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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Region  Bedrooms
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  Preferred Listings
BAMBOO KEY - KEY WEST
  • Key West
  • Condo
  • 2 bedrooms, sleeps 5
  • 2.5 bathrooms
     

    Marathon 2 Bedroom Waterfront Home
    • Marathon
    • House (single)
    • 2 bedrooms
    • Weekly rates
      From $2,995 to $3,995 USD
     

    Enjoy Your Very Own Cozy Florida Key Villa!
    • Duck Key
    • Villa
    • 2 bedrooms, sleeps 2-4
    • 1.5 bathrooms
    • Weekly rates
      From $3,100 to $3,500 USD
     

    100 ft. Dock - Private Pool - Marathon Florida
    • Marathon
    • House (single)
    • 4 bedrooms
    • 4 bathrooms
    • Weekly rates
      From $2,595 to $3,995 USD
     

    Private Island on Marathon in the Florida Keys
    • Marathon
    • House (single)
    • 2 bedrooms
    • 2 bathrooms
    • Weekly rates
      From $3,995 to $5,995 USD
     

    MERMAID'S ROCK - Key West, FL
    • Key West
    • House (single)
    • 4 bedrooms, sleeps 8
    • 3 bathrooms
       

      Marathon 3 Bedroom 3 Bath Gulf Front Home
      • Marathon
      • House (single)
      • 3 bedrooms
      • 3 bathrooms
      • Weekly rates
        From $2,495 to $3,895 USD
       

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

        Key West Suite, Private Jacuzzi, Near Activities Downtown.
        • Key West
        • Suite
        • 1 bedrooms, sleeps 4
        • 1 bathrooms
        • Weekly rates
          From $1,176 to $1,736 USD
         

        Key West Luxury Home
        • Key West
        • Townhouse
        • 7 bedrooms
        • 9 bathrooms
           

          Two-Bedroom Conch Villa In Florida Keys
          • Duck Key
          • Villa
          • 2 bedrooms, sleeps 5
          • 2 bathrooms
          • Weekly rates
            From $1,500 to $2,100 USD
           

          Spectacular Gulf Front Luxury Home on 2.5 Acres property is managed by "American Paradise"
          • Grassy Key
          • House (single)
          • 6 bedrooms, sleeps 16
          • 5.5 bathrooms
          • Weekly rates
            From $5,500 to $11,000 USD
           

          New Waterfront Rental W/Pool & Dock
          • Marathon
          • House (single)
          • 5 bedrooms
          • 4 bathrooms
             

            Tropical Paradise Oceanfront Home with Pool
            • Cudjoe Key
            • House (single)
            • 2 bedrooms, sleeps 6
            • 2 bathrooms
               

              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
                 

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

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

                    Hideaway in Key West with Pool - Near Activities & Restaurants.
                    • Key West
                    • Cottage
                    • 3 bedrooms, sleeps 6
                    • 2 bathrooms
                    • Weekly rates
                      From $2,856 to $3,556 USD
                     

                    Island Oasis Garden Home Vacation Rental - Key West
                    • Key West
                    • Townhouse
                    • 2 bedrooms, sleeps 4
                    • 2 bathrooms
                    • Weekly rates
                      From $1,500 to $2,100 USD
                     

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

                      Grassy Key/Marathon Gulf Front Property - property is managed by "American Paradise"
                      • Grassy Key
                      • House (single)
                      • 4 bedrooms, sleeps 8 Adults +
                      • 2 bathrooms
                      • Weekly rates
                        From $2,800 to $6,200 USD
                       

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

                        Bayside 1st floor Condo on Florida Bay - Islamorada, Florida
                        • Islamorada
                        • Condo
                        • 1 bedrooms, sleeps 2-4
                        • 2 bathrooms
                        • Weekly rates
                          From $0 to $0 USD
                         

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

                          100 ft. Dock, Passes to the Cabana Club Pool & Sandy Beach
                          • Marathon
                          • House (single)
                          • 4 bedrooms
                          • 2 bathrooms
                          • Weekly rates
                            From $2,495 to $3,995 USD
                           

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

                            Classic Key West Estate Vacation Rental
                            • Key West
                            • House (single)
                            • 6 bedrooms, sleeps 12-14
                            • 4 bathrooms
                            • Weekly rates
                              From $5,000 to $7,500 USD
                             

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

                              Victorian Mansion Vacation Rental - Key West
                              • Key West
                              • House (single)
                              • 5 bedrooms, sleeps 10
                              • 3 bathrooms
                              • Weekly rates
                                From $4,450 to $5,350 USD
                               

                              Old Town Key West Pool Home with 2 Off-Street Parking Spaces!
                              • Key West
                              • House (single)
                              • 2 bedrooms, sleeps 6
                              • 2.5 bathrooms
                              • Weekly rates
                                From $2,786 to $3,486 USD
                               

                              "Havana Lane" An Old Town Vacation Rental Retreat
                              • Key West
                              • Cottage
                              • 2 bedrooms, sleeps 4
                              • 2 bathrooms
                                 

                                1 Bedroom Waterfront Home
                                • Marathon
                                • House (single)
                                • 1 bedrooms
                                • 1 bathrooms
                                • Weekly rates
                                  From $2,895 to $3,895 USD
                                 

                                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
                                • Weekly rates
                                  From $6,800 to $9,300 USD
                                 

                                Amelia's Hideaway Vacation Rental - Key West
                                • Key West
                                • Villa
                                • 4 bedrooms, sleeps 2-10
                                • 3.5 bathrooms
                                • Weekly rates
                                  From $3,800 to $4,800 USD
                                 

                                Gorgeous Views - Gorgeous Home - Marathon / Grassy Key property is managed by "American Paradise"
                                • Grassy Key
                                • House (single)
                                • 5 bedrooms, sleeps 14
                                • 4 bathrooms
                                • Weekly rates
                                  From $4,500 to $8,500 USD
                                 

                                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
                                   

                                  Fantasy Resort Villa Vacation Rental - Key West
                                  • Key West
                                  • Villa
                                  • 3 bedrooms, sleeps 8
                                  • 2.5 bathrooms
                                  • Weekly rates
                                    From $3,500 to $4,500 USD
                                   

                                  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)
                                  • 4 bedrooms, sleeps 8
                                  • 3 bathrooms
                                  • Weekly rates
                                    From $2,500 to $5,500 USD
                                   

                                  PRISTINE OCEANFRONT HOME IN ISLAMORADA, THE FLORIDA KEYS - Rent All or Rent Separately
                                  • Islamorada
                                  • House (single)
                                  • 10 bedrooms, sleeps 2-28
                                  • 2-8 bathrooms
                                  • Weekly rates
                                    From $4,900 to $11,000 USD
                                   

                                  Beautiful Florida Key Three Bedroom Cottage Villa
                                  • Duck Key
                                  • Cottage
                                  • 3 bedrooms, sleeps 8
                                  • 2.5 bathrooms
                                     

                                    Ocean View Luxury Vacation Rental - Key West
                                    • Key West
                                    • Condo
                                    • 3 bedrooms, sleeps 6
                                    • 2 bathrooms
                                    • Weekly rates
                                      From $2,000 to $2,800 USD
                                     

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

                                      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
                                       

                                      THE KEYS KOTTAGE has it all - Islamorada, Florida
                                      • Islamorada
                                      • Villa
                                      • 2 bedrooms, sleeps 4-8
                                      • 2 bathrooms
                                      • Weekly rates
                                        From $0 to $0 USD
                                       

                                      8 Bedrooms 6 Bathrooms in 2 Adjacent Gulf Front Homes - 2 100 ft Docks - Private Pool - Passes to the Cabana Club
                                      • Marathon
                                      • House (single)
                                      • 8 bedrooms
                                      • 6 bathrooms
                                      • Weekly rates
                                        From $4,590 to $7,990 USD
                                       

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

                                        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
                                           

                                          Island Village Cottage Vacation Rental - Key West
                                          • Key West
                                          • Cottage
                                          • 2 bedrooms, sleeps 4-6
                                          • 2 bathrooms
                                          • Weekly rates
                                            From $1,850 to $2,550 USD
                                           

                                          Island Rendezvous Vacation Rental - Key West
                                          • Key West
                                          • Villa
                                          • 6 bedrooms, sleeps 14
                                          • 5 bathrooms
                                          • Weekly rates
                                            From $5,850 to $7,500 USD
                                           

                                          Breathtaking Ocean Views with 60ft dock on crystal clean canal
                                          • Cudjoe Key
                                          • House (single)
                                          • 3 bedrooms, sleeps 6 to 8
                                          • 2 bathrooms
                                          • Weekly rates
                                            From $1,000 to $1,125 USD
                                           

                                          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 $1,000 to $1,400 USD
                                           

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

                                            Seabird Key, Private Island, Florida Keys...with a stunning home, 19' Boston Whaler, Kayaks, Hobie Cat, and a long list of unexpected amenities.
                                            • Nautical Maps shown as Russell Key
                                            • Private Island-all to yourself
                                            • 3 bedrooms, sleeps 8
                                            • 3 bathrooms
                                            • Weekly rates
                                              From $5,595 to $6,995 USD
                                             

                                            WATERFRONT Condo, "PARADISE AT GULFPOINTE"-- Heated Pool, Dock, Views
                                            • Marathon
                                            • Condo
                                            • 2 bedrooms, sleeps 4 Ad & 2 Ch
                                            • 2 1/2 bathrooms
                                            • Weekly rates
                                              From $1,000 to $1,600 USD
                                             

                                            Key West Cottage For Two with Hot tub, tiki Bar, Private Yard.
                                            • Key West
                                            • Cottage
                                            • 1 bedrooms, sleeps 2
                                            • 1 bathrooms
                                            • Weekly rates
                                              From $1,375 to $1,876 USD
                                             

                                            38' Houseboat Rental - Houseboat on the Gulf of Mexico
                                            • Marathon
                                            • HouseBoat
                                            • 1 bedrooms, sleeps 4-5
                                            • 1 bathrooms
                                            • Weekly rates
                                              From $2,995 to $4,195 USD
                                             

                                            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
                                               

                                              Florida Key Villa - Santuary Villas
                                              • Duck Key
                                              • House (single)
                                              • 2-4 bedrooms, sleeps 4-8
                                              • 1.5 - 4 bathrooms
                                              • Weekly rates
                                                From $3,000 to $3,500 USD
                                               

                                              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
                                               

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

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

                                               
                                                Rental Locations   (Listed alphabetically by City or Town)
                                               

                                                City BR(s) BA(s) Sleeps Description
                                              Big Coppitt Key 6 BR 3.5 BA 10 Key West Vacation Home, Views of the bay, Private, Tiki Hut.
                                              Big Pine Key 2 to 10 BR 1.5 to 5.5 BA 4 to 20 The San Marco Homes & Bungalow - Big Pine Key
                                              Big Pine Key 2 BR 2 BA 4 Fisherman’s Paradise This Home Will Not Disappoint - Florida
                                              Big Pine Key 2 BR 2 BA 4 Beautiful Home - Great Views - Big Pine Key
                                              Big Pine Key 3 BR 2 BA 6 Gorgeous Views - Big Pine Key
                                              Big Pine Key 3 BR 3 BA 6 Big Pine Key Oceanfront Vacation Home - Atlantis
                                              Big Pine Key 3 BR 2 BA 6 Magnificent Open Water Views - Big Pine Key Vacation Home
                                              Big Pine Key 3 BR 1 BA 8-9 Fabulous Florida Keys Vacation in Port Pine Heights
                                              Big Pine Key 3 BR 2 BA 6 Tropical Bay
                                              Cudjoe Key 1 BR 1 BA 2 Magnificent Cudjoe Key Vacation Home
                                              Cudjoe Key 2 BR 2 BA 6 Tropical Paradise Oceanfront Home with Pool
                                              Cudjoe Key 2 BR 2 BA 4 Vacation in Paradise - Located on Cudjoe Key
                                              Cudjoe Key 3 BR 2 BA 6 Waterfront Vacation Rental - Casa Rosado
                                              Cudjoe Key 3 BR 2 BA 6 Cudjoe Paradise
                                              Cudjoe Key 3 BR 2 BA 6 Quiet Waters - Cudjoe Key
                                              Cudjoe Key 3 BR 2 BA 6 to 8 Breathtaking Ocean Views with 60ft dock on crystal clean canal
                                              Cudjoe Key 3 BR 2 BA 6 Suncatcher's Dream - Paradise in the Beautiful Florida Keys.
                                              Cudjoe Key 3 BR 2 BA 6 Cudjoe Ocean Shores Room for all your water toys
                                              Duck Key 2 BR 2 BA 7 Waterfront Keys to Memories - Duck Key
                                              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 1.5 BA 2-4 Enjoy Your Very Own Cozy Florida Key Villa!
                                              Duck Key 2 BR 2 BA 5 Two-Bedroom Conch Villa In Florida Keys
                                              Duck Key 2-4 BR 1.5 - 4 BA 4-8 Florida Key Villa - Santuary Villas
                                              Duck Key 3 BR 2.5 BA 8 Beautiful Florida Key Three Bedroom Cottage Villa
                                              Duck Key 5 BR BA The Keys Vacation - Tingler Isle Luxury Home
                                              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"
                                              Islamorada 1 BR 2 BA 2-4 Bayside 1st floor Condo on Florida Bay - Islamorada, Florida
                                              Islamorada 2 BR 2 BA 4-8 THE KEYS KOTTAGE has it all - Islamorada, Florida
                                              Islamorada 2 BR 2 BA Oceanfront Islamorada Condo Rentals Located in the Beautiful Florida Keys
                                              Islamorada 2 BR 2 BA 6 Futura Yacht Club - Tropical Paradise - Islamorada
                                              Islamorada 3 BR 3 BA 6 Best Florida Keys Rental - Islamorada
                                              Islamorada 4 BR 3 BA 8-10 The Perfect Getaway with Heated Pool and Jacuzzi - IN THE HEART of ISLAMORADA
                                              Islamorada 10 BR 2-8 BA 2-28 PRISTINE OCEANFRONT HOME IN ISLAMORADA, THE FLORIDA KEYS - Rent All or Rent Separately
                                              Key Colony Beach 2 BR 2 BA 4 Key Colony Sunrise Retreat - Book Now for a $100.00 Gas Credit
                                              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 3 BR 2 BA 8 Bright & Breezy - Very Popular Home - WiFi & Cabana Club Included!
                                              Key Colony Beach 6 BR BA Key Colony Beach Waterfront Pool Home
                                              Key Largo BR BA Key Largo Yacht Rentals - "The Key in Life is to Take the Water"
                                              Key Largo 1 BR 1 BA 2-6 BAY FRONT Cottages & your own FREE 22’ SAILBOAT + Paddle Boats, Kayaks, Canoes, Fishing & Snorkeling Gear, Sun Sets, Dolphins & Manatees Tiki Huts
                                              Key Largo 3 BR 2 BA 8 Key Largo "Manatee Manor "
                                              Key West Studio 1 BA 2 "Casa Atlantica Studio" Experience Breathtaking Ocean Views From This Secluded Private Studio.
                                              Key West BR BA Luxurious Key West Vacation Home
                                              Key West 1 BR 1 BA 4 Key West Cottage - Butterfly Garden
                                              Key West 1 BR 1 BA 2 "Casa Atlantica One" - Breathtaking Ocean Views From This Secluded Private Ocean Front Apartment.
                                              Key West 1 BR 1 BA 2 Land’s End one bedroom one bath cottage available monthly near historic seaport
                                              Key West 1 BR 1 BA 2-4 Key West Suite - Near Beach, Restaurants and Duval Street.
                                              Key West 1 BR 1 BA 2 "Key Lime Calypso "A great vacation home in the heart of Old Town Key West!
                                              Key West 1 BR 1 BA "Buddy Shula's Paradise Place" Spacious 1 Bedroom Key West Vacation Rental
                                              Key West 1 BR 1 BA 2 Key West Cottage For Two with Hot tub, tiki Bar, Private Yard.
                                              Key West 1 BR 1 BA 2-4 Key West Carriage Cottage
                                              Key West 1 BR 1 BA 4 Vintage Luxury Cottage Vacation Rental - Just Off Upper Duval Street with Pool
                                              Key West 1 BR 1 BA 2-4 Key West Garden Suite - Key West, Florida
                                              Key West 1 BR 1 BA 2-4 Key West Studio Suite in the Gardens, Near Restaurants, and The Beach.
                                              Key West 1 BR 1 BA 2 Fabulous Key West Cottage with Art-Deco Interior Design
                                              Key West 1 BR 1 BA 4 Margaret’s Harborside Cottage one bedroom one bath cottage available monthly near Historic seaport
                                              Key West 1 BR 1 BA 2-4 Key West Studio Suite - Peaceful & Serene yet close to city activities.
                                              Key West 1 - 4 BR 1 - 2 BA 4 per "Pete's Cottages" Beautiful Vacation Rental Cottages
                                              Key West 1 BR 1 BA 4 Key West Suite, Private Jacuzzi, Near Activities Downtown.
                                              Key West 1 BR 1 BA 4 Egret one bedroom cottages in the heart of the historic district
                                              Key West 2 BR 2 BA 2-6 Down Island Digs Vacation Rental in Old Town Key West
                                              Key West 2 BR 2 BA 4 Upscale Modern Key West Cottage - Tropical Chill
                                              Key West 2 BR 2 BA 4 "Beach Club #201" Luxurious Oceanfront Condo with Magnificent views of the Ocean
                                              Key West 2 BR 2 BA 6 Suite Paradise - Wonderful Key West Home with Private Pool
                                              Key West 2 BR 2.5 BA 6 Fantastic Key West Vacation Rental - Amelia Home
                                              Key West 2 BR 2 BA 4 Howe St. Hideaway two bedroom two bath home located in the Old Town in a very peaceful area.
                                              Key West 2 BR 2 BA 2-4 Click here to view more details about this property
                                              Key West 2 BR 2.5 BA Foundry on the Waterfront - Key West
                                              Key West 2 BR 2 BA 4 "Havana Lane" An Old Town Vacation Rental Retreat
                                              Key West 2 BR 2 BA 4 Mahogany Breezes
                                              Key West 2 BR 2 BA 6 Tropical Breeze - two bedroom two bath oceanfront condo
                                              Key West 2 BR 2 BA 6 Key West Crown Jewel - Enjoy Key West in STYLE!!
                                              Key West 2 BR 2 BA 4 Island Oasis Garden Home Vacation Rental - Key West
                                              Key West 2 BR 2 BA 2-6 Key West - Cockadoodle Cottage with Pool
                                              Key West 2 BR 2 BA 4 Ocean Front Luxury Condominium at 1800 Atlantic #435
                                              Key West 2 BR 2 BA 6 Fully Renovated Luxury Home in the heart of Old Town Key West.
                                              Key West 2 BR 2.5 BA 6 Artist's House,2 Bedroom Condo,Downtown Key West.
                                              Key West 2 BR 2.5 BA 5 BAMBOO KEY - KEY WEST
                                              Key West 2 BR 2.5 BA 4 "Dockside Villa" - 2 bedroom 2 1/2 bath Townhome with Dockage
                                              Key West 2 BR 1.5 BA 5 Carols Bungalow - Two bedroom one 1/2 bath townhome available monthly
                                              Key West 2 BR 1 BA 4 Aquamarine - two bedroom one bath upstairs condo
                                              Key West 2 BR 1 BA 4 Key West Cottage with Jacuzzi - Ideal for Relaxing.
                                              Key West 2 BR 1.5 BA 4 "Shipyard Palms " Charming Gated Comunity Condo in the heart of HIstoric District
                                              Key West 2 BR 1 BA 4-6 Romantic Garden Cottage in Key West
                                              Key West 2 BR 2 BA 4-6 Key West Southern Sunrise Vacation Rental
                                              Key West 2 BR 2.5 BA CARIBBEAN CHARM - KEY WEST
                                              Key West 2 BR 2 BA 6 Atlantic Retreat- two bedroom two bath oceanview condo on Atlantic
                                              Key West 2 BR 2 BA 6 This great two bedroom two bath condominium at 1800 Atlantic Condominiums offers you a wonderful relaxing garden view.
                                              Key West 2 BR 2 BA 4 Southern Wind - two bedroom two bath home in historic district
                                              Key West 2 BR 2 BA 4 "Beach Club #303" Luxurious Oceanfront Condo with Magnificent views of the Ocean
                                              Key West 2 BR 2 BA 2-4 Cottage in the heart of Key West Bustling Seaport,Private Pool.
                                              Key West 2 BR 2 BA 6 Key West Vacation Rentals
                                              Key West 2 BR 2 BA 4 Catherine St. Getaway- Old Town Home with Pool
                                              Key West 2 - 4 (Vari BR 2 - 4 (Var BA 4 - 10 (Var "Duval Square" Vacation Rental Condo's Conveniently Located
                                              Key West 2 BR 2.5 BA 6 SPINNAKER SAIL - Key West, FL
                                              Key West 2 BR 1 BA 4 Shipyard Condo 'Havana Views' - Key West
                                              Key West 2 BR 2 BA 2-5 Henry's Piece Of Paradise On The Ocean In Key West
                                              Key West 2 BR 2 BA 6 A Zen Garden - Tranquil 2 bedroom 2 bath oceanfront condo
                                               
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                                              Featured
                                              Property Managers

                                              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...


                                              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
                                              Key West, FL
                                              Rates Vary
                                              Rent a private home, cottage, villa, or condo as an alternative to your typical Key West hotel stay.

                                              www.american-paradise.com
                                              Florida Keys, FL
                                              Rates from $1,100 / week
                                              American Paradise Florida Keys Vacation Rentals.

                                              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.





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



                                              Marathon 2 Bedroom Waterfront Home
                                              Marathon House (single), 2 bedrooms Weekly rates from $2,995 to $3,995 USD



                                              Enjoy Your Very Own Cozy Florida Key Villa!
                                              Duck Key Villa, 2 bedrooms, sleeps 2-4, 1.5 bathrooms Weekly rates from $3,100 to $3,500 USD



                                              100 ft. Dock - Private Pool - Marathon Florida
                                              Marathon House (single), 4 bedrooms, 4 bathrooms Weekly rates from $2,595 to $3,995 USD



                                              Private Island on Marathon in the Florida Keys
                                              Marathon House (single), 2 bedrooms, 2 bathrooms Weekly rates from $3,995 to $5,995 USD



                                              MERMAID'S ROCK - Key West, FL
                                              Key West House (single), 4 bedrooms, sleeps 8, 3 bathrooms



                                              Marathon 3 Bedroom 3 Bath Gulf Front Home
                                              Marathon House (single), 3 bedrooms, 3 bathrooms Weekly rates from $2,495 to $3,895 USD



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



                                              Key West Suite, Private Jacuzzi, Near Activities Downtown.
                                              Key West Suite, 1 bedrooms, sleeps 4, 1 bathrooms Weekly rates from $1,176 to $1,736 USD



                                              Key West Luxury Home
                                              Key West Townhouse, 7 bedrooms, 9 bathrooms



                                              Two-Bedroom Conch Villa In Florida Keys
                                              Duck Key Villa, 2 bedrooms, sleeps 5, 2 bathrooms Weekly rates from $1,500 to $2,100 USD



                                              Spectacular Gulf Front Luxury Home on 2.5 Acres property is managed by "American Paradise"
                                              Grassy Key House (single), 6 bedrooms, sleeps 16, 5.5 bathrooms Weekly rates from $5,500 to $11,000 USD



                                              New Waterfront Rental W/Pool & Dock
                                              Marathon House (single), 5 bedrooms, 4 bathrooms



                                              Tropical Paradise Oceanfront Home with Pool
                                              Cudjoe Key House (single), 2 bedrooms, sleeps 6, 2 bathrooms



                                              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



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



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



                                              Hideaway in Key West with Pool - Near Activities & Restaurants.
                                              Key West Cottage, 3 bedrooms, sleeps 6, 2 bathrooms Weekly rates from $2,856 to $3,556 USD



                                              Island Oasis Garden Home Vacation Rental - Key West
                                              Key West Townhouse, 2 bedrooms, sleeps 4, 2 bathrooms Weekly rates from $1,500 to $2,100 USD



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



                                              Grassy Key/Marathon Gulf Front Property - property is managed by "American Paradise"
                                              Grassy Key House (single), 4 bedrooms, sleeps 8 Adults +, 2 bathrooms Weekly rates from $2,800 to $6,200 USD



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



                                              Bayside 1st floor Condo on Florida Bay - Islamorada, Florida
                                              Islamorada Condo, 1 bedrooms, sleeps 2-4, 2 bathrooms Weekly rates from $0 to $0 USD



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



                                              100 ft. Dock, Passes to the Cabana Club Pool & Sandy Beach
                                              Marathon House (single), 4 bedrooms, 2 bathrooms Weekly rates from $2,495 to $3,995 USD



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



                                              Classic Key West Estate Vacation Rental
                                              Key West House (single), 6 bedrooms, sleeps 12-14, 4 bathrooms Weekly rates from $5,000 to $7,500 USD



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



                                              Victorian Mansion Vacation Rental - Key West
                                              Key West House (single), 5 bedrooms, sleeps 10, 3 bathrooms Weekly rates from $4,450 to $5,350 USD



                                              Old Town Key West Pool Home with 2 Off-Street Parking Spaces!
                                              Key West House (single), 2 bedrooms, sleeps 6, 2.5 bathrooms Weekly rates from $2,786 to $3,486 USD



                                              "Havana Lane" An Old Town Vacation Rental Retreat
                                              Key West Cottage, 2 bedrooms, sleeps 4, 2 bathrooms



                                              1 Bedroom Waterfront Home
                                              Marathon House (single), 1 bedrooms, 1 bathrooms Weekly rates from $2,895 to $3,895 USD



                                              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 Weekly rates from $6,800 to $9,300 USD



                                              Amelia's Hideaway Vacation Rental - Key West
                                              Key West Villa, 4 bedrooms, sleeps 2-10, 3.5 bathrooms Weekly rates from $3,800 to $4,800 USD



                                              Gorgeous Views - Gorgeous Home - Marathon / Grassy Key property is managed by "American Paradise"
                                              Grassy Key House (single), 5 bedrooms, sleeps 14, 4 bathrooms Weekly rates from $4,500 to $8,500 USD



                                              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



                                              Fantasy Resort Villa Vacation Rental - Key West
                                              Key West Villa, 3 bedrooms, sleeps 8, 2.5 bathrooms Weekly rates from $3,500 to $4,500 USD



                                              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), 4 bedrooms, sleeps 8, 3 bathrooms Weekly rates from $2,500 to $5,500 USD



                                              PRISTINE OCEANFRONT HOME IN ISLAMORADA, THE FLORIDA KEYS - Rent All or Rent Separately
                                              Islamorada House (single), 10 bedrooms, sleeps 2-28, 2-8 bathrooms Weekly rates from $4,900 to $11,000 USD



                                              Beautiful Florida Key Three Bedroom Cottage Villa
                                              Duck Key Cottage, 3 bedrooms, sleeps 8, 2.5 bathrooms



                                              Ocean View Luxury Vacation Rental - Key West
                                              Key West Condo, 3 bedrooms, sleeps 6, 2 bathrooms Weekly rates from $2,000 to $2,800 USD



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



                                              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



                                              THE KEYS KOTTAGE has it all - Islamorada, Florida
                                              Islamorada Villa, 2 bedrooms, sleeps 4-8, 2 bathrooms Weekly rates from $0 to $0 USD



                                              8 Bedrooms 6 Bathrooms in 2 Adjacent Gulf Front Homes - 2 100 ft Docks - Private Pool - Passes to the Cabana Club
                                              Marathon House (single), 8 bedrooms, 6 bathrooms Weekly rates from $4,590 to $7,990 USD



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



                                              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



                                              Island Village Cottage Vacation Rental - Key West
                                              Key West Cottage, 2 bedrooms, sleeps 4-6, 2 bathrooms Weekly rates from $1,850 to $2,550 USD



                                              Island Rendezvous Vacation Rental - Key West
                                              Key West Villa, 6 bedrooms, sleeps 14, 5 bathrooms Weekly rates from $5,850 to $7,500 USD



                                              Breathtaking Ocean Views with 60ft dock on crystal clean canal
                                              Cudjoe Key House (single), 3 bedrooms, sleeps 6 to 8, 2 bathrooms Weekly rates from $1,000 to $1,125 USD



                                              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 $1,000 to $1,400 USD



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



                                              Seabird Key, Private Island, Florida Keys...with a stunning home, 19' Boston Whaler, Kayaks, Hobie Cat, and a long list of unexpected amenities.
                                              Nautical Maps shown as Russell Key Private Island-all to yourself, 3 bedrooms, sleeps 8, 3 bathrooms Weekly rates from $5,595 to $6,995 USD



                                              WATERFRONT Condo, "PARADISE AT GULFPOINTE"-- Heated Pool, Dock, Views
                                              Marathon Condo, 2 bedrooms, sleeps 4 Ad & 2 Ch, 2 1/2 bathrooms Weekly rates from $1,000 to $1,600 USD



                                              Key West Cottage For Two with Hot tub, tiki Bar, Private Yard.
                                              Key West Cottage, 1 bedrooms, sleeps 2, 1 bathrooms Weekly rates from $1,375 to $1,876 USD



                                              38' Houseboat Rental - Houseboat on the Gulf of Mexico
                                              Marathon HouseBoat, 1 bedrooms, sleeps 4-5, 1 bathrooms Weekly rates from $2,995 to $4,195 USD



                                              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



                                              Florida Key Villa - Santuary Villas
                                              Duck Key House (single), 2-4 bedrooms, sleeps 4-8, 1.5 - 4 bathrooms Weekly rates from $3,000 to $3,500 USD



                                              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



                                              Bright & Breezy - Very Popular Home - WiFi & Cabana Club Included!
                                              Key Colony Beach House (multifamily), 3 bedrooms, sleeps 8, 2 bathrooms Weekly rates from $1,325 to $1,950 USD



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