30 DAY MINIMUM. Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully...
$2,610 - $4,000 / mth
Condo, 1 Bedroom, 1 Bath, Sleeps 2
Platinum
Key West Vacation Rentals in Florida
64 properties found
Nearby rentals: Lower Keys (8 miles), Cudjoe Key (21 miles), Summerland Key (24 miles), Big Torch Key (26 miles), Ramrod Key (26 miles)
This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries,...
$290 - $370 / nt
$1,890 - $3,220 / wk
Home, 2 Bedrooms, 2 Baths, Sleeps 4
Platinum
Duval Square - The Retreat. In the heart of Old Town, Duval Square is located at the "artistic" and quieter end...
$250 - $310 / nt
$1,680 - $2,870 / wk
Condo, 2 Bedrooms, 2 Baths, Sleeps 4
Platinum
Fantastic location combined with casual elegance makes this Key West cottage a great retreat to experience! And...
$450 - $590 / nt
$2,940 - $5,390 / wk
Home, 3 Bedrooms, 3 Baths, Sleeps 6
Platinum
30 DAY MINIMUM. An amazing renovation of mid town historic home with the Washington Street address many desire....
$4,000 - $7,000 / mth
Home, 1 Bedroom, 1.5 Baths, Sleeps 2
Platinum
Enjoy the resort- style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst...
$210 - $290 / nt
$1,400 - $2,660 / wk
Condo, 2 Bedrooms, 2 Baths, Sleeps 4
Platinum
Tucked behind a privacy gate, this garden setting L- shaped home is a perfect escape in the heart of Old Town....
$450 - $590 / nt
$2,940 - $5,100 / wk
This bright and sunny pool home is situated on a quiet street in the Casa Marina district of Key West. Guests can...
$3,200 - $6,500 / mth
Home, 2 Bedrooms, 2 Baths, Sleeps 4
Platinum
Welcome to unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool...
$270 - $400 / nt
$1,820 - $3,360 / wk
Condo, 2 Bedrooms, 2 Baths, Sleeps 4
Platinum
Welcome to the Beach!!!! No this house isn't oceanfront! But in Key West almost anything is possible. This house...
$470 - $660 / nt
$3,150 - $5,600 / wk
Unforgettable! Luxurious! Comfortable! Located at Atlantic Ocean along with breathtaking views, high end furnishings...
Condo, 2 Bedrooms, 2 Baths, Sleeps 4
Platinum
Palm Isle - a room ahead of its time - A truly "green unit". Your room mate or in this case "suite mate" is a...
$168 - $248 / nt
$1,176 - $1,736 / wk
ISLAND OASIS: Take a lot of history and a lot of charm - mix it with a great location and you have the perfect...
$368 - $468 / nt
$2,576 - $3,276 / wk
Cottage, 3 Bedrooms, 2 Baths, Sleeps 6
Premier+
Beautiful landscaped property & contemporary house will offer you a serene- tropical perfect for complete relaxation...
Condo, 2 Bedrooms, 2.5 Baths, Sleeps 5
Premier+
LITTLE PALM - What an idyllic setting! Picture a new cottage with all the must have's for a great Key West vacation...
$198 - $268 / nt
$1,386 - $1,876 / wk
Cottage, Studio, 1 Bath, Sleeps 2
Premier+
The Beach Boys on one of their many trips to the Florida Keys (they are Mojito buds with Jimmy Buffett) stayed...
$368 - $408 / nt
$2,576 - $2,856 / wk
This downtown Key West vacation rental is one block off Duval Street, just around the corner from Sloppy Joe's...
$348 - $448 / nt
$2,436 - $3,136 / wk
This is a non- smoking condo/hotel(you may smoke on the balconey), that "home away from home" comfortable appeal,...
$159 - $169 / nt
Hollinsed guests house is located in the heart of Old Town, is beautiful Key West Victorian home along with Key...
Condo, 2 Bedrooms, 2 Baths, Sleeps 6
Premier+
This Historic Register property enjoys a superior location in the Heart of Old Town - an easy 4 block walk from...
Home, 3 Bedrooms, 2 Baths, Sleeps 6
Premier+
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