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USA Florida Key West Old Town Key West Listing #10751

Almost Southernmost Retreat - Key West, FL

36 reviews
Max occupancy: 14 2 King Bed, 4 Queen Bed, 2 Sofa Bed 5 bedrooms 3.5 bathrooms 4 dog max  (30 lb weight limit) 
415 Truman Ave. and 417 Truman Avenue., 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.

Dog-friendly, colorful cottages w/ pool & hot tub in a fabulous location!

A large group getaway to Key West starts with this pair of charming cottages, which feature a total five bedrooms, three-and-a-half bathrooms, and a max occupancy of 14. The property also includes a private heated swimming pool, a private hot tub, and dog-friendly accommodations.

The cottages sit right on Truman Avenue between Duval Street and Whitehead Street - an unbeatable location offering easy pedestrian access to dozens of shops and restaurants, not to mention the Ernest Hemingway Home & Museum and other notable local attractions. One private parking spot and additional off street parking are available.

One of the cottages has two bedrooms and one bathroom, while the other cottage has three bedrooms and two-and-a-half bathrooms. Both cottages have spacious decks for sunbathing, fully equipped kitchens, cable, and free WiFi. It's also possible to rent each cottage separately if you're traveling with a smaller group - call Vacasa for more information. A dog is welcome for a small nightly fee.

Start planning your Key West vacation and book these cottages 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.




Washer/dryer : Private

Heating & cooling

Central AC

Kitchen & dining








On-site activities

Hot tub : Private

Pool : Private


Beach towels

36 reviews

Elizabeth B. Mar 2020
The location and size of the home were great for our larger group. We did have some issues with the hot tub being dirty and overall cleanliness of the 2 houses, but nothing that ruined the stay. As a family with 2 smaller children the layout did pose a little issue as the 2bed/1bath home isn’t suited for younger children. The rooms are on different floors and we didn’t feel 100% comfortable with the children alone in either option. The 3bed/2.5bath home is better suited for kids. Again, nothing that was a deal breaker. The pool was great for the warm afternoons!
Manager response:
Hello Elizabeth, We apologize that the home and hot tub were not at the high-level cleanliness that we hold ourselves too. We apologize for the inconvenience and do hope you will give us another chance to impress you in the future.
Meghan P. Mar 2020
Great space and location! Perfect for our big group!
Kathleen Q. Feb 2020
The house was nice and comfortable, perfect for our large group. The pool and hot tub were a little dirty. Location was perfect! We had trouble with the lock code but they were quick to help.
Manager response:
Hi Kathleen, we're so glad you enjoyed your stay in our home! We appreciate your feedback regarding the cleanliness of the pool and hot tub, and we have followed up with our housekeeping staff to ensure that our home is being cleaned to our own high standards. We're glad that we were able to help you with the lock code. We hope to host you again soon!
James S. Dec 2019
Loved the shared back patio and proximity to Duval Street!
Jean M. Nov 2019
Had a great time at these beautiful homes....comfortable, clean, perfectly located, great staff, great accommodations.
Jeff M. Nov 2019
Worked out really well for 5 couples and the adjoining patio/pool was great place to lounge and relax.
Jacob V. Sep 2019
Vacasa were flexible with slight alteration to my checkout. Great company, great house.
Shana J. Sep 2019
We have stayed here 3 times now, although this was the first time we rented both houses together. Highly recommend, we had an absolutely wonderful time, and there was plenty of room for all of us. The one upstairs bedroom in 417 Truman is a little tight, but it still comfortable. Hopefully we will be back soon!
Chelsea W. Sep 2019
My friends and I rented these houses for a bachelorette weekend. The houses were perfect for us. We loved having the private pool and hot tub and being able to go from house to house in our own private area. We had a little trouble with plumbing, but Vacasa sent someone within an hour of us calling and fixed the issue. I highly recommend this location and vacasa rentals! We will definitely stay here again!
John R. Aug 2019
Awesome place really enjoyed location. Wish there was grill only complaint. FYI get your pool pump checked out two guys on trip own pools said it was running hard before you have more costly issues.
Manager response:
John, we are glad you enjoyed your stay and we appreciate you taking the time to share your feedback. We will make sure to keep an eye on the pool pump for proper functioning and for any issues that may need to be addressed. We look forward to hosting you again!
Britney J. Aug 2019
We rented both homes and this was awesome for the group we had! Please note that 415 Truman has 1 bed upstairs and 1 bed downstairs with only 1 bathroom. 417 is the much bigger home with a 4 beds and 2.5 bathrooms. We did both of these houses for bachelor/bachelorette and 13 people. The pool and hot tub are awesome, the rooftop sun deck is great for a pretty day and theres 2 outdoor showers! The houses were very clean and the beds were comfortable. If you are tall then the upstairs bedroom in 417 is not for you -- though not a deal breaker! We could have used more towels as it states daily housekeeping but that did not occur. There is 1 parking spot for a sedan/SUV. We had a 15 passenger van that would not fit in the space. However, overall amazing home -- the rooms in the front of the house do hear the cars/roosters but after a night on Duval that won't matter. Will definitely book here again!
Ralph H. Jul 2019
Great location and lots of room. Nice pool and hot tub. The thing I would say negative another the place is the kitchen is doesn’t have many amenities. Other than that the house is great. Great location, right off Duval Street.
Kandy F. Jun 2019
Perfect for large group
Monique B. Jun 2019
Centrally locates—easy walk to activities & restaurants. House was nicely appointed—they even provide clothing detergent for the washer!
Vicky H. Jun 2019
Great location, good accomadations!
Joseph H. Jun 2019
This place was everything we hoped. Tons of space and so close to downtown. The pool was a huge bonus in the FL heat. The only downside was there are a lot is pictures circulating on multiple sites of this place and multiple have pictures of a grill. So the boys were geared up and ready to grill the catch of the day from the fishing expedition but to our surprise there was no grill. Obviously not a trip ruiner and over all would stay again.
Manager response:
Joseph, we apologize for the lack of grill. We are glad it did not ruin your trip or enjoying the fish you caught.We look forward to hosting you again. Thank you!
William G. Apr 2019
Great location!!!
Dustin M. Mar 2019
Fantastic location with great amenities for a good time in Key West with a large group.
Jane W. Jan 2019
Great location. The kitchens and bathrooms have been nicely renovated, but the upstairs bedrooms are VERY basic. The pool and hot tub were quite enjoyable.
Ashley S. Sep 2018
We had the best time. House was clean, so many towels, ac worked great and communication was more than amazing. We would all stay there again.
Mabel R. Aug 2018
The space is perfect for a large group like ours of 12 adults. The sleeper sofa in 417 was very comfortable. The only concern was the parking specially when you have a large group. Parking is trivial and should have at least 1 parking spot for each home.
Michelle A. Jul 2018
Close to the downtown area and the beach. The house was clean and well maintained.
Ben P. May 2018
They staff really bent over backwards to make our cancelled trip from hurricane Irma work out.
William B. Apr 2018
14 of us rented both properties for a 5 day vacation . The location right off of Duval St. Was perfect a short walk to all of key west attractions, Houses were very nice and accommodated our big party perfectly. Only problem was the maid service . They only cleaned 1 house all week and when we finally complained they cleaned the other house once in 5 days.
Carroll/Michael E. Jan 2018
We rented both 415 & 417, and they are just adequate. The tiny pool is nice for soaking, but you could not really swim. Both kitchens are fully stocked with plenty of utensils. Great location, which makes it easy to walk anywhere in town. Our only complaint is the cost which is way more expensive than other comparable beach rentals.
Douglas F. Dec 2017
The houses are quite nice and are even on a tour! The houses were clean and very easy to get around to the key sights in Key West. There is one main bedroom on the main floor. This is quite nice. (One in each houses) . The upstairs rooms in the 417 House are very small. The ceiling is slanted and if you are 6 foot or taller bring aspirin!! I can not count how many times I hit my head. There are not real mattresses there but egg create on wooden slats. Fine for the young but if you have folks who have back problems then forget it. The photos of the inside and out seem to be taken with a creative perspective (thats being nice).

Overall a great place to stay but don't bring too many adults. The beds won't work for most.
Steven G C. Dec 2017
Clean and great location. Perfect for bigger groups with the decks connecting in the back.
Roger G. Nov 2017
Great Location & Awesome Homes for large family!! Be back soon!!