Key West Vacation Rentals

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Check prices for these dates

Tonight
Jul 28 - Jul 29
Tomorrow
Jul 29 - Jul 30
This weekend
Aug 1 - Aug 3
Next weekend
Aug 8 - Aug 10

Vacation Rentals in Key West

1850 Cabin Home, Waterfall, Family Getaway, Corporate Party, Weddings
Water cascades down a stone structure, surrounded by lush greenery and a charming village setting.

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

9.6 out of 10, Exceptional, (25)
"Decent "
The price is ￥32,492
￥43,126 total
includes taxes & fees
Jul 29 - Jul 30
1850 Cabin Home, Waterfall, Family Getaway, Corporate Party, Weddings
Cozy little getaway in the heart of the city. A short drive from Galena.
Enjoy meals at the dining table with matching benches, surrounded by a comfortable sofa and decorative mirror.

Cozy little getaway in the heart of the city. A short drive from Galena.

9.6 out of 10, Exceptional, (170)
"Sure beats a motel!"
Cozy little getaway in the heart of the city. A short drive from Galena.
Private 3BR/2BA Territory Home Nestled in the Trees
Set amidst lush greenery, this secluded home offers a serene retreat.

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

10.0 out of 10, Exceptional, (117)
"Great place for a visit to Galena!!! Clubhouse was great for kids!! "
The price is ￥18,314
￥44,925 total
includes taxes & fees
Jul 31 - Aug 1
Private 3BR/2BA Territory Home Nestled in the Trees
10 Min Walk to Main St., Updated 1840s Historic Home, Stocked Kitchen, W/D,
Enjoy cooking in this well-equipped kitchen with a central island, refrigerator, oven, and dishwasher.

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

10.0 out of 10, Exceptional, (42)
"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,
Charming BRAND NEW 2-bedroom house with Hottub in lovely Galena countryside
Outdoor spa tub

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

10.0 out of 10, Exceptional, (3)
"We were fortunate to be the very first guests at this adorable property!! The owners did a fantastic job renovating the old schoolhouse, blending historic charm with cozy, modern comforts. The décor creates such a welcoming atmosphere, and the home is stocked with everything you could possibly need to make your stay enjoyable.Thoughtful touches like a welcome letter, festive 4th of July bling, baskets of goodies, and cold waters waiting in the fridge were above and beyond—small extras that made...
The price is ￥36,923
￥68,474 total
includes taxes & fees
Aug 3 - Aug 4
Charming BRAND NEW 2-bedroom house with Hottub in lovely Galena countryside
Cozy 1 Bedroom, 2 Bath Townhome in the Galena Territory
Relax in this cozy living space with a comfortable sofa, coffee table, and TV on a stand. Enjoy meals at the dining table with chairs.

Cozy 1 Bedroom, 2 Bath Townhome in the Galena Territory

9.8 out of 10, Exceptional, (116)
"Best place to stay for our 15th anniversary "
Cozy 1 Bedroom, 2 Bath Townhome in the Galena Territory
JUST BUILT! Timber Ranch The Rocky Mountain Spirit Meets Galena, IL 4BR/4+BA
Smart TV, fireplace, video games, DVD player

JUST BUILT! Timber Ranch The Rocky Mountain Spirit Meets Galena, IL 4BR/4+BA

10.0 out of 10, Exceptional, (2)
"I’ve stayed at a lot of rental places in my life but nothing came close to the Timber Ranch. Great communication with the owners, perfect location, and had a ton of space for the bachelor party. Highly recommend staying here! "
JUST BUILT! Timber Ranch The Rocky Mountain Spirit Meets Galena, IL 4BR/4+BA
Welcome to your Galena Get Away!!!
Enjoy meals in the kitchen with a microwave and oven, and dine by the window with a view of the outdoors.

Welcome to your Galena Get Away!!!

10.0 out of 10, Exceptional, (268)
"Plenty of room. Used the grill for meals. Small but useful kitchen. Easy access to the owners club. Will stay here again. "
Welcome to your Galena Get Away!!!
Private Home~Relax at Your Getaway Among the Trees!
Cozy living room with a stone fireplace, two sofas, large windows, and a wooden ceiling with exposed beams.

Private Home~Relax at Your Getaway Among the Trees!

10.0 out of 10, Exceptional, (75)
"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!
Scenic Getaway – Cozy Stay Near Golf & Trails
Relax in this stylish living area with a mezzanine level, comfortable sofa, and dining table.

Scenic Getaway – Cozy Stay Near Golf & Trails

10.0 out of 10, Exceptional, (59)
"Great stay in a peaceful location. The home was in a nice, quiet area but still conveniently close to town. It was clean, comfortable, and had everything we needed for a relaxing stay. Would definitely recommend and stay here again!"
The price is ￥18,609
￥41,590 total
includes taxes & fees
Jul 29 - Jul 30
Scenic Getaway – Cozy Stay Near Golf & Trails
An Artistic retreat in the heart of downtown Galena
Cozy living space with a central staircase, kitchen area, dining table, and seating area.

An Artistic retreat in the heart of downtown Galena

10.0 out of 10, Exceptional, (14)
"Very Cozy and quite stay. My wife and I enjoyed the peacefulness. "
The price is ￥25,587
￥31,947 total
includes taxes & fees
Jul 29 - Jul 30
An Artistic retreat in the heart of downtown Galena
Charming 1-bedroom apartment in fabulous Downtown Galena with WiFi, AC
Fully equipped kitchen with microwave, dishwasher, and oven.

Charming 1-bedroom apartment in fabulous Downtown Galena with WiFi, AC

The price is ￥20,677
￥32,049 total
includes taxes & fees
Aug 3 - Aug 4
Charming 1-bedroom apartment in fabulous Downtown Galena with WiFi, AC
Cozy Hideaway with 3 Season Lake View
Relax by the pool surrounded by lounge chairs and umbrellas, with a large slide for kids to enjoy.

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
Close to Galena, close to perfect. Premier get away. Three beautiful suites.
Traditional two-story house with a welcoming front porch surrounded by lush greenery and mature trees.

Close to Galena, close to perfect. Premier get away. Three beautiful suites.

10.0 out of 10, Exceptional, (122)
"We had a great time. It was a close drive to Galena and still secluded to feel like we had a private getaway. We had deer come to drink by the creek, and a nice area for a bond fire. The home was beautiful and the owners were really nice. We would definitely book again."
Close to Galena, close to perfect. Premier get away. Three beautiful suites.
Two Bedroom + LOFT, Cozy Golf View Villa, Fast WiFi
Residential-style buildings with pitched roofs and a central entrance, set amidst a well-manicured lawn and a meandering pathway.

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
2 Bedroom, 2 bath home in The Galena Territory. Close to Eagle Ridge Resort
Experience the perfect blend of functionality and comfort in this stylish space, featuring a curved staircase, modern kitchen, and cozy seating area.

2 Bedroom, 2 bath home in The Galena Territory. Close to Eagle Ridge Resort

9.4 out of 10, Exceptional, (179)
"We enjoyed our visit"
2 Bedroom, 2 bath home in The Galena Territory. Close to Eagle Ridge Resort
Galena Luxury Rental Suite 200 Downtown w/parking
Enjoy cooking in the well-equipped kitchen with microwave, oven, and refrigerator, and relax in the adjacent living area with a sofa and coffee table.

Galena Luxury Rental Suite 200 Downtown w/parking

9.6 out of 10, Exceptional, (18)
"Very clean, great location. Would stay here again the next time we’re in the area."
Galena Luxury Rental Suite 200 Downtown w/parking
Two Bedroom Apartment Overlooking Main Street with One Designated Parking Spot
Effortlessly prepare meals in this well-equipped kitchen featuring a refrigerator, oven, and microwave.

Two Bedroom Apartment Overlooking Main Street with One Designated Parking Spot

10.0 out of 10, Exceptional, (3)
"Cute place and a great location. The hosts were very kind and let us check in early. It comes with a parking space too which was very convenient. I would definitely stay again!"
The price is ￥36,775
￥63,860 total
includes taxes & fees
Jul 31 - Aug 1
Two Bedroom Apartment Overlooking Main Street with One Designated Parking Spot
Worry Free! / Fireplace / Clean + Quiet / Close to Indoor Pool, Trails, Town
Cozy living area with a fireplace, dining table, and comfortable seating.

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 ￥17,870
￥45,218 total
includes taxes & fees
Aug 25 - Aug 26
Worry Free! / Fireplace / Clean + Quiet / Close to Indoor Pool, Trails, Town
Driftless Get Away
Relax in this inviting living room with a vintage sofa, coffee table, and framed artwork.

Driftless Get Away

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

Best Western Plus Dubuque Hotel & Conference Center

Best Western Plus Dubuque Hotel & Conference Center

10/10 Excellent
"close to everything lots for kids to do"
SCOTT 2-night trip
Posted 2 days ago
Best Western Plus Dubuque Hotel & Conference Center

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.