Key West Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Key West vacation rentals

House (4 Bedrooms) | Interior

Cottage in Dubuque

1 Mi to Downtown Dubuque! Spacious Home
3.0 star property
The price is ￥14,516
￥58,953 total
includes taxes & fees
Mar 9 - Mar 10
1 Mi to Downtown Dubuque! Spacious Home
Pool

Cabin in The Galena Territory

HoneyComb Hideaway Galena Territories
9.8 out of 10, Exceptional, (8 reviews)
"Great, comfy and cozy stay, space was great for a long weekend with family and area is beautiful. Definitely recommend! "
United States
Montse B.
The price is ￥39,977
￥96,211 total
includes taxes & fees
Mar 9 - Mar 10
HoneyComb Hideaway Galena Territories
Outdoor spa tub

Cabin in Bellevue

Drifter Cabin|Riverview+ Sauna+ Hot Tub+ Pickleball
10.0 out of 10, Exceptional, (5 reviews)
"The hosts were very helpful. The cabin was very clean amd comfortable."
United States
Ryan C.
The price is ￥37,276
￥47,050 total
includes taxes & fees
Mar 9 - Mar 10
Drifter Cabin|Riverview+ Sauna+ Hot Tub+ Pickleball
Terrace/patio

Cabin in Bellevue

Mississippi River Cabin
10.0 out of 10, Exceptional, (41 reviews)
"We loved the place great location very clean and we will be back . "
United States
Mary A.
The price is ￥18,744
￥36,368 total
includes taxes & fees
Mar 9 - Mar 10
Mississippi River Cabin
Exterior

Cabin in Saint Donatus

Wooden Head Cabin Early1800's Log Cabin with a View and Modern Amenities
9.2 out of 10, Wonderful, (17 reviews)
"The cabin itself was beautiful and had a lot of charm ,we really enjoyed the surroundings and the overall setup. However, we did have issues with bugs and flies inside the property in both bedrooms which made the stay less comfortable than expected. With a bit more attention to pest control and cleanliness, this place could be an excellent stay."
United States
BRANKA M.
The price is ￥40,045
￥48,177 total
includes taxes & fees
Mar 12 - Mar 13
Wooden Head Cabin Early1800's Log Cabin with a View and Modern Amenities
Pool

Vacation Home in The Galena Territory

Quiet getaway with wooded views
10.0 out of 10, Exceptional, (71 reviews)
"Very clean and beautiful views. "
United States
chandra m.
Quiet getaway with wooded views
Sun loungers, beach towels

Villa in Bellevue

Riverstone Villa #2 - Accessible Family Suite
10.0 out of 10, Exceptional, (6 reviews)
"The history of the building was very unique as well as very clean."
United States
Sarah
The price is ￥21,592
￥40,264 total
includes taxes & fees
Mar 9 - Mar 10
Riverstone Villa #2 - Accessible Family Suite
Indoor pool

Vacation Home in The Galena Territory

Pet-Friendly Wooded Villa w/ Fireplace, Pool & Club Access — Oak Haven Galena
9.8 out of 10, Exceptional, (27 reviews)
"Great place. Clean, nice layout, easy access to activities. Owners were responsive. Would stay there again"
United States
Rich R.
The price is ￥19,091
￥48,126 total
includes taxes & fees
Mar 9 - Mar 10
Pet-Friendly Wooded Villa w/ Fireplace, Pool & Club Access — Oak Haven Galena
Golf

Condo in The Galena Territory

Lakeview, End unit Condo! Golf! Family! Private pool; 3 BR/3 Bath! Sleeps 8
9.8 out of 10, Exceptional, (54 reviews)
"We loved having coffee in the screened in porch! Very clean and comfortable!"
United States
Rose G.
The price is ￥43,390
￥76,084 total
includes taxes & fees
Mar 27 - Mar 28
Lakeview, End unit Condo! Golf! Family! Private pool; 3 BR/3 Bath! Sleeps 8
Property grounds

Villa in Bellevue

Riverview Villa - Hot Tub - Beach - River Views
10.0 out of 10, Exceptional, (11 reviews)
"This property was hands-down on the nicest places we have stayed. The hot tub was super clean and very nice, we also used the outdoor fire pit, which was wonderful. The location is perfect to walk downtown easily, and the view of the river is very nice. This is a beautiful, very large property that is so tastefully decorated. The beds were also super comfortable!"
United States
Kimberly G.
The price is ￥21,592
￥40,264 total
includes taxes & fees
Mar 9 - Mar 10
Riverview Villa - Hot Tub - Beach - River Views
House (3 Bedrooms) | Interior

Cottage in Galena

'the Fiveten Federal' - Downtown Galena Gem!
3.0 star property
The price is ￥17,829
￥63,757 total
includes taxes & fees
Mar 9 - Mar 10
'the Fiveten Federal' - Downtown Galena Gem!
Terrace/patio

Vacation Home in Galena

Hot Tub 2-bedroom 2 full bath all comforts of home in Galena countryside
10.0 out of 10, Exceptional, (22 reviews)
"The house was absolutely adorable! Super clean, well organized, beautifully decorated. We had a wonderful time there."
United States
Denise
The price is ￥37,867
￥71,733 total
includes taxes & fees
Mar 9 - Mar 10
Hot Tub 2-bedroom 2 full bath all comforts of home in Galena countryside
Smart TV, fireplace, table tennis, stereo

Vacation Home in The Galena Territory

New - Country Chic, Corner Unit, Dog Friendly - Only 12 Min to Downtown Galena
10.0 out of 10, Exceptional, (60 reviews)
"Very clean and nice place for a quick weekend get away for my wife, pet and me. "
United States
Anonymous traveler
The price is ￥23,610
￥51,608 total
includes taxes & fees
Apr 8 - Apr 9
New - Country Chic, Corner Unit, Dog Friendly - Only 12 Min to Downtown Galena
Fridge, microwave, stovetop, coffee/tea maker

Cabin in Bellevue

The Eagle's View - Tiny Home 4
9.8 out of 10, Exceptional, (9 reviews)
"Everything was as expected. Thanks for a great stay!"
United States
Kevin W.
The price is ￥21,592
￥36,553 total
includes taxes & fees
Mar 29 - Mar 30
The Eagle's View - Tiny Home 4
Exterior

Cottage in The Galena Territory

Charming & Cozy 2BR Cottage | Fireplace | Dog-Friendly | Amenity Access
10.0 out of 10, Exceptional, (15 reviews)
"Very comfortable & clean. We enjoyed our stay. "
United States
Iris O.
Charming & Cozy 2BR Cottage | Fireplace | Dog-Friendly | Amenity Access
Outdoor dining

Vacation Home in Galena

Lighted Hot Tub w/ 4 BD/2.5 Baths and VERY close to town.
10.0 out of 10, Exceptional, (78 reviews)
"Perfect for small groups and families looking for a weekend getaway."
United States
Ross W.
The price is ￥55,223
￥89,499 total
includes taxes & fees
Mar 9 - Mar 10
Lighted Hot Tub w/ 4 BD/2.5 Baths and VERY close to town.
Indoor pool, outdoor pool

Vacation Home in The Galena Territory

Charming, Farmhouse Chic, Cozy|Fireplace|12 Min to Town|Beautiful View
10.0 out of 10, Exceptional, (42 reviews)
"Beautiful and peaceful location for our girls weekend in Galena."
United States
Alyssa S.
The price is ￥12,629
￥37,796 total
includes taxes & fees
Apr 8 - Apr 9
Charming, Farmhouse Chic, Cozy|Fireplace|12 Min to Town|Beautiful View
Interior

Vacation Home in The Galena Territory

Picturesque Galena Escape | Spacious 5BR | All Ensuites | 2 Fireplaces! Hot Tub!
9.6 out of 10, Exceptional, (66 reviews)
"Few items not working but the property manager was excellent to communicate with. Very spacious - appreciated each bedroom had a bathroom. Warm and inviting. Hope to be back soon!"
United States
christine p.
The price is ￥43,055
￥100,618 total
includes taxes & fees
Mar 9 - Mar 10
Picturesque Galena Escape | Spacious 5BR | All Ensuites | 2 Fireplaces! Hot Tub!
Exterior

Vacation Home in The Galena Territory

Fresh! 2BR Golf Villa w/ King Beds, Dog-Friendly, Amenity Access, Near Trails
10.0 out of 10, Exceptional, (50 reviews)
"My family and I had a great time in this property, it’s cozy, clean and well located."
United States
fernando
The price is ￥17,285
￥47,530 total
includes taxes & fees
Mar 9 - Mar 10
Fresh! 2BR Golf Villa w/ King Beds, Dog-Friendly, Amenity Access, Near Trails
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

Hotel Julien Dubuque

Hotel Julien Dubuque

10/10 Excellent
"Staff was friendly and helpful. "
William 1-night trip
Posted 3 hours ago
Hotel Julien Dubuque

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

Frequently asked questions

Are there vacation rentals in Key West?

Yes, we offer vacation rentals near popular sights in Key West, or you can select a secluded option if you'd like a relaxing place to stay.

What's the top vacation rental in Key West?

Lighted Hot Tub w/ 4 BD/2.5 Baths and VERY close to town.: This vacation home rental near Key West is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

What can I see and do in Key West?

While exploring the area, visit family-friendly sights like National Mississippi River Museum and Aquarium, or get outside and enjoy nature at Crystal Lake Cave. In the larger area, you’ll find Mines of Spain State Recreation Area and University of Dubuque.

What are vacation rentals like in Key West?

Vacation rentals are private properties you can book for a few days or a quick weekend in Key West. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.