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USA Florida Key West Old Town Key West Listing #10752

Almost Southernmost Too - Key West, FL

14 reviews
Max occupancy: 8 1 King Bed, 3 Queen Bed 3 bedrooms 2.5 bathrooms 4 dog max 
417 Truman Ave. , Key West, FL 33040

Worry-free booking

Enjoy peace of mind with flexible options to change or cancel your trip.

If your check-in date is at least 30 days away, you can reschedule your trip, cancel and receive 100% of the cost as a Future Stay Credit, or cancel for a refund (minus the booking fee).

Expert cleaning

Professional housekeepers clean and stock each home, using an EPA-approved disinfectant.

Local support

Each trip is backed by 24/7 customer support and local teams everywhere we operate.


Many Vacasa homes use smart locks or lockboxes for a smooth, contactless check-in.

Colorful, dog-friendly cottage w/ private pool & all the comforts of home

Experience a quintessential Key West vacation when you stay at this historic three-bedroom, two-and-a-half-bathroom cottage. With a private heated pool, home comforts including free WiFi and cable TV, and room for up to eight guests, this home is perfect for a large family or a group of close friends. The family dog is also welcome to join you for an additional nightly fee.

Located on Truman Avenue between Whitehead and Duval streets, this vacation rental is highly walkable and offers easy access to all of the shops, restaurants, and entertainment of downtown Key West. Street parking is available.

When you aren't strolling the city streets, you'll enjoy lounging in the sun on the second-floor deck, people-watching on the front porch, and put together tasty meals in the well-appointed kitchen. If you're traveling with a larger group, this cottage can be rented along with the one next door to accommodate a total of 16 guests - call Vacasa for more information.

Whether you're here to see the sights, eat the foods, or just relax with your loved ones, you can't go wrong with this Key West vacation rental. Book today!

A damage waiver, covering up to $2,000 of accidental damage to the property or its contents, is included in the cost of your reservation.

You must be 25 years or older to rent this property.

Property permit ID: 25230-104726




Washer/dryer : Private

Heating & cooling

Central AC

Kitchen & dining






Internet : Comcast


Cable : Comcast

On-site activities

Pool : Private




Beach towels


14 reviews

Emily S. Aug 2020
We came with our kids 15, 14, 8, and 6. The location was perfect and we could walk so many places. The pool was the perfect way to spend family time. We had such a wonderful vacation!
Mark S. Feb 2020
Perfect location for your KW vacation. Central access to all the fun!
Jennifer H. Apr 2019
We loved the house!! Great location!! We definitely will be back!!
John-Michael E. Mar 2019
This place was perfect for touring the downtown area. The home was spacious and met our needs. Be warned that there is NO parking at the residence and public parking is hard to find in that area. We parked our car at a golf cart rental place and was able to park our golf cart at the house overnight. Overall, the experience was perfect for us.
Albert Z. Oct 2018
Great Downtown Location. Very Clean and well kept. Within walking distance to everything. Will definitely rent again.
Vincent O. Sep 2018
Thank you were GREAT!! And shuttle driver Mike!!
Elizabeth D. Aug 2018
We loved Almost Southernmost Too - it is in the perfect location and we love the dip pool. It is spacious so everyone can spread out. I highly recommend. Only negative - no parking and the lots are pricey.
Amanda J. May 2018
Awesome house! Just beware there are no private parking spots unless you rent this house AND the one next to it. Some of the advertisements aren’t clear. House was perfect and the staff was very nice. Right on Duvall
Cynthia B. Mar 2018
Convenient to everything, great kitchen, comfortable
Olivia B. Feb 2018
Key West recently marked some spaces “resident only” and next to some, when nothing is written then you can park.keep on driving on Truman, cross Duvall Street and park next to the church on Truman.
Other streets are parking only by permit.

I parked on the side of the house for 1 minute to unload the luggages.

Nice place. Very pleasant.
Many dishes provided. It was very convenient.
Easy access to everything and CVS around the corner for forgotten items
Cameron B. Feb 2018
Everything from check-in to check-out was perfect, from the folks at the rental office to the property itself. The location alone cannot be overstated - it is in nearly an ideal spot to explore the best parts of Key West. And the layout and comfort of the property was better than I had expected. We will definitely be renting here again!