A sunny street lined with historic buildings, a 'ONE WAY' sign, and a flagpole with flags.

Key West Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Key West holiday rentals

Front of property

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (192 reviews)
"The bathroom smelled a bit, but we loved the loft and the vibes of the houseboat. It’s hard to find 3 bedrooms at that reasonable price and we have 3 kids that do not want to sleep together so this was perfect. We ate at the bar and really enjoyed watching the jellyfish. It was a cool!"
United States
Emily
The price is HK$890
HK$2,316 total
includes taxes & fees
16 Jul - 17 Jul
Aqua Lodges at Hurricane Hole Marina
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, (132 reviews)
"Great place to stay"
United States
walter l.
The price is HK$660
HK$2,019 total
includes taxes & fees
15 Jul - 16 Jul
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
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, (444 reviews)
"Great location! Close to everything! We biked everywhere and accommodations had everything we needed. "
United States
Richard A.
The price is HK$769
HK$1,863 total
includes taxes & fees
15 Jul - 16 Jul
Steps from Duval, Pool on Site & Bikes Included!
1 bedroom, WiFi

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D
Old Town Key West
9.8 out of 10, Exceptional, (41 reviews)
"Great location"
United States
Glen V.
The price is HK$824
HK$3,105 total
includes taxes & fees
18 Jul - 19 Jul
Pelican Suite | Cozy Cottage, Hot Tubs, Close to D
Beach

Feb 3-10 $245 off the rates close beach full kitchen & patio

Feb 3-10 $245 off the rates close beach full kitchen & patio
Old Town Key West
9.6 out of 10, Exceptional, (253 reviews)
"Loved our stay here!"
United States
Kristin E.
The price is HK$1,090
HK$2,602 total
includes taxes & fees
8 Aug - 9 Aug
Feb 3-10 $245 off the rates close beach full kitchen & patio
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, (105 reviews)
"Not really close to much but a comfortable bed and clean room. The pool and grounds are lovely. Will stay again but rent a golf cart. "
United States
Laura T.
The price is HK$653
HK$1,988 total
includes taxes & fees
15 Jul - 16 Jul
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
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, (38 reviews)
"Fantastic and cozy… and surprisingly right in the middle of Key West fun"
United States
Jay R.
The price is HK$870
HK$2,829 total
includes taxes & fees
13 Aug - 14 Aug
Ricky's Retreat - Truman @ Duval | Ideal Getaway!
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
9.6 out of 10, Exceptional, (38 reviews)
"Very clean and the services are great. "
United States
Rck S.
The price is HK$870
HK$2,798 total
includes taxes & fees
9 Aug - 10 Aug
Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!
Living area

The Grand Cayman | Beautifully Remodeled Key West!

The Grand Cayman | Beautifully Remodeled Key West!
Key West
9.6 out of 10, Exceptional, (19 reviews)
"Clean, comfortable, beautifully decorated. We enjoyed the pool and hot tub. "
United States
Jen R.
The price is HK$1,621
HK$4,292 total
includes taxes & fees
27 Jul - 28 Jul
The Grand Cayman | Beautifully Remodeled Key West!
Property grounds

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

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Key West
10.0 out of 10, Exceptional, (32 reviews)
"Very nice clean place. Had a minor problem with the beds after checking in but property manager was quick to respond and correct issue. Would stay here again. "
United States
Teri K.
The price is HK$1,543
HK$4,055 total
includes taxes & fees
16 Jul - 17 Jul
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
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
8.8 out of 10, Excellent, (55 reviews)
"Things ran smoorhly with booking and check-in. "
United States
Bev H.
The price is HK$931
HK$2,809 total
includes taxes & fees
16 Jul - 17 Jul
Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
Exterior detail

Holly's Hideaway - Truman @ Duval | Charming Hideaway Near Duval!

Holly's Hideaway - Truman @ Duval | Charming Hideaway Near Duval!
Old Town Key West
9.6 out of 10, Exceptional, (51 reviews)
"Great location close to pretty much everything!!!"
United States
Darryl H.
The price is HK$1,239
HK$3,992 total
includes taxes & fees
5 Aug - 6 Aug
Holly's Hideaway - Truman @ Duval | Charming Hideaway Near Duval!
Beach towels

STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST

STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
Old Town Key West
9.8 out of 10, Exceptional, (45 reviews)
"Great place and location. Walking distance to many shops and restaurants. Our flight arrived a few hours before check in, but the place was ready and we were able to get in right away. Would stay here again! "
United States
Heather W.
The price is HK$691
HK$2,780 total
includes taxes & fees
19 Jul - 20 Jul
STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
Exterior

Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is HK$2,083
HK$3,047 total
includes taxes & fees
15 Jul - 16 Jul
Island View 1BR Residence With Balcony
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)
"I liked that it was pretty centrally located to everything very nice Thank you we had a great time "
United States
Patti E.
The price is HK$1,535
HK$4,162 total
includes taxes & fees
21 Jul - 22 Jul
The Cat Island Suite | Charmingly Renovated w/ Pool
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, (68 reviews)
"Great stay"
United States
Lisa H.
The price is HK$1,238
HK$3,992 total
includes taxes & fees
5 Aug - 6 Aug
Duval Delight | Recently Remodeled Condo on Duval!
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, (37 reviews)
"Great place to stay!"
United States
Andrew M.
The price is HK$1,165
HK$3,581 total
includes taxes & fees
13 Aug - 14 Aug
Kingfish Keep | Lively Escape on Duval! Balcony!
Exterior detail

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, (122 reviews)
"Very communicative, property was as pictured and bikes were perfect for getting around. We didn’t need a car but had no trouble parking right next to the front door. Sandy’s had the best coffee and food was delicious! Will definitely come again!"
United States
Emily F.
The price is HK$1,209
HK$2,692 total
includes taxes & fees
15 Jul - 16 Jul
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
A heated pool

Chagall's Corner | Newly Remodeled!

Chagall's Corner | Newly Remodeled!
Old Town Key West
9.0 out of 10, Wonderful, (43 reviews)
"Very nice place to stay, close to many attractions. "
United States
Maria B.
The price is HK$931
HK$2,833 total
includes taxes & fees
23 Jul - 24 Jul
Chagall's Corner | Newly Remodeled!
Terrace/patio

Duval Hideaway | Dog-Friendly w/ Shared Hot Tub

Duval Hideaway | Dog-Friendly w/ Shared Hot Tub
Old Town Key West
9.8 out of 10, Exceptional, (27 reviews)
"Great little condo off Duval St. It is close to many places to eat and great coffee next door. I’d stay there again! "
United States
Chrysten V.
The price is HK$1,239
HK$3,992 total
includes taxes & fees
5 Aug - 6 Aug
Duval Hideaway | Dog-Friendly w/ Shared Hot Tub
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

The Laureate Key West

The Laureate Key West

10/10 Excellent
"Nice hotel, clean and spacious. Definitely enjoyed our stay."
Tamesha 3-night trip
Posted 4 hours ago
The Laureate Key West

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:

  • View our selection of featured holiday rentals in Key West
  • Use the map to find apartments and other holiday homes in the Key West neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday 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 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 lively festivals. While you're in the area, you can also enjoy the scenic seaside and entertainment choices.

What are some of the best holiday rentals that Key West has to offer?

Luxurious Island Pearl-Private Pool - 2BD/2Bath: This highly rated holiday home rental in Key West is located in the city centre, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Some other homes for rent in Key West include Atlantic Paradise by AvantStay | Great Location w/ & Shared Pool and hot tub! and Southernmost Retreat | On Duval! With Hot Tub, Patio.

How many holiday rentals will I find in Key West?

With 997 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. You can also visit some other popular places in town, such as Duval Street and Southernmost Point.

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.