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Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK

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December 2024
January 2025

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Terrace/patio
4 bedrooms, iron/ironing board, WiFi, bed sheets
Property grounds
TV
Fridge, microwave, oven, stovetop

Reviews

9.2 out of 10

Wonderful

Entire cabin

4 bedrooms2 bathrooms151 sq m

Popular amenities

  • Parking available
  • Hot tub
  • Pet-friendly
  • Barbecue grill
  • Kitchen
  • Air conditioning

Explore the area

Map
Key West, FL
  • Duval Street
    1 min walk
  • Ernest Hemingway Home and Museum
    4 min walk
  • Key West Lighthouse and Keeper's Quarters Museum
    4 min walk
  • Key West, FL (EYW-Key West Intl.)
    9 min drive

Room options

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About this property

Entire place

You'll have the entire cabin to yourself and will only share it with other guests in your party.

Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK

Tradewinds

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Rustle up your favorite people for a memorable trip to Key West with these two homey cottages. Sitting side-by-side in a great location, each house features two bedrooms and one bathroom, a private parking space, dog-friendly accommodations, and a tranquil garden with a private hot tub in the back - what's not to love?

Located half a block from all the excitement of Duval Street, you can walk to historical landmarks like the Key West Lighthouse and The Ernest Hemingway Home and Museum, then stroll south to look out to sea from Southernmost Point. A short walk north will reveal more bars and restaurants than you could hope for on an island this size!

Fuel your day with a home-cooked breakfast in your fully equipped kitchen, sip coffee in the tropical garden, and get a morning soak in the hot tub for some extra relaxation. Freshen up using the outdoor shower, have a barbecue using the gas grill, and kill some time browsing the free WiFi or surfing the flatscreen cable TV. A dog is welcome.

Put life on hold for a moment and settle into paradise with these two cottages on Key West - book today!

If you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us. The pet fee is per stay and ranges between $150 and $200, depending on the bedroom count, and will apply for each additional dog.

Parking notes: There is free parking available for 2 vehicles.



Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the "Rental Agreement" on the checkout page.

Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.
Our customers tell us they enjoy the overall property condition at this cabin. During your stay, you're just a quick walk from Duval Street. A spa tub is available. A kitchen and 2 bathrooms are available in the cabin.
  • Air-conditioned cabin with kitchen, 2 bathrooms, and patio
  • Steps from Duval Street and 4 minutes by foot from Ernest Hemingway Home and Museum
This cabin offers its guests a spa tub, barbecue grills, and a garden. The front desk is open around the clock.

This Key West cabin is smoke free.

Property manager

Vacasa of Florida

Languages

English, French, German, Italian, Spanish

Property amenities

Beach

  • Near the beach

Pool/Spa

  • A hot tub

Internet

  • WiFi available

Parking and transport

  • On-site parking

Kitchen

  • Fridge
  • Stovetop
  • Microwave
  • Oven
  • Coffee/tea maker
  • Cookware/dishes/utensils
  • Toaster

Bedrooms

  • 4 bedrooms
  • Bed sheets provided

Bathrooms

  • 2 bathrooms
  • Towels provided
  • Hairdryer

Entertainment

  • TV with cable/satellite service

Outdoor areas

  • Patio
  • Gas grills
  • Garden

Comfort

  • Air conditioning

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property
  • Note from host: Smoking is not permitted anywhere on the premises.

Services and conveniences

  • Iron/ironing board

Safety features

  • Carbon monoxide detector installed (host has indicated that there is a carbon monoxide detector on the property)
  • Smoke detector installed (host has indicated that there is a smoke detector on the property)
  • Fire extinguisher
  • First aid kit

General

  • Unit size: 1620 sq ft (151 sq m)

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • Pets are welcome
  • Service animals are exempt from fees
  • Note from host: Dogs only. Max of 4. Weight limit: 30 lbs each.

Children and extra beds

  • Children are welcome.

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.

Property is also known as

10731

Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 60 out of 93 reviews" "
Rating 8 - Good. 25 out of 93 reviews" "
Rating 6 - Okay. 4 out of 93 reviews" "
Rating 4 - Poor. 3 out of 93 reviews" "
Rating 2 - Terrible. 1 out of 93 reviews" "

9.2/10

Cleanliness

Reviews

10/10 Excellent

Michele G., Eminence, Indiana

Liked: Cleanliness
Stayed 3 nights in Oct 2024

6/10 Okay

Verified traveller

Liked: Cleanliness
Stayed 3 nights in Jun 2024

4/10 Poor

Susanne V.

Liked: Cleanliness
Cute cottages, very poorly managed
These are two very cute cottages, in a great location. Unfortunately, there were multiple issues. Broken a/c, missing items, trouble getting the access codes, locks that repeatedly failed to work, constant and unsatisfactory communication attempts with the managing company. I requested one night's refund for all of the trouble we dealt with, and was offered a grossly inadequate refund. Would have loved to be able to say they'd made it right, but after weeks of communication that I had to initiate, this was not the case. This property is definitely not worth the price attached, despite it's location.
Stayed 4 nights in Jun 2024

6/10 Okay

christine g.

Liked: Cleanliness
tradewinds
These two cottages need some improveing. ceiling fans did not work, bathroom had no fan so when you got done showering you felt like you were in a sauna. Parking was a little hard because my family have a pickup and a jeep I definitely would not rent these cottages again
Stayed 5 nights in May 2024

10/10 Excellent

Susan B.

Liked: Cleanliness
Excellent vacation
Location, location, location. Perfect spot to park and walk. The neighbors were welcoming. Key West was great. The property description was accurate and the property manager was friendly, funny and accommodating. Great property!!!
Stayed 3 nights in Feb 2024

4/10 Poor

Rob F.

AC Issues
Several AC issues caused considerable discomfort during entire stay. One bedroom AC leaked significantly into the bedroom and almost ruined a phone - I called the office and they sent a maintenance tech that temporarily fixed the leaking, but a night later water returned which we had to mop up with towels. Several floor AC units had been placed in hallway, but they did little to cool the hall and living areas, and they were extremely loud which made sleeping difficult. In addition, patio furniture was rusted so had to use towels to avoid staining clothes. Thankfully we only stayed 3 nights.
Stayed 3 nights in Sep 2023

2/10 Terrible

Michelle S.

Disliked: Cleanliness
Find something else
For the price; some updates should be done to the property; here are the issues we had: -unit was dirty, floors were sticky, linens were dirty. -some appliances were outdated -Hole in the window above the bed, mosquito’s kept coming in before the storm hit, I had many bites all over me -Ants in the kitchen -Bed frame broken in one room -beds were uncomfortable they had two divots in each of them where you could tell people had been sleeping in. -The front door of the house had to be timed perfectly to open the door -Door knob falling off in the back door -the ac not working well at all in the bedroom closest to the front door -the windows (able to put your hand through and look into the windows and touch) -no cleaning supplies such as a broom for sweeping the floor due to sand getting everywhere, no extra paper towels, no cleaning spray once we got something in the counter we couldn’t sanitize which brought more ants -fan does not work in the living room -bathroom gets too hot due to the windows again - the ironing board does not stand up or work -the hot tub was not clean -the cleaning lady just showed up during our vacation; if it's our house and we rented it really no one should be coming on the the property because how do we know if people are gonna come in or not and get our stuff and if they do come onto the property then we should get a warning about it. -bathroom main light didn’t work -front light did not work Etc.
Stayed 4 nights in Aug 2023

10/10 Excellent

Marc F.

Liked: Cleanliness
Great spot for the trip to key west
Clean, AC works, good water pressure. We came down for our Twins 21st birthday and had friends come along too. This place was how it is described.
Stayed 4 nights in Feb 2023

10/10 Excellent

Shannon S.

Liked: Cleanliness
Great, central location
Centrally located for a 15 minute walk to Duval Street, the beach, or the ferry.
Stayed 3 nights in Jul 2022

8/10 Good

Dan O., Murfreesboro, TN

Liked: Cleanliness
Great location, but a couple comments
The location couldn’t be better… within walking distance of essentially everything you’d want to do in Key West! One block off Duval St, and very close to some amazing eateries. The checkin process was less than ideal… I kept scouring the VRBO app, the separate Vacasa app that was required to download and create a profile for in order to get the check-in instructions… only to find out that the door/access codes were not contained in either. Nor were these provided in any of the many emails ahead of time. Luckily, the property management company called about two hours before checkin to welcome us to the area (which was nice), but seemed very surprised that we had not been provided with the door codes. They gave them to us over the phone then. The cottages were generally clean/tidy, but it became clear very quickly that the floors were VERY dirty. After walking across the floors barefoot a couple times, the bottom of one’s feet were borderline black from soot. One of the units had a rotting floorboard inside near the front door… this was somewhat alarming, as it was flimsy enough that a misstep and one’s full body weight on the wrong spot would surely result in puncturing the floor to the crawl space beneath. Otherwise, the units were great, the driveway was handy, and the outdoor seating areas were very pleasant. We’d probably consider staying here again if another trip to Key West were in our future.
Stayed 3 nights in Apr 2022

10/10 Excellent

Stella H.

Liked: Cleanliness
Family Vacation
We had the best time visiting Key West! Staying here made our trip all the more memorable and special. Great location and an awesome set up for a larger group as the two cottages allow space for people to spread out.
Stayed 4 nights in Mar 2022

10/10 Excellent

Verified traveller

Liked: Cleanliness
Amazing Location!
Great location!!
Stayed 3 nights in Mar 2022

10/10 Excellent

Verified traveller

Liked: Cleanliness
Great houses
This was our second after Christmas trip with the entire family. The houses are located very close to Duval and are convenient to shopping and restaurants.
Stayed 5 nights in Dec 2021

10/10 Excellent

Christina Z.

Liked: Cleanliness
Perfect properties
We rented both home for our group for the boat races. The check in process was smooth and easy and the homes were perfect! Quaint, cozy yet spacious and clean all with the historic Key West charm. We will be renting these homes from now on. Perfectly located a few steps from Duval. The hot tub was perfect after a long day out! Thank you for having such a great property! Everyone in our party of 8 was pleased!
Stayed 3 nights in Nov 2021

8/10 Good

Brenda L.

Liked: Cleanliness
Enjoyed the houses. Driveway was to tight for larger car. Cleaning crew came to early and were a l
Enjoyed the time
Stayed 2 nights in Sep 2021

10/10 Excellent

mehgan v.

Liked: Cleanliness
Bachelorette trip
We had 11 girls total in the house! We had the best time! The pull out bed needs to be replaced in the cabin on the left and the ac in the living rooms probably do too. The bedrooms were cold though! We enjoyed our trip!
Stayed 3 nights in Sep 2021

4/10 Poor

Heather J.

Liked: Cleanliness
Like the location but AC was terrible in both houses.
Both houses have Air conditioning issues. The living room AC is not enough to cool the area. We could not get it cooled below 80 and the bathroom felt like a sauna. The bedroom ACs cooled as long as the doors were shut but were so loud it would wake you every time it turned on. This was the case in both houses. Probably best not to stay in this property in the summer. Also, even though we had no intention of using the hot tub in the summer we opened the covers just to check them out. One had missing pieces in the seat area and controllers that were so worn you couldn’t tell which button did what and the other was filthy with a funky smell and cloudy water. We liked the location-it was right near Duval but still quiet. The outside gardens in the back were nice and tropical. The houses were also cute-just a shame we we’re miserably hot the entire time. Of note-the street is very narrow with street parking right in front of the driveway that makes I difficult to pull in if you have a truck or large SUV.
Stayed 4 nights in Aug 2021

8/10 Good

Abby M.

Liked: Cleanliness
Young adult women with a week-long stay
We rented the Leeward and Windward cottages for 7 nights. Along with our stay were some positives and negatives. (Beauty is in the eye of the beholder, so these things might not impact some visitors.) Parking found with this rental is rare as most rentals only provide 1 parking space far away or none at all. This property is GREAT for adults or families visiting that want to travel together, but want/need to SPREAD OUT with separate spaces. This rental is near a lot of great fine dining, and a quick walk to the most amazing Coffee/Cuban spot Key West Cuban Coffee (went there five days in a row). Location is good for those who want to be closer to the LGBTQ part of Key West. We rented bikes and it worked out just fine getting to the Northend of Duval. Not so good for light sleepers as the Leeward cottage bedrooms hear the party animals coming/going all night long, along with a bright security light shining into bedrooms that comes on each time a passerby comes along (every 5 minutes). Light sleepers need to stay in the Windward cottage as the bedrooms are not on the driveway side with bright light and noise traveling up the alley. If renting only one of these properties, the Windward is far superior with an open layout for congregating near the kitchen and a cleaned-up back patio. Neither of them are great for very many people gathering for drinks, dinner, or lunch as they do not have a dining room table. Important if you plan to cook and eat with each other. If you are like us and spent most of your time out-and-about then these work great. Items that may not influence most: Really liked the large mirrors in every room for making it easier for multiple people (girls) to get ready for an evening. We didn't use the hot tubs as it was super hot already in April. I'm not sure if that added expense of cottage with a hot tub fee is worth it unless in the winter. I want to note this is the first rental I've stayed in that didn't have a washer and dryer for us to use throughout the stay. Also, limited hangers and space for clothes and no dresser to put away clothes. For longer stays I felt these things are handy for not "living out of a suitcase."
Stayed 7 nights in Apr 2021

10/10 Excellent

Kyler J.

Liked: Cleanliness
Perfect Rental for 8 Adults
Had an incredible experience at this rental property and would definitely visit again. Came down for a bachelor party (8 total guys) and had an absolute blast. Property team was incredibly helpful and easy to work with. GREAT location to everything.
Stayed 3 nights in Apr 2021

10/10 Excellent

Ryan T.

Liked: Cleanliness
Key West
Great place and great location. Has everything you need.
Stayed 3 nights in Mar 2021

10/10 Excellent

Kimberly S.

Liked: Cleanliness
Perfect
There were 10 of us on a girls getaway. The houses were perfectly sized for 5 in each. The hot tubs were used everyday and night. We all loved that we could visit back and forth and sit on the porches. I love that we didn’t have to search for parking on the road We had 2 vehicles and they fit perfectly The location was perfect walking distance to everything We will return and hopefully these houses will be available
Stayed 3 nights in Feb 2021

8/10 Good

CHELSI M.

Liked: Cleanliness
Great location
Walkable to everything, comfortable bed and pillows, adequate kitchen stuff, hot tub needed maintenance and the maintenance guy never showed but the other hot tub worked so not a deal breaker, not a whole lot of living room space for large group but we didn't come to key west to sit in the living room. Overall location most important for us and so glad it worked perfectly!
Stayed 5 nights in Dec 2020

10/10 Excellent

Allison R., Independence, KS

Liked: Cleanliness
Great proximity to Duval!
Location is great! Walk everywhere
Stayed 4 nights in Nov 2020

10/10 Excellent

GABRIELLE S.

Liked: Cleanliness
Perfect location!
The cottages were quaint and very clean. Perfect for groups looking to enjoy all of what Key West has to offer. Great communication. I would definitely stay here again!
Stayed 2 nights in Aug 2020

8/10 Good

Amy B.

Liked: Cleanliness
Cute cottages, great location, would rent again
Great place, clean, enjoyed the hot tubs over New Years. Excellent location. Need new mattresses and couches...old and sagging in the middle. Can hear pretty much everything through the walls, so pick your travel companions wisely.
Stayed 4 nights in Dec 2019