Key West Vacation Rentals

All Vacation Rentals in Key West, FL

Below you will find a list of all of our Key West, Florida vacation rentals, a variety of properties listed alphabetically, along with photo and brief description. You can view additional pictures and detailed information about the property by clicking on the property name. Have fun browsing!!!

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  • Winter rates apply from approximately December 15 -  April 30.
  • Shoulder rates apply from approximately May 1 - May 30 and November 1 - December 14.
  • Summer rates apply from approximately June 1 - October 31.
  • Rates will be higher for special events and holidays.
  • We can only reserve properties 364 days in advance
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87 Properties Returned
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Call For Availability and Pricing
2 Bedrooms
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

EMMA'S SECRET (monthly rental):  Luxurious 2 bedroom 1 bath condominium located in the historic Bahama Village neighborhood of Old Town offers all the amenities of home.  Enjoy the tropical backyard ambience with jacuzzi, pool and tiki hut.   Located in walking distance to Duval Street, the heart of Key West with all the activities, restaurants, speciality shops and nightlife.


Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Private Home
Area: Old Town

AMELIA HOME:  A private Key West vacation home that is only four blocks from one of our most popular beaches on the Atlantic Ocean and one block from all the Duval Street entertainment.  This 2 bedroom 2.5 bath single family home with private pool is located in one of the most interesting neighborhoods in the historic district of Old Town Key West.


Call For Availability and Pricing
3 Bedrooms
2 Baths
Sleeps 6
Type of property: Cottage
Area: Old Town

BOWE CONCH HOUSE: The Bowe Conch House has evolved within the Thomas family, Conchs, born and raised in Key West, for more than 4 generations.  Ethel Bowe-Thomas purchased the house in the 1930's, raised her family there, planted the massive poinciana tree that offers shade in the backyard, and now her family wants to share it with you.  A unique opportunity to experience life in Key West through the eyes of a Conch.


Call For Availability and Pricing
2 Bedrooms
1½ Baths
Sleeps 6
Type of property: Townhouse
Area: Stock Island

WIND SWEPT (monthly rental): Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the only Caribbean golf course in the United States.  This lovely 2 bedroom 1.5 bath townhome is tastefully furnished with a well-stocked kitchen and located a few doors from the community pool.


Call For Availability and Pricing
2 Bedrooms
2 Baths
Sleeps 5
Type of property: Condo
Area: Old Town

TRUMAN'S HIDEAWAY: It's hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. Located in the exclusive Harbour Place complex, it has all the comforts of home and more.  Conveniently located in Truman Annex, within walking distance of all Key West activities, you'll be tempted to return again and again.


Call For Availability and Pricing
3 Bedrooms
3½ Baths
Sleeps 7
Type of property: Private 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.


Call For Availability and Pricing
2 Bedrooms
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

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
3 Baths
Sleeps 6
Type of property: Private Home
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.


Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Condo
Area: Mid Town

Sunshine On The Rocks (Monthly Rental) 
A true island getaway! This stunning townhome has spectacular waterfront views of the bay, travel down to Key West by boat or bring it along because this is one of the only places on the island with open water boat dockage. Sunshine On The Rocks is the hideaway you are looking for when tropical breezes call your name and turquoise waters is where you are heading.


Call For Availability and Pricing
2 Bedrooms
2 Baths
Sleeps 4
Type of property: Townhouse
Area: Old Town

CONCH WIND:   Conch Wind is the property you have been hunting for! This Conch-style townhome located in Old Town Key West is nestled in a quiet, secured compound, featuring 1 bedroom with bath ensuite on the first floor and the Master bedroom with bath ensuite upstairs. A porch and second floor balcony overlook the 50 foot pool, offering lots of room for rest and relaxation.


Call For Availability and Pricing
2 Bedrooms
2 Baths
Sleeps 6
Type of property: Condo
Area: Ocean Side

ATLANTIC PARADISE -- Imagine the ocean only several yards from your balcony, in a secure gated complex, with all the amenities you could ask for -- Olympic-sized pool, Jacuzzi, tennis courts, covered garage parking.  Make the most of visiting our island Paradise by staying on the ocean within a quick bike ride from the action of Duval Street.


Call For Availability and Pricing
2 Bedrooms
3 Baths
Sleeps 6
Type of property: Townhouse
Area: Stock Island

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
1 Bedroom
1 Bath
Sleeps 2
Type of property: Condo
Area: Old Town

CITY CAY: Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This is the place! Centrally located in Truman Annex, smart, sleek and modern with fully equipped kitchen and high-end electronics within two blocks of anything you'll want to do in our island Paradise.


Call For Availability and Pricing
2 Bedrooms
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

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
1½ Baths
Sleeps 4
Type of property: Townhouse
Area: Stock Island

CORAL BREEZE (monthly rental): Imagine yourself living with the vibrant golf course greens in your backyard and cool tropical breezes wafting your way. Coral  Breeze has that and more.  Beautiful townhome with all the modern conveniences located in the exclusive gated Key West Golf Club where you can relax in the serene golf course surroundings or take a quick trip into Old Town Key West for all it has to offer.


 

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