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Holiday Rentals with Pools in Anguilla

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    Travellers to Anguilla are booking April dates now. Secure your holiday home today, and have the perfect trip.
    65 Matching Rentals in AnguillaView all 185 rentals
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    Tequila Sunrise Villa in Anguilla1 / 17
    (5)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Coconut Palm Villa -Twin Palms Villas at Meads Bay1 / 45
    (6)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    10 Bedrooms, 10 Bathrooms, Sleeps 20 Quick View
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    Amenities & Details
    • Waterfront
    • Terrace
    • Balcony
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Indigo Villa, a luxurious Anguillian estate with 9 air-conditioned bedrooms fronted by beautiful white sands and coral reefed blue sea, awaits you. Each room has a view of the Caribbean Sea and the terrace opens to a marvelous patio vista of pool, palms, sea, sand and the Islands beyond. Indigo...
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    Anguilla, Caribbean AI 2640
    Holiday Rental House - 10 Bedrooms, 10 Bathrooms, Sleeps 20
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    Stunning Sea Feathers Villa1 / 29
    (13)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Patio
    • Parking
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Cable/satellite TV
    • Waterfront
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 November 2018
    I am very happy with my experience at Stunning Sea Feathers. If my family and I were to come back to Anguilla any time soon, we would check the availability of this villa...
    Reviewed 25 February 2016
    The views are indescribable. The house is beautiful. The pictures do not do this house justice. I was speechless every morning looking at the ocean. My favorite part of the...
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    About this property
    Take in the beautiful panaromic views of St. Martin, the beautiful ocean and parts of the island while sitting on the deck drinking your morning coffee or cocktail! Large open air living space with dining room, sitting area as well as chaises to enjoy your day. Two large beautifully appointed...
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    Anguilla, Caribbean 00000
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Mangrove Villa at Indigo Reef1 / 12
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Ocean Views
    • Housekeeping Included
    • Patio
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 February 2019
    We had a great stay at Mangrove Villa. We are regulars to Anguilla (I think this was our 15th year.) but renting a free-standing villa was a first for us here. We had the...
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    About this property
    Set into beautifully landscaped gardens, Mangrove Villa is on dramatic West End Bay and just a 5 minute walk from the powder white sands of Shoal Bay West. The magnificent roof top lounge is perfect for sun-bathing or having cocktails while watching the sun go down. The 50 x 20 foot freeform pool...
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    The Valley, Anguilla A1
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    BEST VIEW IN TRUE PARADISE. U WILL NOT WANT TO LEAVE-100% OF PRIOR GUESTS AGREE!1 / 121
    (96)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
    The view from the patio is reminiscent of being in Santorini. You can see for miles. Ships and boats coming and going. And the sunsets!! Oh, and the Castle is not too...
    Reviewed 4 weeks ago
    We returned to Grand Outlook Castle in January 2019, our third visit! The eight of us,four couples, enjoyed a wonderful reunion vacation for 10 days at GOC. Paul and Elise, the...
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    About this property
    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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    Location Information
    Sandy Ground, Anguilla N A
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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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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    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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    Long Bay Village, Anguilla AI 2640
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Terrace
    • Parking
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Separated from the ocean’s shore by Anguilla’s fascinating; limestone rocks, towers Crystal Sunrise Villa. Coastally aligned, this beauty over the horizon offers you the most picturesque views; from its roof top, open deck panoramic patio to the poolside. Why sleep indoors? When you can sleep under...
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    Sandy Hill Bay, Anguilla AI 2640
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Pinnacle Villa - 3 bd luxury, best view and excellent support from owners1 / 18
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Housekeeping Included
    • Ocean Views
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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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    Spyglass Hill Villa1 / 42
    (13)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 December 2018
    We rented spyglass for a month starting nov 8 to dec 10 2018 . We had 3 adult couples for the first 2 weeks and 3 adult children and 3 grandkids for the second 2 weeks. We have...
    Reviewed 23 January 2018
    My family and I returned to Spyglass for the Holidays.We had the most wonderful time. Anguilla is back !!Spyglass Villa even more beautiful!New furniture in dining room...
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    About this property
    Spyglass Hill Villa. Private four-bedroom luxury villa overlooking the Caribbean Sea on the idyllic island of Anguilla. Perfect for a couple, family or group of friends. Spyglass Hill Villa offers all of today’s modern conveniences in a traditional West Indian setting. We invite you to...
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    Anguilla, Caribbean AI2640
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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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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    Ocean Terrace Luxury 2BR Condos, Spectacular Views1 / 10
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Patio
    • Internet Access
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    I stayed at Ocean Terrace for a week and absolutely loved it! From the comfortable beds and furniture to the most wonderful view, our stay could not have been better. Everyone...
    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...
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    About this property
    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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    Mainstay Villa at Elsie Bay1 / 14
    (17)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Ocean Views
    • DVD Player
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Mainstay is a wonderful oceanfront villa in a quiet residential neighborhood. The location makes it easy to get to all of the beautiful beaches and unique restaurants. It was a...
    Reviewed 25 November 2018
    After diligently completing research for an anchorage for our inaugural trip to Anguilla, we were blessed to locate the Mainstay Villa. We just returned after spending 8...
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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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Private Garden
    • Grill
    • Parking
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our retreat, Lockrum Point Villa (LPV). Literally, steps from Lockrum Bay, this amazing two-level Seaside villa sets the stage for luxurious relaxing and entertaining. The villa comes with breath-taking views of the sea and St. Martin, a private pool and a range of luxury amenities for...
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    Little Harbour, Anguilla BWI
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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)
    • 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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    Location Information
    Long Bay Village, Anguilla AI 2640
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Waterfront
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A true tropical oasis, Malliouhana is set on 25 acres of lush, landscaped gardens that merge with one and a half miles of pristine white-sand beaches to envelop your senses and bring to life the true majesty of Anguilla. Enjoy the absolute essence of your destination, discover the healing power of...
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    West End Village, Anguilla 2640
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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. Ambia's Asian-style suites with Caribbean influence are the epitome of style and comfort. Our rooms are furnished with comfortable king size...
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    South Hill, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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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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    Location Information
    East End Village, Anguilla 2640
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 11
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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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    Location Information
    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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    Three Dolphins  Lockrum Bay, Anguilla  BWI1 / 29
    (12)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Housekeeping Included
    • DVD Player
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 October 2017
    Our large family of 5 adults and 4 children vacationed experienced a vacation of a lifetime at Three Dolphins Villa. Upon arrival at the villa, we were greeted by the lovely...
    Reviewed 24 February 2017
    I have been to Europe, Asia, India, Mexico, Bermuda, and Hawaii. I have stayed in some very beautiful homes, but none so stunning as Three Dolphins Villa. For my fiftieth...
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    About this property
    Three Dolphins, Anguilla is an Elegantly furnished Small Estate on the British West Indies Isle of Anguilla and provides a most private escape for the discriminating traveler. Overlooking its own secluded strand of white sand beach directly in front of the house it also has breathtaking views of...
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    Location Information
    Little Harbour, Anguilla A12640
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
    • Secure Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly-Transformed Inside & Out! ----------------------- Grand Opening Special: Book a minimum of 6 nights and get the 7th night rental free when you book by March 31, 2019 for stays in 2019. Excludes US holidays. 12% government tax, 10% service charge and seasonal minimum nights requirement...
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    Location Information
    Long Bay Village, Anguilla A1 2640
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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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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    Location Information
    Sandy Hill Bay, Anguilla 2640
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 11
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    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Amarilla's design is Caribbean with an Italian influence in its yellow stucco walls, turquoise shutters and red tile roof. The cool island interiors by the owners in collaboration with award-winning Dallas interior designer David Salem & Associates have hints of Moroccan flair. With spacious...
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    Location Information
    Island Harbour, Anguilla AI 2640
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    Champagne Shores Villa1 / 13
    (2)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Children's Pool
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    I have stayed and visited Champagne Shores multiple times and even got married there! I have loved each and every one of my experiences there. The service/management is great...
    Reviewed 25 January 2019
    We thoroughly enjoyed our week on Anguilla and our stay at Champagne Shores. The island is filled with friendly and welcoming people. From the moment you disembark at...
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    About this property
    This spectacular Ocean Front Villa has 5 Bedrooms, 4 of which have great ocean views and views of St. Martin. The villa was completely remodeled in 2018 and has all the amenities that you will need while in Anguilla. Daily butler service is included with your stay. Daily continental breakfast...
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    Location Information
    Blowing Point, Anguilla 00000
    Holiday Rental House - 5 Bedrooms, 6 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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    Location Information
    Blowing Point, Anguilla BWI
    Holiday Rental House - 10 Bedrooms, 12 Bathrooms, Sleeps 20
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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 8 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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    Location Information
    West End Village, Anguilla A12640
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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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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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Private Garden
    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our retreat, Lockrum Point Villa (LPV). Literally, steps from Lockrum Bay, this amazing two-level Seaside villa sets the stage for luxurious relaxing and entertaining. The villa comes with breath-taking views of the sea and St. Martin, a private pool and a range of luxury amenities for...
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    Location Information
    Little Harbour, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Luxury 8 bedroom Anguilla villa. Pure Luxury!
    9 Bedrooms, 8 Bathrooms, Sleeps 19 Quick View
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    • Balcony
    • Hot Tub
    • Cable/satellite TV
    • DVD Player
    • Terrace
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    An exhibition of modern architecture and Caribbeanesque vernaculars, the private enclave that is Sheriva Boutique Villa Hotel offers the serenity of understated elegance with contemporary luxuries. The exquisitely appointed interiors by Norma Chase Jobert offer a magnificent haven with a collection...
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    Location Information
    Anguilla, Caribbean AI 2640
    Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 19
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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 15 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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    Location Information
    West End Village, Anguilla A12640
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    9 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Grill
    • Internet Access
    • Washer
    • Balcony
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Considered one of the most luxurious and exclusive beachfront properties in the Caribbean, Cerulean Villa lies on a secluded stretch of beach set amidst tranquil landscaped gardens, creating an ambience of luxury and elegance. Decorated by the renowned New York interior designer Scott Salvator,...
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    Location Information
    Long Bay Village, Anguilla AI 2640
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 18
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Grill
    • Balcony
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 7 Bedroom Villa is also available as a 4 Bedroom Villa at a special rate!   From the moment you set foot on this lush estate, you’ll begin to relax. Whether lounging by your private pool with tranquil views of the sea, or stepping out to the beach from the back porch, you’ll be...
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    Location Information
    Long Bay Village, Anguilla AI 2640
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    • Internet Access
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 6 Bedroom Villa can be rented as a 3/4 or 5 Bedroom Villa at special rates! Both 5/6 Bedroom Villas can also be rented to accommodate up to 24 guests! Gorgeous, mile-long Meads Bay is now the venue of choice for island foodies with its array of beachy and upscale restaurants, bars, anchored...
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    Location Information
    Long Bay Village, Anguilla 2640
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Parking
    • Grill
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 6 Bedroom Villa can be rented as a 3/4 or 5 Bedroom Villa at special rates! Both 5/6 Bedroom Villas can also be rented to accommodate up to 24 guests! Gorgeous, mile-long Meads Bay is now the venue of choice for island foodies with its array of beachy and upscale restaurants, bars, anchored...
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    Location Information
    Long Bay Village, Anguilla 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Balcony
    • Internet Access
    • Washer
    • Grill
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just steps from the sparkling white sands of Long Bay, Anguilla, Sand Villa offers a spectacular Caribbean vista and gentle island breezes. Ensconced in cool elegance, guests will savor indoor/outdoor living with exceptional private service and upscale amenities. Sand Villa offers its own private...
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    Location Information
    Long Bay Village, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Sea Villa at Long Bay Villas Anguilla. Beachfront privacy, luxury services/staff1 / 39
    (1)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 11 Quick View
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    • Housekeeping Included
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Our family spent 10 days at Sea Villa this past January. Prior to visiting - we weren't quite sure what to expect - the property (like many others we considered in the Caribbean...
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    About this property
    Sophisticated Comfort on the Beach - Book 6 Nights Get 7th Free! Details Below!* After a 9-month complete renovation, Sea Villa is now open! This practically-brand-new 5-bedroom villa includes stairs directly to velvet-sand Long Bay Beach where you can swim, snorkel, relax or enjoy a private...
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    Location Information
    Long Bay Village, Anguilla A1 2640
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 11
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • 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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    Location Information
    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    TRULY EFFORTLESS BEACH ACCESS! A MUST SEE! Alegria1 / 42
    (10)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 4 days ago
    We enjoyed a very memorable and perfect week in paradise in this amazing home. The house is beyond comfortable, very well laid out, and it is a beautiful place to relax and...
    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...
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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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    Location Information
    Blowing Point, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Indoor Pool
    • Air Conditioning
    • Secure Parking
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Octagon' is new to the rental market and its unique design is welcoming, homely, elegant and attention to detail can be seen throughout. As soon as you enter one of the entrance gates you are greeted with a sense of tranquility. With three (3) bedrooms all with ensuites, living room, half bath,...
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    Location Information
    West End Village, Anguilla AI2640
    Holiday Rental House - 3 Bedrooms, 4 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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • 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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    Location Information
    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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    • Wi-Fi
    • Parking
    • DVD Player
    • Cable/satellite TV
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Ocean Views
    • 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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    Location Information
    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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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Balcony
    • Ocean Views
    • DVD Player
    • 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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    Location Information
    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Location Information
    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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 2018. This property is centrally located on the Island of Anguilla and is convenient to some of the most sought-after beaches and restaurants in the Caribbean. Ocean Terrace Condos overlooks the Island of St. Maarten, The view is...
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    Location Information
    The Valley, Anguilla AI 2640
    Condo/Apartment - 2 Bedrooms, 2 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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    Location Information
    The Valley, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Sandcastle Villa - Luxury Beachfront (owner)1 / 91
    (1)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Washer
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 March 2016
    If I could give 100 stars I would!I write this review back in reality, missing the dream that is Sandcastle Villa so very much. This house is everything and more. Beautifully...
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    About this property
    Sandcastle is a private oasis, sitting directly on a secluded, white sandy beach of Anguilla. An absolute dream home to delight the most discerning of guests…lounge on the terrace tucked in the colorful garden, lose yourself in the sounds of the ocean from the ‘zen den’ built directly on the...
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    Location Information
    The Valley, Anguilla AI2640
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 10
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