Holiday Rentals in Key West

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Our top choices for Key West holiday rentals

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (179 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
The price is €339
includes taxes & fees
8 Mar - 9 Mar
Aqua Lodges at Hurricane Hole Marina

Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
The price is €872
includes taxes & fees
23 Mar - 24 Mar
Grand Marina Suite by Brightwild Waterfront

The Salt Cay | Updated! Stunning Sunset View, Pool

The Salt Cay | Updated! Stunning Sunset View, Pool
Key West
9.6 out of 10, Exceptional, (41 reviews)
"Great location! We did not really want to stay in the main part of Key West."
United States
Trent B.
The price is €811
includes taxes & fees
14 Mar - 15 Mar
The Salt Cay | Updated! Stunning Sunset View, Pool

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access
Meadows
9.8 out of 10, Exceptional, (40 reviews)
"The condo was nicely cleaned and decorated. Love the huge balcony overlooking the water. "
United States
Trysh W.
The price is €1,104
includes taxes & fees
21 Mar - 22 Mar
Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
10.0 out of 10, Exceptional, (35 reviews)
"Every as described, great stay!"
United States
Bryan W.
The price is €780
includes taxes & fees
1 Mar - 2 Mar
The Cat Island Suite | Charmingly Renovated w/ Pool

Stay at SUNRISE SUITES 203!

Stay at SUNRISE SUITES 203!
Key West
9.2 out of 10, Wonderful, (119 reviews)
"First day was very pleasant really enjoyed staying at the condo AC was cold everything worked well had a wonderful time"
United States
Mike R.
The price is €665
includes taxes & fees
23 Mar - 24 Mar
Stay at SUNRISE SUITES 203!

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Key West
9.8 out of 10, Exceptional, (26 reviews)
"This property is beautiful and the location is great as well. We will be back!"
United States
Patricia K.
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK

Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK
Meadows
9.8 out of 10, Exceptional, (22 reviews)
"Really enjoyed the accommodations. "
United States
Timothy
The price is €804
includes taxes & fees
11 Mar - 12 Mar
Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (120 reviews)
"we had a wonderful room with a great location. It was too cold to use the pool, but it looked very inviting. Would definitely stay again."
United States
Richard
The price is €585
includes taxes & fees
22 Mar - 23 Mar
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

Comfortable Condo with Pool, Private Balcony, & Beach Access

Comfortable Condo with Pool, Private Balcony, & Beach Access
Beachside
8.6 out of 10, Excellent, (140 reviews)
"Beautiful property! Pool was phenomenal. There is a men’s and a Womens sauna separately. The common area greenery is beautiful. Thank you"
United States
Amanda G.
The price is €887
includes taxes & fees
11 Mar - 12 Mar
Comfortable Condo with Pool, Private Balcony, & Beach Access

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Key West
9.0 out of 10, Wonderful, (38 reviews)
"Very enjoyable other than the rooster started crowing at 4:30 AM."
United States
Carol
The price is €561
includes taxes & fees
10 Mar - 11 Mar
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
The price is €491
includes taxes & fees
2 Mar - 3 Mar
Resort View 1BR Suite With Direct Pool Access

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Key West
8.6 out of 10, Excellent, (143 reviews)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (98 reviews)
"Nice property, great location, comfortable bed, lovely pool. "
United States
Candice B.
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

Duval Delight | Recently Remodeled Condo on Duval!

Duval Delight | Recently Remodeled Condo on Duval!
Old Town Key West
9.8 out of 10, Exceptional, (47 reviews)
"Nice clean place in a great area. "
United States
Pat K.
The price is €838
includes taxes & fees
2 Mar - 3 Mar
Duval Delight | Recently Remodeled Condo on Duval!

Dog-friendly suite with pool, hot tub, tennis & full kitchen

Dog-friendly suite with pool, hot tub, tennis & full kitchen
Key West
8.6 out of 10, Excellent, (122 reviews)
"We like this place, It was clean and quiet"
United States
Julie P.
Dog-friendly suite with pool, hot tub, tennis & full kitchen

Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (31 reviews)
"Good condo and staff help me out on phone with me till we found the condo. "
United States
Raamkumaran
The price is €658
includes taxes & fees
1 Mar - 2 Mar
Grand Marina Suite - Poolside & Waterfront Condo

Feb 3-10 $245 off the rates close beach full kitchen & patio

Feb 3-10 $245 off the rates close beach full kitchen & patio
Old Town Key West
9.6 out of 10, Exceptional, (243 reviews)
"Great locationPlace looked like picsGreat host"
United States
derek a.
Feb 3-10 $245 off the rates close beach full kitchen & patio

Completely Renovated Condo with Pool, Hot Tub, & Private Patio - Free Parking

Completely Renovated Condo with Pool, Hot Tub, & Private Patio - Free Parking
Key West
9.0 out of 10, Wonderful, (137 reviews)
"Loved how convenient and quiet this place was. The balcony and view of the pool was a plus. We sat out there each morning and evening."
United States
Angela C.
The price is €625
includes taxes & fees
23 Feb - 24 Feb
Completely Renovated Condo with Pool, Hot Tub, & Private Patio - Free Parking

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
9.8 out of 10, Exceptional, (47 reviews)
"Everything was excellent, awesome host, beautiful vacation!"
United States
Jodi M.
The price is €340
includes taxes & fees
25 Feb - 26 Feb
Living the Dream Key West Style
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, 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 €267 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

Can I find holiday rentals in Key West?

Yes, there are holiday rentals in Key West close to Mel Fisher Maritime Museum, or you can select a more secluded option if you're looking for a relaxing stay. Travellers who like culture and the arts give Key West high marks for its great live music and entertainment choices. While you're in the area, you can also enjoy the scenic seaside and lively festivals.

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

3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West: This highly rated holiday home rental in Key West offers an outdoor pool, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. Make the most of garden in this rental home to help you unwind. Some other homes for rent in Key West include Amelia`s Hideaway - Hidden Key West Courtyard - Steps off Duval w Private Pool and Low Rates.& spec. early & late book spec. & 10% wk stays & close all& beach! .

How many holiday rentals will I find in Key West?

With 1030 Expedia holiday rentals, you're guaranteed to find just the right place for your Key West stay.

What can I see and do in Key West?

Mel Fisher Maritime Museum and Florida Keys Eco - Discovery Center are a couple of the family-friendly sights, whereas cultural attractions include Ernest Hemingway Home and Museum and Key West Lighthouse and Keeper's Quarters Museum. Duval Street and Harry S. Truman Little White House are other places to visit while you're in town.

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 offer extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family trips.