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Anguilla Vacation Rentals

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    Travellers to Anguilla are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    2 Bedrooms, Sleeps 4Quick View
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    10 Bedrooms, Sleeps 20Quick View
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    About this property
    The villa is a contemporary 5 000 square foot 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 retreat that...
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    Anguilla, Caribbean AI 2640
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    5 Bedrooms, Sleeps 10Quick View
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    • Hot Tub
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    Pet friendly
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    Smoking allowed
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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...
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    Rendezvous Bay, Anguilla
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Reviews
    6 Bedrooms, Sleeps 12Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
    About this property
    Like an ivory sculpture on the majestic cliffs overlooking Anguilla’s Little Bay, the six bedroom Ani South has been designed to offer an unforgettable Caribbean vacation. Unique to Ani South is its configuration, accessible to guests via an elevator, roll-in showers, pool lift and wheelchair...
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    Anguilla, Caribbean
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, Sleeps 10Quick View
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    • Satellite TV
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    Pet friendly
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    Smoking allowed
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    Located on the breezy and cool hilltop of Sandy Hill bay at Seafeathers, you'll find Emerald Reef Villa. Here you can truly enjoy nature from the sound of the waves crashing to the singing of birds surrounded by the lush local surroundings complimented by beautiful flowers. This is a great location...
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    Sandy Hill Bay, Anguilla 00000
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    10 Reviews
    5 Bedrooms, Sleeps 11Quick View
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    • DVD Player
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    • Housekeeping Included
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    Pet friendly
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    Smoking allowed
    About this property
    Private and Secluded, VILLA GARDENIA is perfect for a FAMILY, a GROUP OF FRIENDS or COUPLES looking for a retreat in Anguilla. The architectural design is sophisticated, contemporary and has a versatile layout to accommodate your needs. Rent 1,2,3,4,or all five bedrooms Villa Gardenia consists of...
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    Anguilla, Caribbean 2640
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 11
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    2 Bedrooms, Sleeps 4Quick View
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    • Wi-Fi
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    Pet friendly
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    Located on a secluded beach on Anguilla’s southern shore, Tequila Sunrise is a spacious and contemporary beach house on Lover’s Cove in Dropsey Bay. The villa overlooks the Caribbean Sea and offers stunning views of the mountains of St Martin. Known for its pristine white sand beaches and clear...
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    Anguilla, Caribbean V0N 1B2
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    5 Bedrooms, Sleeps 10Quick View
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    • Private Outdoor Pool (Unheated)
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    Villa Modena Cove Bay Anguilla Comfortably Sleeps 10 Guests Villa Modena is private and palatial and  set upon one acre of land near the Cap Juluca Hotel on Cove Bay. A combination of a two storey main house and a one storey clubhouse provides 5 stunning bedrooms with private bathrooms sleeping 10...
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    Anguilla, Caribbean
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    8 Bedrooms, Sleeps 16Quick View
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    • Satellite TV
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    Pet friendly
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    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...
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    Anguilla, Caribbean
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 16
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    3 Reviews
    8 Bedrooms, Sleeps 16Quick View
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    The African Sapphire is a generously proportioned beachfront property with a very large living and entertaining area that allows dining for 18, and offers superb 360 degree views of the Caribbean Sea and St Martin. The African Sapphire is four stories high and 14,000 square feet sumptuously...
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    Anguilla, Caribbean
    Holiday Rental House - 8 Bedrooms, 10 Bathrooms, Sleeps 16
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    1 Bedroom, Sleeps 2Quick View
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    • Balcony
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    Pet friendly
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    Smoking allowed
    About this property
    3-star aparthotel in Shoal Bay with free parkingLocated in the heart of Shoal Bay, this aparthotel is 0.7 mi (1.2 km) from Shoal Bay Beach and within 3 mi (5 km) of Island Harbor Beach and Scilly Cay. Stone Cellar Art Gallery and Captain's Bay Beach are also within 6 mi (10 km).An outdoor pool,...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    10 Bedrooms, Sleeps 20Quick View
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    • Balcony
    • DVD Player
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Air Conditioning
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Indigo Villa, a luxurious Anguillian estate with 9 air-conditioned bedrooms fronted by beautiful white sands and coral reefed blue sea, awaits you. Each room has a view of the Caribbean Sea and the terrace opens to a marvelous patio vista of pool, palms, sea, sand and the Islands beyond. Indigo...
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    Anguilla, Caribbean
    Holiday Rental House - 10 Bedrooms, 10 Bathrooms, Sleeps 20
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    1 Bedroom, Sleeps 2Quick View
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    • Washer
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    The spacious Junior Suite is located on the second floor and offers stunning views of Meads Bay from the private balcony. The Junior Suite is configured as a studio and features a fully-equipped kitchen with cookware and cutlery, a plush king-size bed, as well as a washer and dryer. The bathroom...
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    Anguilla, Caribbean
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    '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...
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    Anguilla, Caribbean
    Holiday Rental House - 5 Bathrooms, Sleeps 1
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    5 Bedrooms, Sleeps 10Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Zenaida Beach & Tennis Estate sits on Anguilla’s highest elevation and is nestled in three acres of lush tropical gardens. The villa is reached entirely by paved road and is famous for its sweeping views of the Caribbean Sea, St. Martin and St. Barthelemy. Enjoy ultimate privacy in this five...
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    Sandy Hill Bay, Anguilla
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 6Quick View
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    • DVD Player
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    Smoking allowed
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    Welcome to Colibri villa, a picturesque island paradise tucked away in the northern Caribbean. Known for its pristine white sand beaches and clear turquoise seas, Anguilla offers a casual island tempo so you can get the rest and relaxation you deserve. Colibri is a striking and spacious villa whose...
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    Sandy Hill Bay, Anguilla AI 2640
    Holiday Rental House - 3 Bedrooms, 6 Bathrooms, Sleeps 6
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    8 Bedrooms, Sleeps 16Quick View
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    • Grill
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    Find your own Caribbean paradise at Nevaeh. Set on a private, gated lot that stretches down to a half-mile of golden sand on Anguilla’s Long Bay, this luxury oceanfront vacation rental boasts stunning views and pampering service. The brand-new villa takes its design cues from local architecture and...
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    Long Bay Village, Anguilla AI 2640
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    3 Bedrooms, Sleeps 6Quick View
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    • Terrace
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Clare Villa is an exceptional retreat for friends and family and is close to the white sandy beaches in Anguilla. The villa features three bedroom suites, three full plus one half bathrooms and comfortably accommodates up to six guests. An expansive terrace with loungers surround the private...
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    Sandy Hill Bay, Anguilla
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    • Waterfront
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    Pet friendly
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    Smoking allowed
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    Like an ivory showpiece glinting in the sun, Sandcastle is your private palace right by the sands of the Caribbean Sea. Welcome to sunny Anguilla, a magical island known for its watersports, nightlife and friendly local vibration. Take in the magnificent views of the ever changing hues of the...
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    Anguilla, Caribbean AI 2640
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    • Grill
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    • Sauna
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    Pet friendly
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    Smoking allowed
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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...
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    Island Harbour, Anguilla AI 2640
    Holiday Rental House - 3 Bedrooms, 7 Bathrooms, Sleeps 6
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    6 Bedrooms, Sleeps 13Quick View
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    • Patio
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    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...
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    Anguilla, Caribbean
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 13
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    Studio, Sleeps 1Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    Nearest Beach: Sandy Ground Beach Proximity: Near the beach/Overlooking from cliffside Fantastic new Cliff Top Villa overlooking the stunning Sandy Ground Village, with 3 bedrooms, 3.5 baths, open floor plan, Furnished with authentic Thai furnishings and artwork with all the amenities you could...
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    Anguilla, Caribbean
    Holiday Rental House - 4 Bathrooms, Sleeps 1
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    1 Review
    Studio, Sleeps 1Quick View
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    • Washer
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    Nearest Beach: Shoal Bay East Beach Proximity: Very close to beach (10 minute walk or a few minutes drive) This ideal and beautiful cliffside villa is situated in Shoal Bay East and minutes away from the beach that was voted one of the best white sand beaches in the Caribbean... Waves offers...
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    Anguilla, Caribbean
    Holiday Rental House - 4 Bathrooms, Sleeps 1
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    6 Bedrooms, Sleeps 12Quick View
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    • DVD Player
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    Part of a private estate that looks out over the stunning Little Bay in Anguilla, the Villa Ani South is a six-bedroom gem that provides guests with a full household staff, premium amenities, and a setting that is both stunning and soothing. Close to the equally lovely Limestone Beach and the most...
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    Anguilla, Caribbean
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    8 Bedrooms, Sleeps 16Quick View
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    • Grill
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    Located on the soft white sands of Meads Bay, The Beach House offers an unparalleled beachfront location and the ultimate in breezy Caribbean living. Book your stay with Luxury Retreats today, and you will soon be in Anguilla on one of the most beautiful beaches in the world. Elegant, modern and...
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    West End Village, Anguilla AI 2640
    Holiday Rental House - 8 Bedrooms, 10 Bathrooms, Sleeps 16
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    10 Bedrooms, Sleeps 18Quick View
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    • Grill
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    Villa Indigo Anguilla. Imagine enjoying a Caribbean holiday in a private 1.5-acre property that looks out on a sheltering reef and picturesque harbor. This is precisely what to expect when you book a visit to Villa Indigo in Anguilla. Sitting above Little Harbour, which is sheltered by Cinnamon...
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    Anguilla, Caribbean
    Holiday Rental House - 10 Bedrooms, 10 Bathrooms, Sleeps 18
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    1 Review
    5 Bedrooms, Sleeps 10Quick View
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    This generous and luxurious beachfront villa features incredible views of the Caribbean Sea and St Martin. The spacious living and dining area is ideal for gatherings of family and friends or for entertaining business associates. Blue Diamond is a 12,000 square foot villa. Guests enter the...
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    Anguilla, Caribbean
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8Quick 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...
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    Anguilla, Caribbean
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8Quick View
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    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...
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    West End Village, Anguilla
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Pet friendly
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    Smoking allowed
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    Cerulean Villa is a spectacular retreat nestled directly on the beach at beautiful Barnes Bay. This private resort has set the standard for service, cuisine, and accommodations, offering its guests the exclusivity of a private home with all the amenities of a five star hotel. The 13,000 square-foot...
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    Anguilla, Caribbean
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 18
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    8 Bedrooms, Sleeps 16Quick View
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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...
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    Anguilla, Caribbean
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    5 Bedrooms, Sleeps 10Quick View
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    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...
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    Island Harbour, Anguilla
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    From its perch atop Long Bay's highest point, Sky Villa is the embodiment of its namesake. Interior hues of aquamarine and royal blue with yellow accents set an ethereal tone throughout its 6 500 square feet of sweeping space. There are four master suites, three of which have private terraces...
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    Long Bay Village, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Nearest Beach: Rendezvous Beach Beach Proximity: On the sea Located at the Callaloo Resort in the beautiful Rendezvous Bay area. Ananke is simply elegant in all ways, The furniture is simple and comfortable and the views are fantastic. The outdoor living spaces are great for entertaining and...
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    Anguilla, Caribbean
    Holiday Rental House - 3 Bathrooms, Sleeps 1
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    Studio, Sleeps 1Quick View
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    Nearest Beach: Long Bay Beach Beach Proximity: On the Beach FOR RENT: Sky Villa one of the three most luxurious rental properties in Anguilla.   Sky is the embodiment of its namesake. Interior hues of aquamarine and royal blue with yellow accents set an ethereal tone throughout its 6,500 sq. ft. of...
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    Anguilla, Caribbean
    Holiday Rental House - 5 Bathrooms, Sleeps 1
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    2 Bedrooms, Sleeps 4Quick View
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    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...
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    Blowing Point, Anguilla
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    7 Bedrooms, Sleeps 14Quick View
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    • Waterfront
    • DVD Player
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    Pet friendly
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    Smoking allowed
    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...
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    Long Bay Village, Anguilla AI 2640
    Holiday Rental House - 7 Bedrooms, 11 Bathrooms, Sleeps 14
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    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 by beautiful sunlight and nights caressed by cool island breezes. Perched picturesquely above the...
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    Sandy Ground, Anguilla AI 2640
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    • DVD Player
    • Grill
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nearest Beach: Rendezvous Beach Beach Proximity: Near the Beach Big fancy Villas not your style, prefer something very Caribbean, Well this is it... Cedars is a charming West Indian style cottage overlooking Rendezvous Bay and just steps away to the beach. Cedars is a private villa and is perfect...
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    Anguilla, Caribbean
    Holiday Rental House - 2 Bathrooms, Sleeps 1
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    • DVD Player
    • Washer
    • Hot Tub
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nearest Beach: Shoal Bay West Beach Proximity: On the Beach Situated on its very own secluded and delightful cove in the West of Anguilla, The Pavilion at Covecastles redefines the standard for superlative villa accommodation in an exclusive tropical setting. Covecastles a luxury resort presents...
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    Anguilla, Caribbean
    Holiday Rental House - 5 Bathrooms, Sleeps 1
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    • Patio
    • Wi-Fi
    • Hot Tub
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Like the extraordinary orange and purple flower with which this residence shares its name, Bird of Paradise Villa is a true gem for the connoisseur. Named one of the “Top 20 Villas in the World” by Islands Magazine, this Anguillan oasis offers the exclusivity of a boutique hotel, the privacy of an...
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    Anguilla, Caribbean AI 2640
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8Quick View
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    • DVD Player
    • Grill
    • Patio
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Like the extraordinary orange and purple flower with which this residence shares its name, Bird of Paradise Villa is a true gem for the connoisseur. Named one of the “Top 20 Villas in the World” by Islands Magazine, this Anguillan oasis offers the exclusivity of a boutique hotel, the privacy of an...
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    Anguilla, Caribbean AI 2640
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This slice of paradise is perched on a hill overlooking the shimmering Crocus Bay on the island of Anguilla. Spectacular architecture and sensational tropical scenery, tasteful furnishings and a deluxe kitchen offers you unequaled comfort in a tropical paradise setting. The villa is sprawled out...
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    Anguilla, Caribbean
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, Sleeps 2Quick View
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    • Hot Tub
    • DVD Player
    • Grill
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Like the extraordinary orange and purple flower with which this residence shares its name, Bird of Paradise Villa is a true gem for the connoisseur. Named one of the “Top 20 Villas in the World” by Islands Magazine, this Anguillan oasis offers the exclusivity of a boutique hotel, the privacy of an...
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    Anguilla, Caribbean AI 2640
    Holiday Rental House - 1 Bedroom, 5 Bathrooms, Sleeps 2
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    3 Bedrooms, Sleeps 6Quick View
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    • Wi-Fi
    • Hot Tub
    • DVD Player
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Like the extraordinary orange and purple flower with which this residence shares its name, Bird of Paradise Villa is a true gem for the connoisseur. Named one of the “Top 20 Villas in the World” by Islands Magazine, this Anguillan oasis offers the exclusivity of a boutique hotel, the privacy of an...
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    Anguilla, Caribbean AI 2640
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 6
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Offering ocean views from a balcony or terrace, these spacious, air-conditioned suites have Caribbean-style décor, full kitchens, a comfortable living space, washer and dryer, and complimentary wi-fi access. There is a king-size bedroom and a separate living room that includes a flat-screen TV and...
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    Anguilla, Caribbean
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    4 Bedrooms, Sleeps 8Quick View
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    • Outdoor Dining Area
    • Balcony
    • Grill
    • Satellite TV
    • Waterfront
    • Internet Access
    • Porch
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7 Palms Villa design is Caribbean Casual with Breathtaking views that juts out for an incredibly living experience. The Caribbean Island interiors and living spaces are perfect for a tropical vacation. With spacious indoor and outdoor living and dining areas, 7 Palms Anguilla offers ample room for...
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    Location Information
    Anguilla, Caribbean 00000
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Studio, Sleeps 1Quick View
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    • Waterfront
    • Washer
    • Satellite TV
    • Grill
    • Internet Access
    • DVD Player
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nearest Beach: Jopsey Bay Beach Proximity: Near the Beach Located on Jopsey Bay, a bay only some people are lucky to come across while on vaction in Anguilla, this villa overlooks secluded Lover's Cove along a dramatic and stunning Anguillian shoreline, Rum Punch Villa is a 7,500 square foot...
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    Anguilla, Caribbean
    Holiday Rental House - 3 Bathrooms, Sleeps 1
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