Keys Vacation Rentals

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These Keys 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.

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  Preferred Listings
The San Marco Homes & Bungalow - Big Pine Key
  • Big Pine Key
  • House (single)
  • 2 to 10 bedrooms, sleeps 4 to 20
  • 1.5 to 5.5 bathrooms
     

    Gated Open-Water Vacation Home - Summerland Key - Comes Equipped w/ All the Thoughtful Touches of Home and So Much More...
    • Summerland Key
    • House (single)
    • 4 bedrooms, sleeps 8
    • 3 bathrooms
       

      Oceanfront Islamorada Condo Rentals Located in the Beautiful Florida Keys
      • Islamorada
      • Condo
      • 2 bedrooms
      • 2 bathrooms
      • Weekly rates
        From $900 to $1,500 USD
       

      The Perfect Getaway with Heated Pool and Jacuzzi - IN THE HEART of ISLAMORADA
      • Islamorada
      • Apartment
      • 4 bedrooms, sleeps 8-10
      • 3 bathrooms
      • Weekly rates
        From $3,000 to $3,500 USD
       

      It's a Great "Package" Deal,as guest have discovered year after year...
      • Key Largo
      • House (single)
      • 3 bedrooms, sleeps 8
      • 2 bathrooms
      • Weekly rates
        From $1,800 to $2,000 USD
       

      Tropical Breeze - two bedroom two bath oceanfront condo
      • Key West
      • Condo
      • 2 bedrooms, sleeps 6
      • 2 bathrooms
      • Weekly rates
        From $225 to $1,905 USD
       

      Key West Crown Jewel - Enjoy Key West in STYLE!!
      • Key West
      • Condo
      • 2 bedrooms, sleeps 6
      • 2 bathrooms
      • Weekly rates
        From $345 to $2,695 USD
       

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

        Enjoy a Marina Home in the Heart of the Keys
        • Marathon
        • House (single)
        • 3 bedrooms, sleeps 6
        • 2.5 bathrooms
        • Weekly rates
          From $1,700 to $1,700 USD
         

        Atlantic Retreat- two bedroom two bath oceanview condo on Atlantic
        • Key West
        • Condo
        • 2 bedrooms, sleeps 6
        • 2 bathrooms
        • Weekly rates
          From $240 to $1,900 USD
         

        1, 2 & 3 bedroom condos on the ocean side overlooking a sandy beach and heated pool. Marathon, Florida
        • Marathon
        • Condo
        • 1-3 bedrooms
        • 1-3 bathrooms
           

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

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

              Private Beach-Ocean View-Pool-Walking Distance to Restaurants - Key Colony Beach
              • Key Colony Beach
              • Condo
              • 2 bedrooms, sleeps 4
              • 2 bathrooms
              • Weekly rates
                From $1,100 to $1,400 USD
               

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

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

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

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

                      In the Heart of "Old Town" Beautiful Vacation Home in Key West, Florida
                      • Key West
                      • House (single)
                      • 3 bedrooms, sleeps 6
                      • 3 bathrooms
                      • Weekly rates
                        From $4,000 to $6,000 USD
                       

                      BAY FRONT Cottages & your own FREE 22’ SAILBOAT + Paddle Boats, Kayaks, Canoes, Fishing & Snorkeling Gear, Sun Sets, Dolphins & Manatees Tiki Huts
                      • Key Largo
                      • Cottage
                      • 1 bedrooms, sleeps 2-6
                      • 1 bathrooms
                      • Weekly rates
                        From $840 to $2,100 USD
                       

                      Bright & Breezy - Very Popular Home - Wireless Internet!!
                      • Key Colony Beach
                      • House (multifamily)
                      • 3 bedrooms, sleeps 8
                      • 2 bathrooms
                      • Weekly rates
                        From $1,325 to $1,950 USD
                       

                      Key Colony Sunrise Retreat - Book Now for a $100.00 Gas Credit
                      • Key Colony Beach
                      • Duplex
                      • 2 bedrooms, sleeps 4
                      • 2 bathrooms
                         

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

                          Fisherman’s Paradise This Home Will Not Disappoint - Florida
                          • Big Pine Key
                          • House (single)
                          • 2 bedrooms, sleeps 4
                          • 2 bathrooms
                             

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

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

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

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

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

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

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

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

                                              PRISTINE OCEANFRONT HOME IN ISLAMORADA, THE FLORIDA KEYS - Rent All or Rent Separately
                                              • Windley Key
                                              • House (single)
                                              • 2-10 bedrooms, sleeps 2-28
                                              • 2-8 bathrooms
                                                 

                                                Dock Your Boat from This Incredible Islamorada Vacation Home - Florida
                                                • Plantation Key
                                                • House (single)
                                                • 3 bedrooms, sleeps 6
                                                • 3.5 bathrooms
                                                   

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

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

                                                      Bayside 1st floor Condo on Florida Bay - Islamorada, Florida
                                                      • Islamorada
                                                      • Condo
                                                      • 1 bedrooms, sleeps 2-4
                                                      • 2 bathrooms
                                                         

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

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

                                                            THE KEYS KOTTAGE has it all - Islamorada, Florida
                                                            • Islamorada
                                                            • Villa
                                                            • 2 bedrooms, sleeps 4-8
                                                            • 2 bathrooms
                                                               

                                                              Open Water - Great View - Great Boating and Fishing
                                                              • Big Pine Key
                                                              • House (single)
                                                              • 3 bedrooms, sleeps 6-8
                                                              • 3 bathrooms
                                                                 

                                                                Key Colony Point borders the waters edge of paradise... offering breathtaking sunsets daily, and an escape to paradise well worth planning every year
                                                                • Key Colony Beach
                                                                • Apts & Townhomes
                                                                • 2-3 bedrooms
                                                                • 2-3 bathrooms
                                                                   

                                                                  2 Bedroom 2 Bathroom Home on Summerland Key
                                                                  • Summerland Key
                                                                  • House (single)
                                                                  • 2 bedrooms
                                                                  • 2 bathrooms
                                                                     

                                                                    Villa Largo - Luxury Oceanfront Estate in Beautiful Key Largo
                                                                    • Key Largo
                                                                    • House (single)
                                                                    • 5 bedrooms, sleeps 12
                                                                    • 6 bathrooms
                                                                    • Weekly rates
                                                                      From $7,999 to $13,999 USD
                                                                     

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

                                                                      BAMBOO KEY - KEY WEST
                                                                      • Key West
                                                                      • Condo
                                                                      • 2 bedrooms, sleeps 5
                                                                      • 2.5 bathrooms
                                                                         

                                                                        Key West Vacation Home - "Colorful Conch" @ The Sanctuary: 3 Bedrooms, 3 Baths & Private Pool in an Exclusive Gated Community @ the Key West Golf Club
                                                                        • Key West
                                                                        • House (single)
                                                                        • 3 bedrooms, sleeps 8
                                                                        • 3 bathrooms
                                                                           

                                                                          This Luxurious Duck Key Vacation Rental Condo Can Be Your Dream Vacation...
                                                                          • Duck Key
                                                                          • Villa
                                                                          • 2-4 bedrooms, sleeps 2 - 10
                                                                          • 1-3 bathrooms
                                                                             

                                                                            Key West Found - 2 Bedroom Townhouse - Historic Section Key West
                                                                            • Key West
                                                                            • Townhouse
                                                                            • 2 bedrooms, sleeps 6
                                                                            • 2.5 bathrooms
                                                                            • Weekly rates
                                                                              From $1,600 to $2,200 USD
                                                                             

                                                                            Suite Paradise - Wonderful Key West Home with Private Pool
                                                                            • Key West
                                                                            • House (single)
                                                                            • 2 bedrooms, sleeps 6
                                                                            • 2 bathrooms
                                                                               

                                                                              Bahama Dreaming - Key West Conch House
                                                                              • Old Town
                                                                              • House (single)
                                                                              • 3 bedrooms, sleeps 8
                                                                              • 2 bathrooms
                                                                              • Weekly rates
                                                                                From $2,700 to $3,600 USD
                                                                               

                                                                              Treetop Villa - Historical Property - Walk to Duval Street
                                                                              • Old Town
                                                                              • House (single)
                                                                              • 5 bedrooms, sleeps 12
                                                                              • 5.5 bathrooms
                                                                              • Weekly rates
                                                                                From $6,500 to $7,000 USD
                                                                               

                                                                               
                                                                                Rental Locations   (Listed alphabetically by City or Town)
                                                                               

                                                                                City BR(s) BA(s) Sleeps Description
                                                                              Duck Key 1 BR 1 BA 4 Welcome to our Vacation rental cottage on Duck Key property is managed by "American Paradise"
                                                                              Duck Key 2-4 BR 1-3 BA 2 - 10 This Luxurious Duck Key Vacation Rental Condo Can Be Your Dream Vacation...
                                                                              Duck Key 2 BR 2 BA 7 Waterfront Keys to Memories - Duck Key
                                                                              Grassy Key 4 BR 2 BA 8 Adults + Grassy Key/Marathon Gulf Front Property - property is managed by "American Paradise"
                                                                              Grassy Key 5 BR 4 BA 14 Gorgeous Views - Gorgeous Home - Marathon / Grassy Key property is managed by "American Paradise"
                                                                              Grassy Key 6 BR 5.5 BA 16 Spectacular Gulf Front Luxury Home on 2.5 Acres property is managed by "American Paradise"
                                                                              Key Colony Beach 2-3 BR 2-3 BA Key Colony Point borders the waters edge of paradise... offering breathtaking sunsets daily, and an escape to paradise well worth planning every year
                                                                              Key Colony Beach 2 BR 2 BA 4 Private Beach-Ocean View-Pool-Walking Distance to Restaurants - Key Colony Beach
                                                                              Key Colony Beach 2 BR 2 BA 4 Key Colony Beach Florida Waterfront Gem - Pets OKAY
                                                                              Key Colony Beach 2 BR 2 BA 4 Key Colony Sunrise Retreat - Book Now for a $100.00 Gas Credit
                                                                              Key Colony Beach 3 BR 2 BA 8 Bright & Breezy - Very Popular Home - Wireless Internet!!
                                                                              Key Colony Beach 6 BR BA Key Colony Beach Waterfront Pool Home
                                                                              Marathon BR BA Private Waterfront Pool Home
                                                                              Marathon 1-3 BR 1-3 BA Varies 1, 2 & 3 bedroom condos on the ocean side overlooking a sandy beach and heated pool. Marathon, Florida
                                                                              Marathon 2 BR 2 1/2 BA 4 Ad & 2 Ch WATERFRONT Condo, "PARADISE AT GULFPOINTE"-- Heated Pool, Dock, Views
                                                                              Marathon 3 BR 2.5 BA 6 Rent a Luxury Beach Home in the Keys
                                                                              Marathon 3 BR 3 BA 6-8 Lovely and beautiful house located three homes from the open water
                                                                              Marathon 3 BR 2.5 BA 6 Enjoy a Marina Home in the Heart of the Keys
                                                                              Marathon 4 BR 3 BA 8 Tropical Pool Home with Tiki Hut
                                                                              Marathon 4 BR 3 BA 8 Splendid Waterfront Haven for a fun family retreat or a romantic getaway
                                                                              Marathon 4 BR 4 BA The Feeling of Seclusion on your own little peninsula overlooking the Gulf of Mexico...
                                                                              Marathon 5 BR 4 BA 8-14 New Waterfront Rental W/Pool & Dock - 33% Off Sept.1-Nov.21,2008

                                                                              Featured
                                                                              Property Managers

                                                                              www.AtHomeKeyWest.com
                                                                              Located throughout Key West many homes, cottages and compounds are open for vacation rentals. These homes offer a private haven in the tropical beauty of Key West Many different styles and amenities are available.

                                                                              Island Breeze Realty
                                                                              Welcome to the Fabulous Florida Keys...Whether you are interested in Buying or Renting one of our Luxury Waterfront Vacation Rental Homes, We are committed to serving you...


                                                                              www.american-paradise.com
                                                                              American Paradise Florida Keys Vacation Rentals.

                                                                              ActionKeysRealty.com
                                                                              Whether you are planning your vacation or planning to move to the beautiful Florida Keys, we have information to help you.

                                                                              www.RentKeyWest.com
                                                                              Rent a private HOME, COTTAGE, VILLA, or CONDO as an alternative to your typical KEY WEST hotel stay.





                                                                              The San Marco Homes & Bungalow - Big Pine Key
                                                                              Big Pine Key House (single), 2 to 10 bedrooms, sleeps 4 to 20, 1.5 to 5.5 bathrooms



                                                                              Gated Open-Water Vacation Home - Summerland Key - Comes Equipped w/ All the Thoughtful Touches of Home and So Much More...
                                                                              Summerland Key House (single), 4 bedrooms, sleeps 8, 3 bathrooms



                                                                              Oceanfront Islamorada Condo Rentals Located in the Beautiful Florida Keys
                                                                              Islamorada Condo, 2 bedrooms, 2 bathrooms Weekly rates from $900 to $1,500 USD



                                                                              The Perfect Getaway with Heated Pool and Jacuzzi - IN THE HEART of ISLAMORADA
                                                                              Islamorada Apartment, 4 bedrooms, sleeps 8-10, 3 bathrooms Weekly rates from $3,000 to $3,500 USD



                                                                              It's a Great "Package" Deal,as guest have discovered year after year...
                                                                              Key Largo House (single), 3 bedrooms, sleeps 8, 2 bathrooms Weekly rates from $1,800 to $2,000 USD



                                                                              Tropical Breeze - two bedroom two bath oceanfront condo
                                                                              Key West Condo, 2 bedrooms, sleeps 6, 2 bathrooms Weekly rates from $225 to $1,905 USD



                                                                              Key West Crown Jewel - Enjoy Key West in STYLE!!
                                                                              Key West Condo, 2 bedrooms, sleeps 6, 2 bathrooms Weekly rates from $345 to $2,695 USD



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



                                                                              Enjoy a Marina Home in the Heart of the Keys
                                                                              Marathon House (single), 3 bedrooms, sleeps 6, 2.5 bathrooms Weekly rates from $1,700 to $1,700 USD



                                                                              Atlantic Retreat- two bedroom two bath oceanview condo on Atlantic
                                                                              Key West Condo, 2 bedrooms, sleeps 6, 2 bathrooms Weekly rates from $240 to $1,900 USD



                                                                              1, 2 & 3 bedroom condos on the ocean side overlooking a sandy beach and heated pool. Marathon, Florida
                                                                              Marathon Condo, 1-3 bedrooms, 1-3 bathrooms



                                                                              "Dockside Villa" - 2 bedroom 2 1/2 bath Townhome with Dockage
                                                                              Key West Townhouse, 2 bedrooms, sleeps 4, 2.5 bathrooms



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



                                                                              Private Beach-Ocean View-Pool-Walking Distance to Restaurants - Key Colony Beach
                                                                              Key Colony Beach Condo, 2 bedrooms, sleeps 4, 2 bathrooms Weekly rates from $1,100 to $1,400 USD



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



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