Key West Holiday Rentals

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Holiday Rentals in Key West

Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, (329)
"First off the communication with Ken was amazing. Always got back to me right away. The property was very clean and just what was needed. Location. Was amazing and having the bikes was awesome. We rode them all over. Would definitely rent here again."
The price is NZ$398
per night
20 May - 21 May
Steps from Duval, Pool & Bikes $129-$299 Night!
Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
8.4 out of 10, Very good, (227)
"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$496
per night
15 May - 16 May
Hyatt Vacation Club at Sunset Harbor, Key West
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$609
per night
14 May - 15 May
Poolside Cottage #411
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Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
9.2 out of 10, Wonderful, (227)
"This property is no frills but provides everything you need. The location is great, the two room split provides privacy, pool was great and the bikes provided allow for cruising around the island. Tanya was very responsive. Would stay here again."
The price is NZ$962
per night
3 Jun - 4 Jun
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (85)
"Aqualodges was a unique, great experience. Really enjoyed the marine life right at our dock. The accommodations were clean and comfortable. Cant wait to come back! "
The price is NZ$624
per night
27 May - 28 May
Aqua Lodges at Hurricane Hole Marina
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$573
per night
20 May - 21 May
The Cozy Little Cottage!
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
9.8 out of 10, Exceptional, (188)
"We had 10 friends staying in the William Skelton Home this past weekend and the home was perfect. Our hosts were helpful and accommodating in letting us store luggage there on our arrival. The house is so close to so much of the action of Key West and yet it's quiet and peaceful when you're back at the home. It's a special place to stay and perfect for large groups."
The price is NZ$2,630
per night
19 May - 20 May
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
9.8 out of 10, Exceptional, (257)
"This property and host exceeded all of our expectations. It was spacious, comfortable, and welcoming with its amazing kitchen, breezy rooms, and friendly neighbors. The hosts were a pleasure to work with and easy to reach whenever we wished to communicate with them. 10/10 would return to this property. I highly recommend it!"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
10.0 out of 10, Exceptional, (9)
"Sunset cruise was amazing around key west with captain lombardi"
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
52' Power Catamaran Yacht at Luxury Resort Marina
10.0 out of 10, Exceptional, (11)
"We had a great time about Blue Jeans! Louie is an amazing host, as responsive as possible, also took us out for a cruise around Key West, AC works great! Easy Golf kart ride from the marina to down town key west. Pool at the marina was nice as well."
52' Power Catamaran Yacht at Luxury Resort Marina
Duval Square in Key West
10.0 out of 10, Exceptional, (12)
"Great location and nice accommodations. Very enjoyable trip. Located right by Duvall Loop free trolly so no reason to pay for the old Town Trolly. Only negative is I don’t like having to wash dishes and put away, having to strip beds and do their laundry. This is my vacation so I could do these things at home. Manager helped 2 old people with our luggage because we thought the elevator was out of order. He even took it up the stairs to our bedroom. So nice and helpful!"
Duval Square in Key West
Tranquility by Smathers and 10 minute bike downtown Key West value savings
9.4 out of 10, Exceptional, (94)
"Nice accommodations. Very clean and comfortable and secure."
Tranquility by Smathers and 10 minute bike downtown Key West value savings
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated pool, and close to Duval!
9.6 out of 10, Exceptional, (181)
"Four Adults comfortably stay at Mango Margarita for a long weekend. The place is very nice and comfortable. We usually stay closer to all of the action of Duval Street, and enjoyed this much better because we found new fun spots! This is blocks away from the Southernmost Point and very close to Blue Heaven, our favorite brunch spot. We would definitely rent this again!"
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated pool, and close to Duval!
34’ Catamaran Sailboat
9.4 out of 10, Exceptional, (23)
"Frank was freindly,knowlable and super accmodating. The facility was clean and close to everything we needed and far enough away from the noise...the locals where freindly and quiet. Just a great stay....WE WILL BE BACK!"
34’ Catamaran Sailboat
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
9.0 out of 10, Wonderful, (213)
"Very enjoyable"
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
9.4 out of 10, Exceptional, (198)
"The inside was as advertised. Great location and the front porch was nice. The inside of the unit was clean."
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
TROPICAL RETREAT ~ 3 Bedroom, 3.5 Bath 1/2 Block From Duval St. w/ Pool!
9.8 out of 10, Exceptional, (55)
"We loved our stay at Tropical Retreat in Key West. The location was perfect with walking distance to tourist spots, bars and restaurants, but far enough away to have privacy and some quiet. The house itself was perfect for 3 couples and the pool was a huge plus to relax in the mornings and afternoons. We will be back!"
TROPICAL RETREAT ~ 3 Bedroom, 3.5 Bath 1/2 Block From Duval St. w/ Pool!
CORTEZ ~ Adults Only, Poolview Suite in Azul Mansion!
9.6 out of 10, Exceptional, (95)
"Beautiful well maintained older home. Available to dine in or sit in the rooms shared space. The bedrooms and bath were lovely. Close to everything. Will return 😊"
The price is NZ$591
per night
12 Jun - 13 Jun
CORTEZ ~ Adults Only, Poolview Suite in Azul Mansion!
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC
9.0 out of 10, Wonderful, (183)
"The area was close to Duval"
The price is NZ$482
per night
7 Jun - 8 Jun
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
9.2 out of 10, Wonderful, (91)
"We enjoyed our short stay. Wish we could have stayed longer. The cottages were conventionally located. Very easy to get around. Hosts were wonderful about communicating and pool was such an added bonus. Loved our stay. ❤️"
The price is NZ$452
per night
13 May - 14 May
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
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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

Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
9.0 out of 10, Wonderful, (1523)
"Very nice property & highly recommend "
The price is NZ$373
per night
21 May - 22 May
Oceans Edge Key West Resort, Hotel & Marina
Havana Cabana at Key West - Adults Only
4.0 star property
8.8 out of 10, Excellent, (1454)
" Chris G front desk employee was amazing with nice attitude and great customer service "
The price is NZ$346
per night
10 Jun - 11 Jun
Havana Cabana at Key West - Adults Only
Margaritaville Beach House Key West
4.0 star property
8.6 out of 10, Excellent, (1748)
"Nice place to sleep , eat and relax. Walking distance to the beach. "
The price is NZ$432
per night
27 May - 28 May
Margaritaville Beach House 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.

How many holiday rentals will I find in Key West?

With 1093 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.