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Vacation Rentals and House Rentals in Anguilla, Caribbean

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    Travelers to Anguilla are booking December dates now. Secure your vacation rental today, and have the perfect trip.
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    About this property
    An exhibition of modern architecture and Caribbeanesque vernaculars, the private enclave that is Sheriva Boutique Villa Hotel offers the serenity of understated elegance with contemporary luxuries. The exquisitely appointed interiors by Norma Chase Jobert offer a magnificent haven with a collection... View all property information
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    Anguilla, Caribbean
    1 / 12
    4 Bedrooms, 5 Bathrooms, Sleeps 1 | Quick View
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    Nearest Beach: Sandy Ground Beach Proximity: Pathway to a secluded cove 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... View all property information
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    Anguilla, Caribbean
    1 / 23
    Island Harbour
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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 / 23
    6 Bedrooms, 6 Bathrooms, Sleeps 1 | Quick View
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    Nearest Beach: Limestone Beach Beach Proximity: Near the beach Los Arcos Villa A Stunning new property that has just been completed with 7800 sq. ft of interior space and 13,000 sq. ft of exterior space and is available for rentals starting January 5, 2010. Beautifully decorated with state of the... View all property information
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    Anguilla, Caribbean
    1 / 26
    10 Bedrooms, 10 Bathrooms, Sleeps 1 | Quick View
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    Nearest Beach: Limestone Bay Beach Proximity: Overlooking the Beach Perched on the breathtaking cliffs overlooking Anguillas Little Bay, Ani Villas Anguilla are the first of an international collection of luxury villas aimed at delivering remarkable vacation experiences. Designed with the highest... View all property information
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    Anguilla, Caribbean
    1 / 12
    3 Bedrooms, 3 Bathrooms, Sleeps 1 | Quick View
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    The Villas at CuisinArt offer the utmost in luxury in a truly spectacular setting. Located at the eastern end of the property, the six villas are private, yet steps away from all Resort facilities. Each has its own entry courtyard graced with a soothing fountain and botanical splendor, transporting... View all property information
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    Anguilla, Caribbean
    1 / 44
    10 Bedrooms, 9 Bathrooms, Sleeps 20 | 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 AI 2640
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    1 / 32
    10 Bedrooms, 10 Bathrooms, Sleeps 20 | Quick View
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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 / 19
    8 Bedrooms, 9 Bathrooms, Sleeps 16 | Quick View
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    About this property
    African Sapphire is ideal for those looking for two Master Suites with two guest rooms that convert to a third suite. It is 14,000 square feet and handicapped accessible, with 8 bedrooms each with en suite bathrooms. The living and dining space is ideal for a group of friends, one or two families... View all property information
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    Anguilla, Caribbean AI 2640
    1 / 7
    4 Bedrooms, 4 Bathrooms, Sleeps 1 | Quick View
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    Nearest Beach: Rendezvous Beach Beach Proximity: Near the Beach Greenguard is a four bedroom Villa with two bathrooms and privately located in the Cul de Sac area. Greengard has wonderful views of Rendezvous bay and the neighbouring island St.Martin and from the deck you can enjoy Anguilla's... View all property information
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    Anguilla, Caribbean
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    Sandy Hill Bay
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Completed in December, 2014 this 4+ bedroom home has gorgeous views of St. Maarten and is a 2 minute drive to Sandy Hill Bay beach or 5 minute walk. You know you have reached somewhere special as you drive up the house and park. The entrance is flanked with twin fountains and as you enter you see... View all property information
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    Sandy Hill Bay, Anguilla
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    Sandy Hill Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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
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    4 Bedrooms, 4 Bathrooms, Sleeps 1 | Quick View
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    Nearest Beach: Shoal Bay East Beach Proximity: On the Sea Patricks Villa is located on the Sea Rocks in the Eastern part of Anguilla, Sea Rocks is an exclusive residential area for full time residents and the villa renters. It is a quiet and beautiful cliff top community. This villa is short 5... View all property information
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    Anguilla, Caribbean
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    Blowing Point
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    Treat yourself to the holiday you deserve in sunny Anguilla. Villa Paradise is a seven bedroom villa located in the coveted Blowing Point area of this idyllic tropical island. The layout and enormous deck spaces of this waterfront residence assure that you will enjoy a stunning view of the... View all property information
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    Blowing Point, Anguilla AI 2640
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    Blowing Point
    3 Bedrooms, 5 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Treat yourself to the holiday you deserve in sunny Anguilla. Villa Paradise is a seven bedroom villa located in the coveted Blowing Point area of this idyllic tropical island. The layout and enormous deck spaces of this waterfront residence assure that you will enjoy a stunning view of the... View all property information
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    Blowing Point, Anguilla AI 2640
    1 / 21
    2 Bedrooms, 5 Bathrooms, Sleeps 4 | Quick View
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    The spirit of Villa Kishti is captured in the elegant luxury offered by the combination of an exceptional location harmoniously blended within an idyllic tropical environment. This unique villa provides a setting of natural beauty in which service excellence and the privacy of guests are paramount.... View all property information
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    Anguilla, Caribbean AI 2640
    1 / 17
    Blowing Point
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Treat yourself to the holiday you deserve in sunny Anguilla. Villa Paradise is a seven bedroom villa located in the coveted Blowing Point area of this idyllic tropical island. The layout and enormous deck spaces of this waterfront residence assure that you will enjoy a stunning view of the... View all property information
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    Blowing Point, Anguilla AI 2640
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    1 / 14
    3 Bedrooms, 7 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Treat yourself to a beautiful beach, pampering service, great contemporary design and five-star shopping and dining at Kishti on Meads East. Not only is the villa set on the sugary sands of Meads Bay Beach, it’s just a short walk from the restaurants and bars along the bay. With sleek interiors by... View all property information
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    Anguilla, Caribbean
    1 / 27
    5 Bedrooms, 5 Bathrooms, Sleeps 1 | Quick View
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    'Songbird' A four bedroom villa situated in Rendezvous Bay one of the Islands premier beaches is just a 5 minute walk away or a 2 minute golf cart ride ( golf cart included) to this beautiful white sanded bay with the clearest most beautiful waters you will ever see. The Architect Lee Skolnick... View all property information
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    Anguilla, Caribbean
    1 / 6
    1 Bedroom, 1 Bathroom, Sleeps 1 | Quick View
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    Nearest Beach: West End Beach Beach Proximity: Near the Beach Unlike the other villas at Indigo Reef, Oleandar is a delightful open plan 1 bedroom cottage with its own private walled garden for that little extra privacy. A roof terrace provides sunrise views over the West End pond with a backdrop... View all property information
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    Anguilla, Caribbean
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    Sandy Hill Bay
    3 Bedrooms, 6 Bathrooms, Sleeps 6 | Quick View
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    Important Note: Please be advised that this region may be affected by the Seaweed Surge that has impacted many Caribbean destinations. Please ask your Villa Specialist for more information. Welcome to Colibri villa, a picturesque island paradise tucked away in the northern Caribbean. Known for its... View all property information
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    Sandy Hill Bay, Anguilla AI 2640
    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 AI 2640
    1 / 32
    Island Harbour
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | 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 AI 2640
    1 / 32
    Island Harbour
    3 Bedrooms, 6 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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 AI 2640
    1 / 15
    Sandy Hill Bay
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Important Note: Please be advised that this region may be affected by the Seaweed Surge that has impacted many Caribbean destinations. Please ask your Villa Specialist for more information. Welcome to Colibri villa, a picturesque island paradise tucked away in the northern Caribbean. Known for its... View all property information
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    Sandy Hill Bay, Anguilla AI 2640
    1 / 21
    3 Bedrooms, 5 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The spirit of Villa Kishti is captured in the elegant luxury offered by the combination of an exceptional location harmoniously blended within an idyllic tropical environment. This unique villa provides a setting of natural beauty in which service excellence and the privacy of guests are paramount.... View all property information
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    Anguilla, Caribbean AI 2640
    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
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    Anguilla, Caribbean
    1 / 14
    Little Harbour
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Sitting on Anguilla's South Shore, Kamique commands stunning views of the secluded cove beach and the mountains of St. Martin. Anani is dramatically nestled in the rolling landscape to form their own special enclaves. The surrounding waters are protected by a reef, which makes for calm waters and... View all property information
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    Little Harbour, 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 / 1
    3 Bedrooms, 3 Bathrooms, Sleeps 1 | Quick View
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    Nearest Beach: Sandy Hill Bay (2 mins drive) Beach Proximity: Near the Beach Las Brisas is a comfortable and modern villa with beautiful views of Sandy Hill Bay. There are two spacious bedrooms with ensuite on the main floor, both with a/c and ceiling fans, well equipped kitchen, laundry room and... View all property information
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    Anguilla, Caribbean
    1 / 20
    6 Bedrooms, 6 Bathrooms, Sleeps 1 | Quick View
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    Nearest Beach: Maundays Bay (2-3 mins drive) Beach Proximity: Near the Beach Mystique villa on its own 1 acre plot of land overlooking the Cove and only two minutes away from the gorgeous white sanded Maundays Bay. Sitting on a lush 10-acre property with stunning views of the Caribbean Sea and... View all property information
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    Anguilla, Caribbean
    1 / 6
    3 Bedrooms, 3 Bathrooms, Sleeps 1 | Quick View
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    Nearest Beach: Blowing Point Beach Beach Proximity: On the Beach Vista is located in the delightful village of Cul de Sac with amazing panoramic views of the Caribbean sea and the mountains of neighbouring island St Martin. This villa is on a very secluded small beach with great snorkelling. Vista... View all property information
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    Anguilla, Caribbean
    1 / 40
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    About this property
    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 / 15
    Sandy Hill Bay
    2 Bedrooms, 6 Bathrooms, Sleeps 4 | Quick View
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    Important Note: Please be advised that this region may be affected by the Seaweed Surge that has impacted many Caribbean destinations. Please ask your Villa Specialist for more information. Welcome to Colibri villa, a picturesque island paradise tucked away in the northern Caribbean. Known for its... View all property information
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    Sandy Hill Bay, Anguilla AI 2640
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 1 | Quick View
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    About this property
    Nearest Beach: Forest Bay Beach Proximity: On the Beach REDUCED... L'EMBELLIE VILLA, Elegant, stylish, private, A 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... View all property information
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    Anguilla, Caribbean
    1 / 24
    West End Village
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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
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    West End Village
    9 Bedrooms, 10 Bathrooms, Sleeps 18 | Quick View
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    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
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    West End Village, Anguilla
    1 / 24
    Shoal Bay Village
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    About this property
    ** Call (617) 755-6875 to inquire about this property SandCastle Pointe Villa, in the heart of Anguilla's famed north coast, is a unique property of stylish contemporary design in one of the world's most beautiful tropical settings. Adorned with contemporary art and thoughtfully chosen furnishings... View all property information
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    Shoal Bay Village, Anguilla
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    5 Bedrooms, 6 Bathrooms, Sleeps 1 | Quick View
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    Nearest Beach: Long Bay Beach Beach Proximity: On the Beach FOR RENT: Sea Villa, The Manager, Concierge and staff stand ready to meet guests every request. Whether making arrangements for snorkeling, scuba, sailing or luxury pampering--our attentive and knowledgeable staff remains dedicated to the... View all property information
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    Anguilla, Caribbean
    1 / 26
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Stretching across the horizon like an ivory sculpture, Seabird villa offers all the perks required for a truly memorable island getaway experience. Allow the sensual features of this private four bedroom villa to overtake your senses and your soul. Located on the remote isle of Anguilla, a tropical... View all property information
    Location Information
    Anguilla, Caribbean AI 2640
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    3 Bedrooms, 3 Bathrooms, Sleeps 1 | Quick View
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    • Shared Outdoor Pool...
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    About this property
    Nearest Beach: Maundays Bay Beach Proximity: Near the Beach Situated in the western part of Anguilla and overlooking Cap Juluca and Altamer, Panarea is just minutes away from two white sandy beaches, the three-bedroom luxury home combines pure elegance with state-of-the-art broadband technology and... View all property information
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    Anguilla, Caribbean
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    2 Bedrooms, 2 Bathrooms, Sleeps 1 | Quick View
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    Nearest Beach: Rendezvous Beach Beach Proximity: On the Sea By the Sea is a two bedroom open-air villa with stunning views of the sea. The beach is a short walk along the water's edge with chairs waiting for you to enjoy and relax. This villa is located in the quiet but residential village of... View all property information
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    Anguilla, Caribbean
    1 / 26
    2 Bedrooms, 4 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Stretching across the horizon like an ivory sculpture, Seabird villa offers all the perks required for a truly memorable island getaway experience. Allow the sensual features of this private four bedroom villa to overtake your senses and your soul. Located on the remote isle of Anguilla, a tropical... View all property information
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    Anguilla, Caribbean AI 2640
    1 / 21
    Island Harbour
    4 Bedrooms, 8 Bathrooms, Sleeps 8 | Quick View
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    Construction Note: Please note that there is construction next door to this villa until further notice. Beachcourt Villa will experience noise, depending on what work is being done at the time. Please enquire with one of our Villa Specialists for further details. Built on a hill forty feet above... View all property information
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    Island Harbour, Anguilla AI 2640
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    8 Bedrooms, 5 Bathrooms, Sleeps 1 | Quick View
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    About this property
    Nearest Beach: Shoal Bay West (Steps away) Beach Proximity: On the Beach The 14,000 sq. ft. African Sapphire is named for its furnishings, including a chandelier and table centerpiece handmade in Africa from half a million beads. HIGHLIGHTS: * Two master bedrooms each with private terrace, office,... 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
    Nestled on Lockrum Bay, Solaire’s world-class accommodations are coupled with some of the most beautiful ocean vistas you’ll find anywhere. Tideswept beaches and crystal-blue waters are only a stroll away from any of our Caribbean villas, making the Solaire village a travel destination you must see... View all property information
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    Blowing Point, Anguilla
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    4 Bedrooms, 5 Bathrooms, Sleeps 1 | Quick View
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    Nearest Beach: Island Harbour (Five minutes drive) Beach Proximity: On the Sea Desert Rose is a luxurious 11,000 square foot 1.35 acres (does not include the tennis court and some surrounding land which may also be purchased separately) Perched on top of a cliff offering breathtaking views of the... View all property information
    Location Information
    Anguilla, Caribbean