Key West Holiday Rentals

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Holiday Rentals in Key West

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (121)
"We enjoyed the small deck that allowed us to watch the boat activity. The shower was so slick it was dangerous to use. It was a little inconvenient to either walk on the short gravel path or walk on the decking and step over all the hoses that were used by the fishing boats. Overall, it was about what we expected from the web site description."
The price is AU$514
includes taxes & fees
12 Mar - 13 Mar
Aqua Lodges at Hurricane Hole Marina

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (375)
"Thank you"
Steps from Duval, Pool on Site & Bikes Included!

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (289)
"I had a great experience with my family!"
The price is AU$735
includes taxes & fees
1 Apr - 2 Apr
Hyatt Vacation Club at Sunset Harbor, Key West

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (807)
"Great property for families. Only downside - if you have a room about be, you can hear everything. So ask for higher rent rates m. Great location, spacious chairs nod and super clean. Loved self cater/clean unit!! "
Coconut Mallory Resort And Marina By Kees Vacations

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (119)
"This cottage was amazing for so many different reasons. Location, quiet, and detail to guests needs. Marcela was a great communicator. No need to communicate too much, everything worked great! We are returning next year!"
Heart of Downtown Key West Cottage With Off-Street Parking

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

9.6 out of 10, Exceptional, (212)
"Great location. The room met our needs. It was clean and comfortable. The owner did a great job of communicating everything we needed to know. Everything was walkable, which we appreciated. "
Feb 3-10 $245 off the rates close beach full kitchen & patio

Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

10.0 out of 10, Exceptional, (3)
"I didn’t really know what I was getting into, but I’m glad I didn’t cancel. This was such a beautiful experience to have shared with just myself. The bed was comfortable and I slept really well both nights. The second night, I had to rent a kayak from the marina (40) to get to the house. It was a beautiful sunset paddle. It’s easy enough, but even as an experienced paddler, it’s about 20 minutes . I had to leave around 5am to catch my flight and paddled back to the marina in pitch black. It was...
The price is AU$447
includes taxes & fees
31 Mar - 1 Apr
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

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

10.0 out of 10, Exceptional, (4)
"Was just a teaser initial trip to Key West but staying on the water was awesome! Beautiful views and great amenities. Kevin and Captain Philip were great throughout the whole process including great local recommendations! One thing to note, if you are 6’ plus, will need to watch your head and the steps downstairs require concentration. As a shorter person (barely 5’!) it all worked perfectly for me! Look forward to staying again and taking the boat out next time! "
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

9.8 out of 10, Exceptional, (281)
"Most impressive condo and grounds - heated pool and huge hot tub and very friendly people! This condo had the best information/directions (and even labeled lightswitches) of anywhere we have ever stayed!"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

Resort View 1BR Suite

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is AU$1,022
includes taxes & fees
1 Apr - 2 Apr
Resort View 1BR Suite

Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach

9.0 out of 10, Wonderful, (158)
"Our stay was great. Marilyn provided us with all necessary information. The house itself is very clean but tiny. It is good for a couple or two people. It was perfect for our needs ! :)"
Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach

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

9.2 out of 10, Wonderful, (254)
"Perfect little getaway"
The price is AU$1,019
includes taxes & fees
20 Mar - 21 Mar
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, (122)
"The property was lovely and very peaceful and quiet. It was delightful to take a dip in the warm pool after a busy day at Dry Tortugas N.P. or mid-day between shopping and going to dinner. The kitchen was very convenient for preparing a light breakfast or lunch"
The price is AU$614
includes taxes & fees
13 Mar - 14 Mar
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

9.2 out of 10, Wonderful, (188)
"This was a great property. Nice and quiet. Gated for privacy. Would use again and will recommend. "
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

Captain's Daughter: Oversized home for the whole family w/private pool & dock

9.8 out of 10, Exceptional, (122)
"Our stay was absolutely incredible. The condo was bigger than we were expecting so we had plenty of room to spread out and relax. The property management website was super helpful and the customer service was amazing as well! Nothing but good reviews from everyone who stayed there!"
Captain's Daughter: Oversized home for the whole family w/private pool & dock

Poolside Cottage #411

9.8 out of 10, Exceptional, (38)
"Quiet area close to everything we were looking for. "
The price is AU$844
includes taxes & fees
20 Mar - 21 Mar
Poolside Cottage #411

EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

9.8 out of 10, Exceptional, (90)
"Clean, roomy, comfortable. Adequate seating and dishes for 6 adults. Great mattresses and pillows. "
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

9.0 out of 10, Wonderful, (37)
"As a mom I liked the cleanliness of kitchen, basic supplies, clean sponge, dish soap etc. it was very cute place. Perfect for three people! Location was good to get to Key West. Stock Island has several good restaurants we didn’t get to try them.all. Had fun using bikes to bike to Starbucks! Beds are comfortable. "
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

TIDES ON SIMONTON ~ Perfectly located just off Duval and all the fun!

9.2 out of 10, Wonderful, (168)
"Excellent location. Main issues were most windows did not open and most were smoked glass so not much natural light. The bedroom was in the front on a busy street so quite noisy.Overall we loved the location and the process interacting with the property manager. "
TIDES ON SIMONTON ~ Perfectly located just off Duval and all the fun!

Cozy & modern guest house in Key West with AC, WiFi

Cozy & modern guest house in Key West with AC, WiFi
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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Other types of properties in Key West you may be interested in

Beachside Resort & Residences

3.5 star property
8.4 out of 10, Very good, (1002)
"Nice property! Dining hall over priced and not willing to change/substitute menu items. The sty itself was very nice!"
The price is AU$512
includes taxes & fees
1 Apr - 2 Apr
Beachside Resort & Residences

Southernmost Beach Resort

4.0 star property
8.6 out of 10, Excellent, (2311)
"Beautiful "
The price is AU$927
includes taxes & fees
13 Mar - 14 Mar
Southernmost Beach Resort

Oceans Edge Key West Resort, Hotel & Marina

4.0 star property
8.8 out of 10, Excellent, (1598)
"Would totally come back!"
The price is AU$704
includes taxes & fees
31 Mar - 1 Apr
Oceans Edge Key West Resort, Hotel & Marina
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.

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?

Feb 3-10 $245 off the rates close beach full kitchen & patio: This highly rated holiday home rental in Key West is located in the city centre, and offers a patio, air conditioning and cable TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Some other homes for rent in Key West include Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach and Poolside Cottage #411.

How many holiday rentals will I find in Key West?

With 1340 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.