Key West Vacation Rentals
101 rentals with 459 photos.Most Popular
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Key West
4 bedroom, 2 baths ocean front home with a dock and an in-ground heated pool. Central air, all kitchen and bath amenities, to include washer and dryer. Located only 15 miles from Key West and all attractions.
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per night
4 beds
2 baths
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Key West
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per night
1 bed
1 bath
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Truman Annex
Truman Annex is located in the heart of Key West's Old Town. Walking or biking distance from all the shops, restaurants, bars & attractions, you don't even need a car. Fly in and take a taxi from the Key West airport or...
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per night
2 beds
2 baths
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Listings
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Key West
Our best Key West vacation ever is just a phone call away! My charming Key West Vacation rental is a houseboat named Ramrod. It is permanently docked at the modern and immaculately maintained Sunset Marina - the perfect...
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per night
2 beds
2 baths
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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
Island Wind welcomes you to a tropical sun drenched oasis in the heart of Old Town. This charming Bahamian style townhome with tin roof and white spindled decks reminiscent of old Key West is located a block off Duval S...
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per night
2 beds
2 baths
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Galleon
This condo is the only one like it at the Galleon Resort. This unit is located on the 6th floor and has 1245 SF of living area, including a huge bedroom with a king bed and windows for viewing ships docked at Mallory Sq...
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per night
1 bed
1 bath
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Galleon
We own a timeshare in Key West and will not be going down there for our week this year. The week is Aug 30-Sept 6 (Labor Day week), at the Galleon Resort, very short walking distance to Duval Street. http://www.galleonr...
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per night
2 beds
2 baths
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Key West
1 BR, 1 BA Private Cottage in thefront of a small compound of cottages that share a Pool and Jacuzzi. Separate from the other units with it's own Covered Front Porch for People Watching! Located just 1/2 block off Duval...
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per night
1 bed
1 bath
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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
The Heron is one of several of the Colony Suites in historic Key West, Florida. A conch style cottage nestled in the heart of Historic Old Town Key West, just two blocks from the world famous Duval Street with its incre...
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per night
1 bed
1 bath
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Key West
Beautifully remodeled, 1374 sq. ft,2 bedroom (King Beds) 2 Bathroom condo- Beautifully landscaped & Located On The Ocean-Sleeps 6. (Right Next To Smathers Beach!) Visit: http://www.coconutpalmsofkeywest.com/ To view rat...
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per night
2 beds
2 baths
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Key West
Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One and Origami Sushi Bar), Casa Maria is a second story paradise just steps from the sights, sounds, and excitement ...
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per night
2 beds
2.5 baths
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Duval Square
Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One, Origami Sushi Bar and NY Pasta Garden), Duval Square Penthouse is a second story paradise just steps from the si...
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per night
2 beds
2.5 baths
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Key West
Steps from Duval Street, on a quiet hidden lane two blocks long, The Family House is hidden in a tropical oasis, a gated compound. The view from the front door is a fish/lily pod with the relaxing sounds of a waterfall....
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per night
2 beds
1.5 baths
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Key West
Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One, Origami Sushi Bar and NY Pasta Garden), Havana Hideaway is a second story paradise just steps from the sights, s...
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per night
2 beds
2.5 baths
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Key West
Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One and Origami Sushi Bar), Casa de Mango is a second story paradise just steps from the sights, sounds and excitemen...
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per night
2 beds
2.5 baths
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Key West
415 Truman Avenue is the perfect location, located between Duval Street and Whitehead St. Just around the corner from Hemingway's House and the Historic Lighthouse Museum, Almost Southernmost is a perfect example of sho...
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per night
2 beds
1 bath
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Key West
The Webster Dictionary dates windward back to 1549; defined as, the side or direction from which the wind is blowing. Our Windward Isle is to landlubbers what windward gusts are to sea captains: a means to easy travel a...
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per night
2 beds
1 bath
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Key West
Conch Casa is a cigar maker's cottage circa 1884 that sits in a historic residential neighborhood half a block from Duval Street. This romantic hideaway is the quintessential conch cottage - both removed and integrated ...
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per night
2 beds
1 bath
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Key West
Less than one block from Duval Street, this delightful, spacious two Queen bedroom suite welcomes you with amenities usually not found at this price point! Bahama Breeze features all the amenities of home, and then some...
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per night
2 beds
1 bath
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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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