Rating 5 (75)

KW33A - Leeward Isle


2 bedrooms
Bathroom 1 baths
Dog Friendly Dog Friendly

  • Address: 529 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


Description Description
Bask in the peaceful sunshine of Key West and feel all your stress melt away when you stay at this cozy dog-friendly cottage right in town. With a private hot tub in the garden area out back plus all the conveniences of home, what's not to love?Sitting only half a block from all the fun and excitement of Duval Street, park your car in the private space and forget about it - you'll be able to walk or bicycle everywhere you want to go. Head to the Southernmost Point and check out the Key West Butterfly and Nature Conservatory while you're at it, then head north to check out Mallory Square and other historical landmarks along the way.Spend quiet mornings in the garden, sipping coffee and eating a delicious breakfast prepared in your fully equipped kitchen. After a full day of exploring, come back for a relaxing soak in the hot tub, watch a show on the flatscreen cable TV, and surf the free WiFi to find activities for tomorrow. A dog is welcome. Make sure your Florida vacation is exactly how you imagine - book this charming cottage today!

Location Location

Reviews Rating 5 (75) Reviews
Rating 5
Great location, wish we had more time to enjoy the hot tub/back patio.
Amy P. -
Rating 5
Very clean and comfortable. Property is pet friendly and plenty of room them as well. Price was affordable and decent for the location. We hope to be able to go back next year.
rose s. -
Rating 5
Love Key West
Christine F. -
Rating 5
They Delivered on the promise!
This was a perfect spot for us to stay and I would recommend it for 1-2 couples. More would be crowded and you would need to use the sofa sleeper. Location, location, location. Close enough to walk everywhere. (We did!) but far enough away to be mostly quiet at night. And the hot tub was the icing on the cake. 5+Stars. Well done.
henry -
Rating 5
House was clean and the location was great. Easy walk to all the fun on Duval street and beyond. House is charming, with comfortable beds, but it is showing its age. We had not planned on cooking and probably would not have cooked in the kitchen. Appliances are old and rusty. If you are just coming for the fun you will be more than happy in this house.
Lynn V. -
Thank you for your feedback. We are happy you enjoyed this home. We sincerely apologize for the issues you have encountered during your stay. We'll continue to work closely with both our local staff and the homeowner to make improvements to this home, and we look forward to welcoming you back for another wonderful getaway in the future.
Seven Keys Vacations staff
Rating 5
Keywest
Our key code d didn't work in the middle of our stay. We called the rental company and it was fixed without a headache. They did great
Margaret -
Rating 5
Loved the location and the private back yard.
Margaret -
Rating 5
Ideal location to walk to a lot of tourist attractions. Would highly recommendz
Angela C. -
Rating 5
Location was perfect. Walkable to almost everything. Host uses Vacasa to manage the listing, they don’t reply to messages on VRBO. Parking guidance was confusing.
krishna y. -
Thank you so much for sharing your feedback. We're delighted to hear that the location was perfect and conveniently walkable to many spots. We sorry to hear that the parking guidance was confusing. Regarding communication, since the host uses Vacasa to manage the listing, we’re here to assist you directly. We thank you for your feedback, as it helps us improve our guests' experiences. We hope to have the opportunity to better serve you in the future.
Seven Keys Vacations staff
Rating 5
Tomie G. -
Rating 5
Great place - clean - no issues. Easy in and easy out.
Ron S. -
Rating 5
Excellent location!
Walk to everything. Had a great stay in this cute key west cottage. Beds were very comfortable and needed after a long day of fun. Would stay here again.
Trista -
Rating 5
Excellent location!
Walk to everything. Had a great stay in this cute key west cottage. Beds were very comfortable and needed after a long day of fun. Would stay here again.
Trista P. -
Rating 5
Amazing property, questionable management
I love this property but I found the property management to be extremely mediocre. There were a lot of issues, two big ones. First, and most fatal, the hottub was AGGRESSIVELY over chlorinated. We couldn’t use it, as soon as we got in we choked on fumes. We tried over multiple days but it was toxic. Second, when we arrived, the full garbage and recycling were physically blocking the entryway. We had to drag them aside just to get through the gate. They were full so this wasn’t placed by the collection people. The other issues were minor but paint a picture. A welcome pack including dishwasher detergent and laundry detergent, and instructions to “start the dishwasher”, but there is no dishwasher and the laundry facilities weren’t working. No drying rack for the dishes. No hand soap in the bathroom. Loose light fixtures. Amazing property and many thanks to the owner, but extremely disappointed in Vacasa.
Adrian -
Rating 5
Amazing property, questionable management
I love this property but I found the property management to be extremely mediocre. There were a lot of issues, two big ones. First, and most fatal, the hottub was AGGRESSIVELY over chlorinated. We couldn’t use it, as soon as we got in we choked on fumes. We tried over multiple days but it was toxic. Second, when we arrived, the full garbage and recycling were physically blocking the entryway. We had to drag them aside just to get through the gate. They were full so this wasn’t placed by the collection people. The other issues were minor but paint a picture. A welcome pack including dishwasher detergent and laundry detergent, and instructions to “start the dishwasher”, but there is no dishwasher and the laundry facilities weren’t working. No drying rack for the dishes. No hand soap in the bathroom. Loose light fixtures. Amazing property and many thanks to the owner, but extremely disappointed in Vacasa.
Adrian P. -
Hello Adrian, thank you for taking the time to share your experience with us. We truly appreciate your honest feedback, as it helps us grow and improve. I’m sorry to hear about the issues you encountered, especially with the hot tub and the garbage blocking the entryway. We always hope guests will communicate with us about any problems during their stay so our local team can address them promptly and help make things more comfortable. We’d love the opportunity to host you again and provide a much better experience in the future.
Seven Keys Vacations staff
Rating 5
😍😍
Beautiful property, excellent location, clean, good communication
Bairon -
Rating 5
😍😍
Beautiful property, excellent location, clean, good communication
Bairon S. -
Rating 5
Vacay
Great lication
Lisa A. -
Rating 5
Even better than the photos!
Lovely house and great location.
Natalie D. -
Rating 5
key west trip
a very nice stay
Diana E. -
Rating 5
529 Olivia Street
Cute little house. Old but taken care of. Close to everything. Would do it again in a heartbeat.
Steve B. -
Thank you, Steve, for your feedback. We are happy you enjoyed this home. We sincerely apologize for the issues you have encountered during your stay. We will continue to work with both our local staff and homeowner to make improvements to this home, and we hope you'll give us a second chance to impress you.
Seven Keys Vacations staff
Rating 5
Although an older house, it was updated and decorated nicely. Very convenient to Duval Street. The only minor drawback was the keypad lock on the front door- it sometimes took 2 or 3 times for the combination to be accepted. We would definitely stay there again.
Patrick -
Rating 5
Mary P. -
Rating 5
We loved this place. So cute. Larger than the pictures let on. Although some fixtures, etc. are antiquated, I find this with most places in KW. Very clean and in a great spot. The hot tub was luke warm. We didn’t investigate how to turn it up as it was our last day. I’d definitely stay here again.
Susan -
Rating 5
Key West Stay
I had the pleasure of taking my family to Key West for the weekend. And we had the fortune of staying at this wonderfully located house. It is the perfect distance from everywhere in this beautiful island. The check-in and checkout were seamless and we thoroughly enjoyed our stay. I highly recommend this location to anyone coming down to Key West. Looking forward to doing so again.
Luis R. -
Rating 5
Key West Authentic
Adorable house in a great location that is a block or so off Duval St. It gets a little warm during the day with it being 100 degrees outside, but part of the charm with it being an older wood frame home. Beds are comfortable and Vacasa staff are accommodating. Outdoor shower is a plus too.
Mark C. -
Rating 5
Cozy cottage
Cute place. Good size rooms. Great location convenient to restaurants shopping and attractions.would stay again.
joseph G. -
Rating 5
Adorable!
Cutest little property! Hit tub had no water & the microwave and side of the fridge were a little dirty, but the rest was spotless! Wish we could've stayed longer!
Jennifer S. -
Rating 5
Key West Experience
Great location to take in the culture of Key West. Thoroughly enjoyed the location which made exploring the island by foot simple.
Heather V. -
Rating 5
Cool place in a great location
Clean, comfortable beds, nice back patio and just off Duval St. Would stay again!
John H. -
Rating 5
Great property
Had a very enjoyable stay. Will stay here again.
Kenneth V. -
Rating 5
Great house and location
Cute, clean and convenient to duval st.
Ashley R. -
Rating 5
Perfect Stay with Friends
We rented this home and our friends rented the house beside us. It was perfect for a fun beach trip with friends. Easily able to walk to restaurants on Duval, the southernmost point, Hemingway house, and lighthouse. All within just 10 mins or less walking. House was clean and exactly what we needed! If we ever find ourselves in Key West again, we will definitely be staying here! If you’re planning a trip with friends or family, so as we did and rent both houses!
Sylvia J. -
Rating 5
Like the cleaness
Liangce -
Rating 5
Great Location
We really enjoyed our visit to Key West and the location of the house made it easy. We were able to walk to almost everything we wanted to do during our stay. It was very close to Duval Street. Having a parking spot at the house was a big plus for us since we had rented a car and drove from Maimi. The house was just as described and we all thought the two king beds were very comfortable. We also used the hot tub every night to relax after a long day and evening of walking everywhere. We all agreed we would definitely rent this house again when we return.
Deborah W. -
Rating 5
cottage close to downtown
perfect place for first timers to stay to be close to downtown
Kara R. -
Rating 5
Great location
Great location. Close to everything. Parking spot is a huge plus.
Jeremy J. -
Rating 5
2 blocks off Duvall easy walk to restaurants and shops . Excellent location
Check in easy great communication with owners. Will stay again
kevin h. -
Rating 5
Great respite
Very cute house, beds were big and comfy, loved the location and jacuzzi!
Noelle I. -
Rating 5
Great Place
Very good place to stay for two couples! Easy walking everywhere, great Cuban coffee/food right around the corner, one minute to Duval. Highly recommend. We will be back
Collin D. -
Rating 5
Perfect Spot to see it all!
This was a perfect house that is much larger than the pictures make it look. The bedrooms were big with extremely comfortable beds. The front porch made the perfect spot to enjoy a morning coffee or afternoon cocktail. Evenings were spend in the hot tub relaxing after walking up and down Duval street, seeing every tourist site and even spending time on the beach. Nothing is more than a 15 minute walk away!
Samantha F. -
Rating 5
Cute cottage
We will be back next year!!
Amber N. -
Rating 5
Weekend getaway
It was hard to get ahold of the property management. Did not receive my check in info on time. Other than that the place was perfect!
Kaley B. -
Rating 5
Perfect location
Charming house in a perfect location. Can walk to anywhere and the house was very nice. The bed and bedding was very comfortable as well.
Patrick M. -
Rating 5
Awesome house!
Awesome location! Enjoyed every minute of our stay!
Verified traveler -
Rating 5
Wonderful house walking distance to Duvall and attractions. Super Stay!
location of house and hot tub
Randy H. -
Rating 5
Great Place
We only stayed one night but we love this place. Located a short walk from Duvall Street, which leads to everything. Loved the hot tub, and honestly one of the most comfortable beds every!
Howard K. -
Rating 5
Loved it!
Clean comfortable beds, lots of towels. Good air conditioning and the off street parking is a BIG plus.
ERIC P. -
Rating 5
Super clean and great location.
Located perfect distance from everything whether it be Duval or the beaches on the other side. Super clean and roomy. Only thing to keep in mind is the Bobby’s Monkey Bar gets jamming on the weekend so there will be noise from that. With that said our 16 month old slept right through it so no biggie. Would definitely stay here again!
Michael D. -
Rating 5
Great place to stay!
We had a great time in Key West and loved our stay at Leeward Isle. The home is clean and has everything you need for your stay. We were fortunate to meet the owner during our stay and he was very nice and asked if there was anything we needed. The beds are comfy and the outside shower is fantastic! Perfect location and easy to get to anywhere. I would definitely recommend this rental and would stay here again. Vacasa made the rental experience easy!
Jen S. -
Rating 5
Nice get away
Nice place to stay and walk old key west
Leonard P. -
Rating 5
Relaxation with 100% fun
House was awesome, location fantastic, had A1 time.
Martin M. -
Rating 5
Great house!!!
Great Place to stay! For a two bedroom 1 bath it’s very spacious. Would rent here again!!!
Michael F. -
Rating 5
529 Olivia
Cute
Diane M. -
Rating 5
Nice House
This house is great for 4-6 guests. Very comfortable. Only one bathroom but we managed fine. Cute little kitchen with coffee pot, fridge and stove. Walking distance to all the bars and restaurants.
Richard D. -
Rating 5
wonderful 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: The house was perfect for 4 adults. I think 6 would have been tight. We were about 1/2 block to mid Duval ST. We enjoyed our stay and had no problems whatsoever. Tanner at KW Vacation Rentals went above and beyond to accommodate us.
Anonymous -
Rating 5
Nice stay!
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: Nice 2-bedroom (both King beds) cottage one half-block from the middle of Duval. Hot tub and outdoor shower a nice amenity. Didn't use the kitchen, but is stocked with housewares you'd need during your stay (as well as towels, pillows, sheets, etc). A bar at the end of the block can get loud late at night, but the white noise from the a/c pretty much blocked out the south be (light sleepers bring earplugs and eyeshades!)
Kathy S. -
Rating 5
Perfect vacation home
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: You want comfort? You want clean?You want the best bed I ever slept in? You want convenience to the main stream of Key West yet quiet. This is the place to stay.
deb h. -
Rating 5
What a charming place!
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: Leeward Isles was an absolutely charming place to stay. The location was great...mid island, and close enough to Duval to be able to easily walk everywhere, but far enough away to get away from the hustle and bustle when you wanted. The house was cool, cutely furnished, comfortable and welcoming.
Sandra P. -
Rating 5
Nice getaway
Rating Details: The property manager was more than 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 little getaway. We had 5 people in our party and all had a good time. One bathroom is challenging but as long as your all friends or family it's doable.
Donna M. -
Rating 5
Perfect location and not loud!
Rating Details: The property manager was very helpful. The vacation rental was 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: This was the perfect location. We loved our little house! It was a great size for the 4 of us, was right off of Duval but still private! People aren't kidding, the beds are SUPER comfortable and we loved having the front porch and back sitting area! The little bamboo shower outside is cool too - I showered outside every day! They come in everyday to give you clean towels etc. but it would be nice if they actually cleaned during your stay. Overall, we would totally stay here again!
Nicole P. -
Rating 5
Good time 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 very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This is a great location for prowling Duval St. It was very rainy and cool while we were there, that had nothing to do with the accommodation which were comfortable. The cool weather necessitate a call for space heaters and they were provided in a timely manner and definitely took the chill out of the air.
Patrick K. -
Rating 5
Great House, Great Location
Rating Details: The property manager was very helpful. The vacation rental was very clean. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Myself and 4 others stayed at Leeward Isle for 5 nights. The house was great, very comfortable for the 5 of us and very clean throughout. The backyard was great to sit back and relax with the hot tub and outside shower. Being just one block from Duval Street, the house had an ideal location. The windows were older and couldn't quite fully shut in some of the rooms, which made it a little difficult to block out the roosters early in the morning. Overall we had a great stay at this house and would definitely stay there again!
Nick P. -
Rating 5
Great experience!
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: The place was clean and the perfect location! The rental company was so accommodating. It was pouring rain one day durning our stay and we didn't bring umbrella's, they dropped off umbrellas for our use and we went on our way. Will definitely rent from them again!
Anonymous -
Rating 5
I would rent again
Rating Details: The property manager was more than 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: Nothing fancy, but everything you need and more. Great location at an affordable price.
Lewis T. -
Rating 5
Didn't want to leave ever!
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: My guests and I were very pleasantly surprised with this place! It had everything we needed to have a great time and the location was prime! Loved the outdoor shower and hot tub! The beds were SO comfortable and I slept like a baby. I will definitely be renting this place again!!! Thank you!!
Heather B. -
Rating 5
Can't wait to come back !!
Rating Details: The property manager was very helpful. The vacation rental was very clean. I was more than 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 were very happy with the house and the location. Never made it to the pool locations. The manager was very helpful there was a small disturbance the one night and the manager was there at a moments notice. And when I checked out the next day he came out to make sure we were ok. I would use Key West Vacation Rentals for my next visit and will suggest them to friends and family.
Dianne B. -
Rating 5
Great place
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Awesome place for 2 couples
Anthony L. -
Rating 5
Relaxation and fun in a home away from home.
The property was clean and nicely decorated. Very comfortable beds! Well stocked kitchen and plenty of towels. The hot tub was heavenly. Great location! Close to shopping, Duval Street and excellent restaurants. You can walk everywhere from the property. We would definitely stay here again!
Sara J. -
Rating 5
Dream house
Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: It was an incredible stay in super house!
Julia S. -
Rating 5
Great place! Awesome 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: Loved the property, the management was great! Check in was a breeze. The hot tub was serviced half way through the stay. Which I though was above and beyond. All in all I would recommend to anyone. We will be back that's for sure!
colin c. -
Rating 5
Sweet Historic Key West Cottage
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: Everything about this little historic "shotgun: cottage was perfect and in keeping with everything we wanted from Key West. KW Vacation Rentals, particularly Craig, was efficient and cordial. We could not have asked for a better first time experience.
Rigney C. -
Rating 5
Amazing weekend getaway!!
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: We had a fabulous time in this house - the beds were soooo comfortable and the pillows too. It was perfectly situated just off Duval and close to everything else we wanted to do. Thanks again guys for your great service. The staff are excellent!! The only reason I gave a 4 for cleanliness was for the floors apart from that..... perfect!
Janet M. -
Rating 5
Key West Vacation
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 wonderful stay!!!!
David A. -
Rating 5
A little bit of Paradise
Rating Details: The property manager was very helpful. The vacation rental was very clean. I was more than 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 loved our stay at Leeward Isle. The beds were the most comfortable we've ever slept on. Things at night are a little noisy, keep the AC running it helps muffle the noise. The water in the bathroom sink is reversed hot on right -that took a while to get use to. Loved the fact you could walk everywhere. We hated to leave our little paradise house!
Susan M. -
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