Midtown / Newtown

If you're looking to come to Key West to soak up some sun, relax and enjoy a more slowed down pace, then we suggest checking out our Midtown & Newtown homes. The main benefits of Midtown/Newtown is the centralized mid-island locations, quiet residential streets and parking(!!!). You’ll be away from the hustle & bustle of Duval St, yet only be a short 10 minute drive or Uber ride down to the heart of the action. There’s plenty of off-street parking, which if you've stayed in Key West before, you know is not easy to find in Old Town.


Properties Available 5 properties available
Spanning an exclusive corner lot in the desirable Midtown neighborhood of Key West is a stunning compound-style home designed as the ultimate vacation destination for a family or group of friends seeking privacy and quiet only a short bike ride or walk from the bustling downtown Old Town area of Key West. In addition to four spacious bedrooms, this
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A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Midtown Mosaic
Private Home Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (12)
73 PALMS is a beautifully renovated two-story home offering the perfect blend of luxury, comfort, and island charm. As its name suggests, the property boasts a remarkable 73 swaying palm trees, creating an unparalleled tropical ambiance that immediately transports you to paradise. This meticulously designed 3 bedroom home features a large swimming
Hot HOT 34
Monthly Rental Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
73 Palms
Private Home Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (1)
SUNFLOWER MELODIES captures the feeling of a childhood summer, like your bare feet on freshly cut grass, the summer sun gently kissing your skin or the sweet, subtle scent of a field of wildflowers in bloom. A month in Key West is defined by a simpler way of life, with low stress, high fun, and heaps of relaxation - which SUNFLOWER MELODIES provide
Monthly Rental Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Sunflower Melodies
Private Home Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (1)
The moment you arrive at this midtown mansion, you’ll know your time in Key West is going to be special. The circular driveway and covered portico provide a grand entrance, which set the stage for what awaits you inside. At over 3,900 square feet, ISLAND OPULENCE is one of the largest private residences in Key West. This impressive ranch-style home
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Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Island Opulence
Private Home
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 11 guests
Welcome to CASA DEL MONO, a spacious coastal retreat where island living unfolds at an easy, graceful pace. It’s the kind of place that invites you to slow down, settle in, and stay awhile. With five bedrooms and four bathrooms, plus expansive wraparound porches upstairs and down, this beautifully appointed home offers plenty of room to spread out
Hot HOT 32
New Property New Property
New Property
Monthly Rental Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Casa Del Mono
Private Home
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 10 guests

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