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Holiday Rentals with Pools in Sandy Hill Bay

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    Sandy Hill Bay is popular with travellers just like you. Don’t let them get your perfect place first—book today!
    27 Matching Rentals in the Sandy Hill Bay AreaView all 77 rentals
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    Sandy Hill Bay
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Beach Villa with Two Pools, Four Living/Dining Areas and Optional Chef1 / 45
    (2)Excellent
    Sandy Hill Bay
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    The following rentals are within 10 kilometres of Sandy Hill Bay.
    Oceana Villa Anguilla - Brand New 2 bedroom1 / 92
    (15)Excellent
    The Valley
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    South Hill
    5 Bedrooms, 5 Bathrooms, Sleeps 1 Quick View
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    Amenities & Details
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocassa Villa Anguilla 5 Bedrooms overlooking Sandy Bay This is a stunning villa overlooking lovely Sandy Bay on the west coast of Anguilla. The villa has 5 double bedrooms with sumptuous furnishings and cool, cotton bedlinens. Living Room opens onto Infinity Pool & Balcony The living room has vast...
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    AI 2640, South Hill, Anguilla
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 1
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    Imperial Penthouse, New Oceanview w/H.Pool&Package1 / 19
    (5)Excellent
    South Hill
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Housekeeping Included
    • Air Conditioning
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Wi-Fi
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 December 2017
    Our stay was amazing and we can’t wait to do it again! The hospitality we received was outstanding, the place was very clean and beautifully decorated, and the views from the...
    Reviewed 5 December 2013
    The stars twinkling, venus shining with the harbour lights shimmering to the rhythm of the waves and the beat from “pumphouse” floating across the bay, combined with the aroma...
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    About this property
    Exclusively situated for viewing this most iconic scenic spot in Anguilla, this modern penthouse atop a luxurious gated resort home offers the best in luxury, location and lifestyle. Awaken to a beautiful view of St. Martin or the Bay; enjoy a light breakfast made from your fridge stocked with our...
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    AI 2640, South Hill, Anguilla
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    The Valley
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    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...
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    AI 2640, The Valley, Anguilla
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    The Valley
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Oceana Villa Anguilla Close to Sandy Beaches Anguilla famously has 33 beaches and Oceana is close to several: one of the nearest is Crocus Bay.  Viewed from Oceana and just a five minute drive this is a long, relatively untouched, quiet beach, except for the Da Vida...
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    AI 2640, The Valley, Anguilla
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Zenaida - Anguilla1 / 10
    (1)Excellent
    East End Village
    8 Bedrooms, 9 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 May 2016
    The delightful staff was phenomenal - very welcoming and they all delivered exceptional service. We were made to feel special and like family. The villa and grounds were...
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    Zenaida East End Village Anguilla A luxury Private Estate with Beach and Tennis courts and wonderful service on the East End of Anguilla. Everything is Cool about the location - guests have the advantage of the most elevated point on Anguilla. Zenaida is one of...
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    AI 2640, East End Village, Anguilla
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 14
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    Shoal Bay Village
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Black Pearl Villa Shoal Bay East Anguilla Mediterranean Pergolas, Domes & Verandas Black Pearl Villa has been designed in a cool Mediterranean style and features an exotic dome roof, a curved barrel roof, romantic pergolas and breezy verandas. 4 Bedroom Suites with...
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    AI 2640, Shoal Bay Village, Anguilla
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    South Hill
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ambia is centrally located in Anguilla with spectacular views overlooking Sandy Ground and minutes away from the Island's 33 magnificent white-sand beaches. The Villa is newly renovated and available for rental beginning December 1, 2016. Ambia's Asian-style suites with Caribbean influence are the...
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    AI 2640, South Hill, Anguilla
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Three Dolphins  Lockrum Bay, Anguilla  BWI1 / 51
    (12)Excellent
    Little Harbour
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 October 2017
    Our large family of 5 adults and 4 children vacationed experienced a vacation of a lifetime at Three Dolphins Villa. Upon arrival at the villa, we were greeted by the lovely...
    Reviewed 24 February 2017
    I have been to Europe, Asia, India, Mexico, Bermuda, and Hawaii. I have stayed in some very beautiful homes, but none so stunning as Three Dolphins Villa. For my fiftieth...
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    About this property
    Three Dolphins, Anguilla is an Elegantly furnished Small Estate on the British West Indies Isle of Anguilla and provides a most private escape for the discriminating traveler. Overlooking its own secluded strand of white sand beach directly in front of the house it also has breathtaking views of...
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    A12640, Little Harbour, Anguilla
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    The Valley
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lotus Blossum Villa The Valley Anguilla 2 Double Bedrooms & 1 Double Studio Lotus Blossum is a peaceful, relaxing property, prisitne, light and beautifully finished with 2 double bedrooms and a self contained studio on the lower level. The bedrooms have contemporary art on the...
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    AI 2640, The Valley, Anguilla
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    The Valley
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    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...
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    Location Information
    AI 2640, The Valley, Anguilla
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    The Valley
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Terrace
    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    • Internet Access
    • Balcony
    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fantastic, well-appointed 2BR 2BA condo available for December 2018. This property is centrally located on the Island of Anguilla and is convenient to some of the most sought-after beaches and restaurants in the Caribbean. Ocean Terrace Condos overlooks the Island of St. Maarten, The view is...
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    AI 2640, The Valley, Anguilla
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Island Harbour
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quixotic Villas, Harbour Ridge, Island Harbour, Anguilla Quixotic Villas are a collection of private retreats that nestle amongst Harbour Ridge offering stunning ocean views and relaxing, comfortable Caribbean accommodations. There are four definitive villas, Villa Amor, Villa...
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    AI 2640, Island Harbour, Anguilla
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Island Harbour
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Amarilla Island Harbour Anguilla Italian Influenced Design Designed by the Anguillan architect Carl Williams, this villa combines a Caribbean approach with Italian influences such as yellow stucco walls, turquoise shutters and a red tile roof. Award...
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    AI 2640, Island Harbour, Anguilla
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Pinnacle Villa - 3 bd luxury, best view and excellent support from owners1 / 18
    (3)Excellent
    South Hill
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Housekeeping Included
    • Ocean Views
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 December 2017
    Our hosts arranged for our rental car to be delivered to the lot. Once we made it to the top of the stairs are jaws dropped, the view was absolutely incredible. The Villa is...
    Reviewed 11 December 2017
    Truly the best getaway I’ve had with my family. Beautiful villa, very spacious, modern and private, surrounded by amazing beaches. Great food and friendly people in this island...
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    About this property
    Exclusively situated for viewing this most iconic scenic spot in Anguilla, this modern penthouse atop a luxurious gated resort home offers the best in luxury, location and lifestyle. Awaken to a beautiful view of St. Martin or the Bay; enjoy a light breakfast made from your fridge stocked with our...
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    Location Information
    AI 2640, South Hill, Anguilla
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Island Harbour
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Patio
    • Grill
    • Waterfront
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    AI 2640, Island Harbour, Anguilla
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    Little Harbour
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Terrace
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Private Garden
    • Grill
    • Parking
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our retreat, Lockrum Point Villa (LPV). Literally, steps from Lockrum Bay, this amazing two-level Seaside villa sets the stage for luxurious relaxing and entertaining. The villa comes with breath-taking views of the sea and St. Martin, a private pool and a range of luxury amenities for...
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    BWI, Little Harbour, Anguilla
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Wesley House - Anguilla1 / 10
    (1)Excellent
    Island Harbour
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 February 2013
    We really enjoyed our stay In Wesley House, the entire house is perfect in every way, well equippted, spacious, clean and indeed very comfortable, the outside decks are well...
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    About this property
    Wesley House Near Captain's Bay, Anguilla Beautiful location Located 150 feet above sea level, Anguilla's Wesley House is a private, luxury property.  It has amazing...
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    Location Information
    VC0400, Island Harbour, Anguilla
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Island Harbour
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kiki Villa Shoal Bay Anguilla 10 minute stroll from Shoal Bay Beach This stunning property built in the mediterranean villa style has a pristine white exterior, a pool, terraces and sun deck overlooking Shoal Bay in the distance. Shoal Bay Beach is just a 10 minute stroll away from...
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    Location Information
    AI 2640, Island Harbour, Anguilla
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Island Harbour
    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Amarilla's design is Caribbean with an Italian influence in its yellow stucco walls, turquoise shutters and red tile roof. The cool island interiors by the owners in collaboration with award-winning Dallas interior designer David Salem & Associates have hints of Moroccan flair. With...
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    AI 2640, Island Harbour, Anguilla
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    The Valley
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sand Castle Villa Limestone Bay Anguilla Beachfront 4 Bedroom Villa Sand Castle Villa boasts 4 bedrooms, 2 kingsize, 1 Queensized and a twin room, perfect for a group of friends or large family to enjoy. Close to the stunning Anguillan coast and blessed with its own beautiful pool...
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    AI 2640, The Valley, Anguilla
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    COUPLES ONLY RETREAT - Stunning Panoramic Ocean Views - Private Pool1 / 38
    (59)Excellent
    Island Harbour
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Waterfront
    • Housekeeping Included
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2017
    Paradise accommodations on a Paradise Island. We loved the huge wrap around outdoor patio with sun and shade, the pool and sitting at the high table overlooking the...
    Reviewed 9 June 2017
    This Villa was a real find!!!!!. This is my husband's and I second trip to Almond Tree Villa, and now I remember why I came back, Enjoyed breakfast and cocktails everyday on...
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    About this property
    IMPORTANT UPDATE: Almond Tree Villa was not damaged by Hurricane Irma and is currently booking guests for all of 2018 and 2019 at our LOW SUMMER rate. Please use the money you save to offset increased airfare and supporting local businesses on Anguilla! A couples only retreat, offering stunning...
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    Location Information
    AI 2640, Island Harbour, Anguilla
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Little Harbour
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Private Outdoor Pool (Heated)
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perched 150 feet above sea level on the east end of Anguilla, the Wesley House features complete privacy, luxury, and a panoramic view of five islands. Air-conditioned bedrooms, a uniquely designed tropical architecture, expansive bougainvillea covered decks and plush eclectic and British colonial...
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    AI 2640, Little Harbour, Anguilla
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    The Valley
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Ocean Views
    • Housekeeping Included
    • Patio
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set into beautifully landscaped gardens, Mangrove Villa is on dramatic West End Bay and just a 5 minute walk from the powder white sands of Shoal Bay West. The magnificent roof top lounge is perfect for sun-bathing or having cocktails while watching the sun go down. The 50 x 20 foot freeform pool...
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    Location Information
    A1, The Valley, Anguilla
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Little Harbour
    10 Bedrooms, 10 Bathrooms, Sleeps 20 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Le Bleu Villa, Anguilla — a stunning beachfront luxury villa for rent. Le Bleu Villa, a luxury tropical estate on Anguilla in the British West Indies, is a lush two-acre compound with a grand main house and a guesthouse — Petite Le Bleu. This gorgeous villa rental features ten...
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    Location Information
    AI 2640, Little Harbour, Anguilla
    Holiday Rental House - 10 Bedrooms, 10 Bathrooms, Sleeps 20
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