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 |
|---|---|---|---|---|---|
Jan 01 - Mar 31 2026 | $19,600 | 28 nights | |||
Apr 01 - Apr 30 2026 | $17,600 | 28 nights | |||
May 01 - May 31 2026 | $11,600 | 28 nights | |||
Jun 01 - Sep 30 2026 | $10,600 | 28 nights | |||
Oct 01 - Oct 31 2026 | $12,600 | 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 November 25, 2025
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