|Minimum Stay||3 nights|
Suitable for childrenYes
Suitable for the elderlyYes
|Theme||Budget, Historic, Romantic, Beach, Downtown, Tropical|
Description from the manager
Opposite Windward Isle , the Leeward Isle sits at 529 Olivia Street, right in the center of Old Town Key West, just 1/2 block from Duval Street. This superb example of shotgun style architecture is complimented with original Dade County pine floors and walls. It has 2 King bedrooms, living room with Q sleeper sofa, 1 bath with tub, full kitchen, private rear yard with outdoor dining, gas BBQ grill and a private spa! Plus Private Parking!!!!
Check-In: 3:00 pm
Check-Out: 11:00 am
Leeward Isle - Sleeps 6, PRIVATE SPA & PARKING!
Key West, Florida
Additional Location Information
Location Type Beach, Downtown, Tropical
Rates shown in $ USD (change)
Get 10% off your total stay See Details »
|Rate Summary||$258 - $448||$258 - $448||$0||$0||3 nights|
|Dec. 15 2012 - Apr. 30 2013
|May. 1 2013 - Jul. 31 2013
|Aug. 1 2013 - Sep. 18 2013
|Sep. 19 2013 - Sep. 23 2013
|Sep. 24 2013 - Oct. 17 2013
|Can't find rates for your travel dates? Contact the manager|
|Oct. 18 2013 - Oct. 27 2013
|Oct. 28 2013 - Nov. 30 2013
|Dec. 1 2013 - Dec. 14 2013
|Dec. 15 2013 - Dec. 24 2013
|Dec. 25 2013 - Dec. 31 2013
|Jan. 1 2014 - Apr. 30 2014
|All Other Dates||$258||$258||-||-||3 nights|
|View all 12 Rate Periods|
- Bed Tax - 13% of rental - Tax
- Rate Based on 4 - $25 / person - Per-Person Adjustment - Per person per night
- Pet Fee - $20 / day - Fee - Per Pet
- Damage Protection Plan - $49 / stay - Security Deposit
- Reservation Fee - $30 / stay - Fee
Additional notes from owner
A 3 night min. applies on weekends in Summer/Shoulder Season. A 5 night min. applies during Winter Season. Higher rates and min. stay requirements apply for Christmas, New Years, Yacht Race Week, 4th of July, Poker Run, Fantasy Festival, Parrot Head, Super Power Boat Races, Thanksgiving.
AvailableUnavailable Last updated: May 01, 2013 ◀▶
What Past Guests Are Saying
Cape Coral, FL
helpful and courteous
The service we received was excellent. The check in was easy to find and the help was very friendly and courteous. We loved the fact that we could leave our luggage between check in and check out time instead of having to carry it around with us. The home we stayed in was very clean and had everything we needed extra for our stay. We would highly recommend there services.
Linda, Tommy & Ann
Prince George, VA
Wonderful little place to stay in a great location.
Leeward Isle was exactly as pictured on the website. Had everything we needed and more. It was in a wonderful location and we were able to walk everywhere. Very clean and comfortable.
Too noisy, too small, too expensive...but great location!
Bar next door was way too loud until wee hours of night. The sound was very loud even with earplugs and a/C running! Neighborhood was run down and house was a bit run down too (lamps did not work and furniture was uncomfortable and somewhat dirty). Grill did not work except on low and dinner was mostly ruined, but we cooked steaks in oven--threw out grilled veggies. King sized bed had center collapsed and we both rolled to the middle! However it was in a great location. For this price, I would have expected much more and friendlier staff (when the rental agency clerk asked how the accommodations were and we replied "fair," she said "great"!
Terre Haute, Indiana
Key West Getaway
Our first trip to Key West. We were a little unsure of the safety and security of the location, especially given the number of locks and warnings posted! After a day or so of exploring KW, we felt much more comfortable and did truly felt safe and enjoyed our stay.
The property was very clean and well appointed. We needed nothing but food and libation. Also some very nice touches with games, DVD player, books and bathroom amenities included. Centrally located and convenient to all attractions. Could easily walk or bike anywhere. We really enjoyed the flora and fauna of the property. The back yard with hot tub were wonderful! Clean and well tended.
Property is billed as central air and is cool but NOT central air that most of us know. Window AC units are located in three of the five rooms that add white noise that isn't so bad because it covers the street noise that comes through uninsulated walls and windows.
Those little flying ants are a problem. The first two days, they were under control. By the last day I was bitten several times in my sleep. Tough to control!
All in all a good KW experience and a good place to have it in. Thanks for keeping these wonderful old historic properties up. They are a treasure!
VERO BEACH FL/ PHILADELPHIA PA
WE COME TO KW OFTEN
USUALLY FOR MUCH LONGER PERIODS OF TIME
I ESPECIALLY LIKE THE FACT YOUR RENTALS
CAN BE UTILIZED FOR LONG WEEKEND STAYS.
HOUSE WAS GREAT, LOCATION GREAT, BEDS VERY COMFORTABLE....NEAT HOUSE. RENTAL PROCESS VERY EASY.
WILL DEFINITELY BE RETURN RENTERS. WE CHECKED OUT A FEW OF THE OTHER LOCATIONS LISTED ON THE SITE. WE'LL BE BACK. THANKS
Great house, trouble with housekeeping
The location was great, the house was beyond our expectations, and the management staff was exceptionally helpful. I would (and have already) recommend this place to friends. The only complaint I have is that the housekeeping staff was rude. There was a laundry room attached to the house and we assumed that it meant it was available for our use as well. Instead the housekeeper locked the door with our clothes inside. When we asked her to open the door, she held our clothes hostage until she finished scolding us that it was for housekeeping only. The next day she came by in the morning (we signed up for the 3 - 6pm servide) and left a note on the door saying that there would be no service that day. We were leaving early the next morning so didn't see the piont in complaining. Again, this was the only complaint to an otherwise great trip.
We truly enjoyed the convenience of Leeward Isle. In the center of restaurants, near Duval, CVS,etc. Also enjoyed hot tub and no stairs with old charm feel of the bungalow. Would love to stay here again.
A perfect setting to spend a week. Rooms were just the right size. We even entertained guest without a problem. The kitchen was stocked with the items we needed to enjoy the week. The backyard was very relaxing. We loved the hot tube! The backyard gas grill stayed busy with the stakes that we had shipped in to the managment office for us. And to top it off, we were in walking distance to all the hot spots that we wanted to get to. We would stay here again!
Leeward Isle - Great Location
Leeward Isle home was at a great location - right near Duval and within walking distance of all the action. The house was clean and homey. We particularly liked the hot tub out back - very relaxing. You really get your money's worth here!
a good nights sleep
The house we stayed at was very pleasant and the facilities were excellent, the issue we have with it is the position of a bar approx 100yards away which played VERY loud music until 4.a.m. and beyond making sleep an impossibility.
I think this should have been pointed out before we booked.
For people who want a quieter holiday I would suggest sourcing a cottage with no bars in the vicinity.
SARASOTA , FL
WE HAD A GREAT TIME IN KEY WEST. THE VACATION RENTAL WAS PERFECT. IT WAS CLEAN. VERY CLOSE TO EVER WHERE YOU WANT TO GO. YOU CAN PARK YOUR CAR AN WALK. PLAN ON COMING BACK AND STAYING AGAIN.
We liked the interior and the private backyard. Typical vaca style. BUt the hot
tub broke. The area can be loud at night. Pools nearby a plus
Our vacation started out staying at the Double Tree Resort on the island, as my husband went on a weekend charter fishing experience to the Dry Tortugas. He came back Sunday and we checked in to the Leeward Isle. What a great place! It was fixed up so nicely and such a home away from home. When you pull up to the house, your first thought is that the house is no big deal, but once we entered I was in love with the place. I always think about what a great time we had. There is a bar across the street called the Monkey bar, which is awesome; my husband and I closed the place at about 5am. Our kids loved Duvall St. which is about 6 houses away from the house. My husband brought tons of fish back from the fishing excursion and the backyard was a great place to cut up the fish and bag to take home. We had a fish fry and invited everyone over (our family was all down in the Keys that week, as well. The backyard was equipped with a grill, jacuzzi, and patio set which all accomodated the our vacation very well. Everyday maids drove around on mini scooters and came to clean the house and restock fresh towels. It was like having a hotel room, but the luxury of a house. I highly recommend the Leeward Isle and can not wait to go back, very soon.
Key West Bungalow
Today's date is July 2, 2009. I stayed at this bungalow a few years ago and they are asking me (now?) to review it.
If memory serves, it is a two bedroom unit located close to Duvall street. It has a hot tub and limited parking in back.
The unit had a nice fit and feel with a decor appropriate for Key West and was located such that we could walk to most of our destinations.
What a great little place!!!
Fantastic location, a block off Duval!! :) Wonderful place to stay...cool little
"private" backyard. Clean, well tended property. Very clean inside and comfy
beds. Would stay there again in a heart beat!!!
An extremly nice getaway
I have been vacaitoning in Key West every year for the past 7 years and this was the "homiest" place I have stayed. Very convenient to Duval and Old Town Key West. Extremly clean and cozy with all essetials for "living" on your vacation. Only problem was locating the pool but a phone call to the staff straitened that out. Would recomend this place to anyone.
melbourne , florida
very clean but ac didnt cool place off !!!!!
it was very nice but had alot of issues with ac when the people came to fix it none of the workers spoke english . over all key west is a fun place can wait to go back . plus i think they should put some basic cable in for the people that would like to wind down at night . but i did have alot of fun sitting on the porch that was nice !!!!
Great for Pets - Several Maintenance issues
We have visited Key West with our dogs many times and enjoy this location, the property has a small backyard which is nice for the dogs. We have stayed at the Windward Isle the house next door several times and have been very happy. This is the second time we stayed in the Leeward Isle and were disappointed in the upkeep of the property. I think someone needs to have a maintenance overhaul on the property. The Air conditioner in the living room does not cool. The Gas Grill did not ignite automatically. The toilet water main broke the night before we left. Overall we would come back but would hope that some of the listed items were fixed.
Just what we were looking for
I visited Key West with 3 friends for my birthday. It was an amazing time, our location of our cottage was perfect! The cottage was just what we needed, we wanted to get away from hotels and that's what we did! It was small, but also had enough room. The beds were soo comfortable.. we even joked about strapping the mattresses to the roof of the car and bringing them home! The next time I visit the Keys I will make sure to use this company again and I have told several friends about it. Thank you for helping make my birthday weekend in the Keys enjoyable!!!
Leeward and Windward Isle Side by Side
We've stayed in both of them and wouldn't stay anywhere else. If the Atlantic end of Duval is your area, both these houses are ideal locations and they are both very nice. The accomodations are great, love the private parking and private courtyards in back. They're great for splitting with another couple!!
I am a Florida native who has been to Key West many times but always on "day"trips. Made to decision to come on vacation with my wife and stay in a romantic setting in one of the cottages here, and was not disappointed. Check in was a breeze, the cottage was wonderful and the location just off Duvall perfect. We cooked dinner twice and grilled outside once. In short order we learned how to walk everywhere right from our doorstep. Highly recommend, no it is not a luxury hotel but it has charm, romance, and history, plus the AC works great. Come on, don't stay at the same old hotel enviroment, experience Key West like a native 80 years ago but with a few modern touches.
Nice place - but no working hottubs
We stayed in tow units over three nights, but neither place had working hottubs. Not a big deal, but you'd expect that one out of two places would be good to go.
HOME AWAY FROM HOME
My husband and I with our border collies visit Key West every Thanksgiving week and love to stay in the Leeward Isle home on Oliva. It is close to everything but off the main area to enjoy evenings with the local neighbors. The back yard, off street parking and front porch gives us everything we want in a home away from home.
Everything you could want in a Key West Vacation. Location, price, hot tub, grill, kitchen. I try to rent the Leeward and the Windward properties everytime I come to Key West. No reason to stay anywhere else.
Jessie Hippie Pants
AWESOME HOUSE IN AN AWESOME LOCATION
This house is great, because you get that old school Key West cottage feel while being really close to Duval St. This house is super cute and the beds are so comfortable! The backyard is also a nice feature. You get a sparkling hot tub surrounded by lush plants and tropical flowers. The property owners were also very chill and easy to deal with. My friends and I rented bikes and did not even get back into our car until we left. We had so much fun we do not even remember some of it. ;P
staniel cay lady
Beautiful peaceful home away from home. Only thing that would've made it better was if the hot tub had worked, but it was still a wonderful visit. Really enjoyed drinking my coffee out at the table on the back patio and watching the little lizards run around.
A Great Week At Key West
We thoroughly enjoyed staying at the Leeward Isle residence. The room was very convenient to everything we wanted to do. Even though it was in the heat of summer, the rooms stayed very cool and the amenities were great!! We will stay again when we plan our next trip to Key West. Highly recommend this property for a family rental.
Get 10% off your total stay
Last Minute Spring Special!
Take 10% off our entire collection of vacation rentals with our Last Minute April/May Special. It's never been easier to get down to paradise. Compare our rates and amenities to local hotels and you'll find Key West Vacation Rentals is the only place to stay in paradise. Valid from April 25, new and direct bookings only