Key West Holiday Rentals

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Holiday Rentals in Key West

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (162)
"The stay was beautiful "
The price is NZ$436
includes taxes & fees
29 Sept - 30 Sept
Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (314)
"Great hotel with excellent location "
Hyatt Vacation Club at Sunset Harbor, Key West

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (402)
"this was exactly as advertised and close to all the action"
The price is NZ$389
includes taxes & fees
30 Sept - 1 Oct
Steps from Duval, Pool on Site & Bikes Included!

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (183)
"Great location; excellent property management "
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

8.8 out of 10, Excellent, (231)
"Property was cute and in a great location! "
The price is NZ$352
includes taxes & fees
29 Sept - 30 Sept
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

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

7.8 out of 10, Good, (22)
"Loved everything about the stay, "
The price is NZ$875
includes taxes & fees
28 Sept - 29 Sept
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (22)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is NZ$540
includes taxes & fees
2 Oct - 3 Oct
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Perfect Location, Private Heated Pool, Pristine Luxury Home!

10.0 out of 10, Exceptional, (189)
"Outstanding place to stay, centrally located!"
The price is NZ$3,067
includes taxes & fees
30 Sept - 1 Oct
Perfect Location, Private Heated Pool, Pristine Luxury Home!

RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!

9.6 out of 10, Exceptional, (188)
"Bucket list trip. Great location. Property was just what was expected. Perfect for 2!"
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

9.6 out of 10, Exceptional, (141)
"This property was great, it had everything needed, extremely clean and walking distance to Davual st.The pool area is wonderful and it was the perfect temperature!Would highly recommend."
The price is NZ$417
includes taxes & fees
8 Oct - 9 Oct
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (819)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (136)
"Great Location, Free Parking, comfortable beds"
Heart of Downtown Key West Cottage With Off-Street Parking

Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

6.6 out of 10, (12)
"Unfortunately this stay was very disappointing. The marina was awesome. Tessa was awesome. The boat itself was disgusting. The pictures are very deceiving. What you see is not what you get. "
The price is NZ$604
includes taxes & fees
28 Sept - 29 Sept
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

Living the Dream Key West Style

9.8 out of 10, Exceptional, (24)
"Great hosts and great accommodations!"
The price is NZ$592
includes taxes & fees
8 Oct - 9 Oct
Living the Dream Key West Style

DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

10.0 out of 10, Exceptional, (4)
"Beautiful property, perfectly located, and one of the best VRBO experiences we have ever had."
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

1-bedroom boat at the Perry with AC, fitness room and 2 swimming pools

The price is NZ$589
includes taxes & fees
28 Sept - 29 Sept
1-bedroom boat at the Perry with AC, fitness room and 2 swimming pools

GATO ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen w/ Shared Heated Pool!

9.6 out of 10, Exceptional, (17)
"Short walk to Duval street, quiet and very clean and comfortable."
The price is NZ$408
includes taxes & fees
6 Oct - 7 Oct
GATO ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen w/ Shared Heated Pool!

Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

9.2 out of 10, Wonderful, (279)
"Great location for our quick weekend"
The price is NZ$1,009
includes taxes & fees
28 Sept - 29 Sept
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

9.6 out of 10, Exceptional, (146)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This darling Conch house in the heart of the island was very comfortable and clean. Will definitely book again."
The price is NZ$405
includes taxes & fees
2 Oct - 3 Oct
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

TRUMAN ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen & Shared Heated Pool

9.6 out of 10, Exceptional, (19)
"Great place will rent again "
The price is NZ$402
includes taxes & fees
6 Oct - 7 Oct
TRUMAN ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen & Shared Heated Pool
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, 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$352 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 entertainment choices and lively festivals. While you're in the area, you can also enjoy the scenic seaside and great live music.

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

Perfect Location, Private Heated Pool, Pristine Luxury Home!: This highly rated holiday home rental in Key West is located in the city centre, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Some other homes for rent in Key West include DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town! and LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool.

How many holiday rentals will I find in Key West?

With 1106 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.