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Key West Vacation Rentals

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Key West vacation rentals

Exterior

Wooden Head Cabin Early1800's Log Cabin with a View and Modern Amenities

Wooden Head Cabin Early1800's Log Cabin with a View and Modern Amenities
Saint Donatus
9.4 out of 10, Exceptional, (18 reviews)
"Perfect night, Great Cabin!!!!!!!!!!!!"
United States
will m.
The price is ￥57,658
￥69,286 total
includes taxes & fees
Jun 10 - Jun 11
Wooden Head Cabin Early1800's Log Cabin with a View and Modern Amenities
Outdoor dining

Lighted Hot Tub w/ 4 BD/2.5 Baths and VERY close to town.

Lighted Hot Tub w/ 4 BD/2.5 Baths and VERY close to town.
Galena
10.0 out of 10, Exceptional, (87 reviews)
"Clean and comfortable - hot tub was a big hit."
United States
Julie C.
The price is ￥64,064
￥100,925 total
includes taxes & fees
Jun 16 - Jun 17
Lighted Hot Tub w/ 4 BD/2.5 Baths and VERY close to town.
Indoor pool, a heated pool

Spacious 5BR Retreat with Hot Tub, Fireplace & Game Room | Galena Territory

Spacious 5BR Retreat with Hot Tub, Fireplace & Game Room | Galena Territory
The Galena Territory
9.8 out of 10, Exceptional, (231 reviews)
"This is our second stay here. It’s perfect for our growing family! "
United States
Hollie M.
Spacious 5BR Retreat with Hot Tub, Fireplace & Game Room | Galena Territory
Smart TV, fireplace, video games, foosball

Secret Room-Hot Tub-Billards-Firepit-Games-Pool access

Secret Room-Hot Tub-Billards-Firepit-Games-Pool access
The Galena Territory
10.0 out of 10, Exceptional, (19 reviews)
"Wonderful stay!"
United States
amy a.
Secret Room-Hot Tub-Billards-Firepit-Games-Pool access
Outdoor spa tub

Drifter Cabin|Riverview+ Sauna+ Hot Tub+ Pickleball

Drifter Cabin|Riverview+ Sauna+ Hot Tub+ Pickleball
Bellevue
10.0 out of 10, Exceptional, (6 reviews)
"The hosts were very helpful. The cabin was very clean amd comfortable."
United States
Ryan C.
The price is ￥42,042
￥53,186 total
includes taxes & fees
Jun 11 - Jun 12
Drifter Cabin|Riverview+ Sauna+ Hot Tub+ Pickleball
Terrace/patio

Shady Haven - Tiny Home 1

Shady Haven - Tiny Home 1
Bellevue
9.8 out of 10, Exceptional, (14 reviews)
"We found the tiny home exceptional, was stocked with everything needed and very clean. Host was friendly and answered any silly questions I had promptly. Spent relaxing evenings by the fire watching barges going through the locks. "
United States
Debra P.
The price is ￥19,027
￥34,047 total
includes taxes & fees
Jun 17 - Jun 18
Shady Haven - Tiny Home 1
Smart TV, stereo

Ranch styled home, in a quiet neighborhood, totally remodeled in 2020.

Ranch styled home, in a quiet neighborhood, totally remodeled in 2020.
Bellevue
9.6 out of 10, Exceptional, (120 reviews)
"Everything was as advertised and we had a great stay visiting family. Very easy access from the highway and very cozy and comfortable."
United States
Lance R.
The price is ￥13,550
￥32,217 total
includes taxes & fees
Jun 10 - Jun 11
Ranch styled home, in a quiet neighborhood, totally remodeled in 2020.
Sun loungers, beach towels

Riverstone Villa #2 - Accessible Family Suite

Riverstone Villa #2 - Accessible Family Suite
Bellevue
10.0 out of 10, Exceptional, (7 reviews)
"The history of the building was very unique as well as very clean."
United States
Sarah
The price is ￥28,159
￥48,759 total
includes taxes & fees
Jun 14 - Jun 15
Riverstone Villa #2 - Accessible Family Suite
Terrace/patio

Mississippi River Cabin

Mississippi River Cabin
Bellevue
9.8 out of 10, Exceptional, (43 reviews)
"Great place"
United States
Greg G.
The price is ￥28,829
￥49,509 total
includes taxes & fees
Jun 14 - Jun 15
Mississippi River Cabin
Indoor pool

Pet-Friendly Wooded Villa w/ Fireplace, Pool & Club Access — Oak Haven Galena

Pet-Friendly Wooded Villa w/ Fireplace, Pool & Club Access — Oak Haven Galena
The Galena Territory
10.0 out of 10, Exceptional, (31 reviews)
"My family and I enjoyed our stay in this property. It was as advertised."
United States
Erman
The price is ￥19,379
￥49,021 total
includes taxes & fees
Jun 15 - Jun 16
Pet-Friendly Wooded Villa w/ Fireplace, Pool & Club Access — Oak Haven Galena
Fridge, microwave, stovetop, coffee/tea maker

The River's Edge - Tiny Home 3

The River's Edge - Tiny Home 3
Bellevue
10.0 out of 10, Exceptional, (13 reviews)
"Had a wonderful time."
United States
Christina S.
The price is ￥18,710
￥33,871 total
includes taxes & fees
Jun 24 - Jun 25
The River's Edge - Tiny Home 3
Exterior

Fresh! 2BR Golf Villa w/ King Beds, Dog-Friendly, Amenity Access, Near Trails

Fresh! 2BR Golf Villa w/ King Beds, Dog-Friendly, Amenity Access, Near Trails
The Galena Territory
10.0 out of 10, Exceptional, (55 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 ￥23,207
￥55,380 total
includes taxes & fees
Jun 10 - Jun 11
Fresh! 2BR Golf Villa w/ King Beds, Dog-Friendly, Amenity Access, Near Trails
Smart TV, fireplace, foosball, table tennis

Luxury Meets Comfort Instagram-Worthy,12 Min 2 Town, Pools, Trails

Luxury Meets Comfort Instagram-Worthy,12 Min 2 Town, Pools, Trails
The Galena Territory
10.0 out of 10, Exceptional, (20 reviews)
"Great stay - great location!"
United States
Jason B.
Luxury Meets Comfort Instagram-Worthy,12 Min 2 Town, Pools, Trails
Interior

Galena Spring Escape - Hot Tub & Cozy Nights

Galena Spring Escape - Hot Tub & Cozy Nights
The Galena Territory
10.0 out of 10, Exceptional, (18 reviews)
"Nice property, good host will rent again."
United States
Anonymous traveler
The price is ￥39,111
￥93,605 total
includes taxes & fees
Jun 23 - Jun 24
Galena Spring Escape - Hot Tub & Cozy Nights
Property grounds

Riverview Villa - Hot Tub - Beach - River Views

Riverview Villa - Hot Tub - Beach - River Views
Bellevue
10.0 out of 10, Exceptional, (12 reviews)
"Great relaxing place "
United States
Nathan A.
The price is ￥31,127
￥52,262 total
includes taxes & fees
Jun 15 - Jun 16
Riverview Villa - Hot Tub - Beach - River Views
Indoor pool, a heated pool

Spacious 3BR*Ensuites | Hot Tub*Fire Pit*Game Room*Coffee Bar*Stunning Sunsets!

Spacious 3BR*Ensuites | Hot Tub*Fire Pit*Game Room*Coffee Bar*Stunning Sunsets!
The Galena Territory
10.0 out of 10, Exceptional, (66 reviews)
"Amazing location - pristine, cozy home with all the amenities. "
United States
Kelsey K.
The price is ￥39,619
￥91,810 total
includes taxes & fees
Jun 10 - Jun 11
Spacious 3BR*Ensuites | Hot Tub*Fire Pit*Game Room*Coffee Bar*Stunning Sunsets!
Smart TV, fireplace, table tennis, stereo

New - Country Chic, Corner Unit, Dog Friendly - Only 12 Min to Downtown Galena

New - Country Chic, Corner Unit, Dog Friendly - Only 12 Min to Downtown Galena
The Galena Territory
10.0 out of 10, Exceptional, (65 reviews)
"Enjoyed our stay. Great host"
United States
Justin D.
The price is ￥28,259
￥57,616 total
includes taxes & fees
Jun 15 - Jun 16
New - Country Chic, Corner Unit, Dog Friendly - Only 12 Min to Downtown Galena
Interior

Valleywood Villa | 5 Ensuite Bedrooms | Hot Tub | Fireplace | Galena Territory

Valleywood Villa | 5 Ensuite Bedrooms | Hot Tub | Fireplace | Galena Territory
The Galena Territory
9.8 out of 10, Exceptional, (71 reviews)
"Exactly what we needed!"
United States
Olivia S.
The price is ￥61,500
￥124,601 total
includes taxes & fees
Jun 14 - Jun 15
Valleywood Villa | 5 Ensuite Bedrooms | Hot Tub | Fireplace | Galena Territory
Indoor pool, a heated pool

Picture Perfect Galena Getaway on Golf Course | 4 Bed 4 Bath | Hot Tub & FirePit

Picture Perfect Galena Getaway on Golf Course | 4 Bed 4 Bath | Hot Tub & FirePit
The Galena Territory
10.0 out of 10, Exceptional, (312 reviews)
"Great place. Plenty of room for everyone. "
United States
Joshua H.
The price is ￥77,910
￥145,363 total
includes taxes & fees
Jun 28 - Jun 29
Picture Perfect Galena Getaway on Golf Course | 4 Bed 4 Bath | Hot Tub & FirePit
Exterior

Charming & Cozy 2BR Cottage | Fireplace | Dog-Friendly | Amenity Access

Charming & Cozy 2BR Cottage | Fireplace | Dog-Friendly | Amenity Access
The Galena Territory
10.0 out of 10, Exceptional, (18 reviews)
"We had a great stay. Brian was very responsive to several questions I had during the stay. The house was very clean and comfortable. It is very quiet out at The Settlement this time of the year and we loved it. Definitely would stay again."
United States
Valorie H.
Charming & Cozy 2BR Cottage | Fireplace | Dog-Friendly | Amenity Access
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

Days Inn by Wyndham Dubuque

Days Inn by Wyndham Dubuque

2/10 Terrible
"I reported a water leak in the room and was told “I told maintenance”. No apology, no option to switch rooms and no attempt to remedy"
Jay 1-night trip
Posted 2 hours ago
Days Inn by Wyndham 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?

1850 Cabin Home - Large BYard-Waterfall- 22' Movie Screen-Family-Event Travelers: This vacation home rental near Key West is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a private yard and a selection of books.

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 University of Dubuque and Five Flags Center.

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.