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Beautiful Villa on the water at Tom's Harbor - Unbeatable Sunsets!

Duck Key, FL, USA
  • Villa900 sqft
  • Bedrooms2
  • Sleeps6
  • Bathrooms2
  • Half Baths0
  • Minimum Stay2 - 3 nights

2 Bedroom, 2 Bathroom

The property is recovering from Hurricane Irma, however, our Villa did not receive any damage from the storm.

This Villa is located on Duck Key with Tom’s Harbor at your back door where you can relax and overlook the water from the first or second floor patio, or enjoy the water directly from your Villa by walking just a few steps where boats, jets skis, paddleboards, and kayaks may be anchored. Boat dockage may be rented from the Grassy Key Marina, or in Marathon.

Duck Key is located in the middle of the Florida Keys at Mile Marker 61, between Islamorada and Marathon, approximately two hours from the Miami or Fort Lauderdale Airports. Key West is about one hour south from the Villa.

This is a townhome style villa with a full kitchen supplied with utensils and cookware. There is a dining area and living room on the first floor with a TV, satellite cable access, and a DVD player; and direct ocean access to Tom’s Harbor from the first floor patio.

There are two bedrooms and two bathrooms located on the second floor with queen sized beds. Each bedroom has a bathroom attached. There is NOT a bathroom on the first floor. This unit is perfect for four people, two in each bedroom. There is however, a sleeper sofa that will accommodate two people. No more than six people maximum are permitted to occupy this rental.

The master bedroom has a patio with a beautiful view overlooking Tom’s Harbor. There are queen size beds in each bedroom, with a TV and satellite cable access. There is a clothes washer and dryer on the first floor. Linens, bath, and beach towels are provided for use during your stay.

The Angler and Ale restaurant is open to the public.

**The below facilities are NOT available at this time due to Hurricane Irma.**

The Marina is located on Duck Key and is in walking distance from this beautiful Villa. The Marina offers every activity that you could want, to include rentals for kayaks, paddleboards, and jet skis. Scuba diving, snorkeling, and fishing are also available. No need to drive anywhere, just walk across Duck Key Drive and you are at the beautiful Marina.

Although our property is located near the Hawks Cay Resort, we are not associated with that facility. Guests staying on our property, or any private rental on this property, do not have privileges on the resort property, such as access to the swimming pools. Poolside bar food and drink service are restricted to non-resort guests. However, you may enjoy dining at the resteraunts a member of the public. If your vacation plans are to primarily spend time at the resort pool/lagoon, receive poolside and bar service, we recommend reserving your stay with the resort.

The Dolphin Connection, and Marina services are open to the public and available to our guests and must be paid for at the time of service. No charges may be made to the Villa.


Jan Dempsey Simkins

Member Since 2013
Response rate:
Response time:
within one hour
Calendar last updated:
Apr 20, 2018
About Jan Dempsey Simkins

Natives of the west and mid-west regions, but love Florida and the Florida Keys enough to retire here. Both love scuba diving, kayaking, fishing, and bicycling and are able to enjoy all of these activities as residents of the Florida Keys. We pride ourselves on being actively involved with our rental properties to ensure a wonderful Florida Keys experience for our guests.

Jan Dempsey Simkins purchased this Villa in 2013

Why Jan Dempsey Simkins chose Duck Key

This property was our home away from home until we retired and now currently live in the Florida Keys. We traveled frequently to this location to vacation and enjoy all that the Florida Keys had to offer. We have worked hard to make this Villa our home away from home, and strive to make this Villa a home for each of our guests while enjoying their vacations.

What makes this Villa unique

This Villa is steps from the beautiful Tom's Harbor. Everything you could wish to do is right out your back door. Swimming, fishing, paddle boarding, kayaking, boating, and jet skiing, just to name a few. The sunsets are amazing every night and can be enjoyed from our back patio. The town of Marathon is ten minutes away with charter facilities of every sort as well. The options are endless for this this middle keys villa.


    • Internet
    • Air Conditioning
    • Heater
    • Satellite or Cable
    • Kids Welcome
    • Washer & Dryer
    • Parking
    • TV
    • No Smoking


      • 2 Bedrooms, Sleeps 6
      • Bedroom 1
        1 queen
      • Bedroom 2
        1 queen
      • There are two bedrooms and two bathrooms located on the second floor; each full size bathroom is attached to each bedroom. The master bedroom has a patio with a beautiful view overlooking Tom’s Harbor. There are queen size beds in each bedroom, with a TV and satellite cable access. Both beds have new pillow top beds, and a sofa sleeper.


      • 2 Bathrooms
        • Two full size bathrooms are attached to each bedroom located on the second floor. There is NOT a bathroom located on the first floor.

        Location Type

          • Ocean View
            This Villa sits on the Tom's Harbor and has beautiful sunsets from the back of the Villa. There is no "beach" access to this water.
          • Oceanfront
          • Water View
          • Waterfront


              • Adventure
              • Away From It All
              • Budget
              • Family
              • Historic
              • Romantic
              • Sports & Activities
              • Tourist Attractions


                  • Guests provide their own meals


                      • Iron & Board
                      • Air Conditioning
                        Central Air Conditioning
                      • Hair Dryer
                      • Heating
                      • Internet
                      • Clothes Dryer
                      • Linens Provided
                        High end bedding provided.
                      • Living Room
                        There is a sofa sleeper in the living room which will accommodate two people.
                      • Parking
                        Parking spaces are available in the front of the Villa
                      • Towels Provided
                        All towels, including beach towels are provided
                      • Washing Machine


                          • Microwave
                          • Coffee Maker
                          • Dishwasher
                          • Ice Maker
                          • Kitchen
                            Full sized kitchen - equipped.
                          • Dishes & Utensils
                            All dishes and utensils are provided.
                          • Oven
                          • Pantry Items
                          • Refrigerator
                            Full sized refrigerator with an ice maker in the freezer.
                          • Stove
                          • Toaster


                              • Dining
                                Table and 4 chairs. There is also a table with 4 chairs on the patio.
                              • Dining Area
                              • comfy seating for 4 people


                                  • DVD Player
                                    DVD player and a small movie selection is provided.
                                  • Satellite / Cable
                                    Cable television is available.
                                  • Television
                                    There are televisions available in the living room and in each bedroom.
                                  • Video Library
                                    A small movie selection is provided.


                                      • Balcony
                                        There is a balcony outside of the master bedroom on the second floor.
                                      • Deck / Patio
                                        There is a patio on the first and second floor, looking out to Tom's Harbor.
                                      • Kayak / Canoe
                                        May be rented at the resort, Grassy Key, or Marathon depending on availability due to Hurricane Irma.
                                      • Lawn / Garden
                                        There is grass located behind the Villa.
                                      • Water Sports Gear
                                        May be rented at the marina once it opens from Hurricane Irma damage.


                                          • Long-term Renters Welcome
                                          • wheelchair inaccessible
                                            There are stairs leading up to the front and back porches of the Villa. Both bedrooms and bathrooms are on the 2nd floor.


                                              • health/beauty spa
                                              • marina
                                              • restaurants

                                                Leisure Activities

                                                  • boating
                                                  • eco tourism
                                                  • paddle boating
                                                  • shopping
                                                  • sight seeing
                                                  • walking

                                                    Local Services & Businesses

                                                      • ATM/bank
                                                      • fitness center
                                                      • groceries
                                                      • hospital
                                                      • laundromat
                                                      • massage therapist
                                                      • medical services

                                                        Sports & Adventure Activities

                                                          • sailing
                                                          • deepsea fishing
                                                          • fly fishing
                                                          • jet skiing
                                                          • kayaking
                                                          • pier fishing
                                                          • fishing
                                                          • scuba diving or snorkeling
                                                          • snorkeling
                                                          • snorkeling/diving
                                                          • surf fishing
                                                          • swimming
                                                          • water skiing


                                                              • A safe is provided for guests to lock their personal belongings. This safe is large enough to place items of value to include a laptop computer. Many guests inquire regarding a outdoor grill. Unfortunately, there is no grilling allowed on the property in accordance with home owner association guidelines. However, there are charcoal grills available for our guests to use at the Hawks Cay Marina, which is directly across from the Villa. We do not participate in the Hawks Cay Resort Rental Management Program, which allows us to offer our villa at reduced rental prices. Consequently, the resort imposes restrictions to their facilities, including the pools to private renters such as VRBO. Bar and poolside food and drink service are also restricted for non-resort guests. If your vacation plans are to primarily spend time at the resort pool/lagoon, receive poolside and bar service, or use the tennis courts, we recommend reserving your stay with the resort.

                                                                House Rules

                                                                Check-in: 4:00 PM

                                                                Check-out: 10:00 AM

                                                                Cancellation Policy

                                                                100% refund if canceled at least 60 days before arrival date. You must contact the owner directly to request cancellation.

                                                                111 Reviews


                                                                Latest reviews

                                                                House was nice, plenty equipped and clean. Porches were super nice and the bay was fantastic.

                                                                Dee B.

                                                                Owners were great, replied extremely promptly and even let us check in early when we arrived.

                                                                Throughout the Keys there is still damage from Hurricane Irma, but it by no means stopped us from doing any activities. There are still some restaurants that are not open, but plenty are back up and running. Great time and great property.

                                                                We enjoyed our stay

                                                                We enjoyed our stay. We like the location in the mid-Keys. Place was clean, kitchen had everything we needed, porch nice. There weren't many other people there when we were there, which was good, as the porches in the complex are right up next to each other. Place is as described. Tight quarters upstairs - no dresser in the second bedroom. Owner responsive and we had a good time there.

                                                                Very nice villa clean neat

                                                                Clifton S.

                                                                Had a great experience to enjoy the property

                                                                Excellent view and Beautiful Villa with lovely decor, large fluffy towels and even beach towels

                                                                Cindy G.

                                                                Very comfortable and immaculate villa with everything you need for a great visit. Owners communicate well and are always available.

                                                                Great property

                                                                Michelle C.

                                                                Nice property, area...had everything we needed

                                                                Great location and town home

                                                                rebecca L.

                                                                Wonderful unit in a great location. Beautiful views!


                                                                Duck Key, FL, USA


                                                                Additional information about rental rates

                                                                Tax Rate

                                                                VRBO fees are not refunded upon cancelation. Cancelations may be made at least thirty days prior to the scheduled stay. Monthly rental cancelations must be made at least sixty days in advance. The cancelation policy is outlined in the rental agreement. Absolutely no more than six persons may reside in this rental under this agreement. Absolutely no smoking.

                                                                111 Reviews
                                                                Wonderful 4.8/5
                                                                Enter dates for accurate pricing
                                                                For booking assistance, call 888-640-7927

                                                                Property # 460750vb