Anguilla Luxury Vacation Rentals

With more than 30 beaches and a coastline shaped by turquoise coves, Anguilla is a masterpiece of understated Caribbean luxury. Each region offers its own rhythm—whether you’re craving tranquil seclusion, world-class cuisine or cultural immersion.

From the iconic shores of Shoal Bay to the sophisticated calm of Long Bay, these distinct locales shape the island’s allure. In this guide, we explore some of the finest areas to stay in Anguilla, all ideal for those seeking the best vacation rentals and a true sense of island ease.

Interested in Anguilla beaches? Here's top 5 beaches in Anguilla.

Blowing Point

Blowing Point is the island’s main arrival hub, home to the ferry terminal for those who ferry over to Anguilla from St. Maarten. Despite its role as a gateway, the village retains a low-key, local charm. Cozy beach bars, casual eateries, and breezy stretches of shoreline make it a perfect first impression of island-of-Anguilla hospitality.

This area is ideal for guests looking for convenience without sacrificing serenity. From here, you’re within easy reach of luxury experiences like private boat charters or even dolphin swims, making it a versatile base for curated vacation experiences.

Crocus Bay

Nestled near The Valley, Crocus Bay blends historical significance with natural beauty. The quiet beach, framed by dramatic bluffs, invites peaceful mornings and romantic sunsets—ideal for travelers seeking reflection or reconnection in a luxury vacation rental.

Seafood-focused dining and waterfront lounging bring a mellow sophistication to this area. For those in search of exceptional villas with panoramic sea views, Crocus Bay is home to some of the best Anguilla villas, including staffed villas like Ani Anguilla with private infinity pools and full-service luxury.

Island Harbor

A vibrant fishing village on the northeast coast, Island Harbor is full of local color and island rhythm. The atmosphere is relaxed but culturally rich, with independent galleries and artisan shops scattered along the shoreline.

Visitors often gather at Scilly Cay, a tiny islet with panoramic views and lobster lunches. For those wanting to visit Anguilla and experience a more authentic side of the island, this area brings together barefoot luxury and vibrant, lived-in charm.

Long Bay

For travelers seeking quiet elegance, Long Bay Villas Anguilla are among the most coveted addresses. The beach itself is an unspoiled stretch of white sand, far from the crowds, with soft breezes and turquoise waves lapping the shore.

Long Bay is where you’ll find some of the most exclusive luxury villa rentals on the island, including Sea Villa, part of a collection of luxury beachfront estates. This is the place to truly unwind—Long Bay Villas often include a private chef service, private pools, and uninterrupted views, creating the epitome of luxury.

Shoal Bay East

Often cited as one of the best beaches on Anguilla, Shoal Bay East offers two miles of powdery sand and a vibrant, laid-back energy. It's a popular destination for those who want to combine beachfront beauty with access to watersports and relaxed dining.

The area is also home to some of the island’s most desirable luxury villas Anguilla has to offer, placing you steps away from snorkeling reefs, sailing excursions, and beach bars with live music. Whether you’re here to relax or explore, this is luxury in Anguilla at its most vibrant.

The Valley

As the capital, The Valley is Anguilla’s cultural and administrative heart. It’s not beachfront, but it provides access to heritage sites like the National Museum and Estate Whim Plantation, along with lush stops like the Botanical Gardens.

While many Anguilla vacation rentals cluster near the coast, staying near The Valley offers a more immersive, local perspective. It’s also ideal for day trips around Anguilla, giving easy access to both eastern and western beaches, as well as key dining and shopping venues.

West End Village

Positioned at the west end of Anguilla, this refined coastal area is known for its natural elegance and access to some of the finest Anguilla resorts and bay villas. It’s home to iconic properties and secluded coves that define Caribbean luxury.

Art galleries, boutique shops, and upscale restaurants create a sense of quiet sophistication. Whether you're seeking Anguilla rentals with direct beach access or planning a dream vacation surrounded by art and sea, West End Village is a timeless choice.

Meads Bay

Meads Bay is a favorite among discerning travelers and a highlight in any guide to Anguilla. This expansive, crescent-shaped beach is known for its calm waters, fine sand, and refined yet unpretentious energy. It’s also home to several luxury resorts, upscale dining venues, and beach clubs that elevate the beach vacation experience.

The area features some of the most sought-after Meads Bay villas, ideal for those seeking luxury Anguilla villa rentals with direct beach access and tailored amenities—including a private chef. With elegant restaurants like Blanchards and access to wellness experiences, Meads Bay blends barefoot ease with the best of luxury Anguilla living.

Anguilla restaurants bring a remarkably sophisticated dining scene. From beachside Italian bistros to artful Asian fusion, the island offers unforgettable meals in settings that match its natural beauty.

Whether you're staying in luxury Anguilla villas or enjoying an extended beach vacation, these standout restaurants deliver culinary experiences that reflect the island’s elevated lifestyle.

Dolce Vita Italian Beach Restaurant & Bar

Set on the sand in Sandy Ground, Dolce Vita brings the flavors of Italy to the Caribbean with a menu that’s both heartfelt and refined. Fresh pastas and delicate seafood are prepared with care—linguine alle vongole and Gorgonzola gnocchi are house favorites, paired with curated Italian wines and beachfront views.

Guests of luxury Anguilla villa rentals in nearby areas often find Dolce Vita a perfect complement to private dining, especially when craving something romantic yet relaxed. It’s an ideal evening stop after a day spent exploring things to do in Anguilla, or simply enjoying the comfort of villas in our portfolio.

Hibernia Restaurant and Art Gallery

Hibernia is more than a restaurant—it’s an experience. Located on the island’s east end, this elegant cottage with Balinese touches offers inventive cuisine with ingredients grown on-site. Signature dishes like long-line fish with local pumpkin and bitter orange essence are plated like fine art.

The adjoining gallery features global treasures collected by the owners, adding a unique cultural touch. For guests staying in shoal bay villas or home in Anguilla near Island Harbor, Hibernia makes for a memorable dinner immersed in style, flavor and the quiet sophistication that makes Anguilla unique.

Mango’s Seaside Grill

A long-standing favorite for Anguilla's luxury travelers, Mango’s Seaside Grill serves up ultra-fresh cuisine in a laid-back yet polished beachfront setting. Dishes like grilled snapper and rum-barbecued chicken are light yet flavorful, complemented by desserts such as warm apple tart or coconut cheesecake.

Mango’s is a short drive from many of the best villas along Meads Bay and Barnes Bay. It’s a quintessential stop for those who rent in Anguilla and want to savor the balance of elevated simplicity that defines this Caribbean island.

Tokyo Bay

Tokyo Bay brings a cosmopolitan edge to the island’s dining scene, with dramatic lighting, teppanyaki theatrics and a sleek sake bar. Ocean-fresh sashimi, Wagyu beef, yakitori and inventive cocktails like the Saketini draw both locals and international guests.

It’s a favorite among chefs and connoisseurs alike, making it a stylish outing for travelers staying in luxury resorts or Anguilla villas with private pools nearby. After a day of sun or sailing, a visit here offers a refreshing contrast and a glimpse into the island’s global sensibilities.

Veya

Veya is the epitome of island chic. Set within a lush tropical garden, the restaurant features glowing lanterns, live jazz and an imaginative menu that spans Caribbean, African and Middle Eastern flavors. Dishes like rum-glazed jerk tuna and Moroccan-spiced shrimp offer bold tastes with elegant presentation.

Perfect for a celebratory night out during your trip to Anguilla, Veya also pairs beautifully with a stay in Meads Bay villas or other nearby properties. It’s a top choice for those curating their own guide to Anguilla, blending local flair with global refinement.

While Anguilla is known for its pristine beaches and luxury living, it also nurtures a quiet but growing cultural movement. Art, history and local craftsmanship are deeply rooted in the island’s identity—offering travelers a thoughtful and enriching dimension to their trip to Anguilla.

Devonish Art Gallery

One of the island’s most respected cultural landmarks, Devonish Art Gallery showcases the vibrant vision of artist Courtney Devonish. Caribbean-inspired paintings, handcrafted jewelry and polished wood sculptures fill the gallery, offering an authentic look at the island’s artistic spirit.

It’s an ideal stop for visitors who want to bring home a piece of the island. The gallery’s curated pieces also make for meaningful, one-of-a-kind gifts for those drawn to local craftsmanship and contemporary Caribbean art.

Heritage Museum

Curated by historian Colville Petty, the Heritage Museum offers a powerful perspective on Anguilla’s complex past. From Arawak-era relics to colonial tools and family heirlooms, this modest space tells the story of an island shaped by resilience and transformation.

For those exploring things to do in Anguilla beyond the beach, this stop provides rare insight into the soul of the island. Petty, who was honored with an OBE by Queen Elizabeth II, adds a personal and passionate voice to the experience—one that elevates this venue into more than just a museum.

When the sun dips below the horizon, Anguilla transforms into a laid-back yet lively destination, with intimate beach bars, upscale lounges, and live music led by local legends. Whether you're enjoying a night out from your villa specialists' curated itinerary or discovering a spontaneous evening near your luxury Anguilla villa rental, the island offers a warm welcome after dark.

Dune Preserve

Perched along Rendezvous Bay, Dune Preserve is an iconic venue built from reclaimed boats and driftwood—infused with the personality of its founder, reggae artist Bankie Banx. Weekend nights come alive with live performances, often featuring Banx himself, making it a must-visit for lovers of roots music and island soul.

It’s a favorite among those who travel to Anguilla looking for authenticity and charm. The atmosphere is relaxed, creative, and unmistakably local—reminding visitors that Anguilla is one of the rare islands where music still comes with a personal connection.

Four Seasons’ Sunset Lounge

At the heart of the Four Seasons resort lies the Sunset Lounge, an elegant terrace with sweeping views over Barnes Bay. Guests enjoy vintage rums, fine cigars and Asian-inspired tapas as the sun sets over the water. With its adults-only infinity pool and live jazz, it’s a refined place to begin or end your evening.

Perfect for guests staying in full-service luxury villas nearby, this lounge delivers a polished experience that aligns with the quiet glamour that defines luxury Anguilla.

Lit Lounge

Lit Lounge turns up the energy with elevated nightlife in the heart of Sandy Ground. Its two-level design features VIP decks, cabanas, a grill and a cocktail bar helmed by renowned mixologist Taffy Hodge. Expect ambient lighting, rhythmic beats and curated drinks that match the vibe.

Whether you’re visiting for the Anguilla Summer Festival or simply looking for an upbeat night out, Lit Lounge offers a chic contrast to the island’s slower daytime rhythm. It’s ideal for guests who want a taste of island nightlife without compromising on sophistication.

Ocean Echo

Situated on Meads Bay, Ocean Echo blends panoramic ocean views with creative mixology and all-day dining. Chief Dillon, the venue’s resident mixologist, crafts signature cocktails like the Rumzie and Dirty Bird—each as vibrant as the scenery.

Ocean Echo offers a seamless transition from lazy afternoon to festive evening, making it a favorite for couples, groups, or families who want to get to Anguilla, unwind and celebrate in style. The location is also convenient for those staying in nearby villa rentals curated by LVH and other villa specialists.

Music, sea and celebration are at the heart of Anguillan life. Throughout the year, the island comes alive with vibrant festivals that bring together locals and travelers in joyful appreciation of heritage, artistry and connection. The following events offer a deeper look into Anguilla's spirited soul.

Anguilla Day

Celebrated annually on May 30th, Anguilla Day marks the island’s declaration of independence in 1967. Locals commemorate the day with a spirited round-the-island boat race and a parade filled with island pride. It’s a meaningful time to travel to Anguilla, with residents and guests alike joining in the festivities.

Expect joyful crowds, historical reflections and a heartfelt appreciation for the island’s sovereignty—all set against the backdrop of warm skies and turquoise seas.

Anguilla Regatta

One of the island’s most anticipated sporting events, the Anguilla Regatta takes place each March at Sandy Ground. Over three days, Anguilla’s finest sailors compete in thrilling boat races while spectators gather at the beach to enjoy lively music, seaside parties and local fare.

Proceeds benefit the Anguilla Youth Sailing Club, which has nurtured hundreds of young sailors over the years, adding purpose to an already electrifying experience on the water.

Festival del Mar

This seaside celebration in Island Harbour honors Anguilla’s deep maritime roots. Held each April, Festival del Mar features seafood cook-offs, fishing tournaments, swimming contests, and beachside concerts. Guests can even take part in dry-land fun like volleyball, arts and games.

It’s a family-friendly event with authentic island energy and an ideal way to experience local flavor, both culinary and cultural, in a laid-back coastal setting.

Moonsplash Reggae Festival

Hosted by iconic Anguillan artist Bankie Banx at Rendezvous Bay’s Dune Preserve, Moonsplash is a beloved reggae festival that blends international talent with unmistakably local soul. The event runs for two nights of open-air concerts followed by beach parties that often last until sunrise.

With its relaxed atmosphere, eclectic crowd and rootsy vibe, Moonsplash is one of the most iconic experiences Anguilla has to offer, especially for those who enjoy live music under the stars.

Summer Festival

Held in late July through early August, the Anguilla Summer Festival is the island’s grandest celebration, merging elements of Carnival with Anguillan flair. The signature event is J’ouvert, a spirited morning street party that gives way to a vibrant beach bash by noon.

From the crowning of the Miss Anguilla Queen to nightly calypso competitions and boat races, the Summer Festival is a high-energy, week-long expression of Caribbean culture at its most exuberant.

For those seeking unforgettable moments beyond the beach, Anguilla offers personalized experiences tailored to your style of exploration. These curated activities provide an immersive way to discover the island’s landscape and soul.

Deep-Sea Fishing Charter

Board a private executive fishing charter for a day at sea in refined style. Premium rums, cigars, onboard entertainment and a personal chef elevate the experience as you chase mahi mahi and wahoo in deep Caribbean waters.

After your catch, return to the chef’s restaurant where your fish is prepared to your liking, followed by sunset dining and live music back onboard. It’s not just fishing, but a celebration of Anguilla’s maritime bounty.

Private Helicopter Tour

See Anguilla from above with a custom helicopter tour offering panoramic views of the island and its surrounding cays. The flight covers scenic landmarks like Rendezvous Bay, Cove Bay and the luminous Meads Bay, with your pilot highlighting hidden gems along the way.

This exclusive aerial journey is perfect for photographers, romantics or first-time visitors wanting a sweeping introduction to the island’s geography and grandeur.

Horseback riding on the beach

Feel the rhythm of the waves beneath you as you ride a well-trained horse along a secluded beach or even through the water itself. Whether you’re an experienced rider or a complete novice, Seaside Stables offers peaceful 30- or 60-minute sessions guided by expert trainers.

This meditative, slow-paced experience offers a gentle way to connect with nature, ideal for couples or anyone seeking serenity and something truly unique.

Private charter diving excursion

With over 20 reefs, seven shipwrecks and five wall dives, Anguilla’s underwater world is nothing short of spectacular. A private diving charter provides complete access to top dive sites, all equipment included, plus options for gourmet lunch stops at islets like Prickly Pear.

After exploring the depths, unwind with grilled lobster and a free-flowing rum punch as you relax on the sand—a perfect blend of exploration and indulgence.

Luxury villas in Anguilla are designed to provide an effortless blend of comfort, privacy and high-end living. Whether you're planning a romantic escape or a multi-generational holiday, the villas in our portfolio are thoughtfully appointed with upscale features that enhance every aspect of your stay.

What amenities are included in Anguilla luxury villas?

An Anguilla luxury villa often includes:

• Infinity pools and heated pools
• Fitness rooms and fully equipped gyms
• Private spa lounges and massage rooms
• Game rooms and pool tables
• Outdoor kitchens and BBQ areas
• Hot tubs and outdoor sound systems
• Walk-in closets and wine storage
• Private elevators and wheelchair access
• Patios, terraces and sun loungers
• Golf carts and bicycles for local exploration

From indoor wellness spaces to outdoor entertainment areas, each Anguilla luxury rental is crafted to reflect the island’s refined, barefoot elegance. Guests can also request such added luxuries as private chef service, butlers and custom excursions, ensuring a fully tailored Caribbean experience.

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