Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK
Cabin in Key West, FL
12 guests · 6 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Free cancellationFull refund if you change your mind
Great for petsBring all your friends and family, even the furry ones
About this cabin rental
Tradewinds
Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'
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 calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'
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.
Amenities
Air conditioner
Pets allowed
Kitchen or Kitchenette
Internet / Wifi
Parking
Balcony or Patio
Hot tub or spa
TV
Garden
Map of Key West, FL
RRRR
Ratings and reviews
10.0 / 10.0
Great location. Parking was a premium part of the house.
4.0 / 10.0
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.
6.0 / 10.0
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
10.0 / 10.0
We had a girls bachelorette trip with 7 of us and it fit us perfectly great location
8.0 / 10.0
Cozy and convenient.
10.0 / 10.0
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!!!
10.0 / 10.0
We had a group of 10 with two cars, and this two cottage location worked out great. Walking distance to almost everything. Our beds were confortable (maybe not the pull out couch so much for one couple), the back yard privacy with hot tub was very nice, and only being a block from Duval St was great. You just need to figure a way to get that rooster from walking down the driveway cackling to us at 6:30 am LOL. We wrote that off as part of the Key West experience!
4.0 / 10.0
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.
2.0 / 10.0
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.
10.0 / 10.0
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.
8.0 / 10.0
The rental properties were very clean and close to everything. Shout out to the cleaning staff who were very kind and did a great job.
The air conditioner in our unit worked fine. The other unit next door had a portable unit connected to the window in addition to window units to make up for the sluggish bedroom air conditioning units. Unsightly but not a deal breaker.
Vacasa was not very helpful in allowing us in to our units even though the cleaning was complete. The code system is not the best and people in our group had trouble off and on our entire stay. When contacting the local vacasa person, they were dismissive and blamed the user when the unit's code box kept locking them out through no fault of their own.
We did like our unit and location but would not use Vacasa in the future.
5.0 / 10.0
The location of the two cottages was fantastic. We loved having both cottagesside by side-by-side with king size beds in all four bedrooms for our large group. The off the road parking was great. Loved the hottubs for late nights and early mornings.
10.0 / 10.0
Honestly this space worked well for our large extended family vacation. We took my mother for her 75th birthday celebration and everything was as pictured and described. Only one small issue and it was addressed quickly and to our comfort and satisfaction. Really appreciate the timely response time!
10.0 / 10.0
Cleanliness, communication, and location was some of the best aspects of the houses.
10.0 / 10.0
We rented these two cottages to celebrate my daughter’s 21st birthday. These cottages are wonderful. Well appointed, AC worked well, and it had everything we needed. We didn’t try the hot tubs, so I can’t speak to that. The employees at the local Vacasa office were wonderful to deal with.
10.0 / 10.0
Centrally located for a 15 minute walk to Duval Street, the beach, or the ferry.
8.0 / 10.0
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.
10.0 / 10.0
Great place
Clean, beautiful homes with new pumping AC units. Grilled our catch and ate it from the hot tub. Comfortable beds. Exceed expectations. Great location.
10.0 / 10.0
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.
10.0 / 10.0
Amazing Location!
Great location!!
10.0 / 10.0
Outstanding Space for a Group
The two cottages are perfectly situated for groups, with two king beds and a pullout couch in each, as well as a hot tub and grill! The location is very walkable to everything and an easy uber from the airport and golf course
10.0 / 10.0
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.
10.0 / 10.0
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!
8.0 / 10.0
Enjoyed the houses. Driveway was to tight for larger car. Cleaning crew came to early and were a l
Enjoyed the time
10.0 / 10.0
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!
10.0 / 10.0
Absolutely wonderful stay
These two houses fit our large group perfectly. And also perfectly located adjacent to Duval. Will be coming back here. Highly recommend
4.0 / 10.0
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.
8.0 / 10.0
Tradewinds Key West Cottages
The location is perfect. In the middle of everything. Just off Duval, up the street from the Hemingway museum, everything less than a mile away. Great layout of two cottages. Four total bedrooms, 2 bathrooms. Nice separation if needed. Only drawback was heat index was 102 and Air Conditioning struggled to keep up. Plus the Hot Tubs need some help, missing a few pieces. Also, two wifi setup, one worked, on didn't. The service was great, anything needed was just a call away, very responsive!
6.0 / 10.0
Tradewinds Weekend
Location was great. Good and bad was bar on nearby corner - great happy hours but not so great for late night noise. House needs a little attention to maintenence do to termites swarming.
4.0 / 10.0
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."
8.0 / 10.0
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."
10.0 / 10.0
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.
10.0 / 10.0
Key West
Great place and great location. Has everything you need.
10.0 / 10.0
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
8.0 / 10.0
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!
10.0 / 10.0
Great proximity to Duval!
Location is great! Walk everywhere
10.0 / 10.0
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!
10.0 / 10.0
Tradewinds bungalows
These are super cute and in a good central location. Houses are in good condition. I have a few suggestions to make it great- the windows in the front there are some broken pains so it rattles and makes it easier to hear then street noise. Furniture could definitely use some updating and the outside foliage need to be trimmed. These homes were very clean and well stocked with towels and even beach towels which was great for us since we flew in. If I cane back to Key West I would stay here again.
8.0 / 10.0
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.
8.0 / 10.0
Great time in Key West, great location!
Cute cottages, have some age on them but very clean. Could definitely use some new mattresses and new couches, sagging in the middle. Loved hanging out on the front porch and in the back yard, especially with the hot tub! Excellent location, very convenient for Duval St., beach, parks, etc. Would definitely rent again.
FAQs
How much does this cabin cost compared to others in Key West?
The average price for a rental in Key West is R 8,645 per night. This rental is R 35,439 above the average.
Is parking included with this cabin?
Yes, parking is listed as an amenity at Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK. For more information, we encourage you to contact the property about where to park.
Is there a pool at this cabin?
We didn’t find pool listed as an amenity for this cabin. It may be worth double checking if a pool is important for your stay.
Is Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK pet friendly?
Yes! This cabin is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.
What amenities are available at Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK?
We found 9 amenities for this rental. This includes air conditioner, pets allowed, kitchen or kitchenette, internet / wifi, and parking.
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