Key West Vacation Rentals

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These Key West vacation homes, condos, villas, cabins, cottages, chalets, and bed & breakfasts are presented by their owners or agents. Please contact them directly with your inquiries. Click on the underlined descriptions below for more details and property photos.
Click Here to review listings ordered by city and # of bedrooms.
 
Premium Listings
BAMBOO KEY - KEY WEST
  • Key West
  • Condo
  • 2 bedrooms, sleeps 5
  • 2.5 bathrooms
     

    Old Town Cottage with Tropical Decor and Pool - Key West
    • Key West
    • Cottage
    • 2 bedrooms, sleeps 4
    • 3 bathrooms
       

      Garden on the Green three bedroom two bath available monthly
      • Key West
      • Apartment
      • 3 bedrooms, sleeps 6
      • 2 bathrooms
         

        "Villa Tropicale" This Magnificent Vacation Rental Home is Best Described as Tropical Seclusion
        • Key West
        • House (single)
        • 4 bedrooms, sleeps 9
        • 5 bathrooms
           

          1800 Atlantic Condominiums ~ Key West
          • Key West
          • Condo
          • 1-3 bedrooms
             

            Golf Club Dr. in The Sanctuary at The Key West Golf Club.
            • Key West
            • Home
            • 3 bedrooms, sleeps 6
            • 2 1/2 bathrooms
               

              Charming Cottage on Oceanfront Property - Near Key West and Big Pine Key
              • Key West
              • Cottage
              • 2 bedrooms, sleeps 6
              • 1 bathrooms
                 

                Ocean View Luxury Vacation Rental - Key West
                • Key West
                • Condo
                • 3 bedrooms, sleeps 6
                • 2 bathrooms
                   

                  Conch Mansion four bedroom three 1/2 bath home available monthly
                  • Key West
                  • House (single)
                  • 4 w/ pool h bedrooms, sleeps 8
                  • 3.5 bathrooms
                     

                    Atlantic Retreat- two bedroom two bath oceanview condo on Atlantic
                    • Key West
                    • Condo
                    • 2 bedrooms, sleeps 6
                    • 2 bathrooms
                       

                      "Beach Club #201" Luxurious Oceanfront Condo with Magnificent views of the Ocean
                      • Key West
                      • Condo
                      • 2 bedrooms, sleeps 4
                      • 2 bathrooms
                         

                        Island Rendezvous Vacation Rental - Key West
                        • Key West
                        • Villa
                        • 6 bedrooms, sleeps 14
                        • 5 bathrooms
                           

                          Key West Crown Jewel - Enjoy Key West in STYLE!!
                          • Key West
                          • Condo
                          • 2 bedrooms, sleeps 6
                          • 2 bathrooms
                             

                            MERMAID'S ROCK - Key West, FL
                            • Key West
                            • House (single)
                            • 3 bedrooms
                            • 3 bathrooms
                               

                              Henry's Penthouse On the Ocean In Key West
                              • Key West
                              • Condo
                              • 2 bedrooms, sleeps 2-6 w/ Pool
                              • 2 bathrooms
                                 

                                Fantasy Resort Villa Vacation Rental - Key West
                                • Key West
                                • Villa
                                • 3 bedrooms, sleeps 8
                                • 2.5 bathrooms
                                   

                                  Key West Coral Country Vacation Rental - Key West
                                  • Key West
                                  • Townhouse
                                  • 2 bedrooms, sleeps 4-6
                                  • 2.5 bathrooms
                                     

                                    Grande Dame Key West Vacation Rental - Exclusive Heart of Old Town Location - Amazing Luxury Mansion Estate - Key West
                                    • Key West
                                    • House (single)
                                    • 7 bedrooms, sleeps 16
                                    • 7 bathrooms
                                       

                                      "Coconut Cabana" A Tropical Vacation Rental Bungalow
                                      • Key West
                                      • House (single)
                                      • 3 bedrooms, sleeps 6
                                      • 2 bathrooms
                                         

                                        "Havana Lane" An Old Town Vacation Rental Retreat
                                        • Key West
                                        • Cottage
                                        • 2 bedrooms, sleeps 6
                                        • 2 bathrooms
                                           

                                          Comfortable Vacation Home in Old Town Key West
                                          • Key West
                                          • House (single)
                                          • 3 bedrooms
                                          • 2 bathrooms
                                             

                                            Tropical Breeze - two bedroom two bath oceanfront condo
                                            • Key West
                                            • Condo
                                            • 2 bedrooms, sleeps 6
                                            • 2 bathrooms
                                               

                                              Spacious Old Town Compound... Just 2 Blocks from Duval
                                              • Key West
                                              • House (single)
                                              • 3 - 6 bedro bedrooms, sleeps 8-16
                                              • 2.5-4.5 bathrooms
                                                 

                                                "Dockside Villa" - two bedroom two 1/2 bath townhome with dockage
                                                • Key West
                                                • Townhouse
                                                • 2 bedrooms, sleeps 4
                                                • 2.5 bathrooms
                                                   

                                                  Classic Key West Estate Vacation Rental
                                                  • Key West
                                                  • House (single)
                                                  • 6 bedrooms, sleeps 12-14
                                                  • 4 bathrooms
                                                     

                                                    Island Oasis Garden Home Vacation Rental - Key West
                                                    • Key West
                                                    • Townhouse
                                                    • 2 bedrooms, sleeps 4
                                                    • 2 bathrooms
                                                       

                                                      In the Heart of "Old Town" Beautiful Vacation Home in Key West, Florida
                                                      • Key West
                                                      • House (single)
                                                      • 3 bedrooms, sleeps 6
                                                      • 3 bathrooms
                                                         

                                                        Amelia's Hideaway Vacation Rental - Key West
                                                        • Key West
                                                        • Villa
                                                        • 4 bedrooms, sleeps 2-10
                                                        • 3.5 bathrooms
                                                           

                                                          Isla Paraiso - Beautiful 4 Bed/ 3.5 Bath Home
                                                          • Key West
                                                          • House (single)
                                                          • 4 bedrooms, sleeps 6-8
                                                          • 3.5 bathrooms
                                                             

                                                            Henry's Piece Of Paradise On The Ocean In Key West
                                                            • Key West
                                                            • Condo
                                                            • 2 bedrooms, sleeps 2-5
                                                            • 2 bathrooms
                                                               

                                                              Victorian Mansion Vacation Rental - Key West
                                                              • Key West
                                                              • House (single)
                                                              • 5 bedrooms, sleeps 10
                                                              • 3 bathrooms
                                                                 

                                                                Beautiful Victorian Home with Heated Pool & Waterfall - Key West
                                                                • Key West
                                                                • House (single)
                                                                • 3 bedrooms
                                                                • 2 bathrooms
                                                                   

                                                                  Island Village Cottage Vacation Rental - Key West
                                                                  • Key West
                                                                  • Cottage
                                                                  • 2 bedrooms, sleeps 4-6
                                                                  • 2 bathrooms
                                                                     

                                                                    Historic Seaport Estate Vacation Rental - Key West
                                                                    • Key West
                                                                    • House (single)
                                                                    • 6 bedrooms, sleeps 12+
                                                                    • 4 bathrooms
                                                                       

                                                                      "Duval Square" Vacation Rental Condo's Conveniently Located
                                                                      • Key West
                                                                      • Condo
                                                                      • 2 - 4 (Vari bedrooms, sleeps 4 - 10 (Var
                                                                      • 2 - 4 (Var bathrooms
                                                                         

                                                                         
                                                                         
                                                                        Rental Locations
                                                                         
                                                                         
                                                                          City BR(s) BA(s) Sleeps Description
                                                                         
                                                                        Key West1 - 4 BR1 - 2 BA4 per"Pete's Cottages" Beautiful Vacation Rental Cottages
                                                                         
                                                                        Key West1 BR1 BA4Egret one bedroom cottages in the heart of the historic district
                                                                         
                                                                        Key West1 BR1 BA4Margaret’s Harborside Cottage one bedroom one bath cottage available monthly near Historic seaport
                                                                         
                                                                        Key West1 BR1 BA2Land’s End one bedroom one bath cottage available monthly near historic seaport
                                                                         
                                                                        Key West1 BR2 BA4Key West Charming - Two bedroom one bath condominium
                                                                         
                                                                        Key West1 BR1 BA2Margaret’s Harborside Cottage
                                                                         
                                                                        Key West1 BR1 BA4Ocean Watch One bedroom one bath oceanview condominium
                                                                         
                                                                        Key West1 BR1 BA2"Key Lime Calypso "A great vacation home in the heart of Old Town Key West!
                                                                         
                                                                        Key West1-3 BR BA1800 Atlantic Condominiums ~ Key West
                                                                         
                                                                        Key West1 BR1 BA2"Casa Atlantica Studio" Experience Breathtaking Ocean Views From This Secluded Private Studio.
                                                                         
                                                                        Key West1 BR1 BA2"Casa Atlantica One" - Breathtaking Ocean Views From This Secluded Private Ocean Front Apartment.
                                                                         
                                                                        Key West1 BR1 BA1-4Key West Gingerbread Cottage Flat Vacation Rentals
                                                                         
                                                                        Key West1 BR1 BA4Vintage Luxury Cottage Vacation Rental - Just Off Upper Duval Street with Pool
                                                                         
                                                                        Key West1 BR1 BA2Shipyard Condo 'Bamboo Cabana' - Key West
                                                                         
                                                                        Key West2 BR2 BA6"Havana Lane" An Old Town Vacation Rental Retreat
                                                                         
                                                                        Key West2 - 4 (Vari BR2 - 4 (Var BA4 - 10 (Var"Duval Square" Vacation Rental Condo's Conveniently Located
                                                                         
                                                                        Key West2 BR2 BA4"La Brisa 405East" Vacation Rental Condo With Beautiful Ocean View
                                                                         
                                                                        Key West2 BR2 BA4"Beach Club #201" Luxurious Oceanfront Condo with Magnificent views of the Ocean
                                                                         
                                                                        Key West2 BR1 BA6Charming Cottage on Oceanfront Property - Near Key West and Big Pine Key
                                                                         
                                                                        Key West2 BR2 BA2-5Henry's Piece Of Paradise On The Ocean In Key West
                                                                         
                                                                        Key West2 BR2 BA2-6 w/ PoolHenry's Penthouse On the Ocean In Key West
                                                                         
                                                                        Key West2 BR2 BA4Ocean Front Luxury Condominium at 1800 Atlantic #228
                                                                         
                                                                        Key West2 BR1 BA4Corner Garden - 2 Bed/ 1Bath Townhome
                                                                         
                                                                        Key West2 BR2 BA6Tropical Breeze - two bedroom two bath oceanfront condo
                                                                         
                                                                        Key West2 BR2 BA6A Zen Garden - two bedroom two bath oceanfront condominium
                                                                         
                                                                        Key West2 BR2.5 BA4"Dockside Villa" - two bedroom two 1/2 bath townhome with dockage
                                                                         
                                                                        Key West2 BR2 BA6Atlantic Retreat- two bedroom two bath oceanview condo on Atlantic
                                                                         
                                                                        Key West2 BR2 BA6Key West Crown Jewel - Enjoy Key West in STYLE!!
                                                                         
                                                                        Key West2 BR BA6Duval Street Hideaway - two bedroom two 1/2 bath townhome in historic district
                                                                         
                                                                        Key West2 BR1.5 BA5Carols Bungalow - Two bedroom one 1/2 bath townhome available monthly
                                                                         
                                                                        Key West2 BR2.5 BA6Spa on Duval - two bedroom two 1/2 bath townhome on Duval St
                                                                         
                                                                        Key West2 BR2 BA4Howe St. Hideaway two bedroom two bath home located in the Old Town in a very peaceful area.
                                                                         
                                                                        Key West2 BR2 BA4Southern Wind - two bedroom two bath home in historic district
                                                                         
                                                                        Key West2 BR2 BA5Conch Condo - upstairs two bedroom two bath in historic district
                                                                         
                                                                        Key West2 BR2.5 BA5Southern Comfort - Two bedroom two 1/2 bath townhome available monthly
                                                                         
                                                                        Key West2 BR1 BA4Aquamarine - two bedroom one bath upstairs condo
                                                                         
                                                                        Key West2 BR2.5 BA6Duval Sea Turtle two bedroom two 1/2 bath on Duval Street
                                                                         
                                                                        Key West2 BR3 BA4Old Town Cottage with Tropical Decor and Pool - Key West
                                                                         
                                                                        Key West2 BR2 BA4-6Island Village Cottage Vacation Rental - Key West
                                                                         
                                                                        Key West2 BR2 BA4Island Oasis Garden Home Vacation Rental - Key West
                                                                         
                                                                        Key West2 BR2.5 BA4-6Key West Coral Country Vacation Rental - Key West
                                                                         
                                                                        Key West2 BR1.5 BA4"Shipyard Palms " Charming Gated Comunity Condo in the heart of HIstoric District
                                                                         
                                                                        Key West2 BR2 BA4"La Brisa 206E" Ocean front condo with beautiful ocean view.
                                                                         
                                                                        Key West2 BR2 BA4"Beach Club #303" Luxurious Oceanfront Condo with Magnificent views of the Ocean
                                                                         
                                                                        Key West2 BR2 BA4"Beach Club #103" Luxurious Oceanfront Condo with Magnificent views of the Ocean
                                                                         
                                                                        Key West2 BR2 BA4Ocean Front Luxury Condominium at 1800 Atlantic #435
                                                                         
                                                                        Key West2 BR1.5 BA2-6Flamboyant Tree Cottage Vacation Rental - off Upper Duval Street with Jacuzzi
                                                                         
                                                                        Key West2 BR2 BA2-6Down Island Digs Vacation Rental in Old Town Key West
                                                                         
                                                                        Key West2 BR1 BA2-5Courtyard Cottage on a Lane - Key West Vacation Renta
                                                                         
                                                                        Key West2 BR2 BA4-6Key West Southern Sunrise Vacation Rental
                                                                         
                                                                        Key West2 BR1 BA2-4Captain's Private Quarters Vacation Rental - Key West
                                                                         
                                                                        Key West2 BR2 BASeaport Suite on Caroline Street
                                                                         
                                                                        Key West2 BR2.5 BASPINNAKER SAIL - Key West, FL
                                                                         
                                                                        Key West2 BR2.5 BABRUBECK COTTAGE - KEY WEST
                                                                         
                                                                        Key West2 BR2.5 BA5BAMBOO KEY - KEY WEST
                                                                         
                                                                        Key West2 BR2 BAIsland Retreat in the Heart of Old Town - Key West
                                                                         
                                                                        Key West2 BR1 BA4Shipyard Condo 'Havana Views' - Key West
                                                                         
                                                                        Key West2 BR2.5 BACARIBBEAN CHARM - KEY WEST
                                                                         
                                                                        Key West2 BR1.5 BAEmerald Sea - Key West, Florida
                                                                         
                                                                        Key West2.5 BR2 BA4Duval on the Square Two bedroom two and one half bath townhome in historic district available monthly only
                                                                         
                                                                        Key West3 BR2 1/2 BA6Golf Club Dr. in The Sanctuary at The Key West Golf Club.
                                                                         
                                                                        Key West3 BR2 BA6"Casa De Cuba" A Vacation Rental House With A Cuban Twist!
                                                                         
                                                                        Key West3 BR2 BA6"Coconut Cabana" A Tropical Vacation Rental Bungalow
                                                                         
                                                                        Key West3 BR3.5 BA6"Duval Roost" A Beautiful Vacation Home With Screened Balcony Overlooking The Pool
                                                                         
                                                                        Key West3 - 6 bedro BR2.5-4.5 BA8-16Spacious Old Town Compound... Just 2 Blocks from Duval
                                                                         
                                                                        Key West3 BR3 BA6"Secret Villa " Secluded Hideaway In The Heart Of Old Town Key West
                                                                         
                                                                        Key West3 BR3 BA6In the Heart of "Old Town" Beautiful Vacation Home in Key West, Florida
                                                                         
                                                                        Key West3 BR1.5 BA6Babalu Cottage - Three bedroom one 1/2 bath home with jacuzzi in historic district
                                                                         
                                                                        Key West3 BR2 BA6Garden on the Green three bedroom two bath available monthly
                                                                         
                                                                        Key West3 BR3 BA8Lighthouse Keep - Three bedroom three bath townhome. GREAT VALUE
                                                                         
                                                                        Key West3 BR3 BA8Sunset Palm - Cottage 24 - 3 bedroom 3 bath cottage "Conch style"
                                                                         
                                                                        Key West3 BR3 BA8Kelly's Cottage Three bedroom three bath townhome
                                                                         
                                                                        Key West3 BR2 BABeautiful Victorian Home with Heated Pool & Waterfall - Key West
                                                                         
                                                                        Key West3 BR2 BAComfortable Vacation Home in Old Town Key West
                                                                         
                                                                        Key West3 BR2.5 BA8Fantasy Resort Villa Vacation Rental - Key West
                                                                         
                                                                        Key West3 BR2 BA6"La Brisa 308North" - Great beach front condo on Salt Pond Nature Preserve
                                                                         
                                                                        Key West3 BR2 BA6Ocean View Luxury Vacation Rental - Key West
                                                                         
                                                                        Key West3 BR2.5 BA6-8Coco's Poolside Retreat Key West Vacation Rental
                                                                         
                                                                        Key West3 BR3 BA7Avant-Garde - Modernistic Luxury Key West Vacation Home
                                                                         
                                                                        Key West3 BR2 BA2-6Island Cosmopolitan Vacation Rental with Private Pool & High Speed Internet
                                                                         
                                                                        Key West3 BR3 BAMERMAID'S ROCK - Key West, FL
                                                                         
                                                                        Key West3 BR2 BA8Shipyard Condo 'Sandcastles' - Key West
                                                                         
                                                                        Key West3 BR3.5 BA6ADMIRAL'S PARADISE - KEY WEST
                                                                         
                                                                        Key West3 BR3 BA8Bay Pointe in Key West Area with Pool
                                                                         
                                                                        Key West3 BR2 BA6Key West Waterfront Vacation Home in Prestigious Key Haven
                                                                         
                                                                        Key West3.5 BR2.5 BAPrivate Pool Garden Villa Vacation Rental
                                                                         
                                                                        Key West4 BR5 BA9"Villa Tropicale" This Magnificent Vacation Rental Home is Best Described as Tropical Seclusion
                                                                         
                                                                        Key West4 BR4 BA14"Southard Street" Quiet, Historic Compound Offers Three Separate Vacation Rental Suites Sharing A Lush, Large, Sunny Pool
                                                                         
                                                                        Key West4 BR3.5 BA6-8Isla Paraiso - Beautiful 4 Bed/ 3.5 Bath Home
                                                                         
                                                                        Key West4 w/ pool h BR3.5 BA8Conch Mansion four bedroom three 1/2 bath home available monthly
                                                                         
                                                                        Key West4 BR3.5 BA2-10Amelia's Hideaway Vacation Rental - Key West
                                                                         
                                                                        Key West4 BR3 BA10Pavilion Villa Vacation Rental - A Private Tropical Paradise - Key West