USA Gulf Coast Florida Key West Listing #10733

Windward Isle - Key West, FL

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28 reviews
Max. occupancy: 6 2 Queen Bed 2 bedrooms 1 bathroom Sleeps 4 comfortably  4 dog max  (30 lb weight limit) 
Address provided after booking

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Expert cleaning

Pro housekeepers clean thoroughly and provide fresh linens before every stay.

Local support

Count on 24/7 guest care and local teams everywhere we operate.


Smart locks or lockboxes at many homes offer smooth, contactless check-in.

Dog-Friendly Cottage with Private Hot Tub & Garden - Great Downtown Location

Dreaming about a tropical vacation? This two-bedroom, one-bathroom cottage in Key West is the perfect destination - a private hot tub, garden, and a great location downtown will make this your best vacation yet!

Located only half a block from the restaurants and bars on Duval Street, you'll have plenty to do within walking or biking distance of this rental, so leave your car in the private parking space provided. Check out the Ernest Hemingway Home and Museum, Fort Zachary Taylor Historic State Park, or say goodbye to land for a while and hop on a sailboat for a romantic cruise into the sunset.

When you need to rest and freshen up, you'll be glad to have a private garden and hot tub in the backyard, a fully equipped kitchen for cooking meals, several flatscreen cable TV's, and free WiFi to browse and upload photos. There's patio furniture out back, as well as a grill to have your own island barbecue. The family dog is also welcome to come along for an additional nightly fee.

You deserve the privacy and comfort of home when you're on vacation, and this charming cottage is the key!

County permit number: 25230-73041

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


Heating & cooling

Central AC

Partial AC

House rules


Kitchen & dining





Internet : Comcast


Cable : Comcast

On-site activities

Hot tub : Private




28 reviews

Renee M. Aug 2022
Loved the cottage. Very comfortable and great location.
Alice L. Nov 2021
Good location, walking distance to restaurants and attractions. Beds were very comfortable and house was clean. WiFi did not work and the hot tub was dirty, emailed company with concerns and didn’t get a response.
Manager response:
Thank you for staying with us, Alice, and for taking the time to provide your feedback! We're happy to hear you enjoyed the location, though we apologize for the issues that prevented you from fully enjoying your stay. It is relayed to guests in our check-in materials that while our local property manager is not on-site to greet guests, our professional, dedicated team is standing by should any need arise. We regret that we did not see your email until after your departure, but please know that our local team is currently working with Comcast to improve the internet at this home. We will ensure that the hot tub is thoroughly cleaned prior to future guests and we appreciate you bringing this to our attention. We look forward to hosting you for a much more enjoyable stay in the future!
Jeana C. Oct 2021
This was the perfect house for my brother and myself, along with our spouses, while visiting Key West for a few days. It was close to everything we wanted to do. We didn't spend much time in the house as we were out exploring, but was just what we needed when we returned each day. The AC kept the house comfortable enabling us to rejuvenate for the next days adventure. The neighbors in the rental next door were also a pleasure.
We'll be back! Thanks Vacasa
Donna M. Jul 2021
Very clean and comfortable house. We enjoyed walking to restaurants, bars and clubs. Would stay here again.
Marianita G. Apr 2021
Lovely 2 Br Home with its own rear parking spot and a few blocks walking distance to Duval St., Simonton St,, Truman Ave. Comfy bed, private backyard with hot tub, pet friendly too. We sat on front porch and enjoyed locals too. Great experience!
Becki T. Feb 2021
We loved the house and the private backyard!
The location is so convenient to Duval Street and walkable to just about everything!
It is in need of new living room furniture but the beds are super comfy
Marlene G. Jan 2021
Very clean and comfortable! Close to everything, we walked almost everywhere we went. Its in a busy part of town so there is some street noise. Enjoyable stay in key west!
Shannon P. Dec 2020
The house located at 531 Olivia was just a quick two block walk From DUVAL Street. It was perfectly located.
We stayed for three nights and thoroughly enjoyed ourselves. The place had a hot tub so when we were tired of the hustle on the main strip we took a quick walk back to the house and had a few beverages in the backyard while enjoying the hot tub. Completely secluded however
The neighbors were sweet~
The beds were very comfortable, the pillows were extremely comfortable and the beds were both king-size so plenty of room. Both bedrooms had TVs and all of the amenities for the kitchen needed. Bathroom was spacious and had good water pressure. 4 of us showered and all still had hot water.
I would however recommend bringing a corkscrew for 🍷 if that’s something you’ll enjoy during your stay.
We did have to call to have toilet paper delivered on the second day because we only had one roll in the house and there were four people staying however they brought that within an hour and a half of us Calling.
We enjoyed our stay and cannot wait til we return.
We will be booking with vacasa again ❤️
Howard B. Jul 2020
Modern conveniences in quaint cottage in an unbeatable location. Enticing back patio area with so much shade you won’t want to go back inside. The front porch is great for people watching and relaxing. The off-street parking space is a plus so you can park the car and forget it. Easily room for 4 with the two separate bedrooms with king beds.
Oh, did I say the price was right, too!
Jack M. Mar 2020
Cute place. Great hot tub! Needs new mattress and some sprucing up however.
Manager response:
Thank you for sharing your feedback, Jack. We hope you enjoyed your stay. We appreciate you letting us know there is room for improvement, and we'll pass your comments to the owner for consideration. We hope to have another chance to impress you in the future!
vicki g. Jan 2020
nice house, clean, well stocked, enjoyed the hot tub
Paul M. Dec 2019
Great location a short block from Duval Street. Cozy classic Key West cottage. Nice amenities.
Lulu L. Nov 2019
We stay here for 3 nights (us and the in-laws), and it has been great. We like the decor and they have everything in house, from plates, coffee maker and filter, beach towels, etc. The location is great, very close to the no. 14 stop of the free Duval loop bus if u don’t like walking. Otherwise it is in the middle of everything within walking distance. I would wish there are two bathrooms, but we make it work with one. It’s a pity that we didn’t get to try the jacuzzi as we are all too tired from the activities during the day. Overall my in-laws and us are all very happy that we got this place.
kenneth R. Dec 2018
The cottage was quaint and cozy, perfect for what we was planning. Close to main st, Duval. We did however wanted to use the hot tub but no instructions were left in how to use or turn on since the unit was shut off from the breaker. Other then that, nice beach cottage.
Manager response:
We are so glad to hear this guest enjoyed their stay! We appreciate and encourage guests to let us know of any questions or concerns that may arise in the home so that we make work to address and resolve them as soon as possible. We would love to host this guest again!
Sam T. Dec 2018
just a block off both Duval and Truman this place was in the perfect location. The accommodations were great and the house had almost everything we needed. I'd recommend it to anyone and we will likely stay there again.
Paula N. Jun 2018
Everyone helped to make our stay enjoyable.
Keith C. May 2018
Great place to stay. Clean and well kept. Beds were not too hard or soft. Good sleeping. Small living area but you don't spend a lot of time there. Great patio out back.
Tara B. Apr 2018
The location was perfect, a quick walk over to Duval for us to venture where we wanted to go. There was plenty of space for our group to enjoy all the house had to offer. The management company was excellent to work with and so accommodating to any of our needs. Highly recommend! We will definitely be back for future trips!
Margaret H. Mar 2018
Our cottage on Olivia was comfortable, with good outdoor space (backyard with hot tub, and a front porch). Very adequate kitchen, with everything you'd need for a weekend or a week. Has one-car off-street parking. It was an easy walk to downtown, and pretty much everywhere else we wanted to go, except for Fort Zachery Taylor, for which you'd need a car or a bike. With just a little more attention to repair details of the house, it would be perfect.
Al H. Jan 2018
Enjoyed our stay, well placed for easy access to sights.
James V D. Dec 2017
Perfect location and comfortable place to stay