Key West Vacation Rentals

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Vacation Rentals in Key West

Charming BRAND NEW 2-bedroom house with Hottub in lovely Galena countryside

10.0 out of 10, Exceptional, (4)
"What a beautiful property. Clean, private, and a perfect get-away for my family. My parents loved the house so much we almost had to drag them out! We loved everything about it, but my favorite part was definitely the hottub and the fire pit outside. Would definitely love to come back in the future!"
The price is CA $344
CA $641 total
includes taxes & fees
Sep 7 - Sep 8
Charming BRAND NEW 2-bedroom house with Hottub in lovely Galena countryside

Cozy 1 Bedroom, 2 Bath Townhome in the Galena Territory

9.8 out of 10, Exceptional, (117)
"Best place to stay for our 15th anniversary "
Cozy 1 Bedroom, 2 Bath Townhome in the Galena Territory

10 Min Walk to Main St., Updated 1840s Historic Home, Stocked Kitchen, W/D,

10.0 out of 10, Exceptional, (43)
"Such a great find! Perfect location. Fun and unique property. Had everything we needed."
10 Min Walk to Main St., Updated 1840s Historic Home, Stocked Kitchen, W/D,

1850 Cabin Home, Waterfall, Family Getaway, Corporate Party, Weddings

9.6 out of 10, Exceptional, (27)
"Was quiet, clean and super comfortable bed. Thank you, deff would stay there again."
The price is CA $302
CA $425 total
includes taxes & fees
Aug 9 - Aug 10
1850 Cabin Home, Waterfall, Family Getaway, Corporate Party, Weddings

An Artistic retreat in the heart of downtown Galena

10.0 out of 10, Exceptional, (16)
"Very Cozy and quite stay. My wife and I enjoyed the peacefulness. "
The price is CA $229
CA $288 total
includes taxes & fees
Aug 11 - Aug 12
An Artistic retreat in the heart of downtown Galena

Two Bedroom + LOFT, Cozy Golf View Villa, Fast WiFi

9.2 out of 10, Wonderful, (62)
"The condo was very clean. All the beds were very uncomfortable, owner should invest in better mattresses. Condo was advertised as golf course view and our unit had no visible golf course views. Also ads showed parking right in front of the unit and our parking was up on a hill with two sets of stairs to haul all our things. "
Two Bedroom + LOFT, Cozy Golf View Villa, Fast WiFi

Private 3BR/2BA Territory Home Nestled in the Trees

10.0 out of 10, Exceptional, (118)
"Great place for a visit to Galena!!! Clubhouse was great for kids!! "
The price is CA $154
CA $399 total
includes taxes & fees
Aug 10 - Aug 11
Private 3BR/2BA Territory Home Nestled in the Trees

Lighted Hot Tub w/Beautiful Sunset & 4 BD/2.5 Baths and very close to town.

2.0 star property
10.0 out of 10, Exceptional, (56)
"This was a beautiful property in Galena and the hosts made us feel so welcome! We would love to come stay again, we had a wonderful time and would definitely recommend!"
The price is CA $481
CA $775 total
includes taxes & fees
Aug 10 - Aug 11
Lighted Hot Tub w/Beautiful Sunset & 4 BD/2.5 Baths and very close to town.

Driftless Get Away

9.8 out of 10, Exceptional, (80)
"Very comfortable. Great location. "
Driftless Get Away

Ulysses Suites, Suite 204

10.0 out of 10, Exceptional, (15)
"We were very pleased with our stay. We will definitely stay here again "
Ulysses Suites, Suite 204

Summer w/ us at Wooded Retreat. Hot Tub & Fire Pit - Fido Friendly!

9.8 out of 10, Exceptional, (115)
"Plenty of privacy, clean, nice floorplan, plenty of things to do if the weather isn't cooperating right within the house."
Summer w/ us at Wooded Retreat. Hot Tub & Fire Pit - Fido Friendly!

Perfect Location! Semi Private Pool, Walk to Golf, Resort, Paths! Dog Friendly!

10.0 out of 10, Exceptional, (40)
"This cute little place was amazing. The host was awesome. Will definitely be back. "
Perfect Location! Semi Private Pool, Walk to Golf, Resort, Paths! Dog Friendly!

Beautiful Golf Villa!

9.8 out of 10, Exceptional, (160)
"Wonderful and reasonable place to stay. Cindy was helpful with troubleshooting questions. "
Beautiful Golf Villa!

Private Home~Relax at Your Getaway Among the Trees!

10.0 out of 10, Exceptional, (76)
"We had a great time and lots fun things to do around Galena Territory. House had a great set up and the enclosed porch overlooking the woods was a great place to grill and relax."
Private Home~Relax at Your Getaway Among the Trees!

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

9.2 out of 10, Wonderful, (15)
"Clean stay and great communication with host"
The price is CA $495
CA $594 total
includes taxes & fees
Aug 8 - Aug 9
Wooden Head Cabin Early1800's Log Cabin with a View and Modern Amenities

Cozy Hideaway with 3 Season Lake View

9.4 out of 10, Exceptional, (14)
"A beautiful cottage in a beautiful community! Everything was perfect for our Honeymoon weekend. Will definitely be there again!"
Cozy Hideaway with 3 Season Lake View

Scenic Getaway – Cozy Stay Near Golf & Trails

10.0 out of 10, Exceptional, (59)
"Great location for 48 hrs"
The price is CA $186
CA $406 total
includes taxes & fees
Aug 10 - Aug 11
Scenic Getaway – Cozy Stay Near Golf & Trails

Worry Free! / Fireplace / Clean + Quiet / Close to Indoor Pool, Trails, Town

9.8 out of 10, Exceptional, (16)
"Very clean and comfortable."
The price is CA $166
CA $424 total
includes taxes & fees
Aug 25 - Aug 26
Worry Free! / Fireplace / Clean + Quiet / Close to Indoor Pool, Trails, Town

The Nook: Downtown Galena Cottage w/ hot tub & fire pit!

10.0 out of 10, Exceptional, (124)
"This property was great for a weekend Galena visit with friends! Close enough to downtown to walk, but far enough away to stay quiet at night. The hosts were communicative and helpful! Would stay here again."
The price is CA $312
CA $627 total
includes taxes & fees
Aug 26 - Aug 27
The Nook: Downtown Galena Cottage w/ hot tub & fire pit!

2 Bedroom, 2 bath townhouse in The Galena Territory.

9.4 out of 10, Exceptional, (158)
"Great place to stay. "
2 Bedroom, 2 bath townhouse in The Galena Territory.
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

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, Waterfall, Family Getaway, Corporate Party, Weddings: 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 Mines of Spain State Recreation Area. In the larger area, you’ll find Crystal Lake Cave 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.