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Vacation Rentals in Anguilla, Caribbean

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    Travellers to Anguilla are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 28
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    10 Bedrooms, 9 Bathrooms, Sleeps 20 | Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    6 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Villa Ani - South, also known as ANI SOU, is a 6-bedroom villa located in Little Bay within minutes of the beach and shopping. This villa sits on the southern side of a cliff, looking directly down onto the bay. The master bedrooms and indoor and outdoor living spaces are oriented towards the... View all property information
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    Anguilla, Caribbean
    1 / 13
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Songbird Villa is a luxurious private villa featuring 4/5 bedrooms. This wonderfully designed and furnished home, created by well-known architect, Lee Skolnick, features a unique blend of contemporary and classic Caribbean architecture and furnishings but, more importantly, provides a true... View all property information
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    Anguilla, Caribbean
    1 / 44
    8 Bedrooms, 9 Bathrooms, Sleeps 14 | 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!Let the lush gardens, white sands and turquoise waters of the Caribbean be the... View all property information
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    Anguilla, Caribbean
    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
    1 / 35
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This elegant and secluded three bedroom luxury villa and cottage is set on one acre of lush tropical gardens and a small sandy beach. The bay has shallow water and is great for snorkeling or enjoying the kayaks which are furnished with the villa. Once you arrive, it is a paradise you will not... View all property information
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    Anguilla, Caribbean
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Tequila Sunrise. The Villa is a contemporary 5000 sq. ft. beach house on secluded Lover's Cove, Dropsey Bay on the southern shore of Anguilla. It overlooks the Caribbean Sea and the mountains of St. Martin beyond. Whilst accessible to all the conveniences of modern living, Tequila is a private... View all property information
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    Anguilla, Caribbean
    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
    Location Information
    Anguilla, Caribbean
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    1 / 25
    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
    1 / 19
    4 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Villa Vista, also known as IDP VIS, is a 4-bedroom villa located in Blowing Point within steps of a small beach. This villa overlooks the sea and enjoys a panoramic view. The interior has been designed to a high standard using European designer furnishings, such as Phillipe Starck, Porta Roma,... View all property information
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    Anguilla, Caribbean
    1 / 26
    11 Bedrooms, 13 Bathrooms, Sleeps 22 | Quick View
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    About this property
    Indulge the senses in this designer-finished contemporary beachfront villa situated with a commanding presence on the white sands of Meads Bay Beach. Emerging from the acclaimed design house of Cecconi Simone, you'll find an air of unpretentious luxury that meets resort-style beachfront comfort at... View all property information
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    Anguilla, Caribbean
    1 / 23
    10 Bedrooms, 10 Bathrooms, Sleeps 20 | Quick View
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    Holiday Exclusive - From December 29, 2016 to January 2, 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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    Anguilla, Caribbean
    1 / 26
    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
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    Long Bay Village
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Immerse yourself in resort-style luxury at this commanding plantation-style estate situated on the white-sandy beaches of Long Bay, along the alluring coastline of Anguilla. Set amidst the splendor of endless turquoise waters and meticulously-manicured gardens replete with towering coconut palms,... View all property information
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    Long Bay Village, Anguilla
    1 / 39
    West End Village
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    West End Village, Anguilla
    1 / 41
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Anguilla’s newest luxury offering, CéBlue Villas & Beach Resort offers paramount privacy but getting away from the world you left behind shouldn’t necessarily mean one has to forego all the fun This slice of paradise is perched on a hill overlooking the shimmering Crocus Bay on the island of... View all property information
    Location Information
    Anguilla, Caribbean
    1 / 28
    Rendezvous Bay
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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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    Rendezvous Bay, Anguilla
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    Sandy Hill Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Located at a distance from the more popular destinations on Anguilla, the stunning Villa Tequila Sunrise is ideal for those who want scenic beauty in a setting that offers many amenities and comforts along with privacy and peace. Overlooking Dropsey Bay, and sitting along the edge of Lover's Cove,... View all property information
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    Sandy Hill Bay, Anguilla
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    1 / 26
    Sandy Hill Bay
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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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
    1 / 23
    Island Harbour
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
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    • x
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    About this property
    Villa Black Pearl on Anguilla is located just steps away from spectacular and sought after Shoal Bay East beach, considered the most magical beach in the entire Caribbean. This lovely private villa is situated at the very tip of the island, offering spectacular panoramic views of the turquoise... View all property information
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    Island Harbour, Anguilla
    1 / 32
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Offering the epitome of luxury services and amenities, the stunning Villa Ani North also provides guests with a truly remarkable setting too. Overlooking Little Bay Beach on Anguilla, it is within moments of Limestone Beach and the most popular golf courses on the islands. Spacious, modern and yet... View all property information
    Location Information
    Anguilla, Caribbean
    1 / 16
    Sandy Hill Bay
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • x
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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
    Location Information
    Sandy Hill Bay, Anguilla
    1 / 9
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Mariga Villa is perfect for your 1, 2 or 3 month stay in Anguilla. <BR><BR>The villa enjoys spectacular breezes, and while there is not a huge sea view, you will feel like you are on a beautiful island. <BR><BR>The villa has two equal size bedrooms with en-suite bathrooms. <BR>Bedroom 1 has a king... View all property information
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    Anguilla, Caribbean
    1 / 21
    The Valley
    3 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Children's Pool
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    • x
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    About this property
    Dear Paradise Researcher, We are very pleased to have your kind interest in our version of True Paradise! 2016 is a milestone for Elise & Paul as it marks their 30th year sharing their unique vacation homes with great folks like yourself. Whether a ski chalet at LOON MOUNTAIN, a bungalow on... View all property information
    Location Information
    The Valley, Anguilla
    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
    Location Information
    Sandy Hill Bay, Anguilla
    1 / 27
    6 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Villa Colibri, also known as RIC COL, is a modern 6-bedroom villa located in Sandy Hill. This villa boasts an expansive sea view and offers a stunning outdoor terrace with a private pool, which has varying depths. The living space is open, light, and airy with ample seating. The adjacent... View all property information
    Location Information
    Anguilla, Caribbean
    1 / 17
    Blowing Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    If you are part of the green revolution and you want to travel but also support those aligned with your cause, then the stunning Villa Solaire Premier in Anguilla is for you. Sitting over Lockrum Bay and offering truly unprecedented views of the sea and the islands in the distance, the two-bedroom... View all property information
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    Blowing Point, Anguilla
    1 / 18
    6 Bedrooms, 9 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Close to Cove Bay and part of the prestigious Sheriva estate, the stunning Villa Mystique easily lives up to its name. It has an immediately impressive appearance thanks to its unique profile and contemporary style. Offering a range of indoor and outdoor living spaces, it ensures that all guests... View all property information
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    Anguilla, Caribbean
    1 / 17
    Blowing Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Are you an eco-friendly person? Most of know we have to start thinking about the environmental impact of many parts of our lives, including travel. This is why the Villa Solaire Standard is the environmentally friendly traveler's ideal find. Set on an astonishingly beautiful area of Anguilla, and... View all property information
    Location Information
    Blowing Point, Anguilla
    1 / 37
    Long Bay Village
    7 Bedrooms, 11 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Santosha, an exquisitely crafted, custom designed villa situated on Long Bay Beach. Where the soft white sands and turquoise waters are just steps away. Hosting seven spacious bedrooms, eight full luxurious baths and three half baths plus staff quarters all spread across five buildings in a... View all property information
    Location Information
    Long Bay Village, Anguilla
    1 / 12
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Villa Ocean Gem, also known as RIC MGM, is a 3-bedroom villa located in Forest Bay within a short drive of the beach, shopping, tennis courts, and a golf course. This spacious villa with 5,000 sq. ft. of living space is nestled on a hill, overlooking the south east coast. The property is situated... View all property information
    Location Information
    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
    Location Information
    Long Bay Village, Anguilla
    1 / 8
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Mystique Villa is reputed to be one of the largest on the island at an astonishning 21,000 sq ft. It is home to five Grand Villa Suites, three pools and full gym. There is also an optional garden suite which is perfectly situated for a guest's personal staff. There are two bridges which lead into... View all property information
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    Anguilla, Caribbean
    1 / 16
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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
    Location Information
    Anguilla, Caribbean
    1 / 24
    West End Village
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The iconic experience of the Caribbean is one that involves the white sands, the turquoise sea, and the brilliant blue sky. This is the essence of a stay at the Villa Element Sky, a luxury villa with private beachfront along Anguilla\'s Long Bay area. Part of a group of luxurious holiday retreats,... View all property information
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    West End Village, Anguilla
    1 / 25
    Rendezvous Bay
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Situated on the white-sandy beaches of Anguilla's renowned Rendezvous Bay, boasting a commanding view of the sparkling turquoise waters of the Caribbean Sea, this sprawling white-washed estate oozes resort style elegance, in a luxurious and private setting. Immerse yourself in a five-star... View all property information
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    Rendezvous Bay, Anguilla
    1 / 33
    8 Bedrooms, 11 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Sink your feet into the warm white sands of Meads Bay Beach right at your doorstep at this newly-built modern architectural beachfront estate located on one of the best stretches of white-sandy beach in Anguilla. Savor picture-perfect views of the turquoise waters of the Caribbean while enjoying a... View all property information
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    Anguilla, Caribbean
    1 / 29
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    • Pet-friendly
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    • x
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    • x
    About this property
    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
    Location Information
    Anguilla, Caribbean
    1 / 27
    West End Village
    9 Bedrooms, 10 Bathrooms, Sleeps 18 | Quick View
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    • Hot Tub
    • Grill
    • Washer
    • Satellite TV
    • Internet Access
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Villa Cerulean on Anguilla captures the essence of the island with comfortable furnishings accented with blue decor. This magnificent villa is just steps from the beach and provides nine individually decorated bedrooms, making it ideal for families or a group of friends traveling together.... View all property information
    Location Information
    West End Village, Anguilla
    1 / 32
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Resting majestically along the white sands of Meads Bay Beach, along the idyllic coastline of Anguilla, immersed in an endless seascape of shimmering turquoise waters and towering coconut palms, this six bedroom contemporary villa provides an immerse luxury experience in the Caribbean. Come enjoy... View all property information
    Location Information
    Anguilla, Caribbean
    1 / 8
    5 of 5 stars (1) Excellent
    Long Bay Village
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Secure Parking
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Private Garden
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • x
    About this property
    Traditional Caribbean home with full gourmet kitchen, two master bedrooms, splash pool, inside and outside dining areas, 5 minute walk or drive to Meads Bay beach and several fine restaurants. Views of sea and St. Martin, a/c in bedrooms included, full-house a/c additional charge, daily maid... View all property information
    Location Information
    Long Bay Village, Anguilla
    1 / 24
    West End Village
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Terrace
    • Hot Tub
    • Internet Access
    • Washer
    • DVD Player
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    An estate-like villa set along the golden sands of Long Bay in Anguilla, are just a few of the words to aptly describe the Villa Element Sand. One of three modern beauties with remarkable architectural style and charm, this villa offers up spacious, comfortable, and luxurious living. Pure white and... View all property information
    Location Information
    West End Village, Anguilla
    1 / 39
    Island Harbour
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
    • Washer
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Villa Amarilla on Anguilla sets the standard of excellence on a tropical island known for upscale accommodations. Enter through a welcoming lanai with a profusion of colorful bougainvillea flowers surrounding the intricately designed wrought iron doorway. Step into the grand foyer and prepared to... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 22
    West End Village
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • DVD Player
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Villa Santosha on Anguilla is a grand beachfront estate situated right at the edge of stunning Long Bay Beach. This magnificent villa features eight luxurious bedrooms, making it the ideal choice for up to 14 guests. For your convenience, a complete staff with butler service and a personal chef... View all property information
    Location Information
    West End Village, Anguilla
    1 / 19
    Blowing Point
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Private Outdoor...
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    A fantastic waterfront villa with classic Caribbean style. Sitting on .83 acre Sea Winds is well designed with an open living room, dining room and kitchen. There are two master suites that are mirror images and located on opposite sites of the main living area. In addition there is a third bedroom... View all property information
    Location Information
    Blowing Point, Anguilla
    1 / 19
    Blowing Point
    7 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Hot Tub
    • Satellite TV
    • Washer
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    With more than three private acres of tropical gardens and grounds, and more than seven thousand square feet of upscale living space, the Villa Paradise on Blowing Point in Anguilla easily matches its name. However, the views of St. Martin in the distance, the long stretch of private beach, and the... View all property information
    Location Information
    Blowing Point, Anguilla
    1 / 10
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • Grill
    • Internet Access
    • DVD Player
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Villa RIC KAM2 is a very spacious contemporary West Indian style 4 bedroom villa which sits on a well landscaped rise overlooking the Caribbean Sea and the mountains of St. Maarten beyond. Villa RIC KAM2 has direct beach access through its own short private pathway to a cove beach. This small cove... View all property information
    Location Information
    Anguilla, Caribbean
    1 / 26
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Designed by a world-renown team of architects and designers, the impressive Villa Kishti Black sites above Black Garden Bay in Anguilla and offers families or groups an unprecedented opportunity for a truly luxurious, private and unforgettable Caribbean holiday. A five-bedroom villa, it has been... View all property information
    Location Information
    Anguilla, Caribbean