Key West Vacation Rentals

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86 Properties Returned
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Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 6
Type of property:
Area: OLD TOWN

DUVAL ON THE SQUARE (monthly rental):  Located at the Duval Square townhomes directly on Duval but above all the hubbub. The townhomes are built on the second and third story of the complex with community pool overlooking Duval Street. This lovely 2 bedroom 2.5 bath townhome is available for a relaxing, luxurious month in Paradise.


Call For Availability and Pricing
2 Bedrooms
2 Baths
Sleeps 4
Type of property: 2 Bed Home - Monthly
Area: OLD TOWN

VERANDAH (monthly rental): Tucked away on Frances Street lies your island escape called Verandah, named for the lanai surrounded by Bahama shutters allowing tropical breezes to waft through. A stunning 2 bedroom 2 bath home with private pool in a quiet residential neighborhood with plenty of space for your family to stay and play!


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4 Bedrooms
4 Baths
Sleeps 8
Type of property: 4 Bedroom Home
Area: TRUMAN ANNEX

BLOOM'N PARADISE: Relax in luxury in this beautiful Truman Annex private home with pool and sun deck. 3 bedrooms and 3 bathrooms in the main house plus a pool house with 1 bedroom 1 bath offers room for friends and family to enjoy peace and solitude while at home, with the chaotic nightlife of downtown Key West just 2 blocks away.


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2 Bedrooms
1 Bath
Sleeps 4
Type of property: 2 Bedroom Condo
Area: TRUMAN ANNEX

SHIPYARD TREASURE: 2 bedroom 1 bath upstairs condo centrally located to all the sights and attractions of Old Town Key West including the beach at Fort Zachary Taylor State Park. Enjoy a cocktail on your balcony while watching the people stroll by and let the tropical breezes refresh your senses. ASK ABOUT OUR SPECIAL MONTHLY RATES DURING SUMMER MONTHS.


Call For Availability and Pricing
2 Bedrooms
1 Bath
Sleeps 4
Type of property: 2 Bedroom Condo
Area: TRUMAN ANNEX

KEY WEST CHARMING: This downstairs 2 bedroom 1 bath Shipyard condo is located in prestigious Truman Annex, a gated community within Old Town Key West. Take advantage of the ideal location and convenience of walking to anything you would want to do while visiting our lovely island. Prepare to be charmed.


Call For Availability and Pricing
2 Bedrooms
1 Bath
Sleeps 4
Type of property: 2 Bed Home - Monthly
Area: OLD TOWN

PERFECT PINEAPPLE (monthly rental): Long considered a sign of hospitality, the pineapple is now widely recognized as a sign of Welcome and Friendship...and so we welcome you to the Perfect Pineapple. This quaint Conch cottage, 2 bedrooms 1 bath has all the amenities for your visit, including a side yard where you can sunbathe, swim and BBQ to your heart's content.


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2 Bedrooms
2 Baths
Sleeps 6
Type of property: 2 Bedroom Condo
Area: OCEAN SIDE

4 PALMS: 2 bedroom 2 bath condominium with sleeper sofa offers your family the peace and tranquility you want while home, within minutes of the hectic lifestyle of downtown. Condo complex offer jacuzzi, pool, BBQ and tennis courts for your vacation pleasure. Located next to Smathers Beach where you can walk to promenade on the Atlantic Ocean witnessing magnificent sunrise.


Call For Availability and Pricing
2 Bedrooms
2 Baths
Sleeps 4
Type of property: 2 Bedroom Condo
Area: OLD TOWN

ISLAND WIND: Welcome to a tropical sun-drenched oasis in the heart of Old Town. This charming 2 bedroom 2 bath Bahamian-style townhome, with tin roof and white spindled decks reminiscent of Old Key West, is located in award-winning Windward Park, a gated and secure compound. Soothe your weary muscles in your private jacuzzi after taking in the sights all day.


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3 Bedrooms
4 Baths
Sleeps 8
Type of property: 3 Bedroom Home
Area: TRUMAN ANNEX

EASY LIVIN': The name says it all! This lovely private 3 bedroom home with pool is located in a secluded cul-de-sac in Truman Annex, a gated community located in historic Old Town Key West. Lounge by the pool in peace and tranquility or take a short walk to Duval Street where you will find the restaurants, bars, and shopping you have heard so much about.


Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 6
Type of property: 2 Bedroom Condo
Area: OLD TOWN

DUVAL STREET HIDEAWAY: A two-story, 2 bedroom 2.5 bath townhome located in the rooftop townhome community of Duval Square. Lounge by the pool catching the rays or maybe read a book. Stroll the length of Duval Street to see the sights and you will know how it got the name People Watching Capital of the World.


Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 6
Type of property: 2 Bedroom Condo
Area: OLD TOWN

DUVAL BREEZE:  Enjoy the great location of  this beautiful 2 bedroom 2.5 bath townhome located in the gated rooftop community of Duval Square. This great location is steps away from fantastic restaurants, nightlife, bars and shopping on Duval Street in Old Town Key West.  Check out chaotic Duval Street, then relax  on your private balcony.  Ahhh...


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1 Bedroom
2 Baths
Sleeps 2
Type of property: 1 Bed Home - Monthly
Area: OLD TOWN

SUNNY VIEW (monthly rental): Adorable, affordable, and a great location! Sunny View is the perfect escape for a couple looking to get away from it all in Paradise. A sweet 1 bedroom cottage with bricked backyard, a perfect spot for your morning cafe con leche. Convenient to downtown and shopping. Live like a local on Key West time.


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2 Bedrooms
3 Baths
Sleeps 6
Type of property: 2 Bedroom Condo
Area: CORAL HAMMOCK

CORAL SUITE: If you're looking for a home away from home that will leave you with money in your pocket, Coral Suite is the place for you. This 2 bedroom 2.5 bath townhome in the gated community of Coral Hammock has all the comforts including flatscreen TVs, washer/dryer, private parking, and convenient to some of our local favorite restaurants, beach and airport.


Call For Availability and Pricing
2 Bedrooms
1 Bath
Sleeps 4
Type of property: 2 Bedroom Condo
Area: TRUMAN ANNEX

SIESTA BAY: Beautiful 2 bedroom 1 bath 2nd floor condo in Truman Annex, just steps away from the shared pool and a short walk to Fort Zachary Taylor State Park. Anything you want to do on our island paradise is within a few blocks. Enjoy quiet solitude in this home in between visits to chaotic Duval Street, then do it again and again.


Call For Availability and Pricing
2 Bedrooms
1 Bath
Sleeps 4
Type of property: 2 Bedroom Condo
Area: TRUMAN ANNEX

LAVENDER JUNGLE: Beautiful 2 bedroom 1 bath downstairs Shipyard condo in Truman Annex with back deck that opens to the entrance of Fort Zachary Taylor State Park, one of the nicest beaches on the island. Truman Annex, a secure gated community within Old Town Key West, is within walking distance of all the favorite hotspots on the island.


 

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