Key West Vacation Rentals
18 matching rentals.Most Popular
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Key West
World-class comfort, lush tropical surroundings and unmatched privacy characterize this deluxe, spacious, two story historic home located across from the famous Key West Cemetery in Key West's finest neighborhood. Exclu...
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per night
3 beds
2 baths
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Key West
These Luxury Oceanfront Villas are among the absolute finest properties available anywhere in the Florida Keys, yet are moderately priced. Convenient location just 5 minutes from all activities by car or taxi.
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per night
3 beds
2 baths
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Key West
Just 3 short blocks from the main guest house, the Amelia House is a recently renovated, painted and decorated 3 bedroom, 2 bath private house located at 505 Amelia Street, (3 houses from world-famous, quiet upper-end D...
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per night
3 beds
2 baths
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Listings
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Key West
Conch Republic Cottage - If you are looking for the spaciousness of a hotel suite, but still want that funky Key West style, the Conch Republic Cottage is just for you. This economical suite guesthouse is centrally loca...
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3 beds
3 baths
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Key West
Just 3 short blocks from the main guest house, the Amelia House is a recently renovated, painted and decorated 3 bedroom, 2 bath private house located at 505 Amelia Street, (3 houses from world-famous, quiet upper-end D...
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per night
3 beds
2 baths
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Key West
Located in Duval Square (between Duval Street and Simonton Street) where fine and varied dining abounds (Square One, Origami Sushi Restaurant and New York Garden Cafe), Casa Key West is a second story, well priced unit ...
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per night
3 beds
2 baths
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Key West
Beautiful Spacious Condo Overlooking The Key West Harbor Waterfront!
Book Online! http://www.anislandoasis.com/condorental.html [1] - This exclusive condo is a part of Harbour Place, a waterfront community within the T...
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per night
3 beds
2 baths
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Key West
You will certainly enjoy this wonderful historic home with recent renovations, perfectly placed pool, separate cottage and plenty of outdoor living space located at 1116 Curry Lane. This home is situated in the heart of...
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per night
3 beds
3 baths
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Key West
You will certainly enjoy this wonderful artist's home with recent renovations, perfectly placed pool, and plenty of outdoor living space located at 325 Catherine Street. This home is situated in the heart of Old Town, j...
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per night
3 beds
2 baths
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Key West
Enjoy a fabulous stay at our beautiful vacation house with your dear ones. This three bedroom retreat is spacious enough to lodge eight guests. The bedrooms include king-size bed, queen-size bed, twin bed and sofa sleep...
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3 beds
2 baths
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Key West
Tropical Retreat, at 519 Catherine Street, is on a quiet lane half a block off the upscale Upper end of Duval St. where there are many sophisticated restaurants, high-end art galleries and shops. Downtown Duval St. is w...
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3 beds
3.5 baths
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Key West
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per night
3 beds
2 baths
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Key West
These Luxury Oceanfront Villas are among the absolute finest properties available anywhere in the Florida Keys, yet are moderately priced. Convenient location just 5 minutes from all activities by car or taxi.
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per night
3 beds
2 baths
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Key West
1, 2, 3, 4, 5, 6 & 7 BR Luxury Villas in Historic Old Town Key West with Heated Pool, Full Kitchens, Parking and adjacent to the best beach in Key West. Quiet and peaceful, yet just 3 blocks from Duval Street and the Su...
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per night
3 beds
2 baths
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Key West
Location! Location! Location! Emma House with Pvt Pool is located in Truman Annex Community which is one of the Best locations in Key West. You can walk to everything! It doesn't get any better than this! Emma House ren...
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3 beds
3.5 baths
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Key West
Newly decorated 3 Bedroom home, 2 bathrooms, screened in porch with Ocean View & table that seats 10 people. Property has 65 ft. sea wall on 10 ft. deep canal, where renters can dock up to a 40 ft. boat; swimming ladder...
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per night
3 beds
2 baths
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Key West
Professionally decorated in a Coastal Living style, this elegant yet very comfortable custom built 3 bedroom, 2.5 bath, 3 story home has a living room (Q sleeper sofa) with rose hardwood floors, a gourmet kitchen with g...
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per night
3 beds
2.5 baths
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Key West
World-class comfort, lush tropical surroundings and unmatched privacy characterize this deluxe, spacious, two story historic home located across from the famous Key West Cemetery in Key West's finest neighborhood. Exclu...
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per night
3 beds
2 baths
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Key West
Located directly behind the world famous Hemingway House grounds, just 2 houses off celebrated Duval Street on quiet, intimate Whalton Lane is this charming private home. One block from Center Court grounds, Hemingway's...
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per night
3 beds
2 baths
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Key West
3 BR, 2 BA Private Home shares the pool with the 2 BR, 2 BA Hangover Cottage (rents separately). Located just 4 blocks off Duval Street and close to Mallory Square and Fort Zachary Taylor Beach.
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per night
3 beds
2 baths
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Key West
Deluxe 3 BR, 3 BA Harborfront Penthouse with Beach, Pool, Bar and Marinacan alsobe rented separately as a 2 BR, 2 BA or a 1 BR, 1 BA. The most perfectly located unit in Old Town just 2 blocks off Duval Street and 3 bloc...
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per night
3 beds
3 baths
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Blog Posts
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April 16, 2013
For a sweet break, step out of the Florida heat and into the coolness of one of the Blond Giraffe’s pie shops. The first location opened in 1999 and, that same year, won first place in the Key West Ke...
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March 18, 2013
Key West is definitely the party town of the Florida Keys. There is plenty of shopping in the narrow streets that remind you of an old but busy village. Have fun in the ocan with snorkeling, scuba div...
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January 30, 2013
There’s one main road between Key Largo and Key West, Overseas Highway, and if you point your car toward west, you’ll run into Betsy the 40-foot-tall, 30-foot-wide lobster sculpture just outside the R...
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January 29, 2013
A little over a week ago I was in the Florida Keys where it was warm and sunny. My husband and I had a great vacation. Here are a few of the highlights. We ate breakfast at Blue Heaven. The omelets we...
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January 22, 2013
In 1979 I went camping with some girlfriends in the Florida Keys. None of us had ever been camping before and we didn’t even know how to put up a tent. Fortunately, we camped next to a group of guys f...
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January 19, 2013
I am joining up with the Alisa and her traveling backpack…this weeks Travel Theme is UP! We will be looking UP at the Key West Lighthouse from outside and also from within…...
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January 10, 2013
We made it to Key West. A tropical paradise or party. Or both. I've never been on a Caribbean Cruise or really anywhere tropical, and Key West really gave me first taste of the tropics, or at least t...
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November 01, 2012
After an early morning walkie with both mom and dad, then breakfast, we went to the Key West Aquarium, which is dog-friendly. We saw LOTS of fishies! Okay, how many large inanimate fish
do I have to...
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October 22, 2012
One of the things that Lori and I were really looking forward to during our time in Florida, was the drive to Key West through the Florida Keys. Island hopping through the Gulf of Mexico along a chain...
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October 22, 2012
The water was fresh and cool and she was VERY nice to me!!! We think Key West people are the nicest people around! That night we had dinner at the Island Dogs Bar. We had a very nice waiter who brou...
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