Villa Alegria Anguilla, barefoot elegance at its best

Villa Alegria, located on the intimate island of Anguilla in the British West Indies, is one of the newest and most desirable private beachfront Caribbean villas available for rent. Villa Alegria was created in 2008 by owners Neil and Wendy Freeman, and impeccably appointed by the same designer as the five-diamond Four Seasons Resort on Nevis. This gracious four-bedroom oasis is inspired by centuries old Tuscan architecture, yet provides the best of today’s modern amenities.

Enjoy personalized service, a private gym, and breathtaking views of the Caribbean Sea and the mountains of St. Martin.  Indigo waters and sugar sand are mere footsteps from Villa Alegria down a paved path. A series of porticos, terraces and baths blur the lines between outdoors and indoors and ensure you are never far from the cooling caress of the Caribbean trade winds.  It’s the perfect place to relax and unwind for couples, families and friends.

Villa Alegria’s West End Cul de Sac location is convenient to all of this unspoiled island’s wonders.  Laze on Anguilla’s secluded white sand beaches, dine on culinary delights, explore world-class snorkeling, diving, hiking, fishing, boating, golfing and more, then return home to the comforts of this spectacular retreat to refresh and revive.

Make Villa Alegria your personal Anguilla oasis

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  • “We had an amazing experience staying at Villa Alegria. From the first point of contact with Christina and Neil to the personal attention of Michelle and staff, we were exceptionally pleased and well taken care of. Pre-trip, the level of communication, professionalism, and flexibility with a last minute change, showed the level of commitment and care you have for your customers. During our stay, the experience was handled beautifully by Michelle and staff. They were available any time we had a need and executed flawlessly. The Villa Alegria is breathtaking!!! Great location! We were just a block from the ferry to St Martin (where we took the ferry to the French side for a day of shopping and delicious food). We could even see the island from our view in the house. Breathtaking! We had a wonderful trip and we have referred everyone we know. Once they saw our pictures, they were blown away! Thank you all so much for a memory of a lifetime!"

    -Guest email for stay May 2013

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  • “It's been a little over a week since we returned from our vacation at Villa Alegria and already we are missing it. The villa is stunning. I cannot say enough about its beauty; from the layout, the furnishing, to the amazing view. It was perfect size for my family and extended family. We each had our own personal space yet were able to enjoy each other every day sitting on the veranda and the around the pool. The staff was wonderful as well. Michelle was very accommodating and helpful. She answered all our questions and was quick to respond during the week when additional questions arose about the house or the island. Angelina is so kind, she made us feel at home. I have to admit were unsure of Anguilla, not knowing much about the island, but after spending a week there we loved it. We have already discussed returning to Anguilla and Villa Alegria. Unfortunately, next year's vacation has been planned, but expect to hear from me again for 2015. Thank you again for sharing your wonderful home (and the wine)."

    -Guest email for stay April 2013 – returned in 2014

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  • “Fantastic! We just returned from an 8 night stay at Villa Alegria in Anguilla for my Father’s 70th birthday. We cannot recommend this villa highly enough, it had all of the amenities you could ever desire and was simply stunning. Michelle the Villa Manager was excellent, always on hand if we had any questions. We also had a housekeeper who was spectacular (always there if we needed anything without being intrusive) gym, fully equipped kitchen, wonderful views and close enough to restaurants etc. if you wanted to venture out. Excellent restaurants and beaches. We were three couples and this property worked perfectly for us, we hope to go back soon we loved Anguilla.”

    -Guest review for stay April 2013 on Flipkey

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  • “I want to thank you very much for the use of your Anguilla home last week. My family enjoyed it very much. The views are fabulous from the moment you walk through the front door. The house is very well-appointed as well. Thanks again.”

    -Guest email for stay April 2013

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  • “We truly enjoyed Anguilla and this amazing home. The views are spectacular and the house is both luxurious and comfortable. A first class property all the way."

    -Guest on for stay April 2013 on 3rd Home – 5 stars

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  • “We are so enjoying Villa Alegria, the house is lovely, Michelle and Angelline fabulous and we feel very at home. We would love to arrange to come back again next year -- and of course invite to stop by in Santa Fe soon.”

    -Guest email for stay January 2013 – Repeat Guest

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  • “We have been coming to Anguilla for many years and always stay in great villas. This past March we stayed at a new villa, Villa Alegria, which we had toured the previous November. It was more amazing than we even expected. First the layout and the floor plan of the villa is amazing with every need and desire carefully thought out. Our kids all had great time in the huge pool and going down to the beach. The staff (housekeeper and manager) was amazingly helpful and very nice. The location and views are superb! I just thought I would pass on this information to anyone looking for a great place to stay. Villa Alegria outshines everything else we've seen.”

    --Guest for stay August 2012 on VRBO

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  • “We definitely want the house for 2 weeks again - this is the nicest place we have ever stayed, it even beats the renovation of La Moumania...which is saying something. We just let people tour it and they are clearly disappointed that we had already indicated this to you.”

    -Guest email for stay January 2012 – Repeat Guest

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  • “I wanted to drop you a note to let you know how much we enjoyed Alegria. It was beautifully appointed and had every need we could think of. We met Dale at Tastys and his face brightened when we told him where we were staying! Michelle and Angelina were very helpful and so sweet with all of our questions. Thanks again for a great stay, we hated to leave!”

    -Guest email for stay June 2012

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  • “The guests love Alegria and everything has been great for their visit. So much so that they are re-booking for this same week next year”

    -Travel agent email for stay December 2012

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