Key West Holiday Rentals

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Our top choices for Key West holiday rentals

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (175 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
The price is HK$1,657
HK$3,174 total
includes taxes & fees
1 Mar - 2 Mar
Aqua Lodges at Hurricane Hole Marina

Balcony, Pool, & Near Duval - Curry House Room 8

Balcony, Pool, & Near Duval - Curry House Room 8
Old Town Key West
9.2 out of 10, Wonderful, (22 reviews)
"Place is perfect"
United States
Ryan S.
The price is HK$1,641
HK$3,503 total
includes taxes & fees
2 Mar - 3 Mar
Balcony, Pool, & Near Duval - Curry House Room 8

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Key West
8.6 out of 10, Excellent, (143 reviews)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
The price is HK$1,711
HK$3,871 total
includes taxes & fees
4 Mar - 5 Mar
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
8.0 out of 10, Very good, (28 reviews)
"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
The price is HK$1,953
HK$3,961 total
includes taxes & fees
9 Feb - 10 Feb
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
2.0 star property
Raccoon Key
The price is HK$13,163
HK$22,403 total
includes taxes & fees
16 Feb - 17 Feb
The Fairhaven House at Solaire Lunara Bay

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, (419 reviews)
"Everything was excellent!"
United States
Susan L.
The price is HK$1,962
HK$3,381 total
includes taxes & fees
4 Mar - 5 Mar
Steps from Duval, Pool on Site & Bikes Included!

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (41 reviews)
"Everything was excellent, awesome host, beautiful vacation!"
United States
Jodi M.
The price is HK$3,282
HK$4,161 total
includes taxes & fees
25 Feb - 26 Feb
Living the Dream Key West Style

COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!

COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (100 reviews)
"We had a fantastic day perfect location we were able to walk and ride our bikes everywhereIt was a wonderful getaway and we will be back"
United States
Rogie & Gail C.
The price is HK$2,139
HK$3,889 total
includes taxes & fees
11 Feb - 12 Feb
COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!

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, (97 reviews)
"Nice property, great location, comfortable bed, lovely pool. "
United States
Candice B.
The price is HK$2,106
HK$3,853 total
includes taxes & fees
9 Feb - 10 Feb
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

"LA DOLCE VITA", OLD TOWN! STEPS TO DUVAL! 3 BLOCKS TO SOUTH BEACH! SLEEPS 2-4!

"LA DOLCE VITA", OLD TOWN! STEPS TO DUVAL! 3 BLOCKS TO SOUTH BEACH! SLEEPS 2-4!
Old Town Key West
9.6 out of 10, Exceptional, (147 reviews)
"Great location and perfect for a 1 or 2 night stay. "
United States
Charles G.
"LA DOLCE VITA", OLD TOWN! STEPS TO DUVAL! 3 BLOCKS TO SOUTH BEACH! SLEEPS 2-4!

OSPREY STUDIO @ The Colony-Sleeps up to 4

OSPREY STUDIO @ The Colony-Sleeps up to 4
Old Town Key West
9.6 out of 10, Exceptional, (54 reviews)
"We loved our stay here. It was calm and quiet--such a nice place to lounge and enjoy a morning coffee when you're not hanging out on Duval or exploring the island! We loved it!"
United States
Dean H.
The price is HK$2,332
HK$5,704 total
includes taxes & fees
11 Feb - 12 Feb
OSPREY STUDIO @ The Colony-Sleeps up to 4

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, (118 reviews)
"Brilliant location… very generous to leave bikes and chairs which was used every day. Well decorated and equipped room and comfy bed . Shower is hot and has great water pressure . Check in and out is easy . Thank you "
United Kingdom
Simon
The price is HK$1,894
HK$3,592 total
includes taxes & fees
10 Feb - 11 Feb
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor & Shared Heated Pool

GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor & Shared Heated Pool
Old Town Key West
9.2 out of 10, Wonderful, (25 reviews)
"Amenities, host, then location"
United States
Tom T.
The price is HK$4,254
HK$6,575 total
includes taxes & fees
28 Feb - 1 Mar
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor & Shared Heated Pool

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (19 reviews)
"The perfect House , everything was good "
United States
CARLOS G.
The price is HK$6,243
HK$13,358 total
includes taxes & fees
12 Feb - 13 Feb
The Seagate Estate at Lunara Bay

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
The price is HK$13,163
HK$22,403 total
includes taxes & fees
16 Feb - 17 Feb
Waterfront Luxury Home - Tidelands House

Sunny Condo with WiFi, Hot Tub, Pool & Tennis

Sunny Condo with WiFi, Hot Tub, Pool & Tennis
Key West
9.4 out of 10, Exceptional, (122 reviews)
"Good amenities, nice for a weekend get away"
United States
Alexander B.
The price is HK$2,742
HK$5,276 total
includes taxes & fees
27 Feb - 28 Feb
Sunny Condo with WiFi, Hot Tub, Pool & Tennis

Studio with pool - 1 block to Duval St shops/restaurants & 2 blocks to beach

Studio with pool - 1 block to Duval St shops/restaurants & 2 blocks to beach
Old Town Key West
9.6 out of 10, Exceptional, (99 reviews)
"Loved the room and the property, we will definitely book again when we return! The outdoor space and pool are amazing 👏🏼 👏🏼 👏🏼"
United States
Marshall G.
The price is HK$2,078
HK$4,092 total
includes taxes & fees
11 Feb - 12 Feb
Studio with pool - 1 block to Duval St shops/restaurants & 2 blocks to beach

3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West

3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West
Stock Island
The price is HK$2,138
HK$3,802 total
includes taxes & fees
12 Feb - 13 Feb
3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Stock Island
9.6 out of 10, Exceptional, (120 reviews)
"Great location, close to everything family had a great time."
United States
rafael m.
The price is HK$3,203
HK$6,042 total
includes taxes & fees
27 Feb - 28 Feb
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

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

Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Old Town Key West
9.8 out of 10, Exceptional, (24 reviews)
"Loved it can’t wait to book it again!!"
United States
Amanda C.
The price is HK$1,940
HK$3,849 total
includes taxes & fees
9 Feb - 10 Feb
Ricky's Retreat - Truman @ Duval | Ideal Getaway!
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

Find out more about Key West

Search for holiday rentals in Key West on Expedia! You can easily find your home rentals, villas, holiday apartments in Key West using one of the methods below:

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Frequently asked questions

Can I find holiday rentals in Key West?

Yes, there are holiday rentals in Key West close to Florida Keys Eco - Discovery Center, or you can select a more secluded option if you're looking for a relaxing stay. Travellers 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 holiday rentals that Key West has to offer?

3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West: This highly rated holiday home rental in Key West offers an outdoor pool, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. Make the most of garden in this rental home to help you unwind. Some other homes for rent in Key West include LADY ADMIRAL ~Sweet cottage & guest house with private heated pool off Duval! and Amelia`s Hideaway - Hidden Key West Courtyard - Steps off Duval w Private Pool.

How many holiday rentals will I find in Key West?

With 1103 Expedia holiday rentals, you're guaranteed 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 the 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 holiday rentals like in Key West?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Key West. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family trips.