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Once a remote, sun-drenched outpost in Britain's colonial empire, today Anguilla holds a spot as one of the most talked about Caribbean vacation destinations. Complete with miles of gentle white sand beaches, this long and flat island lures golf lovers with two well-groomed courses. Gourmands agree, Anguilla restaurants are some of the best in the Caribbean, rivaling St. Barths. With both upscale dining and low-key beach bars humming with live music, Anguilla radiates a casual elegance that appears unaffected by growth and attention. With the recent addition of non-stop flights from San Juan, Puerto Rico, an increase in private jets, commuter flights and ferry service from nearby St. Martin, Anguilla has become an even easier place to visit.

Our Staff Recommends

WIMCO Villas, AL AL2, Anguilla, Shoal Bay West, 5 bedrooms, 7 bathrooms


Located in the exclusive private beachfront Altamer Resort - redefining sophistication with style and luxury

Shoal Bay West, Anguilla
5 br / 7 ba

WIMCO Villas, IDP LEM, Anguilla, Forest Bay, 3 bedrooms, 3 bathrooms


Secluded on small sandy beach, includes kayaks & 10' Walker Bay

Forest Bay, Anguilla
3 br / 3 ba

WIMCO Villas, RIC TEQ, Anguilla, Sandy Hill, 3 bedrooms, 3.5 bathrooms


Refined sophistication, a contemporary villa at Lovers Cove

Sandy Hill, Anguilla
3 br / 3.5 ba

WIMCO Villas, ANI EST, Anguilla, Little Bay, 10 bedrooms, 10 bathrooms


10-bedroom estate with two 5-bedroom fully-serviced villas

Little Bay, Anguilla
10 br / 10 ba

WIMCO Villas, AXA ARU, Anguilla, Rendezvous Bay, 5 bedrooms, 5 bathrooms


Exquisite beachfront property, just steps from a top notch golf course

Rendezvous Bay, Anguilla
5 br / 5 ba

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Anguilla villas are known for their modern architecture, clean white tones, and sprawling infinity pools. Most of them sit directly on the beach, or overlook the tranquil Caribbean waters. Villas are tucked off the main roads, and some feature access to nearby resorts. Tennis lovers can take advantage of a number villas with private tennis courts on the grounds, and families will enjoy both the spacious accommodations, and the proximity to calm beaches.

Featured Villas

WIMCO Villas, RIC PAR, Anguilla, Blowing Point, 6 bedrooms, 5.5 bathrooms


Gated 6br villa located on a spacious & luxurious estate

Blowing Point, Anguilla
6 br / 5.5 ba

WIMCO Villas, RIC SAN, Anguilla, Little Bay, 4 bedrooms, 4.5 bathrooms


Secluded beachside Tuscan inspired 10,000 sq.ft villa, fabulous views

Little Bay, Anguilla
4 br / 4.5 ba

WIMCO Villas, IDP LEM, Anguilla, Forest Bay, 3 bedrooms, 3 bathrooms


Secluded on small sandy beach, includes kayaks & 10' Walker Bay

Forest Bay, Anguilla
3 br / 3 ba

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For some, nothing beats hotel life-the ease of room service and on-site restaurants is a treat in and of itself. Take advantage of our team of hotel specialists, who have spent time at each of the intimate hotels we represent, and who actively reflect client feedback into their recommendations. Our hotel specialists will spend time to understand your group's specific needs and wants, research available rooms, and secure the best available price. In other words, let us do the heavy lifting! Anguilla offers a variety of small hotels-from deluxe Relais & Chateau, to simple (and lovely) boutique options. Our hotel team can book long weekend getaways or full length vacations, and would be thrilled to help arrange destination weddings and honeymoons.

Festive Cap Juluca resort is renowned throughout the Caribbean and commands a broad expanse of Anguilla beachfront on Maunday's Bay. The CuisinArt Resort & Spa features luxury guest villas and a hydroponic, health-centric dining facility. CoveCastles is exclusive and modern, with private hotel bungalows and a first-rate staff.

Featured Hotels

WIMCO Villas and Hotels, Hotel, Viceroy Anguilla, Anguilla, Book now with WIMCO

Viceroy Anguilla

Expansive luxury Caribbean hotel accommodations, gourmet dining, and sea-view wellness spa, to its expert personalized service and relaxed island sophistication - this is the art of the getaway. This is Viceroy.


WIMCO Villas and Hotels, Hotel, Cap Juluca, Anguilla, Book now with WIMCO

Cap Juluca

Located on Maundays Bay, on the southwest coast, this private resort offers first class accomodation. Private beach, golf range, watersports, spa. Choose from the casual elegance of the rooms or suites, from 1 to 5 bedrooms with private pool.


WIMCO Villas and Hotels, Hotel, CoveCastles, Anguilla, Book now with WIMCO


Situated on Shoal Bay West, this villa complex offers the privacy and luxury of a villa with the full service of a first class hotel. Watersports, tennis, bikes, restaurant, full kitchen.


WIMCO Villas and Hotels, Hotel, CuisinArt Resort & Spa, Anguilla, Book now with WIMCO

CuisinArt Resort & Spa

On Rendez-Vous Bay, this Spa resort offers luxury beachfront accommodations. Hydroponics garden, watersports, tennis, pool, beach service, over-sized marble bathroom, private patios or terraces.


WIMCO Villas and Hotels, Hotel, Carimar Beach Club, Anguilla, Book now with WIMCO

Carimar Beach Club

Directly on Mead's Bay, this hotel offers great value, an incredible beach, tennis, fully equipped apartments with patio or balcony. Perfect for families, couples or honeymooners.


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