Rating 5 (151)

KW33 - Tradewinds


4 bedrooms
Bathroom 2 baths
Dog Friendly Dog Friendly

  • Address: 529-531 Olivia St
  • Town: Key West
  • Type: House

Amenities 2 Amenities
Featured Amenities
  • Dog Friendly
  • Hot Tub

Bedding Bedding
Bed
Bedroom 1
1 King

Bed
Bedroom 2
1 King

Bed
Bedroom 3
1 King

Bed
Bedroom 4
1 King

Bed
Living room 1
1 Sleep Sofa

Bed
Living room 2
1 Sleep Sofa


Description Description
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!

Location Location

Reviews Rating 5 (151) Reviews
Rating 5
Great place to stay if you want to travel with a larger number of people. Having the two houses next to each other worked out great. The hot tub did not work, but they were very responsive and took care of it to my satisfaction. Overall, a very good location, clean and what we expected.
Anthony Paul -
Rating 5
The house was in a great location, clean, good ac. Will be staying again. Highly recommend
Tracy C. -
Rating 5
We had a great stay here! Close to everything you’d want to access in Key West. Stay has mostly everything you need to stay a few days comfortably.
Jennifer -
Rating 5
We enjoyed staying here. Washer & dryer would’ve been helpful but overall, great space & location!
Brandy -
Rating 5
.
Debbie -
Rating 5
Nice location within walking distance to many restaurants and bars. Quite neighborhood.Very spacious. Nice off road parking. Very comfortable clean beds.
PAULA A. -
Rating 5
Great spot right near Duvall and downtown
Lucas -
Rating 5
We had a wonderful time visiting with family during our trip! The home is definitely rustic but the location to everything is perfect! The beds were very comfortable and high quality linens. Home was clean but it is an older home. AC worked well! Older homes can always use upgrades but overall we enjoyed it very much!
Widget -
Rating 5
Great Property
Close to Duvall St
Sherri -
Rating 5
Beautiful, charming place! Very comfortable and loved the Hot Tub! Very close to Duval street and all the fun!
Sarah -
Hi, thank you for your valuable feedback. We're delighted to hear that you found the place charming and comfortable, and that you enjoyed the hot tub. Its proximity to Duval Street does make it a great location for fun activities. We look forward to the opportunity to welcome you back for another wonderful stay in the future.
Seven Keys Vacations staff
Rating 5
We rented both cabins with friends next door it made everything so easy sitting on our front porches together. It even had a parking spot for our golf carts.
Jennifer R. -
Rating 5
First time trip to Key West six adults. Cottages are cozy as stated. Had a few minor issues that were fixed same day. Perfect location on quite side street. One block from Deval street within walking distance to mostly everything. Need to go further - golf cart rental around the corner or Uber. We didn't use the extra amenities since we ate out each day. Shower and place to change and regroup. Would stay again.
DANIEL R. -
Rating 5
Cute little houses
Had a wonderful time here with our family. Was cozy enough for family but plenty of room to spread out. Easy walking distance to shopping and restaurants. Would definitely book again. Keep in mind these are rustic houses and while they have everything thing you need it may not be from the past 20 yrs.
Jenny -
Rating 5
Gran alojamiento en cayo hueso. La zona era perfecta, tranquila pero cerca de calles principales y de la playa. Gran sitio para ir grupos de gente ya que son espaciosos y ambas casas están conectadas
Laura -
Hi Laura, we truly appreciate you sharing your wonderful experience with us. It warms our hearts to know that you found the location to be perfect, offering a blend of serenity and convenience to the main streets and beach. It's fantastic that our spacious accommodations suited your group well. We genuinely hope that your visit was memorable, and we would be thrilled to host you again for another exceptional stay in the future!
Seven Keys Vacations staff
Rating 5
We booked both houses for 10 people for a fantasy football draft on/along Duval Street. The houses were located just a block off of Duval and allowed us to walk everywhere. It was a great location. The houses themselves were clean and comfortable. Both houses were mirror images of each other. Two bedrooms on the right of a long hallway that led to a smaller living area and kitchen. Not a lot of hangout space, but we didn't really need it for that. Both houses also had hot tubs. It was already so hot in late-August outside that we didn't need to be around hot water (so we didn't use them)!
Jordan -
Hi Jordan, thank you for taking the time to share your valuable feedback with us. We are glad to hear you enjoyed the amenities and location of our vacation rentals. It's wonderful that the cleanliness and comfort of the houses contributed to your overall experience. We appreciate your insights into the layout and space, and we hope to have the opportunity to welcome you back for another enjoyable stay in the future.
Seven Keys Vacations staff
Rating 5
Great location. walkable to bars and restaurants. yet not right on the busiest street.
Definitely recommend
Kevin -
Hi Kevin, we truly appreciate you sharing your experience with us. It's wonderful to hear that you found the location great, with easy access to bars and restaurants while still enjoying a peaceful environment away from the hustle and bustle. Your recommendation means a lot to us, and we can't wait to welcome you back in the future!
Seven Keys Vacations staff
Rating 5
Good location and easy place to access.
Caleb -
Hi Caleb, thank you for taking the time to share your valuable feedback. We're excited about the opportunity to host you again and deliver another amazing experience!
Seven Keys Vacations staff
Rating 5
Bachelor Trip
Great space for a large party! Having both houses with the driveway in the middle provided a great spot for our weekend!
Ryan F. -
Rating 5
We loved staying here, great location and nice spacious rooms.
Katie -
Hey Katie, thank you for providing us with this valuable feedback, we are so glad that you had a wonderful time at our beautiful home! We look forward to welcoming you back on your next visit!
Seven Keys Vacations staff
Rating 5
These cottages were perfect for our vacation. They were walking distance to everything we needed with enough room for all of us.
Katherine -
Hi Katherine, thank you for sharing your experience! We are pleased to hear that our cottages met your needs for your vacation and that their location was convenient for your group. We hope to welcome you back for another enjoyable stay in the future!
Seven Keys Vacations staff
Rating 5
This was a GREAT stay with a few minor changes that would have made it the BEST stay! Location was perfect, and so much fun for walking! We even rented 2 golf carts and safely and securely kept them in the joining drive way free of worry! We used one of the hottubs (house on left) and that was great! We had 10 girls and both houses and it was a perfect fit. Would definitely do it again
Chelsea -
Hey Chelsea, we appreciate you sharing your experience with us. We’re glad to hear you enjoyed the fantastic location and found the accommodations perfect for your group. Thank you for highlighting the convenience of the golf carts and the enjoyment of the hot tub. Your feedback on potential enhancements is valuable to us, and we hope to welcome you back for another great stay soon!
Seven Keys Vacations staff
Rating 5
Great house's
The location was great. Not to far away from the fun but enough to not hear everything.
MICHAEL -
Rating 5
Great location
These were very quaint cottages and a fantastic location close to everything you’d want to see and experience
Kevin M. -
Rating 5
We loved staying here!!!!
Laurie -
Hi Laurie, we're delighted to hear that you loved staying at our home! Thank you for sharing your experience with us. We look forward to welcoming you back for another memorable visit!
Seven Keys Vacations staff
Rating 5
Michele G. -
Rating 5
Houses were nice enough only thing I think they could do better is have some wiggle room on check in /out people were there 30 minutes early trying to come in
Don -
Rating 5
Excellent stay for a group of 8/12
Great location. Parking was a premium part of the house.
Nikolas C. -
Rating 5
Cute home!
We had a girls bachelorette trip with 7 of us and it fit us perfectly great location
Jaime F. -
Rating 5
Great location on Duval street. The houses are aged but were kept in good condition. We were not given the code to enter ahead of time so we had to spend time on the phone with the help desk (15 min). Otherwise great stay
Garrett -
Rating 5
Great location, could not have been more convenient. Comfortable beds, spacious. Parking was convenient too!
If I had to choose a complaint… which I really don’t have… it would be that if you are looking for a modern and updated experience, this may not be for you. The house is older and not updated, but everything was clean and in working order!
Ellen -
Rating 5
These two houses were very unique close to down town the owners were very responsive with any questions I had I would definitely stay here agin
Dustin -
Rating 5
Great place in a great location!
Kristine -
Rating 5
great place in a perfect location
Jennie -
Rating 5
Vacasa Key west was perfect for my bday extravaganza. Two separate homes side by side with two bedrooms and a sofa bed in each. Location was perfect only a block away from duval st. I had a little trouble getting the key code but after calling the office number a few times I was able to get it. Also, not just one hot tub but two! We couldn’t get one of them to work but all we really needed was one any way. Overall a great stay!
Alanna -
Greetings, Alanna! Thank you for taking the time to review your stay with us. We are delighted to know that you loved the location and the amenities of the home. We hope you had a great stay. We are truly sorry for the trouble you experienced while trying to obtain the key code. Nonetheless, we are happy to hear that you were able to eventually get the code after calling, despite the inconvenience. Alanna, thank you for your valuable feedback, and we look forward to welcoming you back for another wonderful getaway in the future! 
Seven Keys Vacations staff
Rating 5
Great house, awesome location, very walkable
Danny -
Rating 5
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!!!
Susan B. -
Rating 5
Perfect Place for 10
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!
Stuart D. -
Hi, Stuart. Thank you for providing us with this valuable feedback. We are so glad that you had a wonderful time at our beautiful home. We thank you for your feedback, as it helps us improve our guests' experiences. We look forward to welcoming you back for another fabulous getaway in the future.
Seven Keys Vacations staff
Rating 5
Awesome place to stay with a group! Perfect location in the heart of everything!
Julie -
Rating 5
Great location. Many walkable restaurants and bars.
Michael -
Rating 5
Very confusing to get the door code. I called 3 days before check in and I was told I would get the codes 24 hours prior to checking in. That did not happen I called back and I was told I would get the code the morning of Check in by 8am I did not. I called back 4 hours before checking in and finally they put me with this extremely rude girl on the phone who said she had left me a massage the previous day on my cell with the code of course no massage was there. If they remove her from the equation and hire someone who is happy their process will greatly improve and they will receive 5 stars from everyone I fear if they keep her they will run off business like they have me. Her name is Victoria and she is at the vasca office in key west.
Tim -
Thank you for taking the time to provide us with this feedback, Tim, we are so sorry for the poor experience you had while using our services. We truly regret to hear of both the disconnect in the care and the delay in the service you received when communicating with our team. Please know that this is not the high level of customer care that we strive to provide our guests and we make every effort to attend to our guests as quickly and efficiently as able. We welcome your feedback as a means to improve and will be sure to follow up with the appropriate parties regarding your experience so they can work to ensure that our high service standards are fully met. To clarify, we provide the check-in info within your check-in email which is sent out 24 hours before arrival to the email that we have on file. Additionally, this information can be found in the Trip Manager portal that is sent out at the time of booking. We sincerely apologize for the inconvenience this may have caused, and we hope you will give us another chance to better serve you on a future stay.
Seven Keys Vacations staff
Rating 5
Nice place. Walking distance to everything you need.
Joe -
Rating 5
this place was so charming and cute and CLEAN. it’s located a tiny walk from all the fun of duval st. our only “gripe” is that we could not for the life of us figure out how to get the hot tub to a lower temperature, but we enjoyed it anyway - even if it was cooking us like soup. would definitely stay here again.
Kelly -
Rating 5
Great location, fun times
Harrison -
Rating 5
Great place to stay.
Michael -
Rating 5
It was an amazing stay. The dual cabins were great. It was a quick walk to everything. Vacasa was very helpful from the beginning til the end. Thank you very much.
Carlo -
Rating 5
We had a great stay at the twin cottages in Key West. The host was very responsive. 8 of us stayed between the two units which worked perfectly. Our favorite part about these units is they are only two blocks from Duval St. and half a block from Simonton St. which basically made it possible for us to walk wherever we wanted to go. The huge propane grill was a plus and so we’re the hot tubs. Would highly recommend these units.
Brant -
Rating 5
Due to the price, this place was worth every penny! It was very inexpensive and relatively comfortable for 12 people. Had it been a more expensive stay, I’d probably consider a lower rating. Unfortunately, there is zero wiggle room with check-in and check-out, even 20-30 minutes and getting back in if something was left behind is seemingly difficult. Bring trash bags and paper towels if you are staying for longer than a weekend. Also, no cooking supplies or dishwasher so grocery shop accordingly! Overall, the place was great and I would definitely book again.
Ally -
Rating 5
Photos did not do this rental justice! Such a lovely space, much bigger than expected. Perfect location about 2 minute walk to Hemingway Home
Catherine -
Rating 5
Excellent location
Kayla -
Rating 5
Killer place! Easy walk to Durval, great place to stay at.
Colby -
Rating 5
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.
Marc F. -
Rating 5
Really we couldn't have asked for more! Met all our expectations!
William -
Rating 5
Great location and lovely space!
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!
Chantal M. -
Rating 5
Walkable, good location.
Amber -
Rating 5
Great location! We could walk or bike the whole island. Many great restaurants and walking distance to Highs Beach. We had both cottages for eight adults and 2 kids; plenty of room. Loved sitting on porch to people watch.
Outside hot tub and showers were wonderful. Just needed a little more info on check out expectations.
Kimbra -
Rating 5
Nice place for the weekend
Eli -
Rating 5
Great spot, great beds, cool back yards, close enough to walk to Duval, also very close to moped rental place that’s great as well
Justin -
Rating 5
Absolutely perfect as described!! Perfect location for exploring the city. Would recommend to anyone. We will be back if the houses is available.
Ronald -
Rating 5
Fantastic Home
Connor -
Rating 5
Clean with great location
Cleanliness, communication, and location was some of the best aspects of the houses.
Andrew B. -
Rating 5
This house was perfect for us! We had 10 girls for a bachelorette party and it fit us perfectly! So close to everything we had planned so we were able to walk everywhere. Definitely a good space for a large group and super conveniently located! Would love to come back!
Kelsey -
Rating 5
great location
Jeanette -
Rating 5
Perfect location
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.
Paula S. -
Rating 5
Great, central location
Centrally located for a 15 minute walk to Duval Street, the beach, or the ferry.
Shannon S. -
Rating 5
Walking distance to EVERYTHING. This was absolutely perfect for a bachelor party of 10. We were able to park a van, a car, and multiple mopeds in between the houses. Ideal situation for mobility and walking.
Justin -
Rating 5
Location was amazing and everything you could want when staying in Key West
Brian -
Rating 5
Perfect location
Morgan -
Rating 5
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.
Ryan R. -
Rating 5
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.
Stella H. -
Rating 5
Amazing Location!
Great location!!
Verified traveler -
Rating 5
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
Connor E. -
Rating 5
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.
Verified traveler -
Rating 5
The houses were great and exactly what we needed! Check out and check in we’re not flexible but i think that is to be expected with a vacation property management company. The location was perfect and the houses were exactly as described!
Lauren -
Rating 5
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!
Christina Z. -
Rating 5
Awesome homes with great location
Eric -
Rating 5
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!
mehgan v. -
Rating 5
Enjoy the morni g breezes and sunrise on the porch. Great outdoor shower area, super for beach days. Backyard BBQ under the evening sky and the a short walk to Duvall Street.
D -
Rating 5
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
George C. -
Rating 5
Cottages were great! Location was perfect!
Payton -
Rating 5
Great location if going to Duvell street is your idea. Lovely karaoke bar across the street. Good communication but wasn’t able to check in early or late which caused some issues with us luggage wise. Large clean beds.
Stephanie -
Rating 5
Great stay!
Emely -
Rating 5
A great place to stay. just a block a half off of Duval street. nice quiet street.
Doug -
Rating 5
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.
Kyler J. -
Rating 5
We loved our stay at Vacasa Key West! Beautiful place with awesome amenities - the outdoor shower is a must! The property was close to everything, we will definitely be back to enjoy this beautiful place.
Carlos -
Rating 5
Key West
Great place and great location. Has everything you need.
Ryan T. -
Rating 5
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
Kimberly S. -
Rating 5
This place was amazing. The owners where very fast at responding to any issues I had. Also the places was in walking distance to all the local hot spots
Christian -
Rating 5
Great location for walking and biking exploring both sides of the key. Well stocked and clean. Communication with management company was easy and friendly
Linda -
Rating 5
Great proximity to Duval!
Location is great! Walk everywhere
Allison R. -
Rating 5
Great place. Good for a multi-family trip or a large family. If you have pets, there is no grass. My dog was a little confused by this but she caught on. There is a privacy fence closing off each backyard from the parking area. Made it a little difficult for family gatherings but we managed. There are gates opening to the parking area from each backyard. Both houses were clean at check in. Overall, it was a great place to stay and I would definitely stay there again. Five star accommodations.
Charles -
Rating 5
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!
GABRIELLE S. -
Rating 5
I rented this airbnb for my dad’s birthday weekend getaway. This airbnb is very convenient and it was cozy. Highly recommended to other families who wants to get away in Key West!
Bao Anh -
Rating 5
You can not go wrong with this property! Two houses, that each have two bedrooms. Exceptionally clean, air conditioner worked perfectly (very important when visiting the Keys). Loved having breakfast and coffee on the front porch in the morning. Bed was very comfortable, and bedding was soft. Beach towels were available as well as bathroom towels and wash cloths. Just the cutest place we have ever stayed at. This will become an annual thing!!
Chris -
Rating 5
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.
Amy C. -
Thank you for your review, Amy. We are glad you enjoyed this home and we appreciate you bringing these issues to our attention. We will work with our local team to ensure these items are corrected for future guests, and we hope to host you again in the near future!
Seven Keys Vacations staff
Rating 5
Very neat little houses. Centrally located and perfectly clean.
Communication is fast, however, the service isnot great. Check-in after 4 p.m.. When we asked to park the cars earlier, obviously noone was at the partment by that time, they just said no without comprehensive explanation. It was also rather difficult to receive the necessary codes to enter the houses.
Christoph -
Thank you for staying with us, Christoph! We ask our guests to refrain from parking at the home before check-in time to ensure that our housekeeping team can easily access the home, we apologize that this was not communicated when you inquired. We hope to have another opportunity to host you!
Seven Keys Vacations staff
Rating 5
These two cottages are so charming. The back yards and tubs are really nice too. The interiors are a little rough, but very accommodating. I'd stay again in a heartbeat. The location cannot be beat!! We rented bikes for our entire stay and highly recommend the same to you.
Karen -
Rating 5
Excellent location! One block to scooter rentals, restaurants (Better Than Sex Desserts and Little Pearl), and easy walk to Duval (shopping and fun people watching) and the wharf. Far enough away from the main walkway to be private.
Celetse -
Rating 5
Excellent spot close to everything w in walking distance. Will stay again if we have the chance to come back to Key West!
Abby -
Rating 5
Running to stand still
We visited key west for the marathon. Coming home to these cute houses and comfy beds with hot hot tubs after the run made the whole experience so much better!!!!
Kristina R. -
Rating 5
Wonder home in a great location😁
The houses were clean and well layed out. The location was perfect
Jean-Paul L. -
Rating 5
Our group of six (two couples and two singles) enjoyed our Key West weekend and stay in the rustic cottages. Check-in was clearly communicated and easy. The location is great for Key West nightlife and sites. The spaces are comfortable and functional, and the air conditioning made the house a comfortable place to come back to on hot summer days.
August -
Rating 5
The house is in a great location and they are super cute little houses, both having a hot tub and a grill in the back. They were the perfect houses to celebrate my brothers birthday at and would definitely recommend this house to anyone looking to have a great key west experience. We did have a few issues and the host were quick to respond and have it fixed.
Emily -
Rating 5
This place was amazing I would definitely recommend it to anyone that is going to the keys. The location was PERFECT! Walking distance to everything we will be coming back for sure
Mike -
Rating 5
We Had an amazing time. This place is great for a big group I loved the location being so close to Duval was great we could go out all night long and only had a short walk back, loved that. Also loved the outdoor shower it was so nice to take a shower outside in the morning in such a beautiful backyard. The hot tub was great too being as it was summer it was nice the water temperature was only 88 degrees. The inside of the house was nice and comfortable great beds and had everything you needed to cook . The only problem we had was parking we came In a 12 passenger van and couldn’t fit in the driveway, we tried and it wasn’t happening it wasn’t too bad we found a spot on the street close by. Thanks again for an amazing stay we had a great trip and would highly recommend this place and stay here again.
Anthony -
Rating 5
Clean, comfortable, and quaint
We had an awesome stay at this property. It was clean and comfortable and in a nice neighborhood close to stores, restaurants and shops. It fit our party of 7 without issue and very comfortable.
Karen D. -
Rating 5
Perfect for a large family
We loved the cottages! They had everything we needed, we brought our adult children and their significant others and our parents. Everyone was comfortable! We had plenty of room, loved the hot tubs, grill worked perfectly and the outdoor shower was a plus!
Penny F. -
Rating 5
Everything was very easy from check-in to check-out. Both units were very clean and we did not have to worry about having enough soap or clean towels. We could tell comfort was a top priority for Vacasa and it was very much appreciated.
Nick -
Rating 5
Perfect location, very easy check-in/check-out process, great spot to stay in Key West!
Brett -
Rating 5
Was very inviting
We enjoyed staying at the Old Town cottages. It was very nice to be able to stay close to the action but still able to get away and be with our group and sit around on the patio.
Amy B. -
Rating 5
We rented both houses for a recent vacation. Location is great although it is about a 20 minute walk to reach Mallory Square. If you are interested in see all of Duval and don't mind walking, it will be a perfect spot. Houses are what we expected, older but fully functioning and met all of our needs.
Cheryl -
Rating 5
A very nice little spot in Key West with a lot of authentic atmosphere! It had everything we hoped for and with the little garden and grill, there plenty of room to house a small diner party.
Thank you!
Mads -
Rating 5
Nice layout
Loved the location, loved the outside shower, if you could add a toilet and mirror outside it would be perfect..
kelly s. -
Rating 5
Place was very clean and in great location. Did not have to use my rental car at all once I got there. Had a great time with family including kids and definitely recommend it.
Kanak -
Rating 5
Convenient to everything downtown. Walking distance to everything, but does have off street parking if you do have a vehicle. Plenty of towels and toiletries. We didn’t do any onsite cooking, but did see the normal cooking utensils. Very nice BIG beds to fall into each night.
Dixie -
Rating 5
Good Place
Quiet part of town. Bar across the street gets a little loud but, AC units inside run constantly so they pretty much drown out the noise. Well kept, clean and has just about everything you need. One suggestion would be to keep salt and pepper shakers in the house for tenants to use. Overall, great location to DuVal Street. Process was very easy and staff was friendly and helpful!
William D. -
Rating 5
A+ we will be back. The houses are adorable, the pics really don’t do them justice. Comfy king sized beds in every room. We absolutely loved our time here.
Morgan -
Rating 5
Excellent location, spacious and ideal for up to 8 people.
John Bryan -
Rating 5
Great price value and location. 2 separate houses make it nice when you have 2 families.
Nick -
Rating 5
Would Stay Again just like the photos.
Our group had an overall good experience at this property. This property is in an ideal location. We parked our cars and didn't drive until we left from our trip. We walked and rode scooters everywhere. The cottages are just a block away from Duval. We went out to eat and used the kitchen which was well stocked with pans and utensils. Note: At the time we stayed the listing said we had a grill in the backyard. When we got there the was no grill. The local property manager said the fire marshal made them remove it. Just in case you were planning to grill out. The little backyards gardens were delightful, and the hot tubs were nice and clean. The cottages were just like the photos, A/C worked well, and there TVs in each bedroom. Planning a trip for 2020 and would love to stay here again!
Amber E. -
We hope you come back in 2020!! Thank you for the wonderful review.
Seven Keys Vacations staff
Rating 5
Super comfortable stay, very clean, we had a great time!
Jackie -
Rating 5
These cottages were perfect! The location was great (right off Duval) and everything was as expected, even nicer than I thought I would be. There are 2 king beds in each cottage which are VERY comfortable. The hot tubs and outdoor showers were an awesome addition to our stay. Additionally, there was an issue with one of the hot tubs, that was quickly resolved. I have nothing but good things to say about Vacasa Key West!
Lauren -
Rating 5
Great location steps away from Duval street, so you are less than a mile from anything you want to see in Key West: Southernmost point, Hemingway House, the Lighthouse, Mallory Square, bars, shops and restaurants. Early risers can find breakfast at the nearby Dennys (open 24 hrs), or Banana Cafe opens at 7:30am. If you can wait till 8:00am, there are two places that serve croissants and/or french pastries. Park your car in the private off-street spaces (room for 2 cars), and then walk everywhere!
Patricia -
Rating 5
Another Great Key West Spot
We loved having the two cottages next to each other. Convenient location, clean neat home. We would definitely stay again!
Christopher W. -
Rating 5
Business Trip
Company Sales Meeting in KW and we had an amazing time. The property was great for 4 people and could sleep four couples perfectly. I would recommend this location to anyone wanting to stay close to Duvall St and all the fun places around there.
Chukwuka A. -
Rating 5
This place was in a great location off Duval street. They allowed us to check in early. The place was nice and clean. The hot tubs were a nice touch!
Nikki -
Rating 5
Fun place!
The houses are really cute and so close to everything! They are right across the street from a happening bar and they party all night!! We went over and joind in the fun, but if you're looking for peace and quiet you may want to stay further from duvall st!
James S. -
Rating 5
Colin
Great Home and location.
Colin C. -
Rating 5
Labor Day Weekend
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The rental experience at Tradewinds was better than I imagined. We even got to check-in a couple hours early which was great since we traveled far by car. We were able to park the cars in the driveway and unload our stuff. The houses were perfect for two separate families on vacation together. It gave us the ability to have our own space but still be close. The houses were right off Duval street in the center of all the fun. They were clean and spacious with king size beds. The backyards were great to relax and unwind in the hot tubs. We throughly enjoyed our stay at the Tradewind houses.
Jena M. -
Rating 5
Awesome
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our stay at the Tradewinds exceeded our expectations!! The homes were in a perfect location. Amentities were great! Would definitely stay here again. The only down fall was the hot tubs were not clean so we did not enjoy that part or our stay as we hoped to.
Sharon P. -
Rating 5
Chinn Family Thanksgiving
Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: All good - great facility and a great time had by all
Stephen C. -
Rating 5
Great little home for a couple or two
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The rental company was great and the homes were exactly as described. We rented both of the sister homes and lived it. Thanks.
richard e. -
Rating 5
Great place for large group!
Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a great stay with 10 girls in both of the Tradewinds houses. It was nice to be able to split up and have room to move around instead of 1 bigger house for all of us. There was plenty of space to have 5-6 girls in each house. Plenty of mirrors to get ready in! It was a good location, a short walk to everything, but far enough to not hear noise constantly. Overall, I would recommend for a large group!
Jessica C. -
Rating 5
Great place for a large group!
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: These places were a great place to gather with a large group. The homes comfortably slept 4 in each house but with the pullout bed, 6 people in each home was a tight squeeze. But you can't beat the location and the coziness of the places. Clean and inviting homes with some small maintenance issues that could be addressed to make the experience a little better, but nothing that overshadowed the stay. I would rent these places again when I go back to EYW.
Jeff M. -
Rating 5
30th Birthday Bash
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our stay was great! Location was perfect and close to everything. Only called maintenance to fix the lock on the bathroom door. Everyone in my party enjoyed their stay as well. Complete success!
Rebecca K. -
Rating 5
PERFECT PERFECT PERFECT
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Only stayed for one night on a mini trip to Key West after a Caribbean Cruise. How nice that the rental agency did not have a minimum stay at these fantastic houses. They were perfect in every aspect. Location was phenomenal, houses were decorated beautifully and the beds gave us the best night's sleep during our entire vacation. Very sad we stayed just one night but do plan to rent the same houses when we return to Key West for a longer vacation. Rick at Key West Vacation Rentals was awesome. Very kind and accommodating. Allowed us to park our cars in his parking lot after we checked out so we could sightsee. Very impressed by entire experience. Highly recommend.
Patricia G. -
Rating 5
Girls Key West Trip
Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The houses were just wonderful. Location was great.The only complaint I have is they need to replace the pull out sofas. The mattress were horrible.They advertise the houses to sleep 6 to a house. The bedrooms beds were very comfortable.OVERALL I GIVE THESE HOUSES A 8. If they replace the sofas I would give them a 9.
Carla W. -
Rating 5
Great location!
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This place was extremely close to everything you would want to do in Key West! We had both houses for 10 girl and it was perfect! We all had our own areas to get ready and we were walking distance to everything! They brought extra towels every day and if you called they would bring extra linens. We had a great stay and would stay here again!
Amanda H. -
Rating 5
Ultimate vacation rental
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We could not ask for anything more perfect. Great house great location and wonderful concierge service. We always come back to rent through your company.
Marilyn M. -
Rating 5
4th of July weekend at Tradewinds Group
Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We booked both units for a group of 12 for 4th of July weekend. We were pleasantly surprised to see how much parking we had between the 2 cottages because it was a major concern of ours. We got all 4 cars in with room to spare. The Leeward cottage's kitchen was a lot smaller than Windward but it was fine because we all congregated in Windward for get togethers. The 4 bedrooms were ample in size and comfortable. Loved the wide, long hallways to store large items! The bathrooms were also good sized which helped with such a large group. The only negative comment I can think of was that the floors were not clean as well as the area rug. If you walked barefoot, your feet were black. The sofas could also use a cleaning. We all really enjoyed the location and the charm of these 2 cottages and I would highly recommend for a large group like ours. I would rent one or both of these again for sure.
Michele S. -
Rating 5
Amazing Stay!!
Great place to stay. 1/2 block from Duval Street near local pubs, restaurants, shopping, activities, etc.
Ed G. -
Rating 5
Great Time
Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a Great time and the rentals were clean, organized and homey!
Shelly B. -
Rating 5
Reasonably priced place to stay in Key West
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Location of property was very close to Duval St. and all of the local activities. King sized beds were very comfortable, and room space was adequate. Shrubbery around hot tub could use some trimming, and there were some minor maintenance issues in the bathroom and kitchen. Bedroom was lacking a closet and dresser for storing clothes, and the safe didn't work. But overall the stay here was very nice.
John B. -
Rating 5
Fun time in KW
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great vacation! Perfect accommodations and location.
Ed G. -
Rating 5
Very nice place
Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Very nice place for the money close to duval street
Joshua S. -
Rating 5
Great place to stay with a large group!
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 2 homes close together, hot tub in each backyard, grill and patio in each backyard, 4 bedrooms and 2 sofa beds, 1.5 blocks from Duval, easy to deal with staff makes it a highly recommended place to stay.
Chris M. -
Rating 5
The Best of Key West
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We were a group of 7 people leasing these 2 cottage homes.The location could not have been better only 1 block off Duval St within walking distance to everything. The homes were clean , and fully equipped. We had trouble with a TV in one of the homes and the rental staff came quickly the next day and switched it out for a brand new TV. The cleaning staff came daily to make beds and add towels. We had a terrific stay in Key West and will definitely be back to lease these great cottage homes.
John R. -
Rating 5
Keywest vacation rentals stay in 3 nights
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Loved the property's and location. Very well maintained and stock. The two pools around the corner are awesome. I definitely would recommend them for your next vacation stay.
Robert G. -
Rating 5
Wonderful home(s), Fantastic Experience!!
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Beautiful home away from home - all the comforts of home, well stocked kitchen, clean and roomy! We were here with a group of friends who had traveled from all over, and we were delighted to have such a friendly, comfortable, personable space to call home! *Perfect* location, both off the beaten path but right in the middle of it all! We could not have been happier!!
Kaitlyn B. -
Rating 5
Great stay at the Tradewinds!
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The Tradewinds was an excellent property! It was a short walk from Duval Street and all of the bars. The daily maid service cleaned up the house and also made the beds. We would definitely consider coming back!
Tim W. -
Rating 5
Bachelorette Party
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a great time! Plenty of space for everyone, clean houses, convenient location, awesome concierge, and a wonderful place to visit! I can't think of a single thing I would have changed!
Anonymous -
Rating 5
GREAT PLACE in KW!
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The Tradewinds cottages were the perfect place for the 6 of us to stay in Key West. Location, location, location! Superb! Walked to many places. But also had off street parking! Delightful housing, took advantage of everything there. Loved the neighborhood and porches. Even though was "spring break" we were never bothered by any noise. Close to everything important to us!!!
Anonymous -
Swipe Swipe for More Reviews

Have a question? Customer Questions & Answers Have a question? Customer Questions & Answers

Want to know specifics? Ask anything about this specific property that you would like to know...


Request More Info Request More Info

Want to know specifics? Ask anything in reference to vacationing at this property that you would like to know...

I agree