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 most desirable private beachfront Caribbean luxury villas available for rent. Villa Alegria Anguilla 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. You’ll feel like you are vacationing in your own private luxury Anguilla resort.

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,  fishing, boating, golfing and more, then return home to the comforts of this spectacular luxury Anguilla villa to refresh and revive.

Anguilla has introduced new entry pre-approval, testing, in-bubble vacation strategy and other health and safety protocols to keep the island COVID-free while ensuring travelers have a relaxing and fun-filled vacation experience. Learn more>

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  • Absolutely spectacular from start to finish! We spent four wonderful nights at Villa Alegria with four couples and everything was absolutely spectacular! The concierge service was great at helping set up everything so the trip was absolutely seamless. The villa is large, spacious and even more beautiful than the pictures. The view is priceless! During our stay we chartered a private boat for the day which was incredible and a must do. We ate out at Tasty's and Smokey's and both were great. The best meal by far was hiring a private chef to prepare dinner at the villa. Chef Dale is an artist and does not disappoint! We will not hesitate to book Villa Alegria on a future trip and are already looking at possible dates for our next visit!

    -Guest Review for Stay Oct 2015

  • Not sure where to start with why don’t I say “wow”...what a wonderful week and great experience. We are thankful to our hosts Neil and Wendy for sharing their island home with us. This is our second experience at Villa Alegria and every bit as good as the first. Let’s start with the island...Anguilla is a wonderful island that is away short flight or boat trip away from the crowds over on St. Maarten. The island itself boasts countless white sand beaches, 33 to be exact, with crystal clear turquoise waters and great restaurants. Our favorite beaches, all close driving distance from the villa were Shoal Bay East - home to a number of casual beach bars, white sand and turquoise waters and Rendezvous Bay – also home to white sand and turquoise waters, but also the Bankie Banx Dune Preserve if you are into some afternoon music. Both beaches have ample opportunity for activity and fun or if you wanted...just peace, quiet and relaxation. This is of course not to mention a beautiful sandy beach that is all but a short 100 yard walk down a path from the villa to the ocean In terms of restaurants, for a small island Anguilla boasts a range of fine-dining, mid-range and casual dining options. It is truly unlike any other island we have been to and cater to those who appreciate a great dining experience. Our favorite restaurants were Blanchard’s and Barrel Stay. We liked Blanchard’s for their lively atmosphere and great food. Barrel Stay was an unknown to us but turned out to be a great experience. When we first got there we did not have high expectations as the outward appearance was more of a casual beach bar. However, we were literally blown away with the meal...from the service, to the appetizers, main course and dessert it was fine dining at its best. Graham is clearly a top notch chef with a passion for excellence in cuisine. In terms of the is situated on the highly desirable west side of the island in a quiet residential neighbourhood and is central to all amenities. Close to the ferry terminal and a short drive from the small island airport. So the trip to the villa, if anything, was an easy and short drive down an unassuming road to the edge of the ocean. The villa itself is stunning, beyond comparison and well over 7,000 square feet. It boasts stunning ocean views of the turquoise waters from each of the four bedrooms, great room and kitchen and 30 foot ceilings, if not higher, in the grand entrance and great room. The kitchen is without doubt a chef’s kitchen and has top end appliances, granite counter tops, a wine fridge and has ample room for preparing meals while enjoying the views of the ocean. The great room has floor to ceiling doors and windows which fully open to enjoy the trade winds with a walkout to an outdoor lounge area and with additional seating for lunches and dinner. All of this overlooking a large waters-edge infinity pool with an attached whirlpool. In addition there are ample lounge chairs and umbrellas situated around the pool to enjoy the perfect south exposure and great views of St Maarten in the distance. In a a separate building was a fully equipped fitness studio for those who wanted to balance relaxation with fitness. The villa also had a separate media room/office, which I personally found quite useful when balancing vacation with work priorities and checking the occasional email and making a phone call. The four bedrooms were exquisite and well located in the four corners of the house allowing our group of eight (four couples in our mid-fifties) with more than ample privacy. The bedrooms were so private that at night we felt like we had the villa all to ourselves without knowing the other was there. Each bedroom had stunning ocean views, a luxurious and well equipped bathroom, and comfortable beds with soft linens that provided for a restful sleep. Two of the bathrooms had both indoor and outdoor showers and the master bathroom had a soaking tub. Should the evening breezes not be enough to cool us each bedroom also had a separate air conditioning unit. The bottom line for us...this is wonderful villa and we highly recommend it. Exceptional accommodation, exquisite infinity pool overlooking the turquoise ocean waters, perfect southern exposure, beautiful beaches, no crowds, great restaurants and most importantly wonderful hosts, an attentive house manager and a diligent housekeeper. We appreciate Villa Alegria and look forward to our return.

    -Repeat Guest Review for stay November 2014

  • “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

  • “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

  • “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

  • “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

  • “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

  • “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

  • “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

  • “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