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Properties Available 47 properties available
COLORS OF THE KEYS is a bright and vibrant townhome that embodies Key West’s colorful & tropical spirit. Located within Truman Annex, Key West's most exclusive gated community, this home is within walking distance of all that Key West has to offer: restaurants, shopping, attractions, and nightlife. In addition to a prime location, COLORS OF THE
Hot HOT 25
Colors of the Keys
Townhome
$350.00 - $1,278.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating 5 (62)
SERENITY ON SOUTHARD is a beautifully renovated 1 bedroom second floor condo with a full kitchen and washer and dryer. This condo is located in the Truman Annex, a gated community located in the heart of the island - just steps from Mallory Square, Duval Street and all the attractions Key West has to offer. Yet, you'll have a peaceful retreat withi
Serenity on Southard
Condo
$200.00 - $982.00 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 2 guests
Rating 5 (46)
SHANG-RI-LA is a term for a utopia designed for life-long learning, happiness and fulfillment. There is no better place to find your happiness and fulfillment than a waterfront oasis on a little island at the farthest Southern tip of the US. This water view condo has been meticulously furnished with a modern coastal feel, with a front row seat to y
Hot HOT 59
Shang-Ri-La
Condo
$220.00 - $1,403.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (325)
SEA CAPTAIN'S HAVEN is an immaculately furnished villa at the Porter Court Complex in Truman Annex, Key West's most desirable gated community, right in the middle of Old Town. At SEA CAPTAIN'S HAVEN, you'll be close to all of Key West's best restaurants and attractions, including Mallory Square and Fort Zachary Taylor State Park.THE LIVING AREA...S
Sea Captain's Haven
Townhome
$315.00 - $1,264.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating 5 (115)
What could be better than spending your tropical vacation in a newly built waterfront home that offers spectacular views and easy access to the beautiful waters of the Florida Keys. POSTCARD POINT is an elevated 2 bedroom home that allows you to enjoy the luxury of brand-new construction in the waterfront location you've been searching for. Picture
Postcard Point
Private Home
$244.00 - $977.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (48)
Formerly La Bonne Vie, SMOOTH SAILING has been meticulously furnished with a modern coastal feel, and the only beauty that competes with the interior is the spectacular views from your private oceanfront balcony. You'll be able to enjoy quiet afternoons with those balmy Key West breezes wafting through the floor-to-ceiling glass doors from the livi
Smooth Sailing
Condo
$233.00 - $1,588.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (238)
WALKING ON SUNSHINE is a modern, tastefully decorated penthouse condo featuring a large wrap-around balcony that offers a front row seat to those famous Key West sunsets and overlooks the peaceful nature preserve and Atlantic Ocean beyond. Best of all, WALKING ON SUNSHINE is located in an upscale private community within walking or biking distance
Walking on Sunshine
Condo
$315.00 - $1,626.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (175)
Located across the street from Blue Heaven, above the delicious La Creperie French Cafe, sits THE PIRATE’S PENTHOUSE. This hidden gem is ideally located in the heart of Bahama Village and within walking distance to everything Duval has to offer. THE PIRATE’S PENTHOUSE has touches of maritime decor sprinkled throughout this spacious condo, complet
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The Pirate's Penthouse
Condo
$333.00 - $1,722.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (49)
A stay at the DUKE OF CATHERINE is fit for a Queen to bring her King! From the crisp, clean decor to the large hot tub and the spacious master bedroom, the DUKE OF CATHERINE has everything his Majesty could desire. This freshly built, professionally designed home is the perfect size for a weekend rendezvous or an extended stay with the royal family
Hot HOT 30
Duke of Catherine
Private Home Pet Friendly
$375.00 - $1,779.00 / per night
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (42)
THE COZY STARFISH is a newly furnished and decorated first floor condo located in the Truman Annex, a private gated community situated in the heart of the island. Despite being only steps away from all that Old Town Key West has to offer, THE COZY STARFISH is a peaceful retreat within a private gated community that offers access to a large, shared
Hot HOT 28
The Cozy Starfish
Condo
$290.00 - $1,026.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (9)
There’s no doubt you’ve heard of Duval Street; phenomenal restaurants, eclectic shops and legendary nightlife. This immaculate condo is just a half block away, giving you access to everything Duval Street has to offer while still allowing you to get a restful night’s sleep. SOUL OF DUVAL truly captures the essence of what makes Key West so special,
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Soul of Duval
Condo
$240.00 - $1,173.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (94)
This colorful two story Old Town cottage is just right for a delightful stay in the Conch Republic. VILLA CUBANA is located right in Old Town, one block away from Duval Street and smack dab in the center of the fun. You couldn't be any closer to the nightlife and attractions of downtown, yet you are tucked away in a quiet gated community you would
Villa Cubana
Townhome
$300.00 - $1,393.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (194)

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