Historic Key West Vacation Rentals

We loved our experience renting through this rental company. They employ a concierge who we went through to book snorkeling and who made knowledgeable recommendations and flawless reservations. Everyone on the team exhibited upmost professionalism, care and interest for our time on the island. They checked in to ensure our stay was smooth and enjoyable.nnConstructively, I wish they took Amex for payment. I also wish checkout could be rolled back later than 10am. Even still, we would definitely book through them on our next visit to the Southernmost City.

As a property manager myself, it's a tremendous joy to deal with professionals like the fine folks at Historic Key West Vacation Rentals. Their service & responsiveness was top notch and the home we stayed in was well cared and made for a lovely stay! Thanks!

I am really disappointed in this company and we will be sure to avoid them when we come to Key West. We booked with them back in November of 2019 to experience our first Fantasy Fest in October of 2020. The whole trip was planned for that event and had been a trip my husband has always wanted to take. Sadly, because of covid, the event got canceled. We booked 2 other hotels in Key West, both that were nonrefundable, but under the circumstances both hotels offered us a refund. Historic Key West said we could cancel 60 days in advance and lose our travel insurance money (over $200 that we were highly pressured to purchase - it did not cover our trip being derailed since our event was canceled) plus a $500 cancelation fee. We did agree to this policy, but had no intentions of canceling the trip. I emailed the company multiple times (reservations, that I was told to contact, never replied to me after multiple emails) and finally got a nice lady, Jennifer, to respond. She's my reason for giving the company 2 stars rather than 1. I was told, after asking for this request, that they'd allow me to move my reservation to next year, considering our unique circumstances. Otherwise, they were only offering to allow a date change through the end of 2020. I was excited to hear this and even agreed to paying the higher 2021 prices..... until I read what those new prices were. They were going to charge me $1100 more for a total of 6 nights because our event was delayed 1 year. $183 per night increase! That was a total of over $4000 for 6 nights for 2 people to sleep in a room near Duval Street. It is probably a great place, but I can stay in an over water bungalow in Bora Bora for that price, and that includes meals! After hearing this news, I still tried to find another solution, including them taking the $500 cancellation fee and allowing us to apply it to a future trip when we are sure we will be able to travel again. The request was not even addressed. I also asked if I was misunderstanding the extreme price increase but that wasn't addressed either. They were kind enough to cancel my reservation and will be crediting me for my deposit paid, minus over $700 of fees that I can't get back. We will be supporting Havana Cabana and Parrot Key Hotel for future Key West visits. I'm sure this company is wonderful as long as you have no problems with your booking. Sadly, we weren't so lucky.

Absolutely love the cottage we stayed in and this rental management company is amazing. Cindy was great every step of the way. Our cottage was clean, comfortable and private. We will absolutely be using this rental company for all of your rentals in a Kay West going forward. Thank you for making our trip easy and memorable.

We stayed at the Chick-a-pea cottage and LOVED IT. Very clean and many nice amenities. The office is very responsive and helpful if you need anything. Will use them again for future travel.