Key West Vacation Rentals

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86 Properties Returned
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1 Bedroom
1 Bath
Sleeps 2
Type of property: 1 Bed Home - Monthly
Area: OLD TOWN

CONCH CABANA (monthly rental): Check into Conch Cabana and leave your worries behind. Simple yet so comfortable for just the two of you in this lovely historic Conch studio cottage. Centrally located in Old Town, just steps from Hemingway's home and the Lighthouse Museum, one block from Duval and a quick bike ride to the beach. Everything you want is here waiting for you.


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3 Bedrooms
3½ Baths
Sleeps 8
Type of property: 3 Bedroom Home
Area: OLD TOWN

BAHAMA HOUSE: Location, location, location! New and totally gorgeous, this spacious house is conveniently located on a quiet street in the heart of Old Town Key West only half a block from the fabulous shops, activities, restaurants and nightlife on Duval Street. Lounge at the pool in total privacy and solitude by day; take the walk around the corner to experience Key West nightlife.


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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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2 Bedrooms
3 Baths
Sleeps 6
Type of property: 2 Bed Home - Monthly
Area: MID TOWN

CAYO HUESO SUNSHINE (monthly rental): A brand new 2-bedroom 3-bath home with den in a new Key West neighborhood -- quiet and secluded yet so accessible to the wonders of our island.  A block from Higgs Beach on the Atlantic Ocean, one of the best locations you'll find, with lots of extras to make you want to return again and again.


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2 Bedrooms
2 Baths
Sleeps 4
Type of property: 2 Bed Condo - Monthly
Area: OCEAN SIDE

SEASIDE ESCAPE (monthly rental): The name says it all. Stay for a month at Seaside Escape and enjoy the ocean views, balmy breezes and casual lifestyle that is the essence of Key West living.  This condo is sure to delight your family and friends, enticing you to return again and again.


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5 Bedrooms
5½ Baths
Sleeps 12
Type of property: 5 Bedroom Home
Area: OLD TOWN

THE VICTORIA HOUSE: This gracious historic property, dating from the early 20th century, was built by prominent cigar manufacturer, William Otis Johnson. 5 bedrooms 5.5 baths with pool and jacuzzi offers your friends and family the finest of acccommodations. Conveniently located on Truman Avenue, 2 blocks from Duval Street. This home has it all!


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

CORAL GARDEN: A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this home offers the finest accommodations for you and your family. Open and airy, with private balconies, a grand 52" flat screen TV in the living room and well-equipped kitchen. A short walk to the community pool and a short drive to favorite local watering holes.


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2 Bedrooms
2 Baths
Sleeps 4
Type of property: 2 Bed Home - Monthly
Area: OLD TOWN

NAUTICAL DREAMS (monthly rental): Here's the perfect spot for whatever you desire, parties or peace & quiet. This 2 bedroom 2 bath home, in a small compound of 8 cottages, opens from each bedroom and the living room onto a grand private deck with ample space for entertaining or relaxing with a book. Walking through this well-established local neighborhood is an added bonus.


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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: 2 Bedroom Condo
Area: TRUMAN ANNEX

KEY WEST FOUND:   A striking 2 bedroom, 2.5 bath townhome located in the historic  Foundry building in Truman Annex. This 3-story townhome has all the comforts of home.  Conveniently located within walking distance of all the best of Key West -- tourist attractions, beach, Duval Street, Sunset celebration -- you will never want to leave.


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3 Bedrooms
3 Baths
Sleeps 8
Type of property: 3 Bedroom Condo
Area: CORAL HAMMOCK

CORAL VILLA -- Located right in the middle of the action, Coral Villa is a beautiful 3-bedroom townhome in the gated community of Coral Hammock. Just off U.S. 1, across from the golf course and around the corner from many of our local favorite restaurants and marinas.  A quick 10-minute drive to Old Town, 5 minutes to Smathers Beach and the airport.


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2 Bedrooms
2 Baths
Sleeps 6
Type of property: 2 Bedroom Home
Area: OLD TOWN

KEY WEST GINGER HOUSE: An absolute jewel a few doors from Duval Street, this single family home is named for the breathtaking ginger plants blooming in our tropical paradise. Featuring 2 bedrooms and 2 full baths with a private jacuzzi in the garden. Soothe your muscles after a full day of partying downtown.


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1 Bedroom
1½ Baths
Sleeps 4
Type of property: 1 Bedroom Home
Area: OLD TOWN

TRANQUILITY: This charming split level cottage offers 1 bedroom 1 full bath upstairs with sleeper sofa and half-bath downstairs. Cozy furnishings, soothing colors and modern conveniences make this the perfect spot for your visit to Key West. Stay in the heart of Old Town and walk to all there is to see on our island Paradise.


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2 Bedrooms
2 Baths
Sleeps 5
Type of property: 2 Bedroom Condo
Area: TRUMAN ANNEX

PARROT PERCH: Located in the gated community known as Truman Annex, you are in walking distance of all the activities to experience while visiting our island paradise. This 2nd floor condo with 2 bedrooms 2 baths and sleeper sofa offers a welcome respite in a great location and a great value for a great vacation.


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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: 2 Bedroom Home
Area: TRUMAN ANNEX

ARTIST GARDEN:  A bright and breezy 2 bedroom 2.5 bath private home located in the prestigious Admirals Lane neighborhood of Truman Annex, a gated community within Old Town Key West. This property is in the ideal location, in walking distance to all Old Town has to offer, including the beautiful beach at Fort Zachary Taylor State Park.


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

CROWNER'S JEWEL: Experience the finest in Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome. Located in Truman Annex, a secluded gated community within Old Town Key West, everything you want to do is within easy walking distance -- tourist attractions, beach, bars, restaurants.


 

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