CoolVacay
Real Places. Real Vacations. Really Easy.
Join the CoolVacay Family
Whether you're beach-bound or mountain-minded, CoolVacay helps you find the right rental for your crew—without the stress. No fluff, no fuss. Just great spots, clear details, and support from real people who've actually been there. We're a small (but mighty) team obsessed with good vacations. The kind where the view is even better than the pics, and you don't have to scroll through 4000 listings to find your perfect fit. CoolVacay is designed to make trip planning feel like part of the fun. From Florida beaches to boardwalk towns to cozy mountain vibes, we hand-pick every rental we list. Got a question? Need a recommendation? Our team's been there (literally), and we're happy to help.
Rental Management
Welcome to CoolVacay, where your property's success is our priority. Partner with us and discover how our expert team and cutting-edge technology can elevate your vacation rental or timeshare to new heights. Together, we'll maximize your property's potential and ensure a seamless, rewarding experience for you and your guests. Let's make every stay exceptional—join the CoolVacay family of managed resorts today
1.5k
Listed Properties
2.5k
Happy Customers
5 ★
Star Reviews
450
Daily Transactions
Cool guests, cooler reviews.
Real feedback from returning guests who value the location, service, and experience year after year.
Clean, Bright, and Welcoming
The resort (York Beach Club) is always clean, bright, and welcoming. The location is perfect, with easy access to beaches and other attractions.
James R
A Quiet, Pet-Friendly Stay
We really enjoyed our stay at the Bay Club. It was very quiet, and we love traveling with our dog - he really enjoyed his stay too. The staff, other dogs, and other guests were all very nice.
Molly N
Best Place in the Keys
All office staff were friendly - the place has never looked better or had better office personnel. It's great to have continuity in the management and the same friendly faces welcoming and assisting you. The best place in the Keys. Been staying here for 20 years and never been better.
Lyle A
A 20-Year Tradition
We have been coming here to Calini for nearly 20 years. Wonderful location, well-maintained facility, and helpful, friendly staff, plus polite and respectful guests. We've made good friends here who come back year after year. We are not interested in going anywhere else.
Ronald F
Our Favorite Stay
The Inn at Comanche Harbor is now our favorite place to stay whenever we're visiting the St. Augustine/Jacksonville area. The location is perfect, the ambiance superb, and the staff exceptional. We had friends visit from Jacksonville, and they were so impressed by the Inn that they have already scheduled a mini vacation.
Craig L
Very Relaxing and Always Enjoyable
We have been coming there for many years (Village of Winnipesaukee). We find it very relaxing and just love it there.
Paul M
