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Top Holiday Rentals in Key West

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

9.6 out of 10, Exceptional, (27)
"Cool place, great host, and a really nice and unique back yard. Absolutely would stay again."
The price is £234
includes taxes & fees
28 Aug - 29 Aug
1850 Cabin Home, Waterfall, Family Getaway, Corporate Party, Weddings

Newly renovated 2-bedroom house with Hottub in lovely Galena countryside

10.0 out of 10, Exceptional, (6)
"This place is just the best!!!! Amazing to think it was a schoolhouse at one point. The beds were so comfortable! Close to things but still very quiet and private. And we loved having an equal number of bathrooms to bedrooms ratio. That is very difficult to find at properties. "
The price is £317
includes taxes & fees
27 Aug - 28 Aug
Newly renovated 2-bedroom house with Hottub in lovely Galena countryside

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

9.2 out of 10, Wonderful, (63)
"This property was perfect for a short family getaway. The area was safe and the condo is situated close to Galena and the surrounding area. I would definitely stay here again. "
Two Bedroom + LOFT, Cozy Golf View Villa, Fast WiFi

Driftless Get Away

9.8 out of 10, Exceptional, (80)
"Close to shopping and restaurants!"
Driftless Get Away

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 £173
includes taxes & fees
27 Aug - 28 Aug
An Artistic retreat in the heart of downtown Galena

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

10.0 out of 10, Exceptional, (49)
"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,

Cozy 1 Bedroom, 2 Bath Townhome in the Galena Territory

9.8 out of 10, Exceptional, (122)
"Best place to stay for our 15th anniversary "
Cozy 1 Bedroom, 2 Bath Townhome in the Galena Territory

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

2.0 star property
10.0 out of 10, Exceptional, (60)
"Beautiful home. Tons of space. Owners very helpful and excellent communication. Beds were very comfortable. View was awesome. Loved the grazing sheep."
The price is £429
includes taxes & fees
27 Aug - 28 Aug
Lighted Hot Tub w/ 4 BD/2.5 Baths and VERY close to town.

JUST BUILT Timber Ranch! Time for fall colors! 4BR/6BA/HOTTUB/EV/GOLF/RELAX

10.0 out of 10, Exceptional, (5)
JUST BUILT Timber Ranch! Time for fall colors! 4BR/6BA/HOTTUB/EV/GOLF/RELAX

New Owners- 3 BR 3 BA Getaway - Galena Territory & Owners' Club Privileges

10.0 out of 10, Exceptional, (171)
"The six of us (all senior ladies) had a great time - The place was beautiful - Couldn't have asked for more - Would definitely book again - Dianne"
New Owners- 3 BR 3 BA Getaway - Galena Territory & Owners' Club Privileges

1 Bedroom, 2 bath townhouse in The Galena Territory.

9.6 out of 10, Exceptional, (95)
"Clean, well maintained villa close to amenities and tucked away in the country. Very enjoyable stay, well furnished and well maintained."
1 Bedroom, 2 bath townhouse in The Galena Territory.

Summer Bliss @ Gazette Suites on Commerce St! Steps 2 Main St! Parking Spot!

10.0 out of 10, Exceptional, (50)
"Fabulous location and super clean. Comfy beds, too!"
Summer Bliss @ Gazette Suites on Commerce St! Steps 2 Main St! Parking Spot!

Downtown Galena Luxury Rentals Suite 3 Parking New

9.8 out of 10, Exceptional, (9)
"Great host, awesome location, wonderful apartment!"
Downtown Galena Luxury Rentals Suite 3 Parking New

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

10.0 out of 10, Exceptional, (122)
"Great place for a visit to Galena!!! Clubhouse was great for kids!! "
The price is £243
includes taxes & fees
8 Sept - 9 Sept
Private 3BR/2BA Territory Home Nestled in the Trees

Cozy Hideaway with 3 Season Lake View

9.4 out of 10, Exceptional, (15)
"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

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

9.8 out of 10, Exceptional, (21)
"Great end unit, private and very clean. Plenty of towels, pillows, toilet paper and coffee. 😁😁"
The price is £231
includes taxes & fees
9 Sept - 10 Sept
Worry Free! / Fireplace / Clean + Quiet / Close to Indoor Pool, Trails, Town

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

9.8 out of 10, Exceptional, (122)
"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, (41)
"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!

Waterfront cabin with amazing views- Short drive to Dubuque,IA

9.8 out of 10, Exceptional, (9)
"We have stayed here the past 3 years during Thanksgiving week. Great location for our activities. "
Waterfront cabin with amazing views- Short drive to Dubuque,IA

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

9.4 out of 10, Exceptional, (3)
"Cute little apartment in a great location. We highly recommend!!"
The price is £173
includes taxes & fees
28 Aug - 29 Aug
Charming 1-bedroom apartment in fabulous Downtown Galena with WiFi, AC
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

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, apart-hotels, 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 £173 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?

Charming BRAND NEW 2-bedroom house with Hottub in lovely Galena countryside : This holiday home rental outside of Key West is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

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 wider area, you’ll find Crystal Lake Cave 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.