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Holiday Rentals with Pools in Anguilla

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    Travellers to Anguilla are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    143 Matching Rentals in AnguillaView all 295 rentals
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    Stunning Sea Feathers Villa1 / 29
    (12)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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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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    Imperial Penthouse, New Oceanview w/H.Pool&Package1 / 19
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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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 25 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 7 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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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    • Hot Tub
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bonne View Villa is located on South Hill Anguilla with a beautiful view of St Maarten and St Barts Recently completed Villa, fully private property with a gated entrance • Two (2) Bedroom Villa, with the possibility of linking them together, with a total surface area of 3000 sq ft , and sleeps up...
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    South Hill, Anguilla PO BOX 5179
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 1 Quick View
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    • Grill
    • Cable/satellite TV
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nearest Beach: Meads Bay Beach Proximity: On the Beach Meads Bay Beach Villas is an intimate Caribbean resort consisting of four luxurious villas situated directly on picturesque Meads Bay, Anguilla - one of the top-rated beaches in the entire Caribbean. A setting sun over crystal blue water is the...
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    Anguilla, Caribbean
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 1
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    LUXURY VILLA 'B ON THE SEA' IN ANGUILLA, 5 ENSUITE BEDROOMS, 2 DECKS, 2 POOLS1 / 61
    (16)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Washer
    • Children's Pool
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2017
    If you’re looking for a Paradise vacation, you should reserve the Luxury Villa 'B on the Sea' Oceanfront. It is perfect for sharing with family, friends with 5 spacious...
    Reviewed 2 July 2017
    We absolutely loved Anguilla and "B on the Sea". The house was stunning, perched up on the hill on a gorgeous bay overlooking St Marteen and the other islands. We were...
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    About this property
    Villa 'B on the Sea' is a luxurious villa overlooking the Caribbean Sea with expansive views of surrounding island! The villa is specificaly designed to be the ultimate entertainment Mecca for an exceptional paradise experience. This exclusive villa features simple luxury, breathtaking views and...
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    Anguilla, Caribbean ANGUILLA
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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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 6 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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    Long Bay Village, Anguilla AI 2640
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • 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 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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    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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    Anguilla Bow Green Villa on Rendezvous Bay Beach1 / 22
    (3)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Air Conditioning
    • Housekeeping Included
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 May 2017
    The villa is just a few minutes walk from Rendevous Beach, the best beach on the Island with fine golden sands and clear turquoise sea, the ideal setting where we chose to hold...
    Reviewed 13 June 2015
    Overlooking a stunning 2 mile long powder white sandy beach, named Rendevous Bay, stands Bow Green Villa which is set within half an acre of private land. The exclusivity of the...
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    About this property
    Bow Green is walking distance to Rendezvous Bay Beach which is one of the best beaches in Anguilla. Great views of St Martin and close to Anguilla Great House, Sun Shine Shack and Cuisinart Golf Resort. It is three bedroom villa and sleeps six and has a very private large walled swimming pool....
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    West End Village, Anguilla A12640
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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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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    4 Bedrooms, 5 Bathrooms, Sleeps 1 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Hot Tub
    • Waterfront
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nearest Beach: Long Bay Beach Beach Proximity: On the Beach FOR RENT: Sky Villa one of the three most luxurious rental properties in Anguilla.   Sky is the embodiment of its namesake. Interior hues of aquamarine and royal blue with yellow accents set an ethereal tone throughout its 6,500 sq. ft. of...
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    Anguilla, Caribbean
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 1
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    5 Bedrooms, 6 Bathrooms, Sleeps 1 Quick View
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    • Grill
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nearest Beach: Shoal Bay East Beach Proximity: Inland Overlooking the vast Atlantic Ocean is the stunning villa Tamarind, named after a local tree that grows on the Island and situated in the area of Shoal Bay East a five minute drive to one of the most stunning beaches in Anguilla and the...
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    Anguilla, Caribbean
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 1
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Terrace
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Hot Tub
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Caribbean is Sea Villa's muse. Its interiors mirror the serene waters' spectrum of blue and green hues, drawing the eye and soul beyond windows and terraces to the horizon, the infinity edge pool and back in seamless transitions. There are four master suites with terraces facing the sea and...
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    Anguilla, Caribbean
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Bonne View Villa1 / 30
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    • DVD Player
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 May 2016
    We are currently staying here as I write this. It happens to be raining most of this week which is not the norm for Anguilla. This villa is super clean, modernized with a full...
    Reviewed 23 December 2014
    Perfect vacation get away for honeymoon. I stayed there with my family and it was great. Private property and swimming pool. The perfect place if you want extreme privacy. Thank...
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    About this property
    Bonne View Villa is located on South Hill Anguilla with a beautiful view of St Maarten and St Barts Recently completed Villa, fully private property with a gated entrance • Two Bedroom Villa, with a surface area of 1500 sq ft, sleeps up to 6. Master bedroom, King size Bed and private bath,...
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    South Hill, Anguilla PO BOX 5179
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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 21 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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    Zenaida - Anguilla1 / 10
    (1)Excellent
    8 Bedrooms, 9 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 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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    About this property
    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 Anguilla’s highest villas this...
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    East End Village, Anguilla AI 2640
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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 2017. 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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    The Valley, Anguilla AI 2640
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 1 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    • Grill
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nearest Beach: Meads Bay (10 mins walk) Beach Proximity: Inland Zebra Villa located in the West of Anguilla and overlooks the scenic and beautiful Meads Bay Beach.  Zebra Villa offers luxurious and spacious indoor/outdoor living experiences with glorious panoramic views. The Master Suite is the...
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    Anguilla, Caribbean
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 1
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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
    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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    Blowing Point, Anguilla AI 2640
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Zenaida Beach and Tennis Estate1 / 21
    (4)Excellent
    8 Bedrooms, 14 Bathrooms, Sleeps 16 Quick View
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    • Waterfront
    • Hot Tub
    • Wi-Fi
    • Mountain Views
    • Ocean Views
    • Air Conditioning
    • Cable/satellite TV
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2016
    An absolutely wonderful property that has everything you potentially need. Very private and the service staff are incredible. Would definitely go back again.
    Reviewed 23 July 2016
    Our family of "10" had the vacation of a lifetime at the beautiful Zenaida Beach and Tennis Resort. From the moment of our arrival, we were taken in by the warmth of...
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    About this property
    Nestled in three acres of lush tropical gardens, where a 17th century Dutch fort once stood, Zenaida Tennis and Beach Estate offers gracious island living. Enjoy ultimate privacy in two separate villas and an adjoining garden cottage, all handsomely appointed featuring a total of seven...
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    Anguilla, Caribbean A12640
    Holiday Rental House - 8 Bedrooms, 14 Bathrooms, Sleeps 16
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    3 Bedrooms, 3 Bathrooms, Sleeps 1 Quick View
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    • Internet Access
    • Hot Tub
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Villas at Cuisinart Resort Spa offer you the utmost in luxury in a truly spectacular setting. Located at the eastern end of the property, the six villas are private, yet steps away from all Resort facilities. Each has its own entry courtyard graced with a soothing fountain and botanical...
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    Anguilla, Caribbean
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 1
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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 19 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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    Anguilla, Caribbean 12345
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Ocean Views
    • Wi-Fi
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    • Washer
    • 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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    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
    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 this villa...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 1 Quick View
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    • Hot Tub
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Grill
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nearest Beach: Maundays Bay (2-3 mins drive) Beach Proximity: Near the Beach Mystique villa on its own 1 acre plot of land overlooking the Cove and only two minutes away from the gorgeous white sanded Maundays Bay. Sitting on a lush 10-acre property with stunning views of the Caribbean Sea and...
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    Anguilla, Caribbean
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 1
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    5 Bedrooms, 5 Bathrooms, Sleeps 1 Quick View
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    • Waterfront
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Grill
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nearest Large Beach: Rendezvous Bay (approx 6-10 mins drive) Beach Proximity: On the Sea (With a small little bay/cove) NEWLY ADDED 5TH BEDROOM... ON THE GROUND FLOOR! ADDED RECENTLY - A BRAND NEW POOL TABLE!! This luxurious villa is located on the Lockrums Estate and sits on .6 of an acre on the...
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    Anguilla, Caribbean
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 1
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 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
    Perfect Villa Layout This 4 bedroom villa offers the perfect layout for a relaxed, entertained, worked out and pampered experience in Anguilla. At the heart of the villa is a cool and impressive atrium area. The top floor houses the 2 master suites each with kingsize beds, ensuite bathrooms and...
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    Sandy Ground, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Mainstay Villa at Elsie Bay1 / 14
    (13)Excellent
    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 8 August 2017
    If you are planning a trip to Anguilla (first or return visit) this is a must Villa to stay. Great view of St Marteen while you relax in the pool with a beverage. Close...
    Reviewed 27 July 2017
    My wife and I, along with another couple, stayed at Mainstay Villa and were blown away by the place! To wake up every day to that view is amazing. The housekeeper was helpful...
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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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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Location Information
    Blowing Point, Anguilla AI 2640
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    BEST VIEWS- ANGUILLA BWI... TRUE! 86 REVIEWS... Just read reviews & just VISIT1 / 98
    (88)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 3 weeks ago
    We just returned from a two week stay at the Grand Outlook Castle for my wife's 50th Birthday and we absolutely loved the island and the accommodations!!! Elise & Paul went...
    Reviewed 27 June 2017
    This was our second stay in beautiful Anguilla with Paul and his fantastic team. This time we had the pleasure of staying at the G.O.C. and it certainly did not disappoint...
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    Dear Paradise Researcher, before you do read on, know the safe and serene island of Anguilla and the stunning Grand Outlook Castle WILL exceed you and your party's expectations. No image or description can ever replicate the experience of the beauty and friendly people of Anguilla and the event...
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    Sandy Ground, Anguilla N A
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Bow Green Rendezvous Anguilla1 / 20
    (2)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 January 2017
    Bow Green was the ideal place to enjoy Anguilla for a number of reasons:Location - situated less than 100m from Rendez-vous beach (my favourite beach on the island). There are...
    Reviewed 9 September 2014
    Would recommend this to anyone! Of all the tropical islands I've visited this is my favourite. its the most picture perfect paradise island of them all. I have stayed at Bow...
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    About this property
    Golden sun, aquamarine sea, azure sky, soft white sand, beautiful unspoilt and uncrowded beach at Rendezvous Bay Beach, Bow Green Villa with swimming pool , fantastic haute cuisine of Anguilla near by,and indulgent luxury Spa near by are waiting for you. Bow Green is a beautiful home walking...
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    West End Village, Anguilla A12640
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 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
    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)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 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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    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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    Island Harbour, Anguilla AI 2640
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nearest Beach: Sandy Ground Beach Proximity: Inland Little Butterfly is situated in the quiet area of Little Harbour this one bedroom, luxury apartment is perfect for the solo traveler or a couple, Little Butterfly provides a contemporary and affordable getaway vacation in the heart of Anguilla....
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    Anguilla, Caribbean
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 1
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Property ID: 1769 Additional amenities include: music library, movie/video library, computer available, coffee maker, bbq outside (gas), washer/dryer, pool shower, cd player, tennis on-site, gated community, water sports nearby, french satellite, internet access/wifi, great for 2 couples, great...
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    Anguilla, Caribbean
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    10 Bedrooms, 10 Bathrooms, Sleeps 20 Quick View
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    • Balcony
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Air Conditioning
    • Waterfront
    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
    Holiday Rental House - 10 Bedrooms, 10 Bathrooms, Sleeps 20
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    Three Dolphins  Lockrum Bay, Anguilla  BWI1 / 51
    (12)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • 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 25 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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    Location Information
    Little Harbour, Anguilla A12640
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 1 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Grill
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Songbird' A five bedroom villa situated in Rendezvous Bay one of the Islands premier beaches is just a 5 minute walk away or a 2 minute golf cart ride ( golf cart included, seats 6) to this beautiful white sanded bay with the clearest most beautiful waters you will ever see. Architect Lee Skolnick...
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    Anguilla, Caribbean
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 1
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 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
    Papillon Villa Little Harbour Anguilla 21st Century Family Home This state of the art privately owned family home was designed and built 3 years ago and combines an elegant mix of architectural styles and luxury to provide a spacious and comfortable vacation villa with landscaped gardens, tennis...
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    George Hill, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • 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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    South Hill, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    COUPLES ONLY RETREAT - Stunning Panoramic Ocean Views - Private Pool1 / 38
    (59)Excellent
    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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    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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    Island Harbour, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
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    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 walls, bespoke...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Cable/satellite TV
    • Hot Tub
    • Waterfront
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Villas by CuisinArt offer the utmost in luxury in a truly spectacular setting. Located at the eastern end of the property, the six villas are private, yet steps away from all Resort facilities. Each has its own entry courtyard graced with a soothing fountain and botanical splendor, transporting...
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    Anguilla, Caribbean
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 1
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • 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 inclusive...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waves on Shoal Bay is an oceanfront vacation rental that offers tranquility, splendor, romance, and casually elegant tropical living. The villa’s central location makes it the perfect Anguilla rental, as it is ideally situated between the high-end resorts and restaurants in Shoal Bay, and overlooks...
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    Shoal Bay Village, Anguilla AI 4620
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    8 Bedrooms, 9 Bathrooms, Sleeps 1 Quick View
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    • Washer
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nearest Beach: Maundays Bay (2-3 minutes drive) Beach Proximity: Near the beach Infinity is yet another luxury villa located at Sheriva West End. This seven bedroom property is overlooking the Cove and only three minutes away from beautiful and scenic Maundays Bay. Situated on a lush 10-acre...
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    Anguilla, Caribbean
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 1
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    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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    Location Information
    Little Harbour, Anguilla AI 2640
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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