Key West Holiday Rentals

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Our top choices for Key West holiday rentals

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, (117 reviews)
"Cozy and charming! Simple layout, beautifully decorated, and perfectly located near Potters Mill and downtown Bellevue. Highly recommend!"
United States
Nathan T.
The price is NZ$333
includes taxes & fees
21 Apr - 22 Apr
Ranch styled home, in a quiet neighborhood, totally remodeled in 2020.

Charming, Farmhouse Chic, Cozy|Fireplace|12 Min to Town|Beautiful View

Charming, Farmhouse Chic, Cozy|Fireplace|12 Min to Town|Beautiful View
The Galena Territory
10.0 out of 10, Exceptional, (44 reviews)
"Host was great at communicating! Our stay was peaceful and comfortable."
United States
Michelle H.
The price is NZ$378
includes taxes & fees
22 Apr - 23 Apr
Charming, Farmhouse Chic, Cozy|Fireplace|12 Min to Town|Beautiful View

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
9.8 out of 10, Exceptional, (29 reviews)
"We enjoyed our stay very much!"
United States
Jessica S.
The price is NZ$516
includes taxes & fees
17 Apr - 18 Apr
Pet-Friendly Wooded Villa w/ Fireplace, Pool & Club Access — Oak Haven Galena

The Eagle's View - Tiny Home 4

The Eagle's View - Tiny Home 4
Bellevue
9.8 out of 10, Exceptional, (9 reviews)
"Everything was as expected. Thanks for a great stay!"
United States
Kevin W.
The price is NZ$407
includes taxes & fees
20 Apr - 21 Apr
The Eagle's View - Tiny Home 4

Private entrance/space. Peaceful getaway. Close to events. King bed. Amenities!

Private entrance/space. Peaceful getaway. Close to events. King bed. Amenities!
Dubuque
9.6 out of 10, Exceptional, (28 reviews)
"Check in was easy and the place was very cozy and cute! "
United States
McKenna W.
The price is NZ$208
includes taxes & fees
23 Apr - 24 Apr
Private entrance/space. Peaceful getaway. Close to events. King bed. Amenities!

Mississippi River Cabin

Mississippi River Cabin
Bellevue
10.0 out of 10, Exceptional, (41 reviews)
"Great place"
United States
Greg G.
The price is NZ$523
includes taxes & fees
19 Apr - 20 Apr
Mississippi River Cabin

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, (53 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 NZ$502
includes taxes & fees
19 Apr - 20 Apr
Fresh! 2BR Golf Villa w/ King Beds, Dog-Friendly, Amenity Access, Near Trails

115#202 / Charming Downtown Dubuque Apartment

115#202 / Charming Downtown Dubuque Apartment
Downtown Dubuque
10.0 out of 10, Exceptional, (41 reviews)
"The entire place was spotless and very nice. The location was perfect for downtown activities. I would highly recommend. The restaurant below is a must too! "
United States
Michele
The price is NZ$323
includes taxes & fees
19 Apr - 20 Apr
115#202 / Charming Downtown Dubuque Apartment

The River's Edge - Tiny Home 3

The River's Edge - Tiny Home 3
Bellevue
10.0 out of 10, Exceptional, (11 reviews)
"Had a wonderful time."
United States
Christina S.
The price is NZ$399
includes taxes & fees
29 Apr - 30 Apr
The River's Edge - Tiny Home 3

Riverstone Villa #2 - Accessible Family Suite

Riverstone Villa #2 - Accessible Family Suite
Bellevue
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 NZ$434
includes taxes & fees
27 Apr - 28 Apr
Riverstone Villa #2 - Accessible Family Suite

Scenic Galena Condo - 2 Kings - Golf Views - Close to Lake & Trails - Pools

Scenic Galena Condo - 2 Kings - Golf Views - Close to Lake & Trails - Pools
The Galena Territory
10.0 out of 10, Exceptional, (83 reviews)
"Super cute place to stay, packed with everything you need, in the Galena territory. Mellissa was responsive any time needed. Would stay here again! "
United States
Sara Z.
The price is NZ$405
includes taxes & fees
19 Apr - 20 Apr
Scenic Galena Condo - 2 Kings - Golf Views - Close to Lake & Trails - Pools

Riverview Villa - Hot Tub - Beach - River Views

Riverview Villa - Hot Tub - Beach - River Views
Bellevue
10.0 out of 10, Exceptional, (11 reviews)
"Nice and clean! Great area for a quiet get away! "
United States
Brooke P.
The price is NZ$506
includes taxes & fees
19 Apr - 20 Apr
Riverview Villa - Hot Tub - Beach - River Views

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 NZ$504
includes taxes & fees
23 Apr - 24 Apr
Drifter Cabin|Riverview+ Sauna+ Hot Tub+ Pickleball

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

Private 3BR/2BA Territory Home Nestled in the Trees - Stonecrest
The Galena Territory
10.0 out of 10, Exceptional, (145 reviews)
"Had a great time, perfect location, great setup for a family. "
United States
William R.
The price is NZ$469
includes taxes & fees
19 Apr - 20 Apr
Private 3BR/2BA Territory Home Nestled in the Trees - Stonecrest

Escape to Creekwood Pines - 2 King Beds, Near Golf, Dog-Friendly, Amenity Access

Escape to Creekwood Pines - 2 King Beds, Near Golf, Dog-Friendly, Amenity Access
The Galena Territory
10.0 out of 10, Exceptional, (26 reviews)
"Easy check-in, very clean, nicely updated, comfortable beds. "
United States
Rachel A J.
The price is NZ$504
includes taxes & fees
21 Apr - 22 Apr
Escape to Creekwood Pines - 2 King Beds, Near Golf, Dog-Friendly, Amenity Access

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 traveller
The price is NZ$800
includes taxes & fees
21 Apr - 22 Apr
Galena Spring Escape - Hot Tub & Cozy Nights

The Riverbottom - Tiny Home 2

The Riverbottom - Tiny Home 2
Bellevue
10.0 out of 10, Exceptional, (14 reviews)
"We really enjoyed our 2 nights in the tiny cabin. We cooked, watched a movie (it rained one night), and used the hot tub. It was easy to find, clean, and safe. Thanks!"
United States
Erin H.
The price is NZ$399
includes taxes & fees
29 Apr - 30 Apr
The Riverbottom - Tiny Home 2

Amazing! 2 Bed Townhouse in the HEART of Dbq!

Amazing! 2 Bed Townhouse in the HEART of Dbq!
Dubuque
9.8 out of 10, Exceptional, (48 reviews)
"I can’t say enough-host,amenities,location… everything was perfect!"
United States
Maria C.
The price is NZ$356
includes taxes & fees
21 Apr - 22 Apr
Amazing! 2 Bed Townhouse in the HEART of Dbq!

JACUZZI SUITE 2 Queen Beds Private and Romantic!

JACUZZI SUITE 2 Queen Beds Private and Romantic!
Dubuque
9.8 out of 10, Exceptional, (24 reviews)
"Great place to stay, clean, everything we needed, and the host communication was excellent."
United States
Todd F.
The price is NZ$350
includes taxes & fees
28 Apr - 29 Apr
JACUZZI SUITE 2 Queen Beds Private and Romantic!

Cheerful home by Millwork District/Farmers Market

Cheerful home by Millwork District/Farmers Market
Historic Millwork District
9.6 out of 10, Exceptional, (23 reviews)
"Clean comfortable very nice place to stay "
United States
Dale B.
The price is NZ$341
includes taxes & fees
19 Apr - 20 Apr
Cheerful home by Millwork District/Farmers Market
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

Find out more about Key West

Everything you need to know about Key West holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Key West holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Key West holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Key West holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Key West. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Key West holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Key West holiday rentals we have selected for you start as low as NZ$383 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Key West rentals

At Expedia, we put the best Key West holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Key West rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Key West holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Key West. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Key West?

Yes, there are holiday rentals close to the most popular sights in Key West, or you can select a more secluded option if you're looking for a relaxing stay.

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

Cozy 1 Bedroom, 2 Bath Townhome in the Galena Territory: This holiday home rental outside of Key West is located next to a golf course, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a patio and an arcade/games room.

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 wider area, you’ll find Mines of Spain State Recreation Area and University of Dubuque.

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 provide amenities such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a family trip or a small group gathering.