Make a Florida Upper Keys vacation rental your home away from home in the Florida Keys.

Guests of Islamadora vacation rentals will find great fishing and diving opportunities here. Highlights for guests of Islamadora vacation rentals include hiking along the nature trails at Long Key State Recreation Area and visiting the Windley Key Quarry Fossil Reef State Geologic Site. The Theater of the Sea, on Windley Key, features shows starring dolphins and other sea creatures.

The northernmost island in the Florida Keys, Key Largo is just an hour’s drive south of Miami. Guests of Key Largo vacation rentals will find a number of local operators offering snorkeling and diving trips, as well as plenty of fishing charters. Other attractions for guests of Key Largo vacation rentals include kayaking and bird watching in the nearby Everglades. Tavernier vacation rentals are also a popular choice in the Upper Keys.

You're sure to find the perfect Upper Florida Keys vacation rental for a fabulous Florida vacation. Reserve your Upper Florida Keys vacation rental today!

Expand your search for Florida vacation rentals to include Miami vacation rentals and Ft. Lauderdale rentals in South Florida, Destin vacation rentals and Sanibel Island rentals on the Gulf Coast, or Orlando vacation home rentals near Disney.

While you're here, discover more about the Florida Keys in our vacation ideas section, which includes info on top beaches and topics like long-term rentals in Key Largo.

You have sent
a request for
information to
this owner.
FILTERS
List View
Map View
Cancel Apply Filters
  1.  >
  2.  >
  3.  >
  4.  >
  5.  >

Upper Florida Keys: Houses, Condos & More(853)

sort by HomeAway Sort
Kawama Yacht Club- Oceanfront Private Beach - Sunsets!
    2 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 8
$200 - $300
per night

Kawama Yacht Club- Oceanfront Private Beach - Sunsets!

Book it Now!
3 night Minimum Stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
  1. Upper Florida Keys >
  2. Key Largo Condo
#404942vb
    (17)
    Waterfront Luxury Home with An Incredible View on a Full Acre, Free Secured WiFi
      4 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 8
    $2,400 - $2,550
    per week

    Waterfront Luxury Home with An Incredible View on a Full Acre, Free Secured WiFi

    7 night Minimum Stay
    • 4 BR,
    • 3 BA,
    • Sleeps 8
    1. Upper Florida Keys >
    2. Key Largo House
    #332253
      (26)
      Oceanfront resort condo beautifully renovated. Ocean & Marina views Free WI-FI
        2 Bedrooms,
      • 2 Bathrooms
        • , Sleeps 6
      $1,080 - $1,380
      per week

      Oceanfront resort condo beautifully renovated. Ocean & Marina views Free WI-FI

      7 night Minimum Stay
      • 2 BR,
      • 2 BA,
      • Sleeps 6
      1. Upper Florida Keys >
      2. Key Largo Condo
      #172415
        (25)
        Paradise for Rent in the Florida Keys!! Designer Vacation Home on Deep Water
          3 Bedrooms,
        • 2 Bathrooms
          • , Sleeps 7
        $300 - $350
        per night

        Paradise for Rent in the Florida Keys!! Designer Vacation Home on Deep Water

        3 night Minimum Stay
        • 3 BR,
        • 2 BA,
        • Sleeps 7
        1. Upper Florida Keys >
        2. Islamorada House
        #330045
          (17)
          Beautiful Key Largo Town Home Fully Renovated Top to Bottom
            2 Bedrooms,
          • 2 Bathrooms
            • , Sleeps 6
          $180 - $200
          per night

          Beautiful Key Largo Town Home Fully Renovated Top to Bottom

          3 night Minimum Stay
          • 2 BR,
          • 2 BA,
          • Sleeps 6
          1. Upper Florida Keys >
          2. Key Largo Townhome
          #450084vb
            (8)
            Meagan's Beach House - Bayfront Home with spectacular Sunrises and Sunsets
              2 Bedrooms,
            • 2 Bathrooms
              • , Sleeps 6
            $1,600
            per week

            Meagan's Beach House - Bayfront Home with spectacular Sunrises and Sunsets

            7 night Minimum Stay
            • 2 BR,
            • 2 BA,
            • Sleeps 6
            1. Upper Florida Keys >
            2. Key Largo House
            #265117
              (21)
              World-Class Private Retreat Compound - Over 300' Waterfront- 152' Dock
                7 Bedrooms,
              • 6 Bathrooms
                • , Sleeps 14
              $7,000
              per week

              World-Class Private Retreat Compound - Over 300' Waterfront- 152' Dock

              Book it Now!
              7 night Minimum Stay
              • 7 BR,
              • 6 BA,
              • Sleeps 14
              1. Upper Florida Keys >
              2. Key Largo Estate
              #3482337
                Affordable Key Largo Beach Cottage! Open water location
                  2 Bedrooms,
                • 2 Bathrooms
                  • , Sleeps 6
                $185
                per night

                Affordable Key Largo Beach Cottage! Open water location

                3 night Minimum Stay
                • 2 BR,
                • 2 BA,
                • Sleeps 6
                1. Upper Florida Keys >
                2. Key Largo House
                #107982
                  (6)
                  Waterfront Cottage - Beach and Dockage! Sunset Views!
                    2 Bedrooms,
                  • 1 Bathroom
                    • , Sleeps 4
                  $150
                  per night

                  Waterfront Cottage - Beach and Dockage! Sunset Views!

                  3 night Minimum Stay
                  • 2 BR,
                  • 1 BA,
                  • Sleeps 4
                  1. Upper Florida Keys >
                  2. Key Largo House
                  #225990
                    (3)
                    Ocean Reef Club Pool 36' Seawall Beach Golf Tennis
                      2 Bedrooms,
                    • 1 Bathroom
                      • , Sleeps 5
                    $185 - $400
                    per night

                    Ocean Reef Club Pool 36' Seawall Beach Golf Tennis

                    2 - 7 night Minimum Stay
                    • 2 BR,
                    • 1 BA,
                    • Sleeps 5
                    1. Upper Florida Keys >
                    2. Ocean Reef Club Condo
                    #175223
                      (26)
                      Penthouse Condo Sunsets at Key Largo, Kawama Yacht Club Tower
                        2 Bedrooms,
                      • 2 Bathrooms
                        • , Sleeps 8
                      $950 - $2,095
                      per week

                      Penthouse Condo Sunsets at Key Largo, Kawama Yacht Club Tower

                      7 night Minimum Stay
                      • 2 BR,
                      • 2 BA,
                      • Sleeps 8
                      1. Upper Florida Keys >
                      2. Key Largo Condo
                      #233900
                        (32)
                        A Magnificent, Luxurious 7 Bedrooms, 5 Bath Rent All or Part
                          8 Bedrooms,
                        • 5 Bathrooms
                          • , Sleeps 24
                        $1,200
                        per night

                        A Magnificent, Luxurious 7 Bedrooms, 5 Bath Rent All or Part

                        3 night Minimum Stay
                        • 8 BR,
                        • 5 BA,
                        • Sleeps 24
                        1. Upper Florida Keys >
                        2. Key Largo House
                        #937436
                          (14)
                          Oceanfront Beach Resort - Direct Ocean Views - Free Secured WiFi!
                            2 Bedrooms,
                          • 2 Bathrooms
                            • , Sleeps 6
                          $795 - $1,200
                          per week

                          Oceanfront Beach Resort - Direct Ocean Views - Free Secured WiFi!

                          3 night Minimum Stay
                          • 2 BR,
                          • 2 BA,
                          • Sleeps 6
                          1. Upper Florida Keys >
                          2. Key Largo Condo
                          #130386
                            (5)
                            Elegant Beach Home With Dockage and WIFI in Key Largo! Pet friendly!
                              4 Bedrooms,
                            • 3 Bathrooms
                              • , Sleeps 12
                            $350
                            per night

                            Elegant Beach Home With Dockage and WIFI in Key Largo! Pet friendly!

                            3 night Minimum Stay
                            • 4 BR,
                            • 3 BA,
                            • Sleeps 12
                            1. Upper Florida Keys >
                            2. Key Largo House
                            #916757
                              Oceanfront Beach Resort- Stunning Ocean Views - Free Secured WIFI!
                                2 Bedrooms,
                              • 2 Bathrooms
                                • , Sleeps 8
                              $800 - $1,200
                              per week

                              Oceanfront Beach Resort- Stunning Ocean Views - Free Secured WIFI!

                              3 night Minimum Stay
                              • 2 BR,
                              • 2 BA,
                              • Sleeps 8
                              1. Upper Florida Keys >
                              2. Key Largo Condo
                              #119632
                                (5)
                                Beach House with Open Water views! Dockage Included!
                                  3 Bedrooms,
                                • 2 Bathrooms
                                  • , Sleeps 10
                                $300
                                per night

                                Beach House with Open Water views! Dockage Included!

                                3 night Minimum Stay
                                • 3 BR,
                                • 2 BA,
                                • Sleeps 10
                                1. Upper Florida Keys >
                                2. Key Largo House
                                #314828
                                  (10)
                                  Bay Front Home With Magnificent Views
                                    3 Bedrooms,
                                  • 3 Bathrooms
                                    • , Sleeps 8
                                  $500
                                  per night

                                  Bay Front Home With Magnificent Views

                                  3 night Minimum Stay
                                  • 3 BR,
                                  • 3 BA,
                                  • Sleeps 8
                                  1. Upper Florida Keys >
                                  2. Plantation Key House
                                  #452120vb
                                    2 Reviews
                                    Oceanfront Beach Resort - Hawaiian Island Style Setting - Free WiFi!
                                      2 Bedrooms,
                                    • 1 Bathroom, 
                                    • 1 Half Bath
                                      • , Sleeps 6
                                    $700 - $950
                                    per week

                                    Oceanfront Beach Resort - Hawaiian Island Style Setting - Free WiFi!

                                    3 night Minimum Stay
                                    • 2 BR,
                                    • 1 BA,
                                    • 1 HF BA,
                                    • Sleeps 6
                                    1. Upper Florida Keys >
                                    2. Key Largo Townhome
                                    #130780
                                      2 Reviews
                                      Oceanfront Beach Resort & Marina - Waterfront Villa - Free WiFi!
                                        3 Bedrooms,
                                      • 3 Bathrooms
                                        • , Sleeps 8
                                      $900 - $1,395
                                      per week

                                      Oceanfront Beach Resort & Marina - Waterfront Villa - Free WiFi!

                                      3 night Minimum Stay
                                      • 3 BR,
                                      • 3 BA,
                                      • Sleeps 8
                                      1. Upper Florida Keys >
                                      2. Key Largo Villa
                                      #132539
                                        1 Review
                                        Quite, charming, elegant, tropical, a beautiful setting on the bay
                                          5 Bedrooms,
                                        • 3 Bathrooms
                                          • , Sleeps 16
                                        $900
                                        per night

                                        Quite, charming, elegant, tropical, a beautiful setting on the bay

                                        3 night Minimum Stay
                                        • 5 BR,
                                        • 3 BA,
                                        • Sleeps 16
                                        1. Upper Florida Keys >
                                        2. Key Largo House
                                        #338473
                                          (23)
                                          The Views...Water Water Everywhere...Key Largo Home.
                                            4 Bedrooms,
                                          • 4 Bathrooms, 
                                          • 1 Half Bath
                                            • , Sleeps 10

                                          The Views...Water Water Everywhere...Key Largo Home.

                                          • 4 BR,
                                          • 4 BA,
                                          • 1 HF BA,
                                          • Sleeps 10
                                          1. Upper Florida Keys >
                                          2. Key Largo House
                                          #980977
                                            (3)
                                            Bayfront and Beautiful, A Boater's Dream
                                              3 Bedrooms,
                                            • 3 Bathrooms
                                              • , Sleeps 8

                                            Bayfront and Beautiful, A Boater's Dream

                                            • 3 BR,
                                            • 3 BA,
                                            • Sleeps 8
                                            1. Upper Florida Keys >
                                            2. Key Largo House
                                            #191669
                                              8 Reviews
                                              Key Largo's Premier Oceanfront Resort! 2,3 & 4 Bed Villa's, Free WiFi!
                                                3 Bedrooms,
                                              • 3 Bathrooms, 
                                              • 1 Half Bath
                                                • , Sleeps 9
                                              $1,295 - $1,795
                                              per week

                                              Key Largo's Premier Oceanfront Resort! 2,3 & 4 Bed Villa's, Free WiFi!

                                              3 night Minimum Stay
                                              • 3 BR,
                                              • 3 BA,
                                              • 1 HF BA,
                                              • Sleeps 9
                                              1. Upper Florida Keys >
                                              2. Key Largo Villa
                                              #354110
                                                (5)
                                                'Oceans Edge' -A Luxury Villa with a Spectacular Ocean and Marina View
                                                  3 Bedrooms,
                                                • 3 Bathrooms
                                                  • , Sleeps 8
                                                $1,500 - $1,950
                                                per week

                                                'Oceans Edge' -A Luxury Villa with a Spectacular Ocean and Marina View

                                                7 night Minimum Stay
                                                • 3 BR,
                                                • 3 BA,
                                                • Sleeps 8
                                                1. Upper Florida Keys >
                                                2. Key Largo Villa
                                                #338691
                                                  (30)
                                                  Oceanfront Home Adjacent to Pennecamp Coral Reef State Park
                                                    4 Bedrooms,
                                                  • 3 Bathrooms, 
                                                  • 1 Half Bath
                                                    • , Sleeps 8

                                                  Oceanfront Home Adjacent to Pennecamp Coral Reef State Park

                                                  • 4 BR,
                                                  • 3 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 8
                                                  1. Upper Florida Keys >
                                                  2. Key Largo House
                                                  #312507
                                                    6 Reviews
                                                    The Markeysa, the Ultimate Keys Experience - Private Beach
                                                      4 Bedrooms,
                                                    • 4 Bathrooms
                                                      • , Sleeps 10
                                                    $1,200
                                                    per night

                                                    The Markeysa, the Ultimate Keys Experience - Private Beach

                                                    4 night Minimum Stay
                                                    • 4 BR,
                                                    • 4 BA,
                                                    • Sleeps 10
                                                    1. Upper Florida Keys >
                                                    2. Islamorada House
                                                    #40210vb
                                                      (17)
                                                      Cocomo's
                                                        3 Bedrooms,
                                                      • 4 Bathrooms
                                                        • , Sleeps 14
                                                      $857
                                                      per night

                                                      Cocomo's

                                                      • 3 BR,
                                                      • 4 BA,
                                                      • Sleeps 14
                                                      1. Upper Florida Keys >
                                                      2. Islamorada House
                                                      #969325
                                                        (4)
                                                        Waterfront Key Largo luxury home with Bay access!!
                                                          3 Bedrooms,
                                                        • 2 Bathrooms, 
                                                        • 1 Half Bath
                                                          • , Sleeps 6
                                                        $200 - $310
                                                        per night

                                                        Waterfront Key Largo luxury home with Bay access!!

                                                        3 night Minimum Stay
                                                        • 3 BR,
                                                        • 2 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 6
                                                        1. Upper Florida Keys >
                                                        2. Key Largo House
                                                        #935531
                                                          2 Reviews
                                                          Luxury Oceanfront Resort Home - Voted Best in the Keys!!!
                                                            3 Bedrooms,
                                                          • 2 Bathrooms, 
                                                          • 1 Half Bath
                                                            • , Sleeps 10

                                                          Luxury Oceanfront Resort Home - Voted Best in the Keys!!!

                                                          • 3 BR,
                                                          • 2 BA,
                                                          • 1 HF BA,
                                                          • Sleeps 10
                                                          1. Upper Florida Keys >
                                                          2. Key Largo Condo
                                                          #129473
                                                            (16)
                                                            Private / Oceanfront Estate / Contemporary Interior Design
                                                              5 Bedrooms,
                                                            • 5 Bathrooms, 
                                                            • 1 Half Bath
                                                              • , Sleeps 12
                                                            $700 - $1,500
                                                            per night

                                                            Private / Oceanfront Estate / Contemporary Interior Design

                                                            3 - 7 night Minimum Stay
                                                            • 5 BR,
                                                            • 5 BA,
                                                            • 1 HF BA,
                                                            • Sleeps 12
                                                            1. Upper Florida Keys >
                                                            2. Key Largo House
                                                            #333821
                                                              (3)
                                                              • 1 - 30 of 853
                                                              Advertisement

                                                              Upper Florida Keys