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Vacation Homes Of Key West Welcome to VHKW ~ Vacation Homes of Key West, a locally owned and operated full service vacation rental and vacation property management company. Since 1997 we have helped pave the way for licensed vacation rentals in Key West, Florida. We are three generations of local professionals dedicated to helping visitors discover the lifestyle of Key West by renting authentic privately-owned homes, managing and maintaining these homes for property owners with our hands-on care, and caring for our guests by sharing our unique Key West local knowledge.
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Few world destinations have such a remarkable collection of original century-old Victorian and Caribbean architecture as Old Town Key West. Our company' s success was founded on our belief that the remarkable island homes and neighborhoods are not only an excellent tangible investment in our community heritage and economy, they are one of Key West's most important sustainable resources, to be preserved and enjoyed for generations to come.
Dreaming of your perfect Key West getaway, but don't know where to start? The key to success is to live the island like a local, and the best way to do that is with the help of those who know the island best. Our staff at VHKW has deep roots in the Key West culture, stemming from generations of native Key Westers or "Conchs" as we like to call ourselves.
View our exclusive Key West vacation rentals. Vacation Homes of Key West can help you find the perfect vacation rental for your next Key West vacation. Don't pay booking fees, save money by booking directly with VHKW today. Palm fronds gently dancing in the breeze, orchids hanging in the trees, manicured gardens, a pristine swimming pool set with comfortable lounge chairs.
Are you considering booking a stay in one of our Key West Vacation Rentals? For guaranteed lowest rates and easy on-line reservations, make sure to book directly with us - VHKW ~ Vacation Homes of Key West. While we do advertise many of our exclusive Key West Vacation Rentals on trusted on-line vacation rental and travel booking sites, be aware that these sites add fees on top of our standard rental rates. These additional booking fees are often in excess of 10% of your base rental cost, and offer no added value over what we give you directly at VHKW.
Reviews (11)
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Marguerite Moore
Jun 21, 2022
The Caroline Estates House was Absolutely Beautiful and was Perfect for Our Family and Friends Party of 10. The Pool Cottage was adorable and worked out Great for Us. The pool area was very Tropical and Wonderful for when we all just wanted to stay home and laze around the pool. Location was Fabulous as we were very close to Duval Street and all the activities we did, ie Ghost Tour, Snorkeling, Sunset Sail.

I have been coming to Key West for many years and this was the first time I rented a house and we will definitely be renting through VHKW again. It was very easy to work with them and the check in and check out process was so easy. Fabulous Vacation!
Mitch Dingus
Jun 17, 2022
Great location right on the Atlantic ocean. Beautiful view. Close to everything on both ends of the island. Located in a very quiet gated complex. Nice, well kept pool and grounds. Hotel luggage carts made it nice as did shopping carts for bringing up groceries. Would stay here again.
Amy McIntire
May 29, 2022
What a spectacular getaway in Key West! This house was more than we hoped for. Location is everything in key west and this house provided the perfect walking distance to Duval, it was refreshing to come home to the house and jump in the pool after a hot day/night on Duval. This house accommodated our large group of 10 easily. It came fully equipped with anything you'd need including spices in the kitchen. CVS was close enough we bought a couple extra floats. Will be booking again next year! Thank you VHKW for sharing such an incredible home!
Ted Mahoney
Jan 09, 2022
The entire experience was great. From the time I made an inquiry about renting through the contract process was very easy. Anytime I had a question, someone at the office was helpful in getting the correct answer. The Tropical Tranquility property was perfect for my family. Each family member had their own space and the common areas were large and open enough for all of us. The location was ideal to get around Key West especially with a golf cart. If I return to Key West, I will check on this property first.
Kerrie Reffert
Dec 28, 2021
We were a group of 8 who stayed at the house. My daughter and son in law were on their honeymoon so the cottage out back was perfect for them. The house was absolutely perfect to meet our needs! The kitchen has 2 microwaves, 2 dishwashers, 2 coffee pots, and the best Keurig! The bedrooms are spacious. The house is beautiful and clean. There's a sound system so you can play music throughout the downstairs and pool area which we really loved!

We rented a golf cart which worked out perfectly, especially for grocery shopping. But most of the fun is all within walking distance. I love the keypad on the front door. That way everyone had access to the house and no key to worry about. I took 1 star off because the toilet in the master bathroom didn't fill with water after the first day. My friend who was staying in that room called about it, but no one came.

It was no big deal, the main powder room is right next to that bedroom so we didn't make an issue out of it. The pool was nice. It's small, but deep. The back yard is very private but it doesn't get a lot of sun over the pool. I guess that's good for Florida, but us people from gray Pittsburgh love to see the sun! The last and final reason I took off 1 star was not anyone's fault.

I have a big phobia of bugs so of course the first thing I found was a palmetto bug. I knew the risk of seeing bugs, I was prepared to to not freak myself out, my son got rid of it, and we had the best vacation! That being said- would I rent that house again? ABSOLUTELY! Oh and FYI there's a clothing optional resort next to the house. It was no problem, we just kept our blinds closed.

But if you're planning on bringing Grandma or littles you might want to take that into consideration Vacation Rentals of Key West was great to work with! I needed to make some changes to our dates and they happily accommodated. They recommended a fishing charter which was so much fun! All correspondence with them was prompt and helpful. I am amending my rating to 5 stars.

I just spoke to the person who stayed in the room with the toilet issue. She said someone did come and it worked once. She never called again to say it wasn't working. The property manager did not know there still was an issue.
Con Jay
Dec 04, 2021
Love those iguana visitors we had! Twin cottages were cute, clean and convenient to everything. Staff are superb as well.
Elizabeth Bilotta
Nov 26, 2021
We loved Down Island Digs and would rent again. The house was very clean and perfect size for two couples. The location was perfect and central to everything we wanted to do. You could easily walk anywhere from this location. We did also have a golf cart but found we really didn't need to use it much. Working with VHKW was easy and the check-in and check out prices was very smooth.
Mari Casanova
Oct 31, 2021
Staff is extremely helpful and professional. Our group stayed at Ocean View Luxury Villa in Truman Annex. The house is in a perfect location. The sunsets from the third floor deck were spectacular! Kitchen is fully equipped. The pool and deck area were beautiful (surrounded by lush palms). I do not recommend this house if you have a total of 6 adults. The third floor loft is extremely small and quite frankly, an accident waiting to happen given the location of the stairs and hallway. Very dangerous for children as well.
J. M. Munoz
Jul 28, 2021
Absolutely outstanding! From towels to pool accessories, the amenities were incredible, and the home was very clean and spacious. The company is very professional and organized, and the response time to emails quick and efficient. My family and I will definitely be using this company again in the future! Thank you for a memorable stay!
Michelle McElroy
Jun 25, 2021
We went to Key West on a family vacation with our grown kids. The house was the perfect place to stay in key West. Even though there was no central AC the window units kept the house cool. The master bedroom which doesn't have a window unit so it is the warmest but we got along fine. The house was very clean and had plenty of towels. The porch was very nice to dry out bathing suits and wet towels.

The kitchen was well stocked and we cooked at least once a day. The location is ideal and very good place to park scooters or bikes. Perfect place fora true key west experience!
Sandy & John Bush
Dec 17, 2019
We had a wonderful time at Coco's Poolside Retreat Unit 2. We had 5 in our group and it is a 3 bdrm/2.5 bath house. It is very comfortable and roomy. It was stocked with all the items we needed. It was great having the pool right outside our door. Working with the staff at Vacation Homes Key West was great. Helpful, easy to work with, explained everything and answered any questions we had. Btw, the pictures are a perfect match to the unit.