Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Upper Florida Keys Vacation Home Rentals(387)

387 Results
Book it Now!
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
    1 Review
    Book it Now!
    30 night minimum stay
    • 2 BR,
    • 2 BA,
    • Sleeps 6
      Book it Now!
      7 night minimum stay
      • 4 BR,
      • 3 BA,
      • Sleeps 10
        1 Review
        Book it Now!
        30 night minimum stay
        • 2 BR,
        • 2 BA,
        • Sleeps 6
          7 - 28 night minimum stay
          • 3 BR,
          • 3 BA,
          • Sleeps 8
            1 Review
            7 night minimum stay
            • 3 BR,
            • 2 BA,
            • Sleeps 6
              2 - 7 night minimum stay
              • 2 BR,
              • 1 BA,
              • 1 HF BA,
              • Sleeps 6
                Book it Now!
                • 8 BR,
                • 5 BA,
                • Sleeps 24
                  1 Review
                  • 3 BR,
                  • 2 BA,
                  • Sleeps 10
                    (20)
                    28 night minimum stay
                    • 3 BR,
                    • 2 BA,
                    • Sleeps 8
                      7 night minimum stay
                      • 3 BR,
                      • 2 BA,
                      • 1 HF BA,
                      • Sleeps 8
                        (49)
                        28 night minimum stay
                        • 4 BR,
                        • 3 BA,
                        • Sleeps 8
                          (6)
                          30 night minimum stay
                          • 6 BR,
                          • 5 BA,
                          • Sleeps 15
                            (8)
                            Book it Now!
                            6 night minimum stay
                            • 2 BR,
                            • 2 BA,
                            • Sleeps 6
                              7 night minimum stay
                              • 3 BR,
                              • 2 BA,
                              • 1 HF BA,
                              • Sleeps 6
                                (19)
                                Book it Now!
                                7 night minimum stay
                                • 4 BR,
                                • 3 BA,
                                • 1 HF BA,
                                • Sleeps 8
                                  2 Reviews
                                  Book it Now!
                                  7 night minimum stay
                                  • 6 BR,
                                  • 5 BA,
                                  • Sleeps 12
                                    7 night minimum stay
                                    • 3 BR,
                                    • 2 BA,
                                    • Sleeps 6
                                      2 Reviews
                                      28 night minimum stay
                                      • 3 BR,
                                      • 3 BA,
                                      • Sleeps 8
                                        2 Reviews
                                        7 night minimum stay
                                        • 3 BR,
                                        • 3 BA,
                                        • Sleeps 8
                                          (4)
                                          4 night minimum stay
                                          • 4 BR,
                                          • 4 BA,
                                          • 2 HF BA,
                                          • Sleeps 12
                                            7 night minimum stay
                                            • 3 BR,
                                            • 2 BA,
                                            • Sleeps 8
                                              (35)
                                              28 night minimum stay
                                              • 3 BR,
                                              • 2 BA,
                                              • 1 HF BA,
                                              • Sleeps 6
                                                (26)
                                                7 night minimum stay
                                                • 3 BR,
                                                • 2 BA,
                                                • Sleeps 10
                                                  30 night minimum stay
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • Sleeps 7
                                                    1 Review
                                                    4 - 14 night minimum stay
                                                    • 2 BR,
                                                    • 2 BA,
                                                    • Sleeps 4
                                                      $329 - $350
                                                      per night
                                                      4 - 7 night minimum stay
                                                      • 3 BR,
                                                      • 3 BA,
                                                      • Sleeps 8
                                                        (13)
                                                        • 3 BR,
                                                        • 3 BA,
                                                        • Sleeps 9
                                                          (31)
                                                          7 night minimum stay
                                                          • 5 BR,
                                                          • 3 BA,
                                                          • 1 HF BA,
                                                          • Sleeps 16
                                                            (4)
                                                            7 night minimum stay
                                                            • 6 BR,
                                                            • 4 BA,
                                                            • 1 HF BA,
                                                            • Sleeps 11
                                                               

                                                              Recent Upper Florida Keys Reviews

                                                              Good Property, Great Location

                                                              4 of 5
                                                              First and foremost, I have to acknowledge Janie at Phoenix Rentals/iTrip for being the best and most pleasant rental agent I've ever worked with. She is incredibly quick to respond to any questions and concerns I had leading up to the rental. A+ all the way! Second, the owners were very accomodating in working with my group for a non-standard rental time-frame...thanks much! We couldn't have asked for a better location for our dive group, as we were going out with Conch Republic Divers, located at the marina just a stone's throw away. Plenty of dining, diving, fishing, watersports rental options located very near the house. The house itself is represented accurately in the photos and, having 4 single beds, 1 king and one pull-out, it works very well for groups not wanting to share beds with one another. That being said, having been one of the 3 in our group to stay in the seperate lower-level area, I would advise that this space could use some serious TLC/rehab. It has a ton of potential to be a great little space, seperate from the main living area but it needs work (new shower head, new beds/bedding, and just some more creature comforts to give it more of a homey feel rather than a converted storage area feel). The main, upper level living area was MUCH better though, so don't let that scare you off!!!...just know what to expect. My group was a very low-maintenance bunch of guys so we were fine with it. All in all, awesome location and better option than most of the hotels in the area at a much more reasonable price. We plan on being back in the future!
                                                              • Submitted: Aug 9, 2014
                                                              • Stayed: Jul 2014

                                                              How to "de-stress"

                                                              5 of 5
                                                              We needed to "de-stress". The sunset photo on the site was inviting and the reviews of prior guests appeared to be just what we wanted/needed. The owner (Vivian) was easy to work with and extremely professional. She had prepared a pamphlet on were everything was (supermarket, restaurants, etc.) in the neighborhood. All was ready for our arrival. We got to the house and after a couple of days, my wife and I fell in love with the place. The king size bed was awesome, the furnishings were top notch, the down stairs area was ample and we loved the Jacuzzi. The sunset photo on the site was REAL. In a very short time, the stress was gone. We will return.
                                                              • Submitted: Jul 12, 2014
                                                              • Stayed: Jun 2014

                                                              Vacation of a Lifetime!!!

                                                              5 of 5
                                                              We had a WONDERFUL time in Islamorada and your home is FABULOUS!!! We planned this trip, 6/7/14-6/14/14, to celebrate our 20 year Wedding Anniversary with our 14 year old twin girls. We live in Lexington, SC and drove down, which was not a bad ride. The house was easy to find and your instructions from start to finish were spot on! Your home is extremely comfortable and clean and the views are amazing! The first thing we did was rent 2 Paddle Boards for the week from Cowboy Outfitters, per your recommendation. They were most helpful. We used them every day. We caught several fish, all of which I can not name. The most exciting part of our trip was our Offshore Fishing Charter with Captain Jim! We left Key Largo Fisheries, where he is docked at 7:00am. By 10:30am, we had caught the limit of 50 Mahi Mahi! We also managed to catch 2 large Bull Dolphin and a Baracuda! What an amazing time we had! Needless to say, we have a freezer FULL of fish at home! We are currently working on our next trip out with Captain Jim. Thanks for recommending him! Now, for the food….Here are our top 3: The Green Turtle-Mahi Reuben and you must try the breakfast, especially the shrimp & grits The Island Grill-Tuna Nachos-outstanding! Backyard Grill at Key Largo Fisheries-Lobster BLT-Awesome! Every day, we explored the island and met some amazing people. It had been 9 years since we were in the keys, and we will not be waiting so long next time! I am hoping to book again with you for next year, as we would not stay anywhere else! Thank you for sharing your home with us! The Corley’s, Lexington, SC
                                                              • Submitted: Jun 27, 2014
                                                              • Stayed: Jun 2014