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Villas and Holiday Rentals in Anguilla, Caribbean

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    Travellers to Anguilla are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 28
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    South Hill
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    1 / 15
    4.5 of 5 stars (2) Very good
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    1 / 28
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Villa Tamarind, also known as IDP TAM, is a 5-bedroom villa located in Shoal Bay East. This villa overlooks the ocean on the northeastern end of the island. The upper level offers 3 bedrooms, an open-concept living room, dining area, and kitchen. The open living room has cushioned Rattan... View all property information
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    Anguilla, Caribbean
    1 / 22
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    A shimmering mirage or a feat of modern design? Contemporary architecture, miles of white sand beaches and the ultimate in privacy makes Villa Modena a rare find. When you pass through Modena’s double gated entrances, you are welcomed to over 10,800 square feet of indoor living space and 18,000... View all property information
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    Anguilla, Caribbean AI 2640
    1 / 30
    Long Bay Village
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Villa Zebra is perched atop magnificent Meads' Bay Hill and just a short stroll away from one of the finest beaches in the Caribbean. The home offers the discerning vacationer a blend of cool, eclectic design in a peaceful and tranquil setting. The villa is built on two levels and offers spacious... View all property information
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    Long Bay Village, Anguilla AI 2640
    1 / 14
    11 Bedrooms, 12 Bathrooms, Sleeps 22 | Quick View
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    Double the fun with a stay at Kishti on Meads. With two chic contemporary villas set on the beautiful white sands and turquoise waters of Meads Bay, the property can host the whole family for a Caribbean getaway or act as an idyllic setting for a special event. A full staff and eleven bedrooms... View all property information
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    Anguilla, Caribbean
    1 / 40
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    Viewfort Estate blends the unpretentious spirit of the West Indies with the refined and unparalleled natural beauty of Anguilla. This vacation rental offers the eclectic and effortless charm of an authentic property that has gracefully engaged elements of the island’s cultural heritage. Perched... View all property information
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    Anguilla, Caribbean AI 2640
    1 / 5
    5 of 5 stars (2) Excellent
    Island Harbour
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    La Vanda is a charming romantic cottage. Very private part of a larger estate, with a walled back garden with outdoor shower, bar-b-que dinning area as well as sun bathing loungers. It is not on the waterfront, but is a very short walk about 3 meters to famous Shoal Bay East Beach. The area is... View all property information
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    Island Harbour, Anguilla AI 2640
    Island Harbour
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Villa Soleil at Captains Bay is a fully air conditioned villa with luxury appointments throughout. . From every vantage point, the villa has the most spectacular views of any villa on the island. Breathtaking views of the ocean from the front and rear of the villa; view of seven islands including... View all property information
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    Island Harbour, Anguilla AI 2640
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    1 / 32
    5 of 5 stars (2) Excellent
    Island Harbour
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    Relax and enjoy a view of endless Caribbean blue at the edge Villa Amarilla’s infinity pool. Located in Anguilla, this five bedroom architectural gem boasts a décor as beautiful as the island’s natural surroundings, created in collaboration with award-winning interior designer David Salem. Whether... View all property information
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    Island Harbour, Anguilla
    1 / 14
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    East Quogue Tranquil is an affordable sun filled, fully furnished one to three bedroom, two bath, self catering vacation apartment/villa. The completely separate second floor villa is located above the owners residence and offers commanding views of the Caribbean Sea, St. Maarten, and surrounding... View all property information
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    Anguilla, Caribbean AI 2640
    1 / 11
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    The Sandyhill Beach Club is a small development (24 units) consisting of rentals as well as residents. It is a few steps to Sandyhill Bay beach with excellent snorkeling as well as quiet waters for swimming and sunbathing. The condo is tastefully decorated with custom fabrics in the turquoise... View all property information
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    Anguilla, Caribbean AI 2640
    1 / 35
    8 Bedrooms, 10 Bathrooms, Sleeps 16 | Quick View
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    Holiday Exclusive - From December 20 to December 26, 2016, this villa & travel dates have been reserved for our guests! You won't find availability for those dates anywhere else - inquire today for more information!Located on two and half acres of beautiful tropical gardens, Le Bleu overlooks the... View all property information
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    Anguilla, Caribbean AI 2640
    1 / 18
    11 Bedrooms, 12 Bathrooms, Sleeps 24 | Quick View
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    About this property
    Set directly on the white sands of Meads Bay in Anguilla, the all-new Villas Kishti (East or West) are two matching properties designed as the Kishti Estate. Meant to offer an exclusive and luxurious way to enjoy the very best that the Caribbean has to offer. With a full-service staff in-residence... View all property information
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    Anguilla, Caribbean
    1 / 20
    5 of 5 stars (12) Excellent
    The Valley
    10 Bedrooms, 14 Bathrooms, Sleeps 20 | Quick View
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    • Hot Tub
    • Waterfront
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    About this property
    Ultimate Luxury, pampered and fully serviced - Recently featured in ROBB REPORT, ISLANDS MAGAZINE, HUFFINGTON POST AND MACO... CONDE NAST JOHANSEN'S PREFERRED PROPERTY !!! 30,000 square feet of pure bliss. The Estate consists of 10 Bedrooms, 6 of them are luxuriously oversized Master Suites.... View all property information
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    The Valley, Anguilla AI 2640
    The Valley
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Sur La Plage is ALL about the beach! Anguilla is known as one of the most lovely of the Caribbean Islands, frequented by celebrities and international recluse's alike. Sur La Plage Privately-owned villas directly on Meads Bay Beach, voted one of the top ten beaches in all the Caribbean. Both... View all property information
    Location Information
    The Valley, Anguilla BWI
    Island Harbour
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our ocean front villa is open-air living in contemporary design. Verdant gardens, natural stone swimming pool, plunge pool and seaside gazebo in expansive private grounds. Your private hideaway in the rural tranquility of Island Harbour village. Since we lived in the villa for 15 years, we can... View all property information
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    Island Harbour, Anguilla AI 2640
    1 / 20
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    A wonderfully interesting up to the minute design with three separate pavilions; one for the kitchen which opens onto its own dining terrace by the pool. Another is an ideal option for a family accommodating two doubles located off the living area and the master bedroom, a sensational space beneath... View all property information
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    Anguilla, Caribbean
    1 / 30
    10 Bedrooms, 10 Bathrooms, Sleeps 20 | Quick View
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    • x
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    About this property
    Villa Le Bleu on Anguilla is a magnificent high-end property right on the water overlooking wonderful views of neighboring St. Martin. This fabulous estate is situated in a prime location on a lushly landscaped ten-acre homesite at the edge of Little Harbour Bay. Two private beaches are just steps... View all property information
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    Anguilla, Caribbean
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    1 / 18
    8 Bedrooms, 9 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Villa Harmony on Anguilla is part of the upscale Sheriva estate, the award-winning collection of luxury villas and suites. Villa Harmony provides eight spacious bedrooms and generous living spaces arranged on two floors with easy access to an expansive pool terrace. The living and dining room open... View all property information
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    Anguilla, Caribbean
    1 / 33
    8 Bedrooms, 10 Bathrooms, Sleeps 16 | Quick View
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    • x
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    About this property
    The setting for The Beach House, Meads Bay, Anguilla is as stunning as the design. Built on one acre of prime beachfront land on the powdery white sand of Meads Bay in the island's west end, with just under 17,000 square feet total living space, the Beach House is a modern masterpiece. Set within... View all property information
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    Anguilla, Caribbean
    1 / 26
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Villa Kishti Black Garden Bay on Anguilla was designed by reputed international designers and the architectural firm of Frank Hamilton to be exceptional, and that it is. The word kishti in Urdu connotes an arc, and this stunning property takes us on a journey to paradise. Guests will find absolute... View all property information
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    Anguilla, Caribbean
    1 / 44
    10 Bedrooms, 10 Bathrooms, Sleeps 18 | Quick View
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    Villa Indigo on Anguilla is set within a private tropical garden of approximately 1.5 acres, Indigo is the perfect holiday hideaway. Located within idyllic Little Harbour, Indigo is sheltered by Cinnamon Reef, providing unrivaled panoramic views of the stunning Caribbean sea and the islands of St... View all property information
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    Anguilla, Caribbean
    1 / 28
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Set at the western end of the island of Anguilla, the Villa Arushi provides its visitors with unprecedented views of St. Martin in the distance, the sea in between and the glorious gardens and grounds that surround the five-bedroom property. With beachfront access, it is a rarity among villas and... View all property information
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    Anguilla, Caribbean
    1 / 19
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    With its southwestern position in Lock Rum Bay, the Villa Aquamarie - Kamique in Anguilla offers impressive scenery. A great view of the channel, and even of St. Martin in the distance, guarantees visitors that they have the kind of endless sea, sky, and breezes that define any Caribbean... View all property information
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    Anguilla, Caribbean
    1 / 18
    6 Bedrooms, 9 Bathrooms, Sleeps 12 | Quick View
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    Villa Mystique on Anguilla is part of the upscale Sheriva estate, the award-winning collection of luxury villas and suites. Villa Mystique provides two elaborate master bedroom suites, each featuring a striking oval design, a spa-like master bath, a private lounge and a convenient dressing room.... View all property information
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    Anguilla, Caribbean
    1 / 24
    Sandy Hill Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Villa Tequila Sunrise, is a contemporary 5000 sq. ft. beach house on secluded Lover's Cove, Dropsey Bay on the southern shore of Anguilla, overlooking the Caribbean Sea, St. Martin's hills and beyond. Whilst accessible to all the conveniences of modern living, Tequila is a private retreat that... View all property information
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    Sandy Hill Bay, Anguilla
    1 / 16
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Villa Modena on Anguilla is a majestic estate situated on a full acre on stunning Cove Bay. The premiere West End location is the most prestigious on the entire island. Stunning white architecture offsets the blues of the sky, the inviting swimming pool and the crystal clear waters of the Caribbean... View all property information
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    Anguilla, Caribbean
    1 / 18
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    The luxurious Six Bedroom Villa Coyaba is situated in Lockrum on the scenic southern coast of Anguilla and overlooking the mountains of the neighbouring island of St. Martin/Maarten. The secluded cove is perfect for sunning or swimming and is only a stone's throw away. With its beautiful... View all property information
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    Anguilla, Caribbean
    1 / 29
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Villa Sandcastle on Anguilla is a spectacular grand estate situated right on the beach with 10,000 square feet of living space. Guests will enjoy all the amenities of a classically designed villa along with a full staff ready to provide desired service. Villa Sandcastle is decorated with neutral... View all property information
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    Anguilla, Caribbean
    1 / 18
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Just steps from the white sands of Meads Bay in Anguilla, the modern, luxurious and amazing Villa Kishti West waits for your arrival. With six large and opulent bedroom suites, it can easily accommodate up to twelve visitors. As part of the larger Kishti Estate, it is a spot where an amazing... View all property information
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    Anguilla, Caribbean
    1 / 18
    The Valley
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Holiday Exclusive - From December 29, 2016 to January 5, 2017, this villa & travel dates have been reserved for our guests! You won't find availability for those dates anywhere else - inquire today for more information! Like a towering ivory sculpture perched on the majestic cliffs overlooking... View all property information
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    The Valley, Anguilla AI 2640
    1 / 32
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • x
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    About this property
    Villa Ani South on Anguilla takes luxury to a whole new level. Ani South is a 6 bedroom high end villa, part of private estate composed of two buildings set at the edge of a point overlooking Little Bay and the Caribbean Sea. The villa features impressive and comfortable contemporary design with a... View all property information
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    Anguilla, Caribbean
    1 / 16
    4.5 of 5 stars (2) Very good
    Sandy Hill Bay
    7 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Nestled in three acres of lush tropical gardens, where a 17th century Dutch fort once stood, Zenaida Tennis and Beach Estate offers gracious island living. Enjoy ultimate privacy in two separate villas and an adjoining garden cottage, all handsomely appointed featuring a total of seven... View all property information
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    Sandy Hill Bay, Anguilla AI 2640
    1 / 18
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    If the idea of a full-service, estate-like holiday spot in the Caribbean appeals to you, consider Villa Kishti East, on exclusive Meads Bay in Anguilla, a dream destination. Part of the Kishti Estate, this individual villa is home to six luxurious bedroom suites, a seemingly endless list of... View all property information
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    Anguilla, Caribbean
    1 / 11
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This very spacious contemporary West Indian style 4 bedroom villa sits on a slight landscaped rise overlooking the Caribbean Sea and the mountains of St. Maarten beyond. Anani has direct access through their own short private pathway to a cove with good gentle water which is protected by an outer... View all property information
    Location Information
    Anguilla, Caribbean
    Island Harbour
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Quiet neighborhood. Fully furnished, spacious air conditioned private apartment overlooking Island Harbour village, miles of ocean, and Scilly Cay. Enjoy the ocean view from the master bedroom, master bathroom, living/dining area, kitchen and laundry area. Second bedroom and second bathroom with... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
    1 / 16
    Sandy Hill Bay
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Brand new and designed in an amazingly contemporary and clean style, the Villa Colibri in the Long Pond Bay area of Anguilla will truly take your breath away. Spread out over two levels, the villa features a spacious interior suitable for up to 12 visitors at once. Just steps from the beach, it... View all property information
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    Sandy Hill Bay, Anguilla
    1 / 12
    6 Bedrooms, 6 Bathrooms, Sleeps 13 | Quick View
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    About this property
    With a southwest Anguilla location on Lockrum Bay, the Villa Triton provides visitors with some of the loveliest and most inspiring views. Not only of the constantly shifting spectrum of blue and turquoise sea, but also the rolling blue and purple hills of St. Martin in the near distance. It also... View all property information
    Location Information
    Anguilla, Caribbean
    1 / 32
    10 Bedrooms, 10 Bathrooms, Sleeps 20 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    Villa Ani on Anguilla takes luxury to a whole new level. The high end private estate is composed of two buildings set at the edge of a point overlooking Little Bay and the Caribbean Sea. The villa features impressive and comfortable contemporary design with a pleasing neutral color pallet. Guests... View all property information
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    Anguilla, Caribbean
    1 / 32
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Villa Ani North on Anguilla takes luxury to a whole new level. Ani North is a 4 bedroom high end villa, part of private estate composed of two buildings set at the edge of a point overlooking Little Bay and the Caribbean Sea. The villa features impressive and comfortable contemporary design with a... View all property information
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    Anguilla, Caribbean
    1 / 20
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    Dramatic ocean views and authentic Caribbean decor by Cindy Dzurita -Five master suites with luxurious linens and ensuite bathrooms -5,000 square feet of landscaped exterior entertaining space - Private plunge pool (not heated) with outdoor shower and powder room - Pool is approximately 15' X 16'... View all property information
    Location Information
    Anguilla, Caribbean
    1 / 21
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Dramatic ocean views and authentic Caribbean decor by Cindy Dzurita - Five master suites with luxurious linens and ensuite bathrooms - Additional sleeping area on lower level with a kids' twin-size bunk configuration - 5,000 square feet of landscaped exterior entertaining space - Private plunge... View all property information
    Location Information
    Anguilla, Caribbean
    1 / 17
    Sandy Hill Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    With its location along Long Pond Bay in Anguilla, the large and contemporary Villa White Cedars is a unique find. Though meant to house six visitors in three bedrooms, the spaciousness of this villa is often a surprise. The proportions are perfectly balanced, however, and all of the living spaces... View all property information
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    Sandy Hill Bay, Anguilla
    1 / 26
    Sandy Hill Bay
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    Villa Bird of Paradise on Anguilla is a stunning gated retreat at the water's edge, stretched out over a beautifully landscaped property. Beach access is a five minute walk from the villa. This amazing estate was created with privacy in mind. The entire compound is set back off the entrance, and... View all property information
    Location Information
    Sandy Hill Bay, Anguilla
    Little Harbour
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Descend upon a lush landscape that envelope a stately stature of the 6679 square foot Ocassa Villa. This captivating villa faces west and reveals breathtaking views, a distinctive design and a peaceful sunset. Ocassa Villa offers you a refined island experience, blissfully filled with days kissed... View all property information
    Location Information
    Little Harbour, Anguilla AI 2640
    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
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    About this property
    Luxury at it's best! Try staying in this luxury two bedroom, two bathroom condo with two en-suite bathrooms and a large balcony with far reaching views of Eagle Beach and the turquoise water of the Caribbean ocean. This condo is only a few steps across the road to the white powder sands of Eagle... View all property information
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    Anguilla, Caribbean
    1 / 22
    Long Bay Village
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Set on Rendezvous Bay in Anguilla, Villa Seabird is a truly exclusive and upscale holiday setting. So well stocked with amenities and features, it can easily serve as your only destination on the island as it provides truly amazing scenery as well as an iconic Caribbean experience. Designed as a... View all property information
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    Long Bay Village, Anguilla
    1 / 51
    Blowing Point
    10 Bedrooms, 11 Bathrooms, Sleeps 20 | Quick View
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    • x
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    • x
    About this property
    Large, luxurious, and ideally located are just a few of the terms that can be used to describe the Villa Beaches Edge properties. A group of two upscale villas, they are set directly on the waterfront of Anguilla\'s Pelican Bay and offer amazing sea views, as well as appealing looks at St. Martin... View all property information
    Location Information
    Blowing Point, Anguilla