Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Boats
Condos
Cottages
Estates
Hotels
Homes
Studios
Townhomes
Villas
Yachts
Barns
Bungalows
Cabins
Castles
Chalets
Farmhouses
Lodges

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Upper Florida Keys Pet Friendly Vacation Home Rentals(144)

144 Results
Book it Now!
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
    (14)
    7 night minimum stay
    • 4 BR,
    • 4 BA,
    • Sleeps 12
      (15)
      1 - 28 night minimum stay
      • 4 BR,
      • 5 BA,
      • Sleeps 10
        (4)
        3 - 5 night minimum stay
        • 2 BR,
        • 2 BA,
        • Sleeps 9
          (6)
          2 - 3 night minimum stay
          • 3 BR,
          • 3 BA,
          • 1 HF BA,
          • Sleeps 8
            1 Review
            7 night minimum stay
            • 3 BR,
            • 4 BA,
            • Sleeps 8
              (9)
              Book it Now!
              5 - 7 night minimum stay
              • 4 BR,
              • 4 BA,
              • 1 HF BA,
              • Sleeps 10
                (3)
                Book it Now!
                30 night minimum stay
                • 2 BR,
                • 2 BA,
                • Sleeps 4
                  (7)
                  • 3 BR,
                  • 3 BA,
                  • Sleeps 6
                    (12)
                    3 - 7 night minimum stay
                    • 3 BR,
                    • 2 BA,
                    • Sleeps 10
                      (11)
                      28 night minimum stay
                      • 4 BR,
                      • 3 BA,
                      • Sleeps 8
                        3 night minimum stay
                        • 4 BR,
                        • 3 BA,
                        • Sleeps 12
                          2 Reviews
                          3 night minimum stay
                          • 3 BR,
                          • 2 BA,
                          • Sleeps 8
                            28 night minimum stay
                            • 4 BR,
                            • 2 BA,
                            • Sleeps 14
                              7 night minimum stay
                              • 4 BR,
                              • 4 BA,
                              • Sleeps 10
                                (11)
                                • 3 BR,
                                • 2 BA,
                                • Sleeps 8
                                  (8)
                                  3 - 4 night minimum stay
                                  • 3 BR,
                                  • 2 BA,
                                  • 1 HF BA,
                                  • Sleeps 6
                                    (4)
                                    2 night minimum stay
                                    • 4 BR,
                                    • 4 BA,
                                    • 1 HF BA,
                                    • Sleeps 8
                                      28 night minimum stay
                                      • 3 BR,
                                      • 2 BA,
                                      • Sleeps 6
                                        1 Review
                                        7 night minimum stay
                                        • 5 BR,
                                        • 3 BA,
                                        • Sleeps 12
                                          (10)
                                          7 night minimum stay
                                          • 3 BR,
                                          • 3 BA,
                                          • Sleeps 8
                                            (24)
                                            Book it Now!
                                            3 night minimum stay
                                            • 3 BR,
                                            • 3 BA,
                                            • Sleeps 8
                                              7 night minimum stay
                                              • 2 BR,
                                              • 2 BA,
                                              • Sleeps 6
                                                2 Reviews
                                                7 night minimum stay
                                                • 2 BR,
                                                • 1 BA,
                                                • Sleeps 4
                                                  (10)
                                                  28 night minimum stay
                                                  • 3 BR,
                                                  • 3 BA,
                                                  • Sleeps 8
                                                    2 Reviews
                                                    28 night minimum stay
                                                    • 3 BR,
                                                    • 3 BA,
                                                    • 1 HF BA,
                                                    • Sleeps 10
                                                      (14)
                                                      7 night minimum stay
                                                      • 6 BR,
                                                      • 3 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 14
                                                        (9)
                                                        • 5 BR,
                                                        • 5 BA,
                                                        • Sleeps 14
                                                          (4)
                                                          6 night minimum stay
                                                          • 5 BR,
                                                          • 3 BA,
                                                          • Sleeps 14
                                                            $150 - $175
                                                            per night
                                                            Book it Now!
                                                            2 night minimum stay
                                                            • 2 BR,
                                                            • 1 BA,
                                                            • Sleeps 6
                                                              (3)
                                                               

                                                              Recent Upper Florida Keys Reviews

                                                              BEAUTIFUL AMAZING WONDERFUL STAY!!!!!

                                                              5 of 5
                                                              We rented for my daughters 33rd birthday, The home was very beautifully decorated and very clean. Everything was in its place washer and dryer were perfect the rooms were comfortable , The owner was pleasant and very helpful. The elevator was a plus due to my husbands knee issues so this is a great home if you have any problems going up or down stairs very accommodating. The area is fantastic and you have everything in walking distance if you need it. Love the peaceful area , We definitely would plan to go back again. THANK YOU
                                                              • Submitted: Sep 4, 2014
                                                              • Stayed: Aug 2014

                                                              What an AWESOME Place to stay

                                                              5 of 5
                                                              I am always a little apprehensive when looking for a place to stay on the internet, but with that being said this place is just plain AWESOME!!!!!!!! The pictures that you see are nothing compared to how the house is; the owners really worked with me and I appreciate that because when I was inquiring about the place I was in Afghanistan. The Family and I really enjoyed the house and all it has to offer; everything from the nice comfortable beds to the pool and hot tub to the dock where we parked our boat was just amazing. We originally were going to have the whole family there but it just ended up being the wife, son, and daughter, because our oldest daughter and her husband were unable to come. There is SO much room we probably didn’t use 60% of the house but that is in no way a knock on the place. The owners greeted us when we arrived and showed us everything the home has and they were very nice. The next time we come to the Keys we will definitely stay here again. If I had anything bad thing to say about this place it would be that large alligator statue that greets you when you walk thru the front door; I was not expecting that and we were somewhat disappointed that there were no Coconuts on the trees we really wanted some fresh ones (LOL). All and all this place is 10 out of 10 and we had a blast, thanks so much for having us.
                                                              • Submitted: Aug 31, 2014
                                                              • Stayed: Aug 2014

                                                              Great House, Perfect Location!

                                                              5 of 5
                                                              My family and I just left this great house after a week-long vacation. It's everything the photos and descriptions say it is. The owner is super nice and responsive, and the property manager made sure we had everything we needed. I've already inquired about staying here again next year! I'm a regular VRBO user and I highly recommend this house. Thanks!
                                                              • Submitted: Aug 5, 2014
                                                              • Stayed: Jul 2014