Nightly & Weekly 1-2 Bedrooms
49 properties available
As Neptune was known as the Roman God of the Sea, NEPTUNE'S PENTHOUSE is known as the crown jewel of the 1800 Atlantic complex overlooking the Sea. This Penthouse Condominium has a lavish wrap-around balcony that overlooks the Atlantic Ocean and Community Pool below. You'll be able to enjoy the refreshing Key West breezes from atop your own private
Neptune's Penthouse
Condo
$366.00 - $1,844.00 / per night
2
bedrooms
2
baths
6
guests
5
(254)
ANGELFISH REEF is a stylish townhome featuring a tasteful abundance of local art and flavor located within the Truman Annex, Key West's most exclusive gated community. You’ll be within walking distance of everything Key West has to offer: restaurants, shopping, attractions, and nightlife. In addition to its excellent location, ANGELFISH REEF provid
Angelfish Reef
Townhome
$339.00 - $1,162.00 / per night
2
bedrooms
2
baths
1
half-baths
6
guests
5
(5)
The sound of steel drums, the warm breeze off the water, the palm trees rustling in the sky… the essence of the Caribbean awaits in Key West for your next private vacation. This classic island townhome is located within Truman Annex, Key West's most exclusive gated community. From the Tommy Bahama furnishings and island inspired décor to the tropic
Caribbean Charm
Townhome
$350.00 - $1,238.00 / per night
2
bedrooms
2
baths
1
half-baths
6
guests
5
(66)
This freshly renovated condo is located at 1800 Atlantic Blvd on the beach, just steps from the ocean and sand in your toes. You'll be able to enjoy quiet afternoons at CONCH IN THE TREETOPS with those balmy Key West breezes wafting through the floor-to-ceiling glass doors, while sitting on your private balcony surrounded by the palm tree tops. CON
Conch in the Treetops
Condo
$220.00 - $1,240.00 / per night
2
bedrooms
2
baths
6
guests
5
(341)
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
The Cozy Starfish
Condo
$290.00 - $1,069.00 / per night
2
bedrooms
1
baths
4
guests
5
(9)
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
Duke of Catherine
Private Home
$399.00 - $1,942.00 / per night
2
bedrooms
3
baths
8
guests
5
(38)
Looking to land at the perfect vacation rental to explore Key West and the Lower Keys? Then look no further than THE LARK’S LANDING. Found on the top floor of Sunrise Suites, THE LARK’S LANDING features all new furniture and TVs, a private balcony, Two Bedroom Suites, a comfortable living room, and a full kitchen. With a location near the entrance
The Lark's Landing
Condo
$210.00 - $791.00 / per night
2
bedrooms
2
baths
6
guests
5
(36)
This Old Town condo is perfect for anyone who can't get enough of Key West's famous nightlife scene. CASITA ANGELITA is located right in Old Town, half a block away from Duval Street and smack dab in the center of the entertainment district. You couldn't be any closer to the late-night scene and attractions of downtown. Fair warning... It can get
Casita Angelita
Condo
$268.00 - $1,784.00 / per night
2
bedrooms
2
baths
6
guests
5
(238)
THE BEAMING BARRACUDA is a freshly renovated townhome located within Truman Annex, Key West's most exclusive gated community. You’ll be within walking distance to all that Key West has to offer: restaurants, shopping, attractions, and nightlife. In addition to its excellent location, THE BEAMING BARRACUDA provides an open living area and outdoor co
The Beaming Barracuda
Townhome
$366.00 - $1,229.00 / per night
2
bedrooms
2
baths
1
half-baths
6
guests
5
(42)
Don't miss an exceptional opportunity to spend your Key West stay on the grounds of an incredible estate property in the most ideal Old Town location you could imagine. DARLING OF DUVAL is a two-story guest cottage that offers many of the essentials and comforts of a luxury hotel plus the added benefits of an in-home washer & dryer, a private p
Darling of Duval
Cottage
$425.00 - $2,090.00 / per night
2
bedrooms
2
baths
4
guests
5
(273)
SUITE SANCTUARY is a luxurious penthouse condo that overlooks the ocean and is certain to be your haven from everyday life. This newly renovated condo features many delights throughout, from the vaulted ceilings to the fresh tile floors reminiscent of a walk on the beach. The large balcony offers a place to relax and enjoy the warm Florida weather
Suite Sanctuary
Condo
$329.00 - $1,685.00 / per night
2
bedrooms
2
baths
6
guests
5
(21)
If you dream of waking up to expansive water views and island breezes, and walking out your front door right onto the streets of Old Town Key West in the center of it all - PROMENADE TO PARADISE is everything you are looking for. With a spacious layout, relaxed island-style furnishings, a semi-private gated pool, and three private balconies all you
Promenade to Paradise
Condo
$450.00 - $1,606.00 / per night
2
bedrooms
2
baths
5
guests
5
(160)
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