Key West Vacation Rentals

Midtown ~ Key West Florida Rentals

Midtown is located in the geographical center of the island, and roughly bounded by North Roosevelt Boulevard (U.S. Route 1), Leon Street, Atlantic Boulevard and 1st Avenue.

When tiny Key West proper ran out of development room in the 1940s and ‘50s, Key West simply built more island, adding the Midtown and New Town areas of Key West. Using dredging to create landfill, Key West more than doubled its square miles and opened the city to thousands of new homes and retail development.

There are two distinct areas of Midtown – east and west.  Midtown West, lies between White Street and Palm Avenue or 1st Street, as it’s also known, and stretches from North Roosevelt Boulevard to the Atlantic Ocean. Its homes more closely resemble the Old Town and Meadows architecture of Conch cottages, though most of the homes are more likely to be classified as Mid-Century modern.

Midtown East lies between 1st Street and 9th Street and stretches from North Roosevelt to the Atlantic. Both neighborhoods are home almost exclusively to long-time Key West residents.

  • Best features: Walk to the to beaches. Beautiful examples of Mid-Century modern architecture. Close to Key West’s primary retail shopping and schools. Many residential blocks in the neighborhoods are blessed with large lots and wide streets.
  • Getting around: Great for walking and biking. The farther east you go, the more you’ll need a car or scooter. You can walk to Old Town and the Casa Marina District; it just takes a bit longer.
  • Street boundaries: White Street on the west; 9th Street on the East; Atlantic Ocean on the south and North Roosevelt on the north.
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Call For Availability and Pricing
2 Bedrooms
3 Baths
Sleeps 6
Type of property: Home
Area: Mid Town

CAYO HUESO SUNSHINE (monthly rental): A brand new 2-bedroom 3-bath home with den in a new Key West neighborhood -- quiet and secluded yet so accessible to the wonders of our island.  A block from Higgs Beach on the Atlantic Ocean, one of the best locations you'll find, with lots of extras to make you want to return again and again.


Call For Availability and Pricing
3 Bedrooms
2 Baths
Sleeps 6
Type of property: Home
Area: Mid Town

A SUITE PARADISE (monthly rental) : This lovely 2 bedroom 2 bath home with den is truly a tropical hideaway tucked away in a secluded Key West neighborhood, yet minutes from all the Duval Street entertainment and Historic Seaport. You can relax and be pampered in a superbly appointed and decorated private home that has every amenity you could desire.


Call For Availability and Pricing
3 Bedrooms
2 Baths
Sleeps 8
Type of property: Home
Area: Mid Town

FLAGLER STATION (monthly rental): This one just arrived and it is a true gem! Flagler Station was just remodeled, refurbished and re-furnished. High speed WIFI and state-of-the-art electronics, top-of the-line gourmet kitchen and luxury linens make this home the one you'll return to year after year.


Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Condo
Area: Mid Town

Sunshine On The Rocks (Monthly Rental) 
A true island getaway! This stunning townhome has spectacular waterfront views of the bay, travel down to Key West by boat or bring it along because this is one of the only places on the island with open water boat dockage. Sunshine On The Rocks is the hideaway you are looking for when tropical breezes call your name and turquoise waters is where you are heading.


Call For Availability and Pricing
2 Bedrooms
2 Baths
Sleeps 6
Type of property: Condo
Area: Mid Town

BOATER'S BEACH HAVEN (monthly rental): A truly unique Key West vacation location. Located midtown on Florida Bay, you'll have first row seats for sunset every night. Take advantage of the private boat dock with your own or a Key West boat rental.  A quick bike ride will get you to Old Town, but you may never want to leave home.