearl - Cozy Nightly Rental in the Heart of Key West NEW Listing

527 Fleming Street, Rear Unit, Key West, FL

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

4.9/5Exceptional! (8 reviews)
Island Pearl

"Great location. Angela very easy to work with. Quick responses to questions and great suggestions of things to do. I hope to return soon!!!"…"

Reviewed on Nov. 23, 2020

Island Pearl - Cozy Nightly Rental in the Heart of Key West NEW Listing
Banana's Foster Guesthouse

Banana's Foster Guesthouse

3.5 out of 5
537 Caroline St, Key West, FL
The price is CA $171 per night from Dec 1 to Dec 2

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

4/5Very Good! (33 reviews)

"Great location and great place!"…"

Reviewed on Jun. 22, 2020

Banana's Foster Guesthouse
Yacht in Paradise: Weekly/monthy Rental Available April/may- Special Rates

Yacht in Paradise: Weekly/monthy Rental Available April/may- Special Rates

7005 Shrimp Rd, Key West, FL

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: Weekly/monthy Rental Available April/may- Special Rates
                     TIRED OF BEING INSIDE! Ask about our November specials

TIRED OF BEING INSIDE! Ask about our November specials

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

4.2/5Very Good! (37 reviews)
It was super comfy and in a great location.

"It was far enough from Duvall street but close enough for convenience. It was small but cozy and just right for a quick weekend stay. Would definitely return."…"

Reviewed on Nov. 10, 2020

TIRED OF BEING INSIDE! Ask about our November specials
Southernmost Sanctuary Apartment

Southernmost Sanctuary Apartment

3.5 out of 5
1330 Simonton St, Key West, FL
The price is CA $202 per night from Nov 29 to Nov 30

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

3.8/5Good! (20 reviews)

"I like that the suites were secluded but yet so Close to grocery store and somewhere to eat and the ocean. The furniture needed replacing badly dresser, dining table, hangin lamp all severely beat up Or damaged. Had everything promised though and beds were very comfortable."…"

Reviewed on Jan. 12, 2020

Southernmost Sanctuary Apartment
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 Aquarium ...

You Wont Find a Better Location for Your Key West Stay
Old Town Garden Villas

Old Town Garden Villas

3.5 out of 5
921 Center St, Key West, FL

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
Real World MTV House---not Just a House Your Own Private Resort

Real World MTV House---not Just a House Your Own Private Resort

32 Driftwood Drive, Key West, FL
The price is CA $2,733 per night from Nov 29 to Nov 30

This family-friendly Key West resort is located on the waterfront, within 3 mi (5 km) of Lower Keys Medical Center and Key West Harbour. Key West Golf Club and ...

4.5/5Wonderful! (21 reviews)
50th Birthday Celebration

"Great place for a large group!! Lots to do & fun atmosphere. Needs updates in the kitchen & overall furnishings but if your willing to look past all it's little flaws, totally the place to make great memories!"…"

Reviewed on Sep. 16, 2020

Real World MTV House---not Just a House Your Own Private Resort
Sail Boat Catamaran / House Boat/ Key West

Sail Boat Catamaran / House Boat/ Key West

7009 Shrimp Rd, Stock Island Marina Village, Key West, FL

Situated on the waterfront, this houseboat is 0.6 mi (1 km) from Robbie's and 1.6 mi (2.6 km) from Key West Harbour. Key West Golf Club and Lower Keys Medical ...

4.6/5Wonderful! (20 reviews)
Fun Family Vacation!

"Staying on this boat was definitely a unique vacation experience. The marina it is located in is excellent. We traveled with our two young children (age 7 & 5) so having access to the hotel pool was great! My kids didn't want to leave and keep asking when we can go back!"…"

Reviewed on Jul. 29, 2020

Sail Boat Catamaran / House Boat/ Key West
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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.

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.

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 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?
La Casita: Visitors review this Key West vacation home rental favorably. It has air-conditioning and cable TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a stovetop, a microwave, and kitchenware. Some other homes for rent in Key West include Key Haven Estates’ “papa’s Adobe”; 4br/4.5ba - 2,402 Interior sq ft and Turn lemons into lemonade Nov. & Dec. Prices lowest ever!.
How many vacation rentals will I find in Key West?
With 903 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.

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 CA $166 per night from Nov 29 to Nov 30
Oceans Edge Key West Resort, Hotel & Marina
Southernmost Beach Resort

Southernmost Beach Resort

4 out of 5
1319 Duval Street, Key West, FL
Free cancellationReserve now, pay when you stay
The price is CA $290 per night from Dec 14 to Dec 15
Southernmost 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.