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 ￥33,385
￥57,091 total
includes taxes & fees
May 28 - May 29
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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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
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, (126)
"Really enjoyed staying at this location near Fort Zachary Taylor beach and Duval Street. The place was quiet and simple and served our needs well!"
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."
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, (189)
"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 ￥115,765
￥244,688 total
includes taxes & fees
May 19 - May 20
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
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
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!
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 ￥18,702
￥43,201 total
includes taxes & fees
May 19 - May 20
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)
"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 ￥15,301
￥37,037 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 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!
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 ￥24,730
￥50,755 total
includes taxes & fees
May 29 - May 30
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, (157)
"In the center of 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, (1517)
"We liked that the property overlooked a harbour . It was lovely and quiet. We appreciated other guests had thought this location was better than being downtown Key West, due to the late night noise etc. The resort was a 12 minute Uber ride to Duval street. The 6 swimming pools ensured that they were not overcrowded and had plenty of lounge chairs. The resort had a great layout and the rooms were quite spacious with a simple classic beach vibe. The food on property was excellent. The staff...
The price is ￥33,204
￥46,422 total
includes taxes & fees
Jun 6 - Jun 7
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, (1454)
"Always a good place to stay. The accommodation worked well for our family. "
The price is ￥28,315
￥41,736 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, (1748)
"Hotel was great venue."
The price is ￥40,649
￥55,576 total
includes taxes & fees
Jun 4 - Jun 5
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?

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.

Recent reviews of Key West properties
Expedia verified reviews

NYAH Key West - Adults Only

NYAH Key West - Adults Only

5/5 Excellent
"I was on a motorcycle ride with 3 friends and this was a perfect place to spend the night after a long ride. Breakfast was good and the pool was wonderful. "
A verified traveler from Columbia stayed at NYAH Key West - Adults Only
Posted 4 hours ago
NYAH Key West - Adults Only