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Anguilla Luxury Holiday Homes

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    AU$9,664 Average
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    Travellers to Anguilla are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    31 Matching Rentals in AnguillaView all 208 rentals
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    9 Bedrooms, 10 Bathrooms, Sleeps 18 Quick View
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    Mystique at Sheriva1 / 17
    (1)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    11 Bedrooms, 12 Bathrooms, Sleeps 24 Quick View
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    8 Bedrooms, 10 Bathrooms, Sleeps 16 Quick View
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    About this property
    Set right along the sands of Meads Bay in Anguilla, the stunning and contemporary Villa The Beach House offers classic tropical living with an added note of luxury. From the pool terrace to the interiors, you will find this villa a remarkable experience, and ideal setting for a group holiday. Like...
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    Anguilla, Caribbean
    Holiday Rental House - 8 Bedrooms, 10 Bathrooms, Sleeps 16
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    8 Bedrooms, 10 Bathrooms, Sleeps 16 Quick View
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    • Washer
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
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    Pet friendly
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    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...
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    West End Village, Anguilla
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    10 Bedrooms, 10 Bathrooms, Sleeps 20 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    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...
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    Anguilla, Caribbean
    Holiday Rental House - 10 Bedrooms, 10 Bathrooms, Sleeps 20
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    Ani Villas - Anguilla's Premier Villa Estate1 / 20
    (17)Excellent
    10 Bedrooms, 14 Bathrooms, Sleeps 20 Quick View
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    • Hot Tub
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    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    I stayed here with a group of 21 students from my grad school. Words could not describe how stunning the property and its location is. The staff was so amazing and accommodating...
    Reviewed 23 July 2017
    Stayed at Ani Thailand last year and was equally impressed with Ani Anguilla this year. We stayed in the north villa and were spoiled with amazing ocean views, exceptional...
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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....
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 10 Bedrooms, 14 Bathrooms, Sleeps 20
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    Le Bleu1 / 35
    (1)Average
    10 Bedrooms, 10 Bathrooms, Sleeps 19 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    Please note this region’s beaches may be affected by a seaweed surge. Please enquire with one of our Villa Specialists for further details. Located on two and half acres of beautiful tropical gardens, Le Bleu overlooks the clear turquoise waters of the Caribbean Sea. With a private beach cove,...
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    Little Harbour, Anguilla AI 2640
    Holiday Rental House - 10 Bedrooms, 10 Bathrooms, Sleeps 19
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    10 Bedrooms, 10 Bathrooms, Sleeps 20 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
    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...
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    Anguilla, Caribbean
    Holiday Rental House - 10 Bedrooms, 10 Bathrooms, Sleeps 20
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    10 Bedrooms, 9 Bathrooms, Sleeps 20 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let the lush gardens, white sands and turquoise waters of the Caribbean be the backdrop to a family getaway or special occasion at Indigo. Set in the lee of Cinnamon Reef on Little Harbor, the villa is tucked into 1.5 acres and has its own beach. With ten bedrooms in the main house, Little Indigo...
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    Anguilla, Caribbean AI 2640
    Holiday Rental House - 10 Bedrooms, 9 Bathrooms, Sleeps 20
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    10 Bedrooms, 10 Bathrooms, Sleeps 18 Quick 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...
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    Anguilla, Caribbean
    Holiday Rental House - 10 Bedrooms, 10 Bathrooms, Sleeps 18
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    8 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    About this property
    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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    10 Bedrooms, 10 Bathrooms, Sleeps 20 Quick View
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    • Waterfront
    • Terrace
    • Balcony
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Patio
    Suitability
    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 AI 2640
    Holiday Rental House - 10 Bedrooms, 10 Bathrooms, Sleeps 20
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    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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    Ani Villa South - Private Resort, Sleeps 121 / 24
    (4)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    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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    The Valley, Anguilla AI 2640
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Ani Villa South - Anguilla1 / 25
    (4)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
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    Pet friendly
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    Reviewed 29 March 2018
    Sorry it took me so long but just wanted to say if you are looking for the best of the best, look no father! From the minute you arrive to the moment you are gettingin your car...
    Reviewed 7 September 2017
    We have been lucky to find this lovely Villa and enjoyed every moment of every day spent there. Chef Sweets kept us full and surprised with beautiful dishes every day. The...
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    About this property
    Recently featured in Robb Report, Islands Magazine and Maco. Ani Villas goal is for our guests to leave the everyday world and their worries behind. letting our team help shape memorable escapes of relaxation and adventure. We strive to introduce our guests to the best our destinations have to...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ani South Little Bay Anguilla Sleek Crisp Lines & Comfort for 10 Guests This is a showcase villa perched upon a headland overlooking Little Bay on Anguilla. There are 5 bedrooms, each quite distinctive all with luxurious bed linens, en suite spa quality bathrooms, AC, WiFi and an all inclusive...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 8 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 - 5 Bedrooms, 8 Bathrooms, Sleeps 10
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    8 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • DVD Player
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Nevaeh, Anguilla. Going beyond luxury, the eight-bedroom Villa Nevaeh sets an entirely new bar in terms of opulence and amenities. Located along Long Bay in Anguilla, it features a full household staff, a golf simulator, a tennis and basketball court, and more. The Balinese inspired design...
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    West End Village, Anguilla
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    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...
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    Anguilla, Caribbean
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    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...
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    Anguilla, Caribbean
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    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...
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    Anguilla, Caribbean
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Ani Villas, Anguilla (North Villa)1 / 20
    (2)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    Smoking allowed
    About this property
    Brand new lavish Luxury Estate in Anguilla. PRIVACY Guaranteed 3 Kings + 2 Twins + 2 Full Ultra Luxurious and fully staffed Private Chef and Butler Services Gym and Tennis Court
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Like a towering ivory sculpture perched on the majestic cliffs overlooking Anguilla’s Little Bay, the four bedroom Ani North has been designed and fitted to offer an unforgettable Caribbean vacation. Unique to Ani North is the home’s dramatic stair atrium with massive skylight above and water...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    8 Bedrooms, 9 Bathrooms, Sleeps 16 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Maundays Bay in Anguilla, Infinity at Sheriva villa successfully harmonizes traditional Caribbean style with touches from the Far East. 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...
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    Anguilla, Caribbean AI 2640
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 16
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    8 Bedrooms, 9 Bathrooms, Sleeps 16 Quick View
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    • Washer
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    Smoking allowed
    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...
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    Anguilla, Caribbean
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 16
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    Smoking allowed
    About this property
    Ani North Little Bay Anguilla Sleek Crisp Lines & Comfort for 10 Guests This is a showcase villa perched upon a headland overlooking Little Bay on Anguilla. There are 5 bedrooms, each quite distinctive all with luxurious bed linens, en suite spa quality bathrooms, AC, WiFi and an all inclusive...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Harmony at Sheriva1 / 22
    (2)Excellent
    8 Bedrooms, 9 Bathrooms, Sleeps 16 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Maundays Bay in Anguilla, Harmony at Sheriva villa successfully harmonizes traditional Caribbean style with touches from the Far East. 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...
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    West End Village, Anguilla AI 2640
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 16
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick 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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    Blowing Point, Anguilla AI 2640
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    7 Bedrooms, 9 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Maundays Bay in Anguilla, Harmony at Sheriva villa successfully harmonizes traditional Caribbean style with touches from the Far East. 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...
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    Anguilla, Caribbean AI 2640
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 14
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