Start-to-finish trip planning
Concierge teams coordinate your arrival, departure, and everything in between.
300+ point inspection
Every Luxury Retreats home is personally verified to be in pristine condition.
On-trip care, 24/7
Premium, on-demand assistance for any question, at any time of day.
48 luxury villas and vacation rentals in Anguilla
1 – 18 of 48 places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.
Luxury Retreats - an expert in Anguilla vacations
Where do you go when you’ve experienced so much of what the Caribbean has to offer? To Anguilla, the petite, picture-perfect island, with acres of white sandy beaches and azure blue seas. Nestled near to its well-known island counterparts, St Martin and St Barts, this isle is the place to go to when R&R is top of the agenda. Yes, there is plenty to see and do, with sea kayaking, day cruises, golf, paddle boarding, and tennis all available at a moment’s notice. Yet the lush tropical landscapes, hidden beach coves, white-hot beaches, and cerulean waters are the perfect backdrops for an afternoon (or two) of doing absolutely nothing. Bliss.
As nature intended
There are many ways to explore Anguilla, like spending an hour or two at the Heritage Cultural Museum. Its artifacts and exhibits offer a great intro to Anguillan history. If that whets your appetite, a Heritage or Amerindian Settlement Site Tour by the Anguilla National Trust is a must. The tours cover the heritage sites, important to the history of the first Anguilla settlers, the Amerindians. The Big Spring is a tour highlight, showcasing the carvings on the rock formations surrounding a spring made by the settlers, between AD600-1400. Elsewhere, the East End Pond, part of a wildlife conservation site, is a hotspot for the island’s indigenous birdlife.
Anguilla’s 33 beaches are all well worth a visit. The most secluded is Little Bay, a small cove close to Crocus Bay beach that is never filled with sightseers. Long Bay is a haven for A-listers and the jet set and this silvery beach is the perfect location for picnics and quiet walks. Shoal Bay West is adorned with palm trees and low-key beach bars. Those who like a little shade from the heat of the sun should head to Maundays Bay, where the iconic Sea Grape trees offer plenty of respite from the sunshine. Many of Luxury Retreats’ villas have complimentary water sports equipment, so once you’ve found your dream cove, you and your guests can snorkel to your heart's’ content.
A la carte
The island’s unique location and history mean its cuisine is a fabulous fusion of produce and cultural influences, with Caribbean and French flavors dominating. Fine dining can be had at Jacala or Geraud’s Bakery, both serving delicious seafood dishes, including crayfish, spiny lobster, and mahi-mahi. For a more relaxed meal, look to Blanchards Beach Shack to feast on curried chicken, shrimp salad, and blackened mahi-mahi. With over 100 restaurants to choose from on the island, you will enjoy finding your own personal favorite.
Anguilla’s close proximity to the islands of St Martin and St Barts means a day trip is almost mandatory during your stay. Just a short 30-minute ferry ride from the Blowing Point terminal takes you to St Martin, an island with a mixture of French and Dutch heritage. The French side is famous for its fusion cuisine and pristine beaches. Make a point of visiting Grand Case, a fishing village with several fine dining restaurants, serving delicious seafood dishes. Every Tuesday from January to April, Grand Case village has its own version of Mardi Gras with the main street closing to traffic and arts and craft stalls lining the streets.
St Bart’s 14 beaches are well worth a visit, particularly the Grand Cul de Sac with the O Corail Beach Bar, offering great dishes for a light lunch. The bustling towns of Gustavia and Saint Jean offer great shopping opportunities with avenues of designer boutiques.
Where to stay - Anguilla rentals
With spacious outdoor areas, infinity pools, and direct access to white sandy beaches, Luxury Retreats has an enticing selection of villas to make your stay on the island of Anguilla absolutely wonderful.
The only tricky choice you make when booking a vacation to Anguilla is deciding whichAnguilla beach house will be your paradise home-from-home. At Luxury Retreats, there are over 20 world class villas, mansions, and apartments to choose from all over the island. All situated in some of the most sought-after locations: Long Bay, Little Harbour, Shoal Bay, Meads Bay, and Rendezvous Bay to name a few.
With homes catering for parties ranging from eight to 50 people, whether you are planning a honeymoon, buddymoon, special family get-together or corporate retreat, there is a villa just waiting to greet you. All villas are close to glistening beaches and azure blue seas and if golf is high on the agenda, the villas close to Long Bay and Rendezvous Bay are near to the five star Cuisinart Resort, which has a Greg Norman designed 18-hole course for you to experience.
Likewise, the villas near to Little Harbour bay are close to Sandy Ground, the self-billed entertainment capital of the island, making it a haven for night owls. All villas have fabulous views of the ocean and are arranged so that life can be seamlessly lived outside as well as inside, with floor to ceiling glass doors, marble flooring, and modern furnishings throughout. Bose surround sound speakers, media rooms, infinity pools, hot tubs, alfresco showers and a full roster of staff services ensure this vacation is the most pleasurable yet.
Get away from it all
Lying in one of the most secluded parts of the island are Luxury Retreats’ Shoal Bay East Villas , just a moment’s walk from Shoal Bay Beach and Shoal Bay Village. From spacious Mediterranean-inspired villas to cliff top mansions and modern glass-fronted houses set within the elegant Zemi Beach House Resort, whatever your vacation requirements are, we’ve got the perfect option for you. With properties ranging from two-bedrooms to eight-bedroom estates, no matter who is in your vacation party, there will be something for everyone to enjoy. From private rooftop terraces to private infinity pools, alfresco showers and daily housekeeping as standard, pure relaxation is available twenty-four hours a day. If you can bear to leave the confines of your luxury accommodation, the nearby Shoal Bay Beach is perfect for snorkeling and all other types of water sports activities, while the Temenos Golf Course is a quick car drive away. Culture buffs will be pleased to know the Cultural Heritage Museum and Amerindian Ceremonial Site are a short car journey away, too.
On the beach
Situated on the south west of the island is the popular beach, Maundays Bay Beach, a long white sandy beach, filled with restaurants and bars. It’s a go-to destination for young families and large vacation parties keen to squeeze the most out of their off-duty experience. If you are looking for a vacation home or estate large enough to accommodate all of your vacation team’s needs, theMaundays Bay Villas we have available could be just what you are looking for. You can take over the entire Sheriva Estate which has three state-of-the-art villas, with 22 rooms and sleeps 50 people. These villas, Harmony, Mystique, and Infinity, available to rent separately, are set over three levels with direct access to spacious terraces with views overlooking the ocean and the breath-taking island of St Martin. Private infinity pools, hot tubs, alfresco showers, and a complimentary golf cart to help you whizz around the estate, all come as standard. The decadent interiors, designed by Norma Chase Jobert, include hardwood ceilings, marble floors, and sumptuous furnishings. Housekeeping and night security are on hand and a private chef can be organized by your Luxury Retreats concierge. Close to the complex is the Cap Juluca resort and its popular restaurants, Pimms, Blu, and Spice, are all within walking distance. This location is ideal for intimate wedding parties, as well as corporate retreats.