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Vacation Rentals in Island Harbour, Anguilla

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    $1,197 Average
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    Travelers to Island Harbour are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 24
    4.5 of 5 bubbles (10) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 31
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    1 / 27
    8 Bedrooms, 10 Bathrooms, Sleeps 16 | Quick View
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    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... View all property information
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    Island Harbour, Anguilla AI 2640
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    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... View all property information
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    Island Harbour, Anguilla XXXXXX
    1 / 7
    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
    Location Information
    Island Harbour, Anguilla AL 2640
    5 of 5 bubbles Reviewed 3 weeks ago
    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...
    5 of 5 bubbles 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 life...
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    1 / 29
    5 of 5 bubbles (42) Excellent
    7 Bedrooms, 8 Bathrooms, Sleeps 18 | Quick View
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    About this property
    MOONRAKER - The ultimate villa in Anguilla for Luxury, Seclusion and Value. Rated overall as "5 star” and loved by all our valued customers. Rated "Excellent" on Tripadvisor and awarded "Top Vacation Rental" on Flipkey/Tripadvisor Moonraker Villa awaits you; a signature, 7 suite, 15,500 sq ft... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
    5 of 5 bubbles Reviewed May 23, 2016
    We Just stayed at Moonraker with a group of 15. My husband and I along with our closest friends, my daughters and their boyfriends all helped us celebrate our 10 year...
    5 of 5 bubbles Reviewed August 19, 2015
    We (15) meet together from three states. The house was perfect for us and we had the most amazing time together. We all had space without being on top of each other. The...
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    1 / 32
    5 of 5 bubbles (2) Excellent
    Studio, 6 Bathrooms, Sleeps 10 | Quick View
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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... View all property information
    Location Information
    Island Harbour, Anguilla
    5 of 5 bubbles 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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    1 / 28
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Our ocean front villa is open-air living in contemporary design. Verdant gardens, natural stone swimming pool, plunge pool and seaside gazebo in expansive private grounds. Your private hideaway in the rural tranquility of Island Harbour village. Since we lived in the villa for 15 years, we can... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
    5 of 5 bubbles Reviewed 1 week ago
    The villa is absolutely wonderful. It has all of the amenities of home in a beautiful location right on the water. The pictures don't do it justice. It is situated perfectly for...
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    1 / 25
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
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    1 / 38
    5 of 5 bubbles (57) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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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... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
    5 of 5 bubbles 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 the...
    5 of 5 bubbles 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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    1 / 29
    5 Bedrooms, 7 Bathrooms, Sleeps 10 | Quick View
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    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... View all property information
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    Island Harbour, Anguilla AI 2640
    1 / 17
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    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... View all property information
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    Island Harbour, Anguilla 00000
    1 / 13
    8 Bedrooms, 10 Bathrooms, Sleeps 16 | Quick View
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    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... View all property information
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    Island Harbour, Anguilla
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
    Location Information
    Island Harbour, Anguilla AI 2640
    1 / 32
    Studio, 6 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Sauna
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    • Pet-friendly
    • Child-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... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
    1 / 32
    Studio, 6 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • Hot Tub
    • Waterfront
    • Internet Access
    • Sauna
    • Grill
    Suitability
    • Pet-friendly
    • Child-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... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
    1 / 16
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
    • Private Outdoor...
    • Wi-Fi
    • DVD Player
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    • Air Conditioning
    • Terrace
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    • Pet-friendly
    • Child-friendly
    • ?
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    • Smoking allowed
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    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... View all property information
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    Island Harbour, Anguilla
    1 / 34
    5 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Epic Beachfront Villa is located on a private and secluded beach, offering luxury living in a relaxing setting on the tropical island of Anguilla. This property has its own private helicopter pad where we can arrange for quick trips to St. Martin and St. Barthelemy. Designed to maximize the 20,000... View all property information
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    Island Harbour, Anguilla
    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
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    • x
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    • x
    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... View all property information
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    Island Harbour, Anguilla
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    1 / 43
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    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... View all property information
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    Island Harbour, Anguilla
    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Island Harbour, Anguilla
    1 / 39
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    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... View all property information
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    Island Harbour, Anguilla
    1 / 24
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    Island Harbour, Anguilla BWI
    1 / 18
    3 Bedrooms, 3 Bathrooms, 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... View all property information
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    Island Harbour, Anguilla 00000
    1 / 8
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    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... View all property information
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    Island Harbour, Anguilla
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Island Harbour, Anguilla 00000
    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Island Harbour, Anguilla AI 2640
    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Island Harbour, Anguilla AI 2640
    1 / 33
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    This family-friendly Seaside Villa is sprawled out over 8,000 square feet and features five bedroom suites, five full bathrooms and comfortably accommodates up to 13 guests. The location sits on a private beach shared by only four other villas, and is minutes away from Shoal Bay Beach and close to... View all property information
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    Island Harbour, Anguilla
    1 / 26
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    An oasis of calm and tranquility is complete at Island Breeze Villa located in Island Harbour on the tropical island of Anguilla. It’s here where you’ll enjoy peace and privacy before the stunning backdrop of the turquoise Caribbean Sea. With five bedrooms and plenty of living space to keep you and... View all property information
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    Island Harbour, Anguilla
    1 / 34
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Epic Beachfront Villa is located on a private and secluded beach, offering luxury living in a relaxing setting on the tropical island of Anguilla.This property has its own private helicopter pad where we can arrange for quick trips to St. Martin and St. Barthelemy. This family-friendly villa... View all property information
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    Island Harbour, Anguilla
    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Island Harbour, Anguilla
    1 / 30
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • x
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    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... View all property information
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    Island Harbour, Anguilla
    1 / 25
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
    Location Information
    Island Harbour, Anguilla
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