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Croatia
Escape to the Adriatic coast to experience Croatia - the ideal luxury destination for families and groups of friends. Explore the delights of the Dalmatian coastline. Croatia has so much to offer, from crystal clear waters, sailing opportunities, fresh Mediterranean cooking and a…

Dominican Republic
The Dominican Republic is a Caribbean treasure, renowned for its white-sand beaches, turquoise waters, and vibrant culture, making it an exceptional destination for a luxury villa vacation. This sun-soaked paradise offers the perfect balance of relaxation and adventure, ideal for…

Greece
Head to Mykonos for a hedonistic combination of Hollywood glamour and seductive scenery, where you’ll find the same carefree vibe that attracted the summering starlets of the sixties. Or step back in time through Crete’s many treasures, her depth of…

Algarve
The Algarve is a treasure trove for beach lovers, with its dramatic cliffs, crystal-clear waters, and golden sands. Whether you want to relax and soak up the sun, or indulge in thrilling water sports, the Algarve has it all. Take…

Anguilla
Anguilla is a Caribbean gem, renowned for its luxury, privacy, and natural beauty, making it the perfect destination for villa rental vacations. The island’s serene atmosphere and exclusivity create an idyllic escape for those seeking relaxation or adventure. With 33…

Provence
Whether you’re gazing over rolling rural scenery or strolling fields striped with sunflowers and vines, this diverse landscape provides an irresistible taste of rural France at its finest. Well-heeled Parisians and artists alike have long flocked to this idyllic region,…

Turks and Caicos
Turks and Caicos is a tropical paradise, renowned for its pristine white sand beaches, turquoise waters, and understated luxury, making it an ideal destination for a villa vacation. This stunning archipelago of 40 islands and cays offers a serene escape…

Tuscany
From rolling vine-laced hills cloaked in early morning mist, to the art-rich cities that birthed the Renaissance, Tuscany’s tranquil landscapes offer an unforgettable taste of quintessential Italy. Whether you come for a city-break or countryside escape, you’re sure to be…

Croatia
Escape to the Adriatic coast to experience Croatia - the ideal luxury destination for families and groups of friends. Explore the delights of the Dalmatian coastline. Croatia has so much to offer, from crystal clear waters, sailing opportunities, fresh Mediterranean cooking and a…

Dominican Republic
The Dominican Republic is a Caribbean treasure, renowned for its white-sand beaches, turquoise waters, and vibrant culture, making it an exceptional destination for a luxury villa vacation. This sun-soaked paradise offers the perfect balance of relaxation and adventure, ideal for…

Greece
Head to Mykonos for a hedonistic combination of Hollywood glamour and seductive scenery, where you’ll find the same carefree vibe that attracted the summering starlets of the sixties. Or step back in time through Crete’s many treasures, her depth of…

Algarve
The Algarve is a treasure trove for beach lovers, with its dramatic cliffs, crystal-clear waters, and golden sands. Whether you want to relax and soak up the sun, or indulge in thrilling water sports, the Algarve has it all. Take…

Anguilla
Anguilla is a Caribbean gem, renowned for its luxury, privacy, and natural beauty, making it the perfect destination for villa rental vacations. The island’s serene atmosphere and exclusivity create an idyllic escape for those seeking relaxation or adventure. With 33…

Provence
Whether you’re gazing over rolling rural scenery or strolling fields striped with sunflowers and vines, this diverse landscape provides an irresistible taste of rural France at its finest. Well-heeled Parisians and artists alike have long flocked to this idyllic region,…

Turks and Caicos
Turks and Caicos is a tropical paradise, renowned for its pristine white sand beaches, turquoise waters, and understated luxury, making it an ideal destination for a villa vacation. This stunning archipelago of 40 islands and cays offers a serene escape…

Tuscany
From rolling vine-laced hills cloaked in early morning mist, to the art-rich cities that birthed the Renaissance, Tuscany’s tranquil landscapes offer an unforgettable taste of quintessential Italy. Whether you come for a city-break or countryside escape, you’re sure to be…

Croatia
Escape to the Adriatic coast to experience Croatia - the ideal luxury destination for families and groups of friends. Explore the delights of the Dalmatian coastline. Croatia has so much to offer, from crystal clear waters, sailing opportunities, fresh Mediterranean cooking and a…
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What travelers say about us
Great people to work with before and after our stay.
Concirge service was impeccable
They seem to have a better selection of homes than VRBO and Airbnb. We were very happy with their service and all of the helpful information regarding our trip!
My family has used wheretostay.com for 5 vacations and this will not be our last. I recommend this agency all of the time to friends and acquaintances.
Andrew and Lori were phenomenal to work with and organize our trip. We are return customers and are were again extremely happy with their customer service and attention to detail!!
Amazing once again -this is the 3rd time we've used WhereToStay and have been thrilled each time!
It was a great experience. They were very helpful in picking the right Villa for us in Anguilla. Our concierge was fabulous. Through every step of the way after booking, she provided all the necessary information for our trip to the island and what to expect when we arrived. She was also very helpful in recommending restaurants, activities, and charter boats from St. Martin for our arrival and departure.
I am already looking on this site for my next year trip. This time bringing whole family.
Highly recommend,easy to work with, efficient & prompt to respond to any questions!
We had a great experience with WhereToStay. Very responsive and helpful.
I couldn't have been happier with services provided by the staff at Where To Stay.From the start they made my experience seamless. I would highly recommend them and will continue using them in the future.Thanks!!Tom B
Our vacation was truly special. Jean made our vacation planning effortless and provided exceptional service and made it a once in a lifetime experience.
Wheretostay is now my preferred provider when looking for vacation homes in the Caribbean. I've worked with them twice now and both experiences were excellent.
Fantastic villa rental site, the best I have ever used.
Our trip was great and we had no disappointments in our stay. The information provided was useful and accurate and all went as planned
Fabulous!
I have used WhereToStay and Betsy 3 or 4 times now for houses on St John. They are always professional and courteous to deal with. Very helpful for or info and quick to respond to questions I have. Obviously I can use other companies but I wouldn't even think of using anyone other than Betsy and WhereToStay.
Great experience and will definitely use them again.
Outstanding in every way!
Absolutely perfect! Jean listened to what we wanted and nailed it!
Was perfect for us! Only issue was power outage due to storms and house didn't have generator Will always make sure there is one at a house in future
It's always nerve racking to book online with a company you don't know. And when you're booking in a different country and spending thousands of dollars it makes it even more frightening. However, this company is legitimate. Our agent Betsy Carmichael is a dream to work with and made sure to answer any and all questions. We loved our experience so much that we booked with her again and went back to the same island and the same neighborhood. We would highly recommend wheretostay.com and Betsy!
Wonderful!
I am very happy with the lines of communication from start to finish of renting the villa.
Jean was extremely helpful from start to finish. Everyone we encountered were top notch. Thank you!!
We enjoyed working with Betsy to confirm the Twin Palms villa and get everything set for when we got there. Betsy gave us the recommendations of what to do, where to get our groceries (and alcohol) and everything was set when we walked in the door. All recommendations were amazing!
Wonderful experience in every way
Our experience with Jean and Lori was excellent! From choosing the island and villa to logistics of transportation, we were very well taken care of.
This was my first experience utilizing WhereToStay.com. Initially, I had a little hesitation booking our trip over the internet with a company I hadn't previously heard of in a foreign country. After doing some research and speaking live with WhereToStay team members, my concerns quickly dissipated. The WhereToStay team were excellent to work with throughout the entire process. They regularly communicated with me during the lead up to our trip as well as during our stay. The recommendations provided (especially renting a car) were extremely valuable and made our experience very enjoyable. I cannot say enough positive words about my experience working with the WhereToStay team. I plan to use WhereToStay.com for future vacations as well as recommend them to people I know.
They were great to work with
I could not recommend the firm more highly.Very attentive and professional.
Amazing
Wonderful team, very attentive, everything was perfect
This is our 2nd time using wheretostay & we would definitely use again!
Where To Stay and their staff offer the best in service and products, we just wish they service more locations so we could shop with the best everywhere!! You could not be in better hands for your travel/vacation experience.
Responsive to any / all needs and questions. They anticipate what you'll need to prepare for the trip, what you might need on island, and simply make the holiday experience one to remember.
Responsive. Intuitive. Informative. Great concierge service.
I give WhereToStay.com the highest possible recommendation. This was the easiest Caribbean villa vacation I have ever booked. Jean and Lori anticipated every question and attended to every detail from airport pick-up through departure.
I highly recommend this villa. It is very private comfortable and beautiful. They recommended Jose as a chef and his food was delicious
A great experience
Excellent experience !!
We would definitely use "Where to Stay" again!
WhereToStay did a great job helping us find our villa. They were very helpful and informative. We will use them again
Our overall experience was excellent!
Where to Stay worked closely with the "on Island" managers and they were responsive to the very few questions that arose during our stay.
Property was well maintained with great onsite support. We would book with where to stay again.
Outstanding experience!
Just excellent...a great organization that made our trip so much more enjoyable.
Excellent!
Very professional. Efficient in dealings with me but friendly and helpful too. Planning and organisation of the holiday was excellent. Definitely use again.
Great people to work with before and after our stay.
Concirge service was impeccable
They seem to have a better selection of homes than VRBO and Airbnb. We were very happy with their service and all of the helpful information regarding our trip!
My family has used wheretostay.com for 5 vacations and this will not be our last. I recommend this agency all of the time to friends and acquaintances.
Andrew and Lori were phenomenal to work with and organize our trip. We are return customers and are were again extremely happy with their customer service and attention to detail!!
Amazing once again -this is the 3rd time we've used WhereToStay and have been thrilled each time!
Get inspired!
Traveling is all about sharing experiences and adventures, which is why we launched our travel magazine. Dive into our stories and find inspiration for your next trip!

Christina - 16 Mar 2025
Vibrant Events You Can’t Miss on the French Riviera
When you think of the French Riviera, your mind naturally drifts to visions of the dazzling blue Mediterranean waters, sun-kissed glamorous beaches, and the opulent yachts that line the coast. Beyond the sparkling sea and luxurious surroundings, it’s the ...
read more

Hannah - 16 Mar 2025
Luxury Villa Rentals Europe With Tennis Courts
Luxury villa rentals in Europe with tennis courts combine the thrill of sport with the indulgence of high-end living. These exceptional properties are set in breathtaking destinations, from the sunlit coasts of the Mediterranean to the rolling hills of Tuscany. ...
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