Key West Vacation Rentals

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Vacation Rentals in 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 CA $295
CA $501 total
includes taxes & fees
May 14 - May 15
Poolside Cottage #411
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!
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
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Property grounds
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
Pool
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
10.0 out of 10, Exceptional, (72)
"This home was wonderful! House had all we needed and was very comfortable. Fully gated yard which was perfect for our dog. It was in such a quiet and peaceful part of town that we sat on the deck and enjoyed the small pool every day. We walked into town each day and we explored all of Old Town from the North end (great marina, restaurants and view) to the South end (great views, restaurants and shopping). Would absolutely recommend this home and would we definitely would rent here next time!"
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
Outdoor dining
Two Bed One Bath Ground Floor End Unit in the Heart of Old Town
10.0 out of 10, Exceptional, (125)
"We had a lovely time"
Two Bed One Bath Ground Floor End Unit in the Heart of Old Town
Pool
Bahama Village studio @ the Galleria!
10.0 out of 10, Exceptional, (5)
"It was very clean and nice. The air conditioning worked great. Located close to Duval. The only issue we had was that there was no closet or place to put clothes so after a few days it was hard to keep organized."
The price is CA $243
CA $511 total
includes taxes & fees
May 15 - May 16
Bahama Village studio @ the Galleria!
Outdoor pool, a heated pool
Luxury 62' Yacht! In a Beautiful Resort
10.0 out of 10, Exceptional, (6)
"Everything was great and we would love to visit again!"
Luxury 62' Yacht! In a Beautiful Resort
Pool
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 CA $1,024
CA $2,164 total
includes taxes & fees
May 19 - May 20
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
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
Property grounds
TROPICAL RETREAT ~ 3 Bedroom, 3.5 Bath 1/2 Block From Duval St. w/ Pool!
9.8 out of 10, Exceptional, (56)
"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!
Pool
**SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..
9.8 out of 10, Exceptional, (133)
"Incredible property on the water. The Last Key Realty team is amazing."
**SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..
Outdoor dining
KATE'S KRAWL OFF DUVAL ~ 1 BR, 1 Ba Home w/ Outdoor Area Steps to Duval!
9.8 out of 10, Exceptional, (59)
"If you like being right downtown in the middle of shops, restaurants and entertainment this place is for you. We parked our car upon arrival and never used it until check out. This is the perfect house for two or maybe three people. We really had a great time."
KATE'S KRAWL OFF DUVAL ~ 1 BR, 1 Ba Home w/ Outdoor Area Steps to Duval!
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
Beach nearby
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
9.8 out of 10, Exceptional, (100)
"Beautiful property in a great location. I would definitely stay again."
The price is CA $165
CA $379 total
includes taxes & fees
May 20 - May 21
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, (330)
"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 CA $135
CA $328 total
includes taxes & fees
May 20 - May 21
Steps from Duval, Pool & Bikes $129-$299 Night!
Fridge, microwave, oven, stovetop
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated pool, and close to Duval!
9.6 out of 10, Exceptional, (182)
"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!
Beach nearby
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 CA $230
CA $463 total
includes taxes & fees
May 28 - May 29
CORTEZ ~ Adults Only, Poolview Suite in Azul Mansion!
Beach nearby
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
9.6 out of 10, Exceptional, (156)
"Couldn’t have asked for a better stay!! Comfy bed, quiet, great AC! Loved it all."
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
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
Don't see what you're looking for?
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

View from property
Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
9.0 out of 10, Wonderful, (1523)
"Liked watching the Navy Fighters flying overhead. Disliked people smoking on balconies."
The price is CA $273
CA $387 total
includes taxes & fees
May 21 - May 22
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)
" Chris G front desk employee was amazing with nice attitude and great customer service "
The price is CA $250
CA $369 total
includes taxes & fees
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, (1751)
"Rooms are great and the outside bar was nice"
The price is CA $313
CA $439 total
includes taxes & fees
May 27 - May 28
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 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?

Poolside Cottage #411: This Key West vacation home rental offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a selection of games and a spa tub. Some other homes for rent in Key West include Duval Square in Key West and Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!.

How many vacation rentals will I find in Key West?

With 1093 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.