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1500 sq. ft. Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discerning travelers for over 15 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenities and ideal location the perfect spot to enjoy all that Key West has to offer.
Dos Casas is a unique four bedroom property ideal for groups, families and friends.
Dos Casas is on the 700 block of Fleming Street, the heart of the most beautiful section of Old Town. This lovely 2-house compound is located just a few blocks from Duval Street, Mallory Square and the Seaport. Quiet at night, yet close to the action, this very special neighborhood showcases the best of Old Town Key West --filled with Victorian mansions and historic homes.
Each house has two bedrooms, a shared bath and kitchen facilities. The main house has a large living room, fully equipped kitchen, full laundry , bath with shower, king bedroom with a walk-in closet and a queen bedroom with plenty of closet space and a desk, if you are working remotely. The charming cottage is perfect for up to four with a queen bedroom and a second bedroom with twin beds, both with plenty of closet space, a kitchenette with refrigerator, sink and microwave, as well as a bath with tub and shower.
The spacious private deck area is totally fenced in with a private pool, covered dining area, lounges and comfortable teak chairs. Both houses have front porches with comfy seating -- perfect to enjoy a cocktail and watch the world go by.
Unique Benefits
Two houses make this property ideal for family groups. Often, grandparents take the big house and their children and grandchildren take the other.
Location is amazing, close to the waterfront and Duval, yet it's quiet.
Great front porches that are up above the street allowing some privacy.
High ceilings, spacious rooms, lots of storage make it easy to settle in for a month.
An amazing outdoor shower.
Great for remote working.
Why Kids Love It
The cute turtles in the pool. A local artist made turtle tiles and they are embedded in the stairs and bottom of the pool.
TVs in every bedroom.
If it's your first time in Key West, you'll be delighted with all that it has to offer. It's called Paradise for a reason. Key West is America's only Caribbean city. Old Town Key West is filled with beautiful homes, fantastic restaurants, bars and music venues as well as galleries and museums.
It's different from anywhere in Florida, combining Bahamian, New England and Caribbean influences in a town with roots going back to the early 1800's. Built on fishing, sponging, a Cuban cigar industry, the Navy -- it's a fascinating mix of cultures. Today, whether you're interested in art, theater, fishing, water sports or music, you'll find something new to experience.
Color is everywhere from the turquoise waters surrounding this island city, beautiful sunsets, lush greenery and flowers blooming at every turn. Houses are painted a rainbow of colors, surrounded by lush gardens.
Duval Street
The Seaport
Mallory Square
Sail and Scuba Trips
Dozens of Restaurants
Truman Waterfront Park
Great Music Venues
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| Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
|---|---|---|---|---|---|
May 01 - Dec 31 2026 | $19,600 | 28 nights | |||
Jan 01 - Apr 30 2027 | $25,600 | 28 nights | |||
May 01 - Dec 31 2027 | $19,600 | 28 nights | |||
Jan 01 - Apr 30 2028 | $25,600 | 28 nights |
Fees:
Notes:
The security deposit is fully refundable as long as the house is left in good condition, utilities not abused and within the average range for the rental month.
We ask you about your pet. Most are fine, but some pets are not appropriate for the property.
Last updated on May 26, 2026
Elaina K.Perfect stay
Our family of 5 visited Dos Casas and had an absolutely wonderful stay! We were warmly welcomed and informed about the property-they were very attentive to details. The compound is beautifully maintained and so comfortable. Having 2 houses on the same property was wonderful--it gave us the space we needed, and then some. The amenities exceeded my expectations and the pool was an added bonus! The location was also perfect, making it easy to explore the area while still feeling like a quiet retreat at the end of the day. I would gladly stay here again and highly recommend it to anyone looking for a clean, comfortable, and memorable experience! Thank you so much!
Stayed: November 2025 Submitted: May 09, 2026
Thomas A.Lovely, comfortable, and convenient
Dos Cosas is wonderful being two separate and lovely homes, allowing for guests to have their space and flexibility with arrangements.Amenities were great and the outside patio area and pool were fantastic, with the heated pool in the cooler temperatures being downright awesome. The outdoor shower was something not to sleep on too.The location is primo. 2 blocks from Duvall, across the street from the Library, and situated on a street that parking was never an issue with scooters having spots at the Library, assuming car parking also not a huge issue. Fausto's grocery was a block away, seriously so close food shopping was just that easy. Numerous shops, cafes, restaurants, and other entertainment just steps away.Couldn't recommend this place enough.
Stayed: December 2025 Submitted: May 04, 2026
Carrie H.Perfect location, gorgeous property!
The location of Dos Casas is perfect for walking or biking Key West. The pool and deck area is a dream! My family and I had the best time and cannot wait to visit again and again. Thank you Dos Casas!
Stayed: February 2026 Submitted: May 04, 2026
Brian B.Absolute Perfection
Dos Casas is a little piece of heaven right in the heart of Key West! The location worked perfectly for us as it is close enough to walk to the amazing restaurants, bars, and marina, yet secluded enough to enjoy some quiet relaxation around the pool. The homes are beautifully appointed and extremely well-kept. The homes feel quite updated yet keep the charm and vibe of Key West!Dos Casas is a home run! Well done to the owners, and we will be back.
Stayed: May 2024 Submitted: May 02, 2026
Bianca B.Wonderful stay at Dos Casas
We had the most wonderful time staying at Dos Casas! From the moment we arrived, we felt right at home. We loved spending mornings and evenings on the front porches watching the world go by, cooking in the charming kitchen, and enjoying the outdoor shower, it was a true Key West experience! The flowers throughout the property made everyday feel like we were living in a tropical paradise. The location couldn’t have been more perfect, with walking distance to our favorite restaurants, sunset, the marina, and having Fausto’s a block away. Dos Casas has truly become a special place in our hearts. We made so many beautiful memories here! Thank you for sharing such a Key West magical home with us, we are forever grateful!
Stayed: March 2025 Submitted: May 02, 2026
Terry S.A Visit to Paradise
We had such a wonderful time at this house. It's actually two houses that share the lovely deck and pool area. We stayed in the main house and our friends took control of the other house. It was so nice to have both our own private space and then such lovely space to hang out together. We enjoyed most meals out on the deck and as many cocktails.The location is perfect! Just a short walk to so many things or just to enjoy the area. We walked every day, never using our car until it was time to go home. All-in-all a very lovely stay in paradise!
Stayed: March 2025 Submitted: May 01, 2026
Shane & Carly C.Perfect Key West Rental
Absolutely loved our stay at this Key West rental! From the moment we walked in, we were blown away by how spotless and well-maintained everything was — you can tell the owners truly care about every detail. The location couldn’t have been better: tucked away on a quiet, peaceful street, yet still an easy walk to everything we wanted to see and do.The kitchen was a dream — modern, fully stocked, and perfect whether you’re cooking a full meal or just mixing up drinks before heading out. The beds were incredibly comfortable, making it easy to relax and recharge after long days walking the streets of Old Town.And the pool… easily one of our favorite parts. Private, clean, and the perfect place to unwind. It really felt like our own oasis.The guest house is a perfect place for older kids or extended family members to stay.If you’re looking for the perfect blend of comfort, convenience, and relaxation in Key West, this is it. We’ll absolutely be back!
Stayed: October 2024 Submitted: April 30, 2026
Steven/ Marilyn K.Great place for a large family or with friends
We had seven: the two of us, our adult daughter, son & wife and 2 small kids. We had plenty of space and good privacy for everyone. Daughter and us in bigger house, son's family in smaller house. The huge patio with pool and dining table was our congregating space. The kitchen was plenty big for all of us to help cook, and the grill was a big one. The mini-kitchen in the smaller house was very helpful for the kids needs, extra drinks, and their early morning coffee. The outdoor shower was everyone's favorite and we all used it most of the time. The house was clean, well-supplied with all our needs, and very comfortable. Gorgeous landscaping. The location is perfect. A quiet neighborhood, but easy walk to busy Duval Street and to the marina and all its venues. Grocery a block away. Library across the street (the kids loved). The only issue we had was parking, as most spaces in the 'hood are reserved for homeowners (you can get ticketed) and we sometimes had to park a couple blocks away. But no car is really needed as we walked almost everywhere or took the loop bus that stopped on our corner. It was our second Dos Casas stay, and we really loved it both times.
Stayed: February 2025 Submitted: April 30, 2026
Jack D.Local Alaskan warmed in Key West Dos Casas
We stayed at Dos Casas in the heart of Key West. The location across the street from the public library is beneficial and I liken it to being a local. Living in Alaska year round it was great to see Key West locals as it was close to my hometown of North Pole and very quaint. Walking was the activity of the day along with great biking to local spots. Dos Casas is a gem, its great Lanai/ area between both residences lend it to a Grotto atmosphere with its pool and outdoor shower that is tucked away for privacy. Behind the gate is a quiet atmosphere where one can lounge all day without having to venture out the front gate. Having a total of four guestrooms in two seperate homes is convenient for a group as everyone has their own quiet place to relax. The access to the town of Key West is so easy and not having to rent a vehicle is the ticket at this amazing property. On most days, I did not need to leave the Dos Casas all day and at night we ventured out by walking to all the amazing bars and restaurants in the Key West area. A Gem
Stayed: December 2024 Submitted: April 30, 2026
A. L.Best Location and Ultimate Comfort
If you seek all the creature comforts of home, a pool, and walking distance to all the greatest restaurants in Key West, look no further than Dos Casas. We brought our bikes, or you can rent locally, and were able to explore the whole island super easily. Minutes from the marina and the ultimate sunset views, topped off by outdoor showers and naps by the pool. The grocery store is walking distance, the library is across the street and several seafood markets within minutes if you want to stay home and cook. Location is everything with this property and it can be kid friendly and couples friendly, multi-family and multi-generational family friendly too, whichever floats your boat! Clean, updated, thoughtful, and spacious, look no further for your Old Town vacation home.
Stayed: August 2024 Submitted: April 30, 2026
Pamela F.Perfect spot in Key West!!
This is the perfect location for your Key West get away. It is two, two bedroom homes with a private pool. Everything is very well kept, very clean and brimming with charm. It is quiet, yet a short walk from Duval or the water front.i have been visiting this island for 20 years and this is my favorite place to stay! I highly recommend it!
Stayed: June 2024 Submitted: April 30, 2026
Jerry S.Dos Casas
Beautiful sanctuary centrally located in Old Town. Very comfortable accommodations in a well maintained property. Property manager and Owner were very responsive to any questions or concerns that arose. Full month rental that felt like a second home during our stay.
Stayed: June 2025 Submitted: July 07, 2025
Member since 2022
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