Key West Vacation Rentals

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Vacation Rentals in 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 ￥15,409
per night
May 20 - May 21
Steps from Duval, Pool & Bikes $129-$299 Night!
Outdoor pool
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 ￥46,088
per night
Jun 1 - Jun 2
Hyatt Vacation Club at Sunset Harbor, Key West
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 ￥33,620
per night
Jun 4 - Jun 5
Poolside Cottage #411
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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, (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 ￥46,539
per night
Jun 3 - Jun 4
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
Outdoor dining
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
Restaurant
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 ￥32,531
per night
May 27 - May 28
Aqua Lodges at Hurricane Hole Marina
Property grounds
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!
Pool
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
9.8 out of 10, Exceptional, (190)
"The house location was absolutely amazing. Everything was top notch. I would recommend this house over and over again, the back yard is so tranquil and the layouts of the room worked out well for bigger parties."
The price is ￥108,799
per night
May 22 - May 23
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Fridge, cookware/dishes/utensils, dining tables
34’ Catamaran Sailboat
9.4 out of 10, Exceptional, (24)
"Friendly, easy access and close to desired destination "
34’ Catamaran Sailboat
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 ￥18,834
per night
May 22 - May 23
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
A heated pool
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
Fridge, microwave, oven, stovetop
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
9.6 out of 10, Exceptional, (184)
"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 | 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, (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
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 ￥22,569
per night
May 20 - May 21
The Cozy Little Cottage!
Fridge, microwave, coffee/tea maker, dining tables
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
9.2 out of 10, Wonderful, (91)
"We absolutely loved this VRBO. We walked everywhere we wanted to go and it was conveniently located. If we come back to Key West we will try and stay here again. Only downfall--bathroom size. We were never in our room anyway so it was not a big issue"
The price is ￥18,211
per night
May 20 - May 21
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
Fridge, microwave, oven, stovetop
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
9.4 out of 10, Exceptional, (199)
"Close to everything but just far enough away to be quiet and relaxing. Cute little house. Very walkable location."
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
A heated pool
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
9.8 out of 10, Exceptional, (103)
"Excellent top drawer"
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
Property grounds
TROPICAL RETREAT ~ 3 Bedroom, 3.5 Bath 1/2 Block From Duval St. w/ Pool!
9.8 out of 10, Exceptional, (57)
"We had a very positive stay at Tropical Retreat. The property is in a great location and was very comfortable. It was as presented on the website and the property managers were great to work with."
TROPICAL RETREAT ~ 3 Bedroom, 3.5 Bath 1/2 Block From Duval St. w/ Pool!
Property grounds
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!
9.2 out of 10, Wonderful, (172)
"The location is perfect, and the townhouse was very clean. It does need a coat of paint on the outside though. There are also two supplemental indoor a/c units in the bedrooms upstairs, and the one in the master bedroom is quite loud. Side from that it was a great place to stay and the owner was extremely helpful."
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!
Pool
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
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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

View from property
Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
9.0 out of 10, Wonderful, (1517)
"The shuttle to downtown was great. Ice mace in building 4 was broken."
The price is ￥30,876
per night
May 27 - May 28
Oceans Edge Key West Resort, Hotel & Marina
Outdoor pool, sun loungers
Havana Cabana at Key West - Adults Only
4.0 star property
8.8 out of 10, Excellent, (1456)
"the hotel is amazing and we were so don't care that it is far away from historical part because you have fast and convenient shuttle bus! Food was amazing, nice rooms, lobby is so beautiful. But!! So many caterpillars around the property I've never seen! Around the pool , in and outside the pool bathroom, on the patio. Bbbbrrrr this is not for everyone. I do understand that they will become butterflies but how you can move them away from guest area?"
The price is ￥28,515
per night
Jun 10 - Jun 11
Havana Cabana at Key West - Adults Only
Beach nearby, white sand
Margaritaville Beach House Key West
4.0 star property
8.6 out of 10, Excellent, (1748)
"."
The price is ￥38,290
per night
Jun 2 - Jun 3
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.

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Frequently asked questions

Can I find vacation rentals in Key West?

Yes, there are vacation rentals in Key West close to Mel Fisher Maritime Museum, or you can select a more secluded option if you want a relaxing stay. Travelers 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 vacation rentals in Key West?

Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!: This Key West vacation home rental is equipped with a spa 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 Poolside Cottage #411 and Duval Square in Key West.

How many vacation rentals will I find in Key West?

With 1079 Expedia vacation rentals, you're sure 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 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 vacation rentals like in Key West?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Key West. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for family gatherings.

Recent reviews of Key West properties
Expedia verified reviews

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

5/5 Excellent
"This was a beautiful property. The rooms and public areas were clean and charming, the breakfast was very good with a nice variety of options. Every member of the staff we encountered was very friendjy and helpful. The location was great for walking to shops and restaurants. "
A verified traveler stayed at Winslow's Bungalows - Key West Historic Inns
Posted 2 days ago
Winslow's Bungalows - Key West Historic Inns