Key West Holiday Rentals

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Check prices for these dates

Tonight
22 Jan - 23 Jan
Tomorrow
23 Jan - 24 Jan
This weekend
24 Jan - 26 Jan
Next weekend
31 Jan - 2 Feb

Holiday Rentals in Key West

Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (112)
"We loved staying on the houseboat."
The price is AU$498
includes taxes & fees
28 Jan - 29 Jan
Aqua Lodges at Hurricane Hole Marina
Steps from Duval, Pool on Site & Bikes Included!
Beach towels

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (361)
"Fun little place with a great pool. Ken was very helpful in all aspects. Highly recommended. Be aware its a small place but very comfortable."
The price is AU$552
includes taxes & fees
3 Feb - 4 Feb
Steps from Duval, Pool on Site & Bikes Included!
34’ Catamaran Sailboat
Interior

34’ Catamaran Sailboat

9.4 out of 10, Exceptional, (30)
"We had a wonderful time. It is an older, smaller boat but we enjoyed it. There is a port a pot in the cabin but there is a huge shower and bathroom under the carport. We were able to fish right off the boat. Frank will answer texts pretty quickly. "
34’ Catamaran Sailboat
Poolside Cottage #411
Outdoor dining

Poolside Cottage #411

10.0 out of 10, Exceptional, (37)
"Great little condo - perfect for our family to visit Key West! "
The price is AU$652
includes taxes & fees
28 Jan - 29 Jan
Poolside Cottage #411
Hyatt Vacation Club at Sunset Harbor, Key West
Outdoor pool

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!"
Hyatt Vacation Club at Sunset Harbor, Key West
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Property grounds

SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!

9.8 out of 10, Exceptional, (16)
"Staying on the Grand Admiral was really awesome for my wife and I. The location at Perry Marina was exceptional. The whole process was very easy, working with Kathy for booking, Stephanie for check-in and Captain John for our charter, everything went smooth. "
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
HAVANA VIEJA ~ Adults Only, Poolside Queen Suite w/ Shared Pool!
Beach nearby

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

9.6 out of 10, Exceptional, (118)
"We had a great time. Enjoyed the property very much."
The price is AU$1,129
includes taxes & fees
10 Feb - 11 Feb
HAVANA VIEJA ~ Adults Only, Poolside Queen Suite w/ Shared Pool!
FONTANA ~ Adults Only, Pool Access King Suite at Azul Mansion!
Miscellaneous

FONTANA ~ Adults Only, Pool Access King Suite at Azul Mansion!

9.4 out of 10, Exceptional, (111)
"Great location!"
The price is AU$622
includes taxes & fees
29 Jan - 30 Jan
FONTANA ~ Adults Only, Pool Access King Suite at Azul Mansion!
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC
Fridge, microwave, oven, stovetop

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

8.8 out of 10, Excellent, (205)
"I recently stayed at this property and had a generally pleasant experience. The property itself is nice and well-maintained, with a great location that adds to its appeal. The surrounding area is excellent, making it convenient and enjoyable. However, there were a few downsides to my stay. The internet was not working, which was quite inconvenient. Additionally, while the property is good overall, it could benefit from having a few more amenities. The bathroom, in particular, could use some...
The price is AU$863
includes taxes & fees
20 Feb - 21 Feb
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC
The Caroline Suite | 1 bed, 1 bath condo w/shared pool
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

The Caroline Suite | 1 bed, 1 bath condo w/shared pool

9.4 out of 10, Exceptional, (12)
"Place was clear, ready, and in a great area. If your looking for a good place in key west this is it"
The price is AU$1,102
includes taxes & fees
23 Jan - 24 Jan
The Caroline Suite | 1 bed, 1 bath condo w/shared pool
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
A heated pool

Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing

9.8 out of 10, Exceptional, (117)
"This has been our go to place to stay while in the keys. We love the pool, hot tub and beach. My boys can walk right out into the beach and start fishing. It is out of the hustle and bustle but not too far out. Highly recommend!"
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Fridge, microwave, oven, stovetop

Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

9.4 out of 10, Exceptional, (215)
"Very clean. Could use some updating such as fresh paint. "
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Terrace/patio

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

9.0 out of 10, Wonderful, (33)
"It was just the right place for my family. We really enjoyed the view and close proximity to Key West. "
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
The Crystalmarine Suite – Rustic Luxury on the Sea
Interior

The Crystalmarine Suite – Rustic Luxury on the Sea

10.0 out of 10, Exceptional, (2)
"This VRBO is a dream for those looking to escape the hustle and bustle of everyday life. With its unique location, it provides a perfect blend of adventure and relaxation. Whether you're looking to reconnect with nature or simply unwind in a beautiful setting, this floating house offers an unparalleled experience."
The price is AU$1,417
includes taxes & fees
25 Jan - 26 Jan
The Crystalmarine Suite – Rustic Luxury on the Sea
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort
Aerial view

Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort

9.6 out of 10, Exceptional, (82)
"Great trip with 16 people for a 50th birthday party. Host was very helpful and informative throughout the trip. Great for large groups."
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
Third-party on-site parking

GATED OCEANFRONT CONDO AT SMATHER'S BEACH

9.4 out of 10, Exceptional, (118)
"Good location for us. 2 mile walk to Duval St. uber easily accessible. Grocery Store, sandwich shop, Mexican restaurant, and sports bar a few blocks away. Check in required us to go to different location to pick up keys. A negative for us. Also air conditioner would not cool below 78 degrees last 2 nights. Beautiful property we enjoyed "
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!
Sun-loungers, beach towels

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

9.2 out of 10, Wonderful, (243)
"You cannot beat the location of this property 5 minutes stroll off Duvall. The rooms were clean and well appointed. I was suprised at the small size of the bathrooms the wet shower set up was also a surprise. The orice was good for K.W. I would stay here again."
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!
Feb 3-10 $245 off the rates close beach full kitchen & patio
Exterior detail

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

9.6 out of 10, Exceptional, (208)
"We always stay at this location when available. There’s another one at the rear of the property and it was a good spot but we’re spoiled by this one. We’ve stayed here so much it is almost like a second home. It’s well appointed, the shower is huge and the place is cozy and has the lived in feel to it. There’s plenty of basics in the kitchen, full size fridge and stove, the bed is outstanding and adjustable, and there’s even beach chairs to use while staying. Marilyn is a great host and super...
Feb 3-10 $245 off the rates close beach full kitchen & patio
Bahama Village studio @ the Galleria!
Pool

Bahama Village studio @ the Galleria!

9.6 out of 10, Exceptional, (10)
"Everything was as advertised. Its location was fantastic with easy access on foot to everything Key West has to offer. Only negative is that there is a high top table and two chairs in a space that really doesn’t afford those niceties. The bed was comfortable. The ac was a bit loud."
Bahama Village studio @ the Galleria!
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Outdoor pool, a heated pool

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

9.8 out of 10, Exceptional, (280)
"We had a wonderful week during the Christmas/ New Year break. The condo is exceptional. Very clean including many items that make your stay easy and welcoming. The kitchen is fully stocked, not that one needs much while staying on the island. We relaxed in the condo, enjoyed restaurants and music across the island. "
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
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

Ibis Bay Beach Resort
Outdoor pool, pool umbrellas, pool loungers

Ibis Bay Beach Resort

2.5 star property
8.0 out of 10, Very good, (1721)
"Didn’t have regular TV."
The price is AU$477
includes taxes & fees
23 Jan - 24 Jan
Ibis Bay Beach Resort
Havana Cabana at Key West - Adults Only
Outdoor pool, pool loungers

Havana Cabana at Key West - Adults Only

4.0 star property
8.8 out of 10, Excellent, (1648)
"It was pretty noisy near the pool at night, but super fun during the day! "
The price is AU$497
includes taxes & fees
27 Jan - 28 Jan
Havana Cabana at Key West - Adults Only
The Perry Hotel & Marina Key West
2 outdoor pools, open 8:00 AM to 10:00 PM, pool loungers

The Perry Hotel & Marina Key West

4.0 star property
9.4 out of 10, Exceptional, (1003)
"Beautiful property and extremely nice and accommodating staff. Weather was great and the atmosphere was A ! We would definitely stay at The Perry Hotel again. "
The price is AU$705
includes taxes & fees
29 Jan - 30 Jan
The Perry Hotel & Marina Key West
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 entertainment choices and great live music. 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?

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!: This highly rated holiday home rental in Key West is located on the waterfront, and has a balcony, 1 hot tub and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Some other homes for rent in Key West include Poolside Cottage #411 and Spec. Jan 26-31 --219. lodg + w. 3 night stay close beach.

How many holiday rentals will I find in Key West?

With 1324 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. San Carlos Institute - Casa Cuba and Duval Street 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.