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Vacation Rentals in Island Harbour, Anguilla

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    Travelers to Island Harbour are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 13
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Location Information
    Island Harbour, Anguilla AI 2640
    1 / 12
    4.5 of 5 bubbles (6) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Great for groups! Enjoy breathtaking ocean views, prevailing sea breezes and stargazing nightly on the wrap-around porch. Minutes away from the world's most unspoiled and secluded beaches, crystal clear water, hiking trails and snorkeling.<BR><BR>This space is unique because of its size and... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
    4 of 5 bubbles Reviewed August 24, 2016
    My family and I spend 9 days at this amazing villa. The rooms were spacious enough to hold 10 people comfortably and with room to spare. The house was equipped with everything we...
    5 of 5 bubbles Reviewed July 23, 2016
    Wow what a spectacular villa. With views of St. Martin Flat Island and St Barts. So spacious with bathrooms you would love to sleep in.Great living space for the whole family. The...
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    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 / 24
    4.5 of 5 bubbles (10) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Perfect for 2<BR><BR>James Place Apartments are located in a quiet secure and well maintained community. It is a perfect base from which guests can enjoy the sun, beaches, and relax. The rooms are spacious, modern and comfortable with private balcony's. The floors are finished with Italian tile... View all property information
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    Island Harbour, Anguilla AI 2460
    4 of 5 bubbles Reviewed March 30, 2016
    As a couple who prefer active RnR and a first time travelers to Anguilla, we were looking to ease ourselves into the local element. James Place apartments fit that requirement...
    5 of 5 bubbles Reviewed January 14, 2016
    My husband and I stayed here 3 nights and we really loved it. The apartment was in great condition and the bed was so so comfortable. We got the best sleep of our entire 12 night...
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    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Quiet neighborhood. Fully furnished, spacious air conditioned private apartment overlooking Island Harbour village, miles of ocean, and Scilly Cay. Enjoy the ocean view from the master bedroom, master bathroom, living/dining area, kitchen and laundry area. Second bedroom and second bathroom with... View all property information
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    Island Harbour, Anguilla AI 2640
    1 / 35
    5 of 5 bubbles (57) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    About this property
    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 pool deck area.... 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 / 7
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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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 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 / 10
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
    Location Information
    Island Harbour, Anguilla
    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
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    Island Harbour, Anguilla AI 2640
    1 / 31
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    • Smoking allowed
    • x
    About this property
    The grandeur of Ultimacy Villa belies its warmth and serenity. Ultimacy offers many secluded spots for quiet conversation, reflection and peaceful meditation to the pulse of the calming surf against the rocks. Ultimacy Villa can comfortably accommodate up to 16 guests in 8 bedrooms for small... View all property information
    Location Information
    Island Harbour, Anguilla 11111
    1 / 10
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Quixotic Villas, Harbour Ridge, Island Harbour, Anguilla Quixotic Villas are a collection of private retreats that nestle amongst Harbour Ridge offering stunning ocean views and relaxing, comfortable Caribbean accommodations. There are four definitive villas, Villa Amor, Villa Elegante, Villa... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 32
    5 of 5 bubbles (2) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    • Grill
    • Sauna
    • Internet Access
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    • Pet-friendly
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    • ?
    • ?
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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 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Island Harbour, Anguilla 00000
    1 / 17
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
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    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Island Harbour, Anguilla 00000
    1 / 43
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    • x
    • Smoking allowed
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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 / 22
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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
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    1 / 21
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    • Grill
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    • ?
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    • ?
    About this property
    Built on a hill forty feet above the water, Beachcourt Villa maximizes the stunning ocean views and breezes of Shoal Bay East in sunny Anguilla. Just seconds from the spacious decks of your villa lie the pristine waters, green foliage and white sands of this remote area of the island. Swimming,... View all property information
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    Island Harbour, Anguilla AI 2640
    1 / 21
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    • Grill
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    • ?
    • ?
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    • ?
    About this property
    Built on a hill forty feet above the water, Beachcourt Villa maximizes the stunning ocean views and breezes of Shoal Bay East in sunny Anguilla. Just seconds from the spacious decks of your villa lie the pristine waters, green foliage and white sands of this remote area of the island. Swimming,... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
    1 / 21
    4 Bedrooms, 8 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • ?
    About this property
    Built on a hill forty feet above the water, Beachcourt Villa maximizes the stunning ocean views and breezes of Shoal Bay East in sunny Anguilla. Just seconds from the spacious decks of your villa lie the pristine waters, green foliage and white sands of this remote area of the island. Swimming,... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
    1 / 21
    7 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
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    • Waterfront
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Built on a hill forty feet above the water, Beachcourt Villa maximizes the stunning ocean views and breezes of Shoal Bay East in sunny Anguilla. Just seconds from the spacious decks of your villa lie the pristine waters, green foliage and white sands of this remote area of the island. Swimming,... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
    1 / 21
    2 Bedrooms, 8 Bathrooms, Sleeps 4 | Quick View
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • ?
    About this property
    Built on a hill forty feet above the water, Beachcourt Villa maximizes the stunning ocean views and breezes of Shoal Bay East in sunny Anguilla. Just seconds from the spacious decks of your villa lie the pristine waters, green foliage and white sands of this remote area of the island. Swimming,... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
    1 / 29
    5 Bedrooms, 7 Bathrooms, Sleeps 10 | Quick View
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    • x
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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 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
    • DVD Player
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    • Balcony
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    • Pet-friendly
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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
    1 / 13
    8 Bedrooms, 10 Bathrooms, Sleeps 16 | Quick View
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    • x
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    • x
    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 / 39
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
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    • x
    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 / 32
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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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
    3 Bedrooms, 6 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Hot Tub
    • Patio
    • Waterfront
    • Sauna
    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
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