Key West Holiday Rentals

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Our top choices for Key West holiday rentals

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 AU$293
includes taxes & fees
11 May - 12 May
The Eagle's View - Tiny Home 4

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 AU$348
includes taxes & fees
11 May - 12 May
Charming, Farmhouse Chic, Cozy|Fireplace|12 Min to Town|Beautiful View

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, (118 reviews)
"Great place to stay. "
United States
Michael
The price is AU$280
includes taxes & fees
24 May - 25 May
Ranch styled home, in a quiet neighborhood, totally remodeled in 2020.

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 AU$293
includes taxes & fees
11 May - 12 May
The River's Edge - Tiny Home 3

Mississippi River Cabin

Mississippi River Cabin
Bellevue
10.0 out of 10, Exceptional, (41 reviews)
"Great place"
United States
Greg G.
The price is AU$426
includes taxes & fees
27 May - 28 May
Mississippi River Cabin

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 AU$293
includes taxes & fees
11 May - 12 May
The Riverbottom - Tiny Home 2

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, (30 reviews)
"My family and I enjoyed our stay in this property. It was as advertised."
United States
Erman
The price is AU$428
includes taxes & fees
11 May - 12 May
Pet-Friendly Wooded Villa w/ Fireplace, Pool & Club Access — Oak Haven Galena

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, (54 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 AU$409
includes taxes & fees
12 May - 13 May
Fresh! 2BR Golf Villa w/ King Beds, Dog-Friendly, Amenity Access, Near Trails

Golf View Galena Townhome - 2 Kings - Near Pools, Trails, Lake & Outdoor Fun

Golf View Galena Townhome - 2 Kings - Near Pools, Trails, Lake & Outdoor Fun
The Galena Territory
10.0 out of 10, Exceptional, (85 reviews)
"We had a great time. Melissa was very responsive and accommodating. The the condo was super clean, cozy and was in a great location. Would highly recommend!"
United States
Ben S.
The price is AU$337
includes taxes & fees
11 May - 12 May
Golf View Galena Townhome - 2 Kings - Near Pools, Trails, Lake & Outdoor Fun

Golf Townhouse Near Eagle Ridge | 2 King Suites, Sleeps 2–6, Amenity Access

Golf Townhouse Near Eagle Ridge | 2 King Suites, Sleeps 2–6, Amenity Access
The Galena Territory
10.0 out of 10, Exceptional, (27 reviews)
"Easy check-in, very clean, nicely updated, comfortable beds. "
United States
Rachel A J.
The price is AU$402
includes taxes & fees
11 May - 12 May
Golf Townhouse Near Eagle Ridge | 2 King Suites, Sleeps 2–6, Amenity Access

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 AU$272
includes taxes & fees
7 June - 8 June
115#202 / Charming Downtown Dubuque Apartment

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 AU$361
includes taxes & fees
11 May - 12 May
Riverstone Villa #2 - Accessible Family Suite

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 AU$460
includes taxes & fees
14 May - 15 May
Drifter Cabin|Riverview+ Sauna+ Hot Tub+ Pickleball

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 AU$655
includes taxes & fees
18 May - 19 May
Galena Spring Escape - Hot Tub & Cozy Nights

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 AU$296
includes taxes & fees
11 May - 12 May
Shady Haven - Tiny Home 1

Peaceful Galena Retreat with Scenic Views + Private Deck

Peaceful Galena Retreat with Scenic Views + Private Deck
The Galena Territory
9.8 out of 10, Exceptional, (77 reviews)
"Awesome place, close to everything that’s near and nice amen"
United States
Genaro
The price is AU$358
includes taxes & fees
11 May - 12 May
Peaceful Galena Retreat with Scenic Views + Private Deck

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, (29 reviews)
"Check in was easy and the place was very cozy and cute! "
United States
McKenna W.
The price is AU$173
includes taxes & fees
11 May - 12 May
Private entrance/space. Peaceful getaway. Close to events. King bed. Amenities!

Boutique townhome w/ fire pit, KING bed, mezzanine loft & golf views!

Boutique townhome w/ fire pit, KING bed, mezzanine loft & golf views!
The Galena Territory
10.0 out of 10, Exceptional, (57 reviews)
"Beautiful townhome, great location and clean!"
United States
Dawn M.
The price is AU$318
includes taxes & fees
11 May - 12 May
Boutique townhome w/ fire pit, KING bed, mezzanine loft & golf views!

1129#1- Market view studio/steps Millwork district

1129#1- Market view studio/steps Millwork district
Downtown Dubuque
9.6 out of 10, Exceptional, (45 reviews)
"Great location, clean and had everything I needed."
United States
Christina B.
The price is AU$184
includes taxes & fees
11 May - 12 May
1129#1- Market view studio/steps Millwork district

A MUST SEE! 2BR Lakefront Home w/ Boats & More!

A MUST SEE! 2BR Lakefront Home w/ Boats & More!
East Dubuque
9.4 out of 10, Exceptional, (20 reviews)
"Yes, I was very relaxing."
United States
Larry H.
The price is AU$307
includes taxes & fees
18 May - 19 May
A MUST SEE! 2BR Lakefront Home w/ Boats & More!
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 favourite 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 depend 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 AU$315 per night. Entering your travel dates in the search wizard might find you 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.