Key West Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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
8.8 out of 10, Excellent, (176 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
The price is NZ$677
includes taxes & fees
17 Feb - 18 Feb
Aqua Lodges at Hurricane Hole Marina

Balcony, Pool, & Near Duval - Curry House Room 8

Balcony, Pool, & Near Duval - Curry House Room 8
Old Town Key West
9.2 out of 10, Wonderful, (22 reviews)
"Place is perfect"
United States
Ryan S.
The price is NZ$744
includes taxes & fees
2 Mar - 3 Mar
Balcony, Pool, & Near Duval - Curry House Room 8

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.
The price is NZ$820
includes taxes & fees
4 Mar - 5 Mar
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
7.8 out of 10, Good, (29 reviews)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
The price is NZ$826
includes taxes & fees
10 Feb - 11 Feb
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
2.0 star property
Raccoon Key
The price is NZ$10,123
includes taxes & fees
6 Mar - 7 Mar
The Fairhaven House at Solaire Lunara Bay

Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (419 reviews)
"Everything was excellent!"
United States
Susan L.
The price is NZ$714
includes taxes & fees
4 Mar - 5 Mar
Steps from Duval, Pool on Site & Bikes Included!

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (42 reviews)
"Everything was excellent, awesome host, beautiful vacation!"
United States
Jodi M.
The price is NZ$1,069
includes taxes & fees
9 Mar - 10 Mar
Living the Dream Key West Style

COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!

COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (100 reviews)
"We had a fantastic day perfect location we were able to walk and ride our bikes everywhereIt was a wonderful getaway and we will be back"
United States
Rogie & Gail C.
The price is NZ$804
includes taxes & fees
11 Feb - 12 Feb
COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!

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, (97 reviews)
"Nice property, great location, comfortable bed, lovely pool. "
United States
Candice B.
The price is NZ$871
includes taxes & fees
10 Feb - 11 Feb
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

"LA DOLCE VITA", OLD TOWN! STEPS TO DUVAL! 3 BLOCKS TO SOUTH BEACH! SLEEPS 2-4!

"LA DOLCE VITA", OLD TOWN! STEPS TO DUVAL! 3 BLOCKS TO SOUTH BEACH! SLEEPS 2-4!
Old Town Key West
9.6 out of 10, Exceptional, (148 reviews)
"Great location and perfect for a 1 or 2 night stay. "
United States
Charles G.
The price is NZ$888
includes taxes & fees
22 Feb - 23 Feb
"LA DOLCE VITA", OLD TOWN! STEPS TO DUVAL! 3 BLOCKS TO SOUTH BEACH! SLEEPS 2-4!

OSPREY STUDIO @ The Colony-Sleeps up to 4

OSPREY STUDIO @ The Colony-Sleeps up to 4
Old Town Key West
9.6 out of 10, Exceptional, (54 reviews)
"We loved our stay here. It was calm and quiet--such a nice place to lounge and enjoy a morning coffee when you're not hanging out on Duval or exploring the island! We loved it!"
United States
Dean H.
The price is NZ$1,174
includes taxes & fees
11 Feb - 12 Feb
OSPREY STUDIO @ The Colony-Sleeps up to 4

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Old Town Key West
10.0 out of 10, Exceptional, (118 reviews)
"Brilliant location… very generous to leave bikes and chairs which was used every day. Well decorated and equipped room and comfy bed . Shower is hot and has great water pressure . Check in and out is easy . Thank you "
United Kingdom
Simon
The price is NZ$720
includes taxes & fees
10 Feb - 11 Feb
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor & Shared Heated Pool

GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor & Shared Heated Pool
Old Town Key West
9.2 out of 10, Wonderful, (25 reviews)
"Amenities, host, then location"
United States
Tom T.
The price is NZ$1,347
includes taxes & fees
10 Mar - 11 Mar
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor & Shared Heated Pool

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (19 reviews)
"The perfect House , everything was good "
United States
CARLOS G.
The price is NZ$2,749
includes taxes & fees
12 Feb - 13 Feb
The Seagate Estate at Lunara Bay

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
The price is NZ$4,766
includes taxes & fees
16 Feb - 17 Feb
Waterfront Luxury Home - Tidelands House

Sunny Condo with WiFi, Hot Tub, Pool & Tennis

Sunny Condo with WiFi, Hot Tub, Pool & Tennis
Key West
9.4 out of 10, Exceptional, (122 reviews)
"Good amenities, nice for a weekend get away"
United States
Alexander B.
The price is NZ$1,119
includes taxes & fees
27 Feb - 28 Feb
Sunny Condo with WiFi, Hot Tub, Pool & Tennis

Studio with pool - 1 block to Duval St shops/restaurants & 2 blocks to beach

Studio with pool - 1 block to Duval St shops/restaurants & 2 blocks to beach
Old Town Key West
9.6 out of 10, Exceptional, (99 reviews)
"Loved the room and the property, we will definitely book again when we return! The outdoor space and pool are amazing 👏🏼 👏🏼 👏🏼"
United States
Marshall G.
The price is NZ$859
includes taxes & fees
11 Feb - 12 Feb
Studio with pool - 1 block to Duval St shops/restaurants & 2 blocks to beach

3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West

3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West
Stock Island
The price is NZ$789
includes taxes & fees
10 Feb - 11 Feb
3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Stock Island
9.6 out of 10, Exceptional, (120 reviews)
"Great location, close to everything family had a great time."
United States
rafael m.
The price is NZ$1,250
includes taxes & fees
27 Feb - 28 Feb
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

Ricky's Retreat - Truman @ Duval | Ideal Getaway!

Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Old Town Key West
9.8 out of 10, Exceptional, (24 reviews)
"Loved it can’t wait to book it again!!"
United States
Amanda C.
The price is NZ$912
includes taxes & fees
10 Mar - 11 Mar
Ricky's Retreat - Truman @ Duval | Ideal Getaway!
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.
Save an average of 15% on thousands of hotels when you're signed in

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$517 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 1041 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.