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Holiday Rentals with Pools in Anguilla

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    Travellers to Anguilla are booking December dates now. Secure your holiday home today, and have the perfect trip.
    75 Matching Rentals in AnguillaView all 208 rentals
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    Stunning Sea Feathers Villa1 / 29
    (12)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Ocean Views
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3-star aparthotel in Shoal Bay with free parking Located 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...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Ocean Views
    • Balcony
    • DVD Player
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3-star aparthotel in Shoal Bay with free parking Located 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...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Balcony
    • Ocean Views
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3-star aparthotel in Shoal Bay with free parking Located 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...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Ocean Views
    • DVD Player
    • Wi-Fi
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3-star aparthotel in Shoal Bay with free parking Located 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...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Ocean Views
    • Balcony
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3-star aparthotel in Shoal Bay with free parking Located 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...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Air Conditioning
    • Ocean Views
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3-star aparthotel in Shoal Bay with free parking Located 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...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Ocean Views
    • Cable/satellite TV
    • DVD Player
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3-star aparthotel in Shoal Bay with free parking Located 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...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
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    • Cable/satellite TV
    • Balcony
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tortue Villa (french name for Turtle) is located at Shoal Bay, Anguilla, about 4 minutes drive from Allamanda Beach Club, overlooking the ocean. Stunning views of Shoal Bay Beach and surrounding cays can be enjoyed from both the top and second levels. If one sits around long enough on the large...
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    Shoal Bay Village, Anguilla AI 2640
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Ocean Views
    • Balcony
    • DVD Player
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3-star aparthotel in Shoal Bay with free parking Located 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...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Ocean Views
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Allamanda Beach Club is a 3-star Family oriented Hotel located at Shoal Bay East. Located in the heart of Shoal Bay, this Hotel is a 3 minutes walk to the East side of 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...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Ocean Views
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Allamanda Beach Club is a 3-star Family oriented Hotel located at Shoal Bay East. Located in the heart of Shoal Bay, this Hotel is a 3 minutes walk to the East side of 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...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Ocean Views
    • DVD Player
    • Balcony
    • Wi-Fi
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Allamanda Beach Club is a 3-star Family oriented Hotel located at Shoal Bay East. Located in the heart of Shoal Bay, this Hotel is a 3 minutes walk to the East side of 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...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Ocean Views
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Allamanda Beach Club is a 3-star Family oriented Hotel located at Shoal Bay East. Located in the heart of Shoal Bay, this Hotel is a 3 minutes walk to the East side of 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...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Parking
    • Terrace
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tortue Villa (french name for Turtle) is located at Shoal Bay, Anguilla, about 4 minutes drive from Allamanda Beach Club, overlooking the ocean. Stunning views of Shoal Bay Beach and surrounding cays can be enjoyed from both the top and second levels. If one sits around long enough on the large...
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    Shoal Bay Village, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Ocean Views
    • Wi-Fi
    • Grill
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Allamanda Beach Club is a 3-star Family oriented Hotel located at Shoal Bay East. Located in the heart of Shoal Bay, this Hotel is a 3 minutes walk to the East side of 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...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Parking
    • DVD Player
    • Terrace
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tortue Villa (french name for Turtle) is located at Shoal Bay, Anguilla, about 4 minutes drive from Allamanda Beach Club, overlooking the ocean. Stunning views of Shoal Bay Beach and surrounding cays can be enjoyed from both the top and second levels. If one sits around long enough on the large...
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    Shoal Bay Village, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Ocean Views
    • Balcony
    • DVD Player
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3-star aparthotel in Shoal Bay with free parking Located 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...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Air Conditioning
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3-star aparthotel in Shoal Bay with free parking Located 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...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Ocean Views
    • Balcony
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3-star aparthotel in Shoal Bay with free parking Located 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...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Pinnacle Villa - 3 bd luxury, best view and excellent support from owners1 / 18
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • 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 12 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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    South Hill, Anguilla AI 2640
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Oceana Villa Anguilla - Brand New 2 bedroom1 / 92
    (15)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Patio
    • Wi-Fi
    • Housekeeping Included
    • Ocean Views
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 June 2016
    Oceana is a beautiful villa in a perfect location looking over Crocus bay. My wife and I stayed here for a week during June 2016 and we couldn't have picked a better Villa for...
    Reviewed 2 February 2016
    This is our 3rd year at Oceana and it continues to be a fantastic choice , perfect for two couples, not too big for my husband and me when we're on our own. The site is...
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    About this property
    Oceana, Anguilla offers tranquility, romance, and casually elegant tropical living. The villa's open design maximizes sea views and ocean breezes, inviting you to experience a private vacation retreat. Set on a breezy hillside overlooking picturesque Crocus Bay, this bright and airy villa provides...
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    The Valley, Anguilla NONE
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    3 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private, luxurious, oceanfront, private villa in Sea Feather’s Bay with stunning views of the Caribbean and St Martin. The modern design is ideal for relaxing vacation. Large rooms with private balconies have incredible views, ample outdoors and in-door living spaces, swimming pool and garden....
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    East End Village, Anguilla 2640
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 11
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    Mainstay Villa at Elsie Bay1 / 14
    (15)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • DVD Player
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 weeks ago
    This is a beautiful property with the conveniences of home. Kitchen and living areas are recently updated and we had access to everything we could need for our stay.The...
    Reviewed 4 July 2018
    My husband, daughter and her husband joined us for 4 days and 3 nights at Mainstay. Husband and I stayed for 8 days, 7 nights. We arrived at the dock from St Martin around...
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    About this property
    Mainstay is a privately owned villa situated on a ½ acre right on the Caribbean Sea. It offers 3 bedrooms, 2 full baths and a 1/2 bath. Our lovely pool and large deck offers spectacular southern views of St. Martin & other neighboring islands. Mainstay is a very spacious and well appointed...
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    Anguilla, Caribbean ELSIE BAY
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 3 Bathrooms, Sleeps 11 Quick View
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    • DVD Player
    • Grill
    • Patio
    • Balcony
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private, luxurious, oceanfront, private villa in Sea Feather’s Bay with stunning views of the Caribbean and St Martin. The modern design is ideal for relaxing vacation. Large rooms with private balconies have incredible views, ample outdoors and in-door living spaces, swimming pool and garden....
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    East End Village, Anguilla 2640
    Holiday Rental House - 1 Bedroom, 3 Bathrooms, Sleeps 11
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    Villa Fay Perfect getaway for couples or families1 / 24
    (17)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Patio
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2017
    My family vacation at this beautiful Anguilla property Villa Fay was awesome.The villa was very spacious and was able to accommodate my family of 5 and still feel like everyone...
    Reviewed 18 April 2017
    We had the most wonderful and relaxing week of my sisters wedding last month. Everything was perfect. The location, the bedrooms, the view, the Great Room. It was all amazing...
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    About this property
    This 3700 sf. sprawling compound offers mature landscaping, a master bedroom, two additional bedrooms with private bathrooms, a 1900 sf. Great Room and the Entertainment Deck. Each bedroom offers private decks for sunning or just relaxing with a cocktail. If you don't want to go to the beach...
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    Location Information
    Anguilla, Caribbean 12345
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • 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 Elegante, Villa...
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    Island Harbour, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Coconut Palm Villa -Twin Palms Villas at Meads Bay1 / 45
    (5)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Ocean Views
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Patio
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 June 2017
    This villa was the stay of a lifetime for my husband and I! We were lucky enough to be part of the wedding party for my cousin's wedding. It was truly paradise everywhere we...
    Reviewed 6 June 2017
    We stayed at Coconut Villa the week of our wedding. The villa is spotless, and very beautiful, the views are spectacular and it is very private.. The staff is very friendly and...
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    About this property
    Coconut Palm Villa is the BEST VALUE VILLA rental at Meads Bay in Anguilla. * 3 en-suite bedrooms * private swimming pool * steps from Meads Bay Beach - one of the world's best beaches * beach chairs and umbrellas set up on Meads Bay Beach * fully equipped granite counter kitchen * exquisitely...
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    Long Bay Village, Anguilla AI 2640
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Location, Location, Location! Stunning Villa Azure1 / 27
    (8)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Housekeeping Included
    • Air Conditioning
    • Hot Tub
    • Ocean Views
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2018
    Our family of ten spent 12 incredible nights at Villa Azure, the villa is absolutely breathtaking. As others have said, the pictures simply do not do the property justice. Of...
    Reviewed 9 March 2014
    Villa Azure provides a 5+++ Star vacation accommodation with all the privacy and comfort of a private home. Villa Azure's location and staff are beyond compare. If you are...
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    About this property
    **Quick Villa Azure info: Villa Azure is a 5 Star Luxury Villa overlooking Anguilla's best Beach- Shoal Bay Beach • It is the most luxurious Villa with the most amenities in the Shoal Bay Beach area • The best sea views on the island are framed in each doorway with endless shades of blue •...
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    Location Information
    Shoal Bay Village, Anguilla CARRIBBEAN
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 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
    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 restaurant at its eastern end....
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Twin Palms Villas at Meads Bay1 / 49
    (1)Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Ocean Views
    • Wi-Fi
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
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    • Patio
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Twin Palms VIllas at Meads Bay Feature Two Villas on One Estate: *Coconut Palm (3 bedrooms / 4 bathrooms) *Beach Palm (2 bedrooms / 3 bathrooms) *Connected to each other by a lit garden path *These are the BEST VALUE VILLA RENTALS at Meads Bay. Each villa features: * private swimming pool at each...
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    Long Bay Village, Anguilla AI 2640
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beaches Edge Villa Pelican Bay, Anguilla Sleek Crisp Lines & Comfort for 10 Guests Located close to the sandy beach of Pelican Bay, Beaches Edge Villa has been designed with striking attention to detail and clean contemporary lines throughout both the interior and exterior. Supreme service and...
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    Location Information
    Blowing Point, Anguilla AI 2640
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    TRULY EFFORTLESS BEACH ACCESS! A MUST SEE! Alegria1 / 42
    (9)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Housekeeping Included
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Waterfront
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 2017
    This home, Villa Alegria, in Blowing Point, Anguilla, BWI, was absolutely, positively all that we wanted and thought it would be plus more. From our first entrance into this...
    Reviewed 25 April 2017
    We stayed at Villa Alegria 4/14/17 - 4/21/17. What a truly amazing home. The location could not be more convenient. It was just a couple minutes form the Blowing Point Ferry...
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    About this property
    The beachfront vacation home you've been dreaming about! Villa Alegria, located near Blowing Point and Anguilla's desirable West End, is one of the Caribbean's most beautiful and comfortable beachfront villas with stunning views of the sea and mountains of St. Martin. Unlike most Anguilla villas,...
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    Blowing Point, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    Imperial Penthouse, New Oceanview w/H.Pool&Package1 / 19
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • 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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    Location Information
    South Hill, Anguilla AI 2640
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    BEST VIEWS IN PARADISE... U WILL NOT WANT TO LEAVE-100% OF PRIOR GUESTS AGREE!1 / 110
    (93)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Children's Pool
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 weeks ago
    The Castle was beautiful! The bedrooms all had breathtaking views, bathrooms and even outdoor showers. The pool area was amazing and the infinity pool was perfect. We grilled...
    Reviewed 16 May 2018
    This property is amazing. Even more beautiful and spacious than the pictures show. Paul gave us wonderful advice for a trip and his staff was friendly.The property is immaculate...
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    Dear Paradise Researcher, Thanks for arriving at this special moment; the moment of paradise Anguilla is still True Paradise. PLUS... It' is always summer on Anguilla NOW before you do read on, know the safe and serene island of Anguilla and the stunning Grand Outlook Castle WILL exceed you...
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    Sandy Ground, Anguilla N A
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Nirvana Villa - Anguilla1 / 8
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 July 2017
    After a long search, I chose Villa Nirvana for a friends getaway. This was our 5th trip to Anguilla, but the first for our group of friends. We had such a great time and the...
    Reviewed 20 March 2017
    Getting to our Nirvana Villa was simplified by Paul and Elise who organized all the transfers etc. Our plane was delayed so it was late when we got to the villa. Much to our...
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    Nirvana Villa Shannon Hill aka Seafarer's Ridge Nr Sandy Ground Anguilla 4 Bedrooms 4 Bathrooms Private, Elevated Location above Sandy Ground This beautiful villa has been designed to fit perfectly upon its elevated position and present the best possible panoramic views from every room and terrace....
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    Blowing Point, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
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    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 Outdoor Showers Each air...
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    Shoal Bay Village, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Wesley House - Anguilla1 / 10
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
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    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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    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 panoramic views over 5 islands, and from this rental guests are sure to fall in love with the Caribbean. The nearest beach is a 5...
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    Location Information
    Island Harbour, Anguilla VC0400
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Wi-Fi
    • Patio
    • Balcony
    • Grill
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private, luxurious, oceanfront, private villa in Sea Feather’s Bay with stunning views of the Caribbean and St Martin. The modern design is ideal for relaxing vacation. Large rooms with private balconies have incredible views, ample outdoors and in-door living spaces, swimming pool and garden....
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    Sandy Hill Bay, Anguilla 2640
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 11
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in the golf course of the St Regis Resort, Westgreen villa with its beautiful attention to detail & fabulous open airy feel, is the perfect getaway. Built on two levels, the villa offers tiled floors and tasteful interiors that feature a mix of wood, rattan and upscale fabrics. With three...
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    West End Village, Anguilla AI 2640
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    BestValue1300/5bd/night. Rent 1 bdr or more,  rates adjusted on a sliding scale1 / 52
    (10)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 11 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Waterfront
    • Internet Access
    • Air Conditioning
    • Housekeeping Included
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2016
    Hands down the best vacation I've ever taken! Walking into Villa Gardenia, the first thing you see is an amazing panoramic view. The villa has an enormous amount of space which...
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    About this property
    Private, luxurious, oceanfront, private villa in Sea Feather’s Bay with stunning views of the Caribbean and St Martin. The modern design is ideal for relaxing vacation. Large rooms with private balconies have incredible views, ample outdoors and in-door living spaces, swimming pool and garden....
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    Location Information
    Anguilla, Caribbean 2640
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 11
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    Ocean Terrace Luxury 2BR Condos, Spectacular Views1 / 10
    (13)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Patio
    • Internet Access
    • Grill
    • Shared Outdoor Pool (Unheated)
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    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 February 2017
    Our two week stay at Ocean Terrace on the beautiful Caribbean island of Anguilla was a vacation in paradise. We awoke each morning to sunrise over the ocean with the picturesque...
    Reviewed 17 March 2015
    My wife and I spent an amazing 9 days in Anguilla and so enjoyed our accommodation at Ocean Terrace. The property is slightly off the main roads but all in all centrally located...
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    Ocean Terrace is a small, intimate condominium complex (only 11 units) nestled on a hill on the southeastern shore of Anguilla, offering truly spectacular panoramic views of St. Martin, St. Barths and St. Kitts. Our spacious two bedroom condominium consists of more than 1,500 square feet of space...
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    Anguilla, Caribbean AI 2640
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Beach Palm Villa - Twin Palms Villas at Meads Bay1 / 32
    (3)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Ocean Views
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 April 2017
    The accommodations were absolutely wonderful! The villa was extremely comfortable and spacious. The private pool was a great feature that was used frequently, and housekeeping...
    Reviewed 5 April 2017
    This was a family vacation of nine people. We stayed at these two adjoining villas and had a great time. The Twin Palm Villa was perfectly equipped with everything, from the...
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    About this property
    Beach Palm Villa is the BEST VALUE VILLA rental at Meads Bay in Anguilla * 2 en-suite bedrooms * private swimming pool * steps from Meads Bay Beach - one of the world's best beaches * beach chairs and umbrellas set up on Meads Bay Beach * fully equipped granite counter kitchen * exquisitely...
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    Location Information
    Long Bay Village, Anguilla AI 2640
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
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    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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    South Hill, Anguilla AI 2640
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    WEDDINGS, FAMILIES Enjoy 2 Full Oceanfront Villas!1 / 45
    (5)Excellent
    10 Bedrooms, 12 Bathrooms, Sleeps 20 Quick View
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    • Housekeeping Included
    • Children's Pool
    • Mountain Views
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 July 2017
    We had a fantastic experience at Beaches Edge for our four night vacation with our closest family and friends that culminated in our wedding! Michelle was very responsiveness...
    Reviewed 10 February 2017
    Not easy to find a place that can take care of such a large group. But these villas did that and some. Managers were very helpful lining up rental cars. Fishing trips. Our...
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    About this property
    A PRIVATE RESORT, ALL TO YOURSELVES! ***One of the most affordable 10-bedroom options on Anguilla and near the island's desirable West End!!*** This professionally-managed, two-villa oceanfront estate with a small beach nearby is ideal for family reunions, destination weddings, corporate...
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    Blowing Point, Anguilla BWI
    Holiday Rental House - 10 Bedrooms, 12 Bathrooms, Sleeps 20
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
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    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 Kiki Villa and...
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    Island Harbour, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    NEW EXPANDED POOL & DECK! Oceanfront Beaches Edge East Villa1 / 32
    (4)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Hot Tub
    • Waterfront
    • Wi-Fi
    • Housekeeping Included
    • Children's Pool
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 March 2016
    My husband and I stayed here with our 3 small children and extended family (10 people total) and had an amazing time. The pictures do not lie--the house is really that beautiful...
    Reviewed 11 August 2014
    Words truly cannot describe our stay at Beaches Edge Anguilla. But I will try..From the serene private setting with amazing views of the ocean to the full service staff(which...
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    About this property
    The Beaches Edge Anguilla East Villa is a 5 bedroom/5.5 bath oceanfront villa overlooking Pelican Bay. This contemporary luxury home is away from the crowd. The villa has the most stunning views of the Caribbean Sea and mountains of St. Martin on Anguilla. A small, quiet beach is just a...
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    Location Information
    Blowing Point, Anguilla BWI
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
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    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 Winning Interior Designer The owners in...
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    Location Information
    Island Harbour, Anguilla AI 2640
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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