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Island Harbour Vacation Rentals

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    $1,223 Average
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    Travelers to Island Harbour are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    3 Reviews
    2 Bedrooms, Sleeps 4 Quick View
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    11 Reviews
    1 Bedroom, Sleeps 2 Quick View
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    4 Bedrooms, Sleeps 8 Quick View
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    57 Reviews
    1 Bedroom, Sleeps 2 Quick View
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    • Waterfront
    • Housekeeping Included
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Ocean Views
    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    Reviewed May 23, 2016
    Our trip to the Almond Tree Villa was wonderful. We would have to concur with all the other excellent reviews. We enjoyed every part of the villa, coffee under the patio in...
    Reviewed May 10, 2016
    This was our second visit to Almond Tree Villa and exceeded our expectations once again. Our friends Sue & Joe have thought of everything to make this villa a home away from...
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    About this property
    A couples only retreat, offering stunning panoramic views of the down islands ( St. Maarten, St. Barths, Statia, St. Kitts and Nevis), this luxury 1 Bedroom Villa is among the largest of the 1 bedroom villas on the island with 1100 sq. ft. of living area and nearly 3000 sq. ft. of outdoor patio and...
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    Island Harbour, Anguilla AI 2640
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    2 Bedrooms, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Housekeeping Included
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CATALINA VILLA- Shoal Bay Village, Anguilla; PERFECT FOR ONE OR TWO COUPLES OR A FAMILY WITH 1-3 CHILDREN!! This cute Caribbean Style newly built (2012-14) home has two beautiful Bedrooms and each has its own En Suite Bathroom with Shower and double vanities. Perfect for two couples or one...
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    Island Harbour, Anguilla XXXXXX
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Reviews
    5 Bedrooms, Sleeps 10 Quick View
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    • Grill
    • Sauna
    • Hot Tub
    • Wi-Fi
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 12, 2011
    This villa was quite spectacular. The kitchen was very nice and spacious. All the bedrooms were very big and each had their own balcony which was really nice! The pool are was...
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    About this property
    Relax and enjoy a view of endless Caribbean blue at the edge Villa Amarilla’s infinity pool. Located in Anguilla, this five bedroom architectural gem boasts a décor as beautiful as the island’s natural surroundings, created in collaboration with award-winning interior designer David Salem. Whether...
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    Island Harbour, Anguilla
    Rental Home - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    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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    Island Harbour, Anguilla AI 2640
    Rental Home - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    Kiki Villa Shoal Bay Anguilla 10 minute stroll from Shoal Bay Beach This stunning property built in the mediterranean villa style has a pristine white exterior, a pool, terraces and sun deck overlooking Shoal Bay in the distance. Shoal Bay Beach is just a 10 minute stroll away from Kiki Villa and...
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    Island Harbour, Anguilla
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    8 Bedrooms, Sleeps 16 Quick View
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    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Wi-Fi
    • Washer
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Picturesquely situated on Anguilla's southeast shoreline, Ultimacy Villa is an eight bedroom super villa located in the upscale neighborhood of Sea Rocks, nestled between the villages of Shoal Bay and Island Harbour. This three story home is considered one of Anguilla's largest and most impressive...
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    Island Harbour, Anguilla AI 2640
    Rental Home - 8 Bedrooms, 10 Bathrooms, Sleeps 16
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    4 Bedrooms, Sleeps 8 Quick View
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    • Patio
    • Wi-Fi
    • Waterfront
    • Hot Tub
    • Sauna
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and enjoy a view of endless Caribbean blue at the edge Villa Amarilla’s infinity pool. Located in Anguilla, this five bedroom architectural gem boasts a décor as beautiful as the island’s natural surroundings, created in collaboration with award-winning interior designer David Salem. Whether...
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    Location Information
    Island Harbour, Anguilla AI 2640
    Rental Home - 4 Bedrooms, 7 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Satellite TV
    • Air Conditioning
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    • Grill
    • Waterfront
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Soleil at Captains Bay is a fully air conditioned villa with luxury appointments throughout. . From every vantage point, the villa has the most spectacular views of any villa on the island. Breathtaking views of the ocean from the front and rear of the villa; view of seven islands including...
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    Island Harbour, Anguilla AI 2640
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6 Quick View
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    About this property
    This is a private and tranquil villa located in the Sea Rocks area of the island between Shoal Bay and Island Harbour, 4 minute drive to Shoal Bay beach and situated on the rocky cliff overlooking the sea. Jems Villa offers the discriminating traveler two bedrooms and two bathrooms with walkouts to...
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    Island Harbour, Anguilla 00000
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Amenities & Details
    • Grill
    • Hot Tub
    • Wi-Fi
    • Patio
    • Waterfront
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and enjoy a view of endless Caribbean blue at the edge Villa Amarilla’s infinity pool. Located in Anguilla, this five bedroom architectural gem boasts a décor as beautiful as the island’s natural surroundings, created in collaboration with award-winning interior designer David Salem. Whether...
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    Location Information
    Island Harbour, Anguilla AI 2640
    Rental Home - 3 Bedrooms, 7 Bathrooms, Sleeps 6
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    5 Bedrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Amarilla on Anguilla sets the standard of excellence on a tropical island known for upscale accommodations. Enter through a welcoming lanai with a profusion of colorful bougainvillea flowers surrounding the intricately designed wrought iron doorway. Step into the grand foyer and prepared to...
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    Location Information
    Island Harbour, Anguilla
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Amenities & Details
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Praised in Architectural Digest twice, this ultra modern villa is the ideal vacation spot for the well traveled who appreciate architectural beauty, unspoiled nature, tranquility, privacy, simple elegance and personalized service. Two four bedroom grand villas, four three bedroom villas and...
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    Island Harbour, Anguilla
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    8 Bedrooms, Sleeps 16 Quick View
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    • Satellite TV
    • DVD Player
    • Internet Access
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Living up to its name, the Villa Beachcourt in Anguilla really does hold court over its own private beach in the sparsely populated Shoal Bay. It is considered one of the finest properties on the island and is large enough to house up to 16 guests comfortably in style and total privacy. Large and...
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    Island Harbour, Anguilla
    Rental Home - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    4 Bedrooms, Sleeps 8 Quick View
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    • Terrace
    • DVD Player
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Black Pearl on Anguilla is located just steps away from spectacular and sought after Shoal Bay East beach, considered the most magical beach in the entire Caribbean. This lovely private villa is situated at the very tip of the island, offering spectacular panoramic views of the turquoise...
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    Island Harbour, Anguilla
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in an amazing ocean front location, this exclusive 3 bedroom, 3 bathroom villa is open-air living in contemporary design. Verdant gardens, natural stone swimming pool, Jacuzzi and seaside gazebo in expansive private grounds. You will enjoy your own private hideaway in the rural tranquility...
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    Island Harbour, Anguilla 00000
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 12 Quick View
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    • Waterfront
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Washer
    • Air Conditioning
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Mahal Oceanfront  is located in Black Garden Bay with access to its own secluded beach on the tropical island of Anguilla. Sprawled out over 4,500 square feet of lavishing living space, this contemporary and family-friendly villa accommodates up to 12 guests and makes hosting family...
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    Island Harbour, Anguilla AI 2640
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, Sleeps 8 Quick View
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    • Balcony
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relaxed and comfortably designed, this cozy 4 bedroom new build is perfect for a large family or a group of friends. Situated on the hillside of Shoal Bay East. Kiki Villa offers a 180 degree view of the beautiful, turquoise blue sea. Just a 10 minute walk from the villa to Shoal Bay beach, with...
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    Island Harbour, Anguilla
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8 Quick View
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    • Internet Access
    • Balcony
    • Terrace
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Soleil Villa at Captain's Bay is a new 5,500 square foot vacation villa and features four air conditioned bedroom suites. From every vantage point, the villa has the most spectacular views of Scrub Island, Scilly Cay, Captains Bay and Savannah Bay. Luxury awaits you in every room of the villa. Four...
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    Island Harbour, Anguilla
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    8 Bedrooms, Sleeps 16 Quick View
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    • Washer
    • Satellite TV
    • Hot Tub
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With impressive views of the Atlantic, the Villa Ultimacy is located in Anguilla and rests between Shoal Bay East and Island Harbor. Peaceful and secluded, it is an eight-room masterpiece of luxury and world-class amenities. It is a fabulous place for the ultimate family holiday, but is also...
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    Island Harbour, Anguilla
    Rental Home - 8 Bedrooms, 10 Bathrooms, Sleeps 16
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    4 Bedrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Internet Access
    • Grill
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fountain Beach Villa is located on Shoal Bay East on the tropical island of Anguilla and is a short walk to Shoal Bay Beach. The villa features four bedroom suites each with a private bathroom, an outdoor shower garden, air conditioning and a flat screen TV. Indoor spaces are full of verve and...
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    Island Harbour, Anguilla
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    1 Bedroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Terrace
    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Balcony
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Island Harbour, Anguilla AI 2640
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, Sleeps 6 Quick View
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    • DVD Player
    • Terrace
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    Smoking allowed
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    Island Harbour, Anguilla 00000
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Balcony
    • Patio
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    Pet friendly
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    Island Harbour, Anguilla
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Patio
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    • Hot Tub
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    Pet friendly
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    Smoking allowed
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    Island Harbour, Anguilla BWI
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 10 Quick View
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    • Washer
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    Smoking allowed
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    Island Harbour, Anguilla
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    • Private Outdoor Pool (Unheated)
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    Island Harbour, Anguilla AI 2640
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Reviews
    3 Bedrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Balcony
    • Air Conditioning
    • Parking
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    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 25, 2017
    Villa Jems offers breathtaking blue water views and all the comforts of home. We enjoyed relaxing and dining on the spacious deck overlooking the great pool and the water view...
    Reviewed February 12, 2014
    This is a tranquil vacation spot. The private pool is a perfect place to relax all day with a sun-hat and a good book. I spent 10 days decompressing from the stress of urban...
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    About this property
    'JEMS' is beautifully situated with sweeping ocean views and magnificent sunsets. The villa offers the discriminating traveler 3 main bedrooms and 3 main baths with walk-outs to the lovely pool and galleries from the principal rooms. JEMS Villa has a wonderful garden for alfresco dining. Walk...
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    Location Information
    Island Harbour, Anguilla AL 2640
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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