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Key West Vacation Rentals

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Browse Select Key West Vacation Homes

4br/4.5ba - 2,402 Interior sq ft
Situated in Key West, this vacation home is within 2 mi (3 km) of Key West Golf Club, Key West Harbour, and Saddlebunch Keys. Lower Keys Medical Center and Robbie's ...
5/5Exceptional! (5 reviews)
Wonderful experience
"We will rent again"

Reviewed on Jul. 16, 2021

4br/4.5ba - 2,402 Interior sq ft
Dockside Daydreams @ Coconut Mallory Marina Villa + Last KEY Services
Situated by the sea, this historic vacation home is within 3 mi (5 km) of Key West Golf Club, Smathers Beach, and Higgs Beach. Key West Harbour is 2.4 mi (3.9 ...
4.9/5Exceptional! (26 reviews)
Lovely setting and well maintained property. Enjoyed the Bar, pools and Marina. Pools
"Very nice stay. ,Any problems that arose were handled quickly and satisfactorily. Would rent from the same Real Estate company again (pending reimbursement for broken refrigerator)."

Reviewed on Jul. 8, 2021

Dockside Daydreams @ Coconut Mallory Marina Villa + Last KEY Services
Lazy River Pool, Enchanting Garden, Old Town Key West, Free Wifi, Bikes & Parkin
Located in Key West Historic District, this historic vacation home is steps from Key West Lighthouse and Keeper's Quarters Museum, Duval Street, and Ernest Hemingway ...
5/5Exceptional! (21 reviews)
The Best of Key West!!
"My husband and I have been visiting Key West for over 20 years. Susan’s Cottage was by far the best place we’ve ever stayed. I truly hated to leave the cottage, the courtyard, the phenomenal swimming pool and most of all that sweet, little neighborhood. All the neighbors were so kind and friendly, ..."

Reviewed on Jul. 6, 2021

Lazy River Pool, Enchanting Garden, Old Town Key West, Free Wifi, Bikes & Parkin
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Casa Cove Beautiful Tropical Decorated 3 King Suites Sleeps 8 Pool 2 mi Beach
This family-friendly Key West vacation home is located near the beach, within 1 mi (2 km) of Lower Keys Medical Center and Key West Harbour. Key West Golf Club ...
5/5Exceptional! (97 reviews)
Perfect Property!
"This was a perfect property for our group of 6 (ages 6 - 43). Everyone loved it! The pool was a definite plus and never crowded. We had 2 cars & parking was no issue. The house was clean & the owner has clearly put thought into making sure you have everything you need. We easily made several meals ..."

Reviewed on Jul. 26, 2021

Casa Cove Beautiful Tropical Decorated 3 King Suites Sleeps 8 Pool 2 mi Beach
Spacious Waterfront 4 Bedroom Home With Private Heated Pool
Situated on the waterfront, this vacation home is within 3 mi (5 km) of Higgs Beach, Duval Street, and South Beach. Southernmost Point and Mallory Square are ...
4.9/5Exceptional! (16 reviews)
Good Time at Havana Daydream
"Property was clean & had plenty of towels for bath & pool.. It was nice to have 4 bedrooms with 4 complete baths. Loved that the twin beds could be converted into king beds! Fantastic view of the bay! Pool was clean & just the right size."

Reviewed on Jul. 22, 2021

Spacious Waterfront 4 Bedroom Home With Private Heated Pool
The Grand Maloney Hotel
Located in Key West Historic District, this vacation home is steps from The Oldest House - Key West and Duval Street. Mallory Square and Harry S. Truman Little ...
The Grand Maloney Hotel
Turn Lemons Into Lemonade Jan. Feb. & March. Prices Lowest Ever!
Located in Key West Historic District, this historic resort is within a 15-minute walk of Duval Street, Higgs Beach, and South Beach. Southernmost Point and ...
4.3/5Excellent! (53 reviews)
Engaged unit owner
"Super clean and the owner is quite approachable. Pleasant neighborhood. We should have asked for more towels, however."

Reviewed on Jul. 21, 2021

Turn Lemons Into Lemonade Jan. Feb. & March. Prices Lowest Ever!
Octopus's Garden @ Coral Hammock Spacious Home & Pool + Last KEY Services..
Situated by the sea, this vacation home is within 1 mi (2 km) of Lower Keys Medical Center and Key West Harbour. Key West Golf Club and Robbie's are also within ...
4.9/5Exceptional! (43 reviews)
Great stay - beautiful, clean home away
"We had a wonderful time. The house was very clean (loved the vibrant colors!) and it had everything we would need for a long stay, even beach towels, chairs, and beach toys. The bathrooms and kitchen were spotless and exactly as described. There was plenty if linen and pillows and extra sheets and ..."

Reviewed on Jul. 14, 2021

Octopus's Garden @ Coral Hammock Spacious Home & Pool + Last KEY Services..
Coral Hammock Poolside Home: 3 BR, 3 BA House in Key West, Sleeps 6
Situated in Key West, this vacation home is within 1 mi (2 km) of Lower Keys Medical Center and Key West Harbour. Key West Golf Club and Robbie's are also within ...
4.9/5Exceptional! (26 reviews)
Good and bad
"The good: the complex itself was nice, and walking out to the pool was perfect. The location is quiet and close 10-15 min away from all the attractions on Key West. The living space is functional but definitely a rental property for some time. The bad: sketchy neighborhood with run down trailers ..."

Reviewed on Jul. 26, 2021

Coral Hammock Poolside Home: 3 BR, 3 BA House in Key West, Sleeps 6
@@ Steps From Duval 1 Bedroom Townhouse in Great Complex Hidden Secret @@
Located in Key West Historic District, this vacation home is within a 5-minute walk of Duval Street and Ernest Hemingway Home and Museum. South Beach and Southernmost ...
4.6/5Exceptional! (28 reviews)
Nice Place, Great Location
"Property was exactly as advertised - relatively modest accommodations, pleasant courtyard, great location half a block from Duval. Check in was effortless, just had to remember a couple codes. The condo itself was unremarkable, but clean and and comfortable and everything worked fine. Property Management ..."

Reviewed on Jul. 21, 2021

@@ Steps From Duval 1 Bedroom Townhouse in Great Complex Hidden Secret @@
Recently Renovated Home w/ Shared Pool, Furnished Patio Area - in Town, Dogs ok
The price is CA $188 per night from Aug 18 to Aug 18
Located in Key West Historic District, this vacation home is within a 5-minute walk of Duval Street and Ernest Hemingway Home and Museum. South Beach and Key ...
4.3/5Excellent! (7 reviews)
Great Location!
"We picked this place because of the location and it had a designated parking place which was important since we drove in from Miami. . Probably best to have only 2 people, as the sofa was not very comfortable for sleeping. The bedroom and bath were very small. Would have given all 5 stars, but the ..."

Reviewed on Mar. 4, 2021

Recently Renovated Home w/ Shared Pool, Furnished Patio Area - in Town, Dogs ok
Key Haven Estates' "papa's Adobe"; 4br/4.5ba - 2,402 Interior sq ft
Situated in Key West, this vacation home is within 2 mi (3 km) of Key West Golf Club, Key West Harbour, and Saddlebunch Keys. Lower Keys Medical Center and Robbie's ...
5/5Exceptional! (5 reviews)
Wonderful time!
"The layout of this home worked perfect for our group of 10. We enjoyed the view and pool. Our sandbar charter was able to pick us up from the house which saved us a ton of time! Cute, clean neighborhood. Would stay here again!"

Reviewed on Jul. 21, 2021

Key Haven Estates' "papa's Adobe"; 4br/4.5ba - 2,402 Interior sq ft
Waterfront Home on Florida Bay With Private Heated Pool in Key Cove Landings
Situated on the waterfront, this vacation home is within 3 mi (5 km) of Higgs Beach, Duval Street, and South Beach. Southernmost Point and Mallory Square are ...
4.3/5Excellent! (9 reviews)
Great July stay in Key West
"The property is perfect location if you want to be a short car/uber ride to Duval area. Easy drive to everywhere on the island. A nice bonus is you can walk to Publix, pizza, and a few other restaurants. Views from 3rd floor are great! A great place to stay!"

Reviewed on Jul. 28, 2021

Waterfront Home on Florida Bay With Private Heated Pool in Key Cove Landings
Waterfront 4 Bedroom 4 Bath Home
Situated in Key West, this vacation home is within 3 mi (5 km) of Higgs Beach, Duval Street, and South Beach. Southernmost Point and Mallory Square are also ...
5/5Exceptional! (3 reviews)
Beautiful
"Amazing experience with amazing property- astounding views from gorgeous home with easy access to all things Key West."

Reviewed on Jul. 6, 2021

Waterfront 4 Bedroom 4 Bath Home
Prices Have Never Been Lower!
Located in Key West Historic District, this vacation home is within a 15-minute walk of Duval Street, Higgs Beach, and South Beach. Southernmost Point and Key ...
4.7/5Exceptional! (67 reviews)
Great place
"Highly recommend, small but it was beautiful and super clean. Everything we needed in paradise."

Reviewed on Jul. 29, 2021

Prices Have Never Been Lower!
Casa Calypso- Beautiful Tropical Style House 3 King Beds Pool 2 mi to Beach
This family-friendly Key West vacation home is located by the sea, within 1 mi (2 km) of Lower Keys Medical Center and Key West Harbour. Key West Golf Club and ...
4.9/5Exceptional! (89 reviews)
Family
"We enjoyed our stay."

Reviewed on Jul. 26, 2021

Casa Calypso- Beautiful Tropical Style House 3 King Beds Pool 2 mi to Beach
Luxury Waterfront Home With Private Heated Pool and Lush Landscaping!
Situated on the waterfront, this vacation home is within 3 mi (5 km) of Higgs Beach, Duval Street, and South Beach. Southernmost Point and Mallory Square are ...
4.9/5Exceptional! (16 reviews)
Nice stay
"Property was centrally located. House was clean and roomy. Very disappointed in the pool. It was very dirty and we had to call 3 times to get it cleaned so unfortunately we were not able to enjoy it and that was on of the reason for booking this house."

Reviewed on Aug. 2, 2021

Luxury Waterfront Home With Private Heated Pool and Lush Landscaping!
Modern Newly Renovated "reborn" Home With Private Deck & hot Tub!
Located in Key West Historic District, this vacation home is within a 10-minute walk of Duval Street and Ernest Hemingway Home and Museum. South Beach and Southernmost ...
5/5Exceptional! (2 reviews)
Butterfly Cottage, Key West
"This house was worth every penny we paid for it. The house is clean, new rehab, lovely deck to relax on. We did not use the hot tub but I can imagine that in colder weather it would be great to have. And great location-walking distance to Duval and other areas of Key West. The rental agency followed ..."

Reviewed on Jul. 26, 2021

Modern Newly Renovated "reborn" Home With Private Deck & hot Tub!
Extra Large Conch Style Home in Oldtown With Privavte Pool AND Dock!
Located in Meadows, this vacation home is within 1 mi (2 km) of Nancy Forrester's Secret Garden, Duval Street, and Ernest Hemingway Home and Museum. South Beach ...
4.8/5Exceptional! (41 reviews)
Great place for our first stay in Key West.
"The property was just as described and rooms were larger than they appeared in photographs. It was clean, stocked well (towels,T.P. laundry soap), and check in/out was very easy. My only suggestion for improvement would be to upgrade bed linens."

Reviewed on Jul. 23, 2021

Extra Large Conch Style Home in Oldtown With Privavte Pool AND Dock!
Key Haven Estates' "modern Keys"; 4br/4.5ba - 2,331 Interior sq ft
Situated in Key West, this vacation home is 1.2 mi (2 km) from Lower Keys Medical Center and 1.8 mi (2.9 km) from Key West Harbour. Key West Golf Club and Robbie's ...
4.8/5Exceptional! (5 reviews)
Talk about AMAZING
"This property was beyond amazing! It was a great location that was no more than 15mins from anywhere we visited on the island. The house was simply beautiful and clean. There was 8 ladies and having extra bathrooms was perfect for us! We will definitely be back next year. This house is 100% recommended ..."

Reviewed on Jul. 7, 2021

Key Haven Estates' "modern Keys"; 4br/4.5ba - 2,331 Interior sq ft
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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 property types in Key West

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue, Key West, FL
The price is CA $280 per night from Sep 2 to Sep 2
4.5/5Wonderful! (2,600 reviews)
"GREAT AND NEAR OUR BOAT"

Reviewed on Aug. 3, 2021

Oceans Edge Key West Resort, Hotel & Marina
The Gates Hotel Key West

The Gates Hotel Key West

4 out of 5
3824 N Roosevelt Blvd, Key West, FL
The price is CA $255 per night from Aug 29 to Aug 29
4/5Very Good! (1,076 reviews)
"I visit key west frequently cause i do not live far, this was my first stay here and it was great!"

Reviewed on Aug. 4, 2021

The Gates Hotel Key West
Barbary Beach House Key West

Barbary Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
The price is CA $372 per night from Sep 1 to Sep 1
4.5/5Wonderful! (654 reviews)
"Everything clean, staff friendly, close to airport, beach is a minute away. Very good place to stay."

Reviewed on Aug. 3, 2021

Barbary 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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