Key West Holiday Rentals

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Holiday Rentals in Key West

Outdoor pool
Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
8.4 out of 10, Very good, (228)
"Perfect location - not to far of a walk from Duval Street and the action but tucked away just enough to be able to have some peace!"
The price is NZ$485
per night
29 May - 30 May
Hyatt Vacation Club at Sunset Harbor, Key West
Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, (330)
"My husband and I just got back from Key West. We had a fabulous time and loved where we stayed. Ken, the owner, is terrific. Great communication, excellent tips on things to do and places to eat. It a large house and you have a room to stay in with your own bathroom, small kitchen and bed. It was perfect for us. We will definitely be back next time we visit Key West. Thanks Ken for being a great host!!!"
The price is NZ$392
per night
30 May - 31 May
Steps from Duval, Pool & Bikes $129-$299 Night!
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (16)
"My son and his new wife stayed here for their honeymoon and they absolutely loved it!"
The price is NZ$603
per night
28 May - 29 May
Poolside Cottage #411
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Fridge, cookware/dishes/utensils, dining tables
34’ Catamaran Sailboat
9.4 out of 10, Exceptional, (25)
"Friendly, easy access and close to desired destination "
34’ Catamaran Sailboat
Property grounds
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
10.0 out of 10, Exceptional, (10)
"Sunset cruise was amazing around key west with captain lombardi"
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Restaurant
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (86)
"It’s an experience, it’s not a luxury stay. It’s sort of like staying in a camper with a septic holding tank that can get pretty smelly next to a working marina, with fish charters and a fish cleaning station. One morning we had to use a spare paddle to shoe away a stinky dead fish head so it wouldn’t get trapped under our unit and smell up the place. Staying on the water was unique but in mid May it would have been nice for more shade on the little deck. I’d save it for the slightly cooler...
The price is NZ$504
per night
27 May - 28 May
Aqua Lodges at Hurricane Hole Marina
Pool
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
9.8 out of 10, Exceptional, (258)
"We really enjoyed our stay at this property. The condo was clean and well supplied with essentials. The property is well maintained and safe. We were able to use the included bicycles to get to most locations we wanted to go in old town. Southernmost point was a leisurely 15 min bike ride away. The property owner communicated well with us and answered all of our questions. The only thing we were not prepared for was the traffic noise. The unit does face a busy street, so you can hear vehicles...
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Sun-loungers, beach towels
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
9.2 out of 10, Wonderful, (228)
"Description and pictures accurate. Clean, got what you need, quick response to my questions. Great for me and my husband in a room. Bikes were awesome to have. Couple blocks off Duval. Each room is good for two. Enjoyed the stay!"
The price is NZ$952
per night
3 Jun - 4 Jun
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
2 outdoor pools
Coconut Mallory Resort And Marina By Kees Vacations
3.0 star property
8.2 out of 10, Very good, (789)
"Great property on the water at the Marina . 2 salt water swimming pools and a nice hot tub . Best to rent bikes and go the Stock Island for lunch or dinner. Also can rent kayaks at Stock Island. "
Coconut Mallory Resort And Marina By Kees Vacations
Beach nearby
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
9.4 out of 10, Exceptional, (98)
"We loved it here. Great location and very clean. Would highly recommend if you are visiting key west."
The price is NZ$446
per night
28 May - 29 May
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
Beach nearby
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
9.8 out of 10, Exceptional, (102)
"Beautiful property in a great location. I would definitely stay again."
The price is NZ$459
per night
29 May - 30 May
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
Fridge, microwave, coffee/tea maker, dining tables
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
9.2 out of 10, Wonderful, (93)
"We stayed for a long weekend and really enjoyed the Fontana Room at Azul Mansion. We were able to park on-site and check-in was very easy. It was walking distance to everything: Smathers Beach, the Southernmost Point, and Mallory Square. The pool was nice, and the amenities were great: fresh, cold water always available; Kuerig and pods in the room; plenty of towels including pool towels. Only downside was the pool lights shown into the room at night so room darkening curtains would be good. We...
The price is NZ$488
per night
11 Jun - 12 Jun
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
Pool
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
9.8 out of 10, Exceptional, (191)
"Everything about this place exceeded expectations. The check in was easy and they even let us store our luggage before our check in to make everything more conducive. The house is better than advertised, within walking distance to all the bars and restaurants."
The price is NZ$2,475
per night
27 May - 28 May
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Fridge, microwave, oven, stovetop
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
9.6 out of 10, Exceptional, (185)
"The stay was excellent, a beautiful home with lovely touches to make you feel comfortable. Overall I gave the highest rating, but the TV didn’t work. The manager was attentive but still took a few days to resolve the issue. Also, pool guy arrived unannounced to service the pool, I would have preferred notice. As I said it was overall perfect in terms of location, cleanliness and charm, would recommend it!"
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
Pool
Salvador's Studio by Brightwild | Heated Pool!
8.0 out of 10, Very good, (20)
"So enjoyed it ! Had never stayed in this part of Old Town , and this introduced me to so much. Would absolutely return."
The price is NZ$508
per night
27 May - 28 May
Salvador's Studio by Brightwild | Heated Pool!
Fridge, microwave, oven, stovetop
The Cozy Little Cottage!
8.8 out of 10, Excellent, (3)
"This cozy little cottage was exactly as advertised. The perfect little getaway for me and my spouse, cute decor, great location, quiet and inviting. Had absolutely zero problems. The AC was definitely a necessity and the little details like the origami folded towels was a nice touch! 10/10 would stay here again."
The price is NZ$574
per night
6 Jun - 7 Jun
The Cozy Little Cottage!
Fridge, microwave, oven, stovetop
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
9.4 out of 10, Exceptional, (200)
"A very cozy little cottage in the heart of everything in Key West. In walking distance of everything, although bikes, golf carts and scooters are a great way to get around too. The front porch was nice to relax and sit on to finish out the day. Inside it was very clean, and had everything we needed for a short stay."
The price is NZ$951
per night
24 Jun - 25 Jun
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Beach nearby
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
9.8 out of 10, Exceptional, (55)
"Perfect, loved the pool area, very peaceful, beautiful property"
The price is NZ$848
per night
10 Jun - 11 Jun
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
Property grounds
40'yacht in Paradise Awaits You!
9.6 out of 10, Exceptional, (23)
"We had a really nice couple of days on this boat. We are older (over 60), and we weren't sure if it was going to be our thing. It was good though! The host was amazingly helpful. We loved the private beach and pool right around the corner. We have been to Key West a lot, so we didn't need to do all the tourist stuff. We mostly stayed on Stock Island. It was easy to get Ubers, so we didn't bother with a car or golf cart. If we were staying longer, we probably would have rented a golf cart. The...
40'yacht in Paradise Awaits You!
Property grounds
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
9.8 out of 10, Exceptional, (154)
"Loved this home! (even asked to buy it) plenty of room comfortable beds, great pool and grounds. I have stayed at dozens of properties in Key West and this is hands down my favorite. Location doesn't get much better as well. Overall fantastic"
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
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See all available properties in 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.

Other types of properties in Key West you may be interested in

6 outdoor pools, free pool cabanas, pool umbrellas
Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
9.0 out of 10, Wonderful, (1521)
"Loved this hotel, beautiful and well thought out comforts for travelers coming to Key West. Suite even had microwave we were not expecting. Daily room cleaning included refilling the Kcups and even giving me extra pillows on my bed. Hourly shuttle to Williams St. near Duval was great, and once we mastered the free Duval loop bus, location was great. Loved being able to text hotel staff with any requests and that they checked on your stay. Drive to hotel was through interesting area, but...
The price is NZ$324
per night
10 Jun - 11 Jun
Oceans Edge Key West Resort, Hotel & Marina
Beach nearby, white sand
Margaritaville Beach House Key West
4.0 star property
8.6 out of 10, Excellent, (1762)
"Amazing!!! "
The price is NZ$425
per night
4 Jun - 5 Jun
Margaritaville Beach House Key West
Outdoor pool, pool loungers
Havana Cabana at Key West
4.0 star property
8.8 out of 10, Excellent, (1462)
"A great place to stay, enjoyed every single day the staff the hotel everything was amazing. Definitely staying there again."
The price is NZ$340
per night
10 Jun - 11 Jun
Havana Cabana at 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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Key West holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Key West. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Key West. Seeing all the best attractions is bound to make you fall in love with Key West. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Key West short-term rentals, that won’t be hard to do.

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?

Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!: This highly rated holiday home rental in Key West is equipped with 1 hot tub, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop. Some other homes for rent in Key West include MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval! and TROPICAL RETREAT ~ 3 Bedroom, 3.5 Bath 1/2 Block From Duval St. w/ Pool!.

How many holiday rentals will I find in Key West?

With 1077 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. You can also visit some other popular places in town, such as Duval Street and Dry Tortugas National Park.

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.

Recent reviews of Key West properties
Expedia verified reviews

Havana Cabana at Key West - Adults Only

Havana Cabana at Key West - Adults Only

5/5 Excellent
"A great place to stay, enjoyed every single day the staff the hotel everything was amazing. Definitely staying there again."
A verified traveller stayed at Havana Cabana at Key West - Adults Only
Posted 10 hours ago
Havana Cabana at Key West - Adults Only