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 Rentals(219)

219 Results
Book it Now!
28 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
    (91)
    Book it Now!
    3 - 13 night minimum stay
    • 3 BR,
    • 3 BA,
    • Sleeps 8
      (17)
      Book it Now!
      7 night minimum stay
      • 3 BR,
      • 2 BA,
      • Sleeps 6
        (14)
        Book it Now!
        5 - 7 night minimum stay
        • 3 BR,
        • 2 BA,
        • 1 HF BA,
        • Sleeps 10
          (8)
          3 - 7 night minimum stay
          • 3 BR,
          • 2 BA,
          • Sleeps 10
            (11)
            3 - 7 night minimum stay
            • 2 BR,
            • 2 BA,
            • Sleeps 6
              (5)
              3 night minimum stay
              • 2 BR,
              • 1 BA,
              • Sleeps 4
                (3)
                3 night minimum stay
                • 4 BR,
                • 3 BA,
                • Sleeps 12
                  2 Reviews
                  2 - 3 night minimum stay
                  • 3 BR,
                  • 3 BA,
                  • 1 HF BA,
                  • Sleeps 8
                    1 Review
                    3 - 5 night minimum stay
                    • 2 BR,
                    • 2 BA,
                    • Sleeps 9
                      2 Reviews
                      7 night minimum stay
                      • 3 BR,
                      • 4 BA,
                      • Sleeps 8
                        (9)
                        7 night minimum stay
                        • 4 BR,
                        • 4 BA,
                        • Sleeps 8
                          (15)
                          1 - 28 night minimum stay
                          • 4 BR,
                          • 5 BA,
                          • Sleeps 10
                            (3)
                            7 night minimum stay
                            • 1 BR,
                            • 2 BA,
                            • Sleeps 4
                              (11)
                              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)
                                  28 night minimum stay
                                  • 4 BR,
                                  • 3 BA,
                                  • Sleeps 8
                                    • 3 BR,
                                    • 3 BA,
                                    • Sleeps 6
                                      (12)
                                      28 night minimum stay
                                      • 4 BR,
                                      • 2 BA,
                                      • Sleeps 14
                                        28 night minimum stay
                                        • 4 BR,
                                        • 3 BA,
                                        • 1 HF BA,
                                        • Sleeps 8
                                          3 - 4 night minimum stay
                                          • 3 BR,
                                          • 2 BA,
                                          • 1 HF BA,
                                          • Sleeps 6
                                            (4)
                                            2 night minimum stay
                                            • 3 BR,
                                            • 2 BA,
                                            • 1 HF BA,
                                            • Sleeps 8
                                              7 night minimum stay
                                              • 4 BR,
                                              • 4 BA,
                                              • Sleeps 10
                                                (11)
                                                3 night minimum stay
                                                • 3 BR,
                                                • 2 BA,
                                                • Sleeps 8
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • Sleeps 8
                                                    (8)
                                                    7 night minimum stay
                                                    • 2 BR,
                                                    • 2 BA,
                                                    • Sleeps 8
                                                      (18)
                                                      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)
                                                            $1,300 - $1,800
                                                            per week
                                                            Book it Now!
                                                            7 night minimum stay
                                                            • 2 BR,
                                                            • 2 BA,
                                                            • 1 HF BA,
                                                            • Sleeps 4
                                                              2 Reviews
                                                               

                                                              Recent Upper Florida Keys Reviews

                                                              Excellent stay. Looking forward to going back.

                                                              5 of 5
                                                              My family and I loved it. The home was tastefully decorated and very clean. Everything looked very new. The rooms were spacious, perfect for my wife, myself, my daughter and her school friend.We rented a boat so I really enjoyed the quiet canal access to the bay; not a lot of boats going in and out. The neighbors were friendly and quiet. The owner was very kind and accommodating.The elevator was an added bonus that came in very handy for taking our luggage and our groceries up to the 2nd floor. We had a great time and plan on going back next year.
                                                              • Submitted: Aug 28, 2014
                                                              • Stayed: Jul 2014

                                                              Hammer Point Gem

                                                              5 of 5
                                                              This is our fourth rental in Hammer Point and we really enjoyed this house. House was very clean & well appointed. Everything was as described. The back yard was great and the canal was great for an afternoon dip. The Kitchen/great room was wonderful for the family to cook our catch & hang out with family & friends. Would have liked a TV in the master bedroom to catch up on the evening news, but other than that it was "perfect" nice neighbors also
                                                              • Submitted: Aug 4, 2014
                                                              • Stayed: Jul 2014

                                                              Great Vacation

                                                              5 of 5
                                                              We have stayed at this complex 5 times but this was the first in this unit. We had a great time, the unit was well equipped and clean. Our extended family stayed in a condo down the road but everyone seemed to congregate at the Port of Call unit. It was comfortable with enough seating when the entire "gang" was at our place. We love that fact that they allow dogs because we don't travel without ours! Owner/manager was very easy to deal with during the booking process and accessible for a minor issue that arose while we were there. The neighbor referred to in the previous review was not a problem at all. We have actually rented the unit right next to him and he wasn't a problem that visit either. I cooked numerous meals in the kitchen and it had all the utensils, pots/pans, and kitchen gadgets I needed. The view is spectacular and I enjoyed my coffee on the balcony - I say "I" because my husband was out fishing EVERY morning. Great restaurants close by...you must try Lazy Days for fish and Tower of Pizza (Islamorada location....not Key Largo) for Italian. Stay away from Hog Heaven - service was awful. We will be back!
                                                              • Submitted: Jul 25, 2014
                                                              • Stayed: Jul 2014