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Anguilla Holiday Vacation with Pools

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    Travellers to Anguilla are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    73 Matching Rentals in AnguillaView all 127 rentals
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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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    Mangrove Villa at Indigo Reef1 / 6
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Mainstay Villa at Elsie Bay1 / 14
    (19)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Tequila Sunrise Villa in Anguilla1 / 17
    (6)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Housekeeping Included
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 30, 2019
    Tequila sunrise is a winner. The villa is beautiful with 3 bedrooms, an infinity pool and large indoor / outdoor living space. It’s isolated and private with a view of Saint...
    Reviewed January 25, 2019
    The locations is great. You are a so close to Dropsey Bay and in a central location. You are not far from either end of Anguilla. Robin and Joel have created an unbelievable...
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    About this property
    SECLUDED SERENITY Tequila is a contemporary three master bedroom beach house at secluded Lover’s Cove at Dropsey Bay which is just a leisurely two minute walk along the scenic path. It is a small, white sand, sun bathing adventure beach with a great snorkeling and exploring bay. It is wonderful for...
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    Sandy Hill Bay, Anguilla AI 2640
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Oceana Villa Anguilla - Brand New 2 bedroom1 / 92
    (17)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 July 2, 2019
    Our family of four (2 kids: 10 and 15) stayed at Oceana for our first trip in Anguilla. From the second we walked in we knew we were home. The house cannot be more perfect for a...
    Reviewed May 27, 2019
    We have traveled the caribbean and rented villas. However Oceana beyond surpassed any villa we have rented. First...the personal touches that are evident in every aspect of...
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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
    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 November 12, 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 February 25, 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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    Location Information
    Anguilla, Caribbean 00000
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Coconut Palm Villa -Twin Palms Villas at Meads Bay1 / 45
    (6)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 January 24, 2019
    We enjoyed a full week stay at this fabulous villa just off of Meads Bay Beach. The location allows for ocean and spectacular sunset views and is at most a leisurely two minute...
    Reviewed June 24, 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...
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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
    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 December 11, 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 December 11, 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
    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 July 5, 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 July 2, 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
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 mins to Beach by Ferry Boat Guests can jump on a local Ferry Boat that takes 2 minutes to transfer guests to a nearby sandy beach. watersports are available on the beach Snorkel and sailing tours are available from St Lucia Immaculate Interior This beautiful apartment is tastefully decorated...
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    Location Information
    The Valley, Anguilla AI 2640
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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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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    Amenities & Details
    • 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 April 5, 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 April 5, 2017
    This was a family vacation of nine people. We stayed at these two adjoining villas and had a great time. The Twin Palm Villa was perfectly equipped with everything, from the...
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    About this property
    Beach Palm Villa is the BEST VALUE VILLA rental at Meads Bay in Anguilla * 2 en-suite bedrooms * private swimming pool * steps from Meads Bay Beach - one of the world's best beaches * beach chairs and umbrellas set up on Meads Bay Beach * fully equipped granite counter kitchen * exquisitely...
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    Location Information
    Long Bay Village, Anguilla AI 2640
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Spyglass Hill Villa1 / 42
    (14)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 March 29, 2019
    We arrived just in time to catch a magnificent sunset and enjoy a beautiful breezy evening on the patio with friends. The villa is set up with every comfort for a carefree...
    Reviewed December 10, 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...
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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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    Location Information
    Anguilla, Caribbean AI2640
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Spyglass Hill Villa1 / 10
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 9, 2019
    What a wonderful first visit to Anguilla. The villa has amazing views and is tucked away. Great amenities from beach towels, basic foods and drinks to get you started, plenty of...
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    About this property
    Perfect Villa LayoutThis 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 King Size beds, en suite bathrooms and...
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    Sandy Ground, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ani South Little Bay Anguilla Sleek Crisp Lines & Comfort for 10 GuestsThis 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 staff...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    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 March 3, 2019
    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 February 21, 2019
    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
    3 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private, luxurious, oceanfront, private villa in Sea Feather’s Bay with stunning views of the Caribbean and St Martin. The modern design is ideal for relaxing vacation. Large rooms with private balconies have incredible views, ample outdoors and in-door living spaces, swimming pool and garden....
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    East End Village, Anguilla 2640
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 11
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ani North Little Bay Anguilla Sleek Crisp Lines & Comfort for 10 GuestsThis 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 staff...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    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
    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
    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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    Location Information
    Little Harbour, Anguilla BWI
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Wesley House1 / 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 February 4, 2013
    We really enjoyed our stay In Wesley House, the entire house is perfect in every way, well equippted, spacious, clean and indeed very comfortable, the outside decks are well...
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    About this property
    Wesley House Near Captain's Bay, Anguilla Beautiful locationLocated 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
    Zenaida1 / 10
    (2)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 August 15, 2018
    We had the opportunity to stay at the gorgeous Zenaida estate for 7 days. From the second we stepped onto the property we were met with the friendliest people who took such...
    Reviewed May 18, 2016
    The delightful staff was phenomenal - very welcoming and they all delivered exceptional service. We were made to feel special and like family. The villa and grounds were...
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    Zenaida East End Village AnguillaA 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 AnguillaZenaida is one of Anguilla's highest villas this property...
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    East End Village, Anguilla AI 2640
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 14
    3 Bedrooms, 4 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
    Tropical ParadiseOverlooking the stunning powder white sand beach Rendezvous Bay, Bow Green Villa is situated in beautiful tranquil private gardens with views out toward St Martin and just a moment's walk away from the sea. Breathtaking BeachRendezvous Bay is arguably one of the best beaches on the...
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    Rendezvous Bay, Anguilla 00000
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    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
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kiki Villa Shoal Bay Anguilla - 10 minute stroll from Shoal Bay BeachThis stunning property built in the mediterranean villa style has a pristine white exterior, a pool, terraces and sun deck overlooking Shoal Bay in the distance. Shoal Bay Beach is just a 10 minute stroll away from Kiki Villa and...
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    Location Information
    Island Harbour, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Three Dolphins  Lockrum Bay, Anguilla  BWI1 / 29
    (13)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Ocean Views
    • Cable/satellite TV
    • Wi-Fi
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 31, 2019
    We just completed a 2 week stay at Three Dolphins. For part of our stay, our daughter's family joined us, for part just the two of us. We've developed a clear list of things...
    Reviewed October 24, 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...
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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. The Villa has been lovingly 'restored and refurnished' inside and out Post Irma by her new Owners. Overlooking its own...
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    Location Information
    Little Harbour, Anguilla A12640
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    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 & VerandasBlack 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 ShowersEach air...
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    Shoal Bay Village, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    5 Bedrooms, 6 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 Modena Cove Bay Anguilla Comfortably Sleeps 10 GuestsVilla Modena is private and palatial and set upon one acre of land near the Cap Juluca Hotel on Cove Bay. A combination of a two storey main house and a one storey clubhouse provides 5 stunning bedrooms with private bathrooms sleeping 10...
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    Blowing Point, Anguilla AI 2640
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    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 DesignDesigned 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 DesignerThe owners in...
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    Location Information
    Island Harbour, Anguilla AI 2640
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocassa Villa Anguilla 5 Bedrooms overlooking Sandy BayThis is a stunning villa overlooking lovely Sandy Bay on the west coast of Anguilla. The villa has 5 double bedrooms with sumptuous furnishings and cool, cotton bed linens. Living Room opens onto Infinity Pool & BalconyThe living room has vast...
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    South Hill, Anguilla AI 2640
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    2 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Wi-Fi
    • Patio
    • Balcony
    • Grill
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private, luxurious, oceanfront, private villa in Sea Feather’s Bay with stunning views of the Caribbean and St Martin. The modern design is ideal for relaxing vacation. Large rooms with private balconies have incredible views, ample outdoors and in-door living spaces, swimming pool and garden....
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    Sandy Hill Bay, Anguilla 2640
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 11
    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
    Sleek Crisp Lines & Comfort for 10 GuestsLocated 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 exceptional staff. There are 5 bedrooms, 3...
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    Blowing Point, Anguilla AI 2640
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Ocean Views
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Violet's place is a cozy, intimate apartment with stylish colonial furnishings and a stunning views of the Caribbean sea embedded in a tropical landscape. This property located directly on the sea facing south in Sandy Hill Bay, a quiet peaceful area of the island. Violet’s place is perfect for...
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    Sandy Hill Bay, Anguilla AI 2640
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 3
    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 June 6, 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 April 18, 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
    Crystal Sunrise Villa1 / 10
    (1)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 15, 2019
    What an incredible property. Our group of 10 had a fantastic weeks stay. There are really not enough words to describe this property. It was fantastic! Clean well kept and you...
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    Crystal Sunrise Villa Summary7 bedrooms, 5 full plus 2 half bathrooms, Indoor and outdoor dining areas, Large heated pool with large deck, Roof deck, Double garage, Games room with pool table, Gym, Family room, Media room, Laundry, WIFI, Satellite Television in rooms, Large kitchen with modern...
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    Sandy Hill Bay, Anguilla 00000
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Oceana Villa Anguilla Close to Sandy BeachesAnguilla 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 It's eastern end....
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    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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    Little Harbour, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    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 March 20, 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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    Anguilla, Caribbean 2640
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 11
    Nevaeh Villa Anguilla, 9 bedroom beachfront villa (5, 6, 8 bed rates on request)1 / 37
    (4)Excellent
    9 Bedrooms, 12 Bathrooms, Sleeps 22 Quick View
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    • Private Outdoor Pool (Heated)
    • Housekeeping Included
    • Hot Tub
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 8, 2019
    This house is absolutely beautiful. The beach which is steps from the house is wonderful. The staff could not be better and we will definitely return.
    Reviewed June 12, 2019
    It’s impossible to believe, but the house is even more incredible in person than the photos. The staff is equally as impressive - they catered to our every whim! Once at NEVAEH...
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    About this property
    An exclusive 9-bedroom estate located on beautiful Long Bay with a half mile of powder fine, white sand beach. Nevaeh is heaven spelled backwards and this modern, high-end villa definitely lives up to its name. With 5 bedrooms in the Main House, 3 in the nearby Guest House, plus a free-standing...
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    Long Bay Village, Anguilla AI2640
    Holiday Rental House - 9 Bedrooms, 12 Bathrooms, Sleeps 22
    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 February 24, 2019
    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 January 25, 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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    Blowing Point, Anguilla 00000
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    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! Sky Villa is one of a trio of 5- and 6-bedroom, truly-beachfront homes at Long Bay Villas that can be rented individually or in combination for vacations, beach weddings and corporate events. Long Bay Beach’s velvet sands are just down a private staircase. Warm...
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    Long Bay Village, Anguilla A1 2640
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    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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    The Valley, Anguilla AI 2640
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    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 July 21, 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 February 10, 2017
    Not easy to find a place that can take care of such a large group. But these villas did that and some. Managers were very helpful lining up rental cars. Fishing trips. Our...
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    About this property
    A PRIVATE RESORT, ALL TO YOURSELVES! ***One of the most affordable 10-bedroom options on Anguilla and near the island's desirable West End!!*** This professionally-managed, two-villa oceanfront estate with a small beach nearby is ideal for family reunions, destination weddings, corporate...
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    Blowing Point, Anguilla BWI
    Holiday Rental House - 10 Bedrooms, 12 Bathrooms, Sleeps 20
    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 May 15, 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 June 13, 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
    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 March 30, 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 August 11, 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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    Blowing Point, Anguilla BWI
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • 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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    West End Village, Anguilla AI2640
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    4 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Secure Parking
    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 2640AI
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 11
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sand Castle Villa Limestone Bay Anguilla Beachfront 4 Bedroom VillaSand Castle Villa boasts 4 bedrooms, 2 King Size, 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 It's own beautiful pool this villa...
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    The Valley, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    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 It's 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
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Ocean Views
    • Patio
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in the quiet historic-tourism neighborhood of Cul De Sac - 5 minutes walk to one of the worlds best beaches (Rendezvous Bay), White Sands Anguilla is a Villa-Home with all modern amenities focused on providing you with the comfort and cleanliness of home with access to all Anguilla has to...
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    Location Information
    Blowing Point, Anguilla AI2640
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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