We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Island Harbour, Anguilla

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    $0
    $1,292 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travelers to Island Harbour are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 15
    4.5 of 5 stars (10) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    1 / 12
    4.5 of 5 stars (6) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    1 / 35
    5 of 5 stars (57) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
    Show Prices
    1 / 10
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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 / 10
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • 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... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 29
    5 of 5 stars (42) Excellent
    7 Bedrooms, 8 Bathrooms, Sleeps 18 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Satellite TV
    • Private Outdoor...
    • Washer
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    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 stars 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 stars 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...
    See all reviews
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Private Yard
    • Satellite TV
    • Patio
    • Parking
    • Ocean Views
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Island Harbour, Anguilla AI 2640
    1 / 5
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Private Yard
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    La Vanda is a charming romantic cottage. Very private part of a larger estate, with a walled back garden with outdoor shower, bar-b-que dinning area as well as sun bathing loungers. It is not on the waterfront, but is a very short walk about 3 meters to famous Shoal Bay East Beach. The area is... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
    5 of 5 stars Reviewed March 13, 2016
    We stayed at Lavanda from February 20 through March 5, 2016.....the pictures don't do the place justice! It was perfect for the two of us, we had never been to Anguilla before and...
    5 of 5 stars Reviewed January 28, 2016
    My wife and I absolutely loved Lavanda Cottage and would not hesitate to stay there again. We have traveled to many islands in the Caribbean and felt like Shoal Bay, and Lavanda...
    See all reviews
    1 / 32
    5 of 5 stars (2) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Parking
    • Air Conditioning
    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
    5 of 5 stars 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...
    See all reviews
    1 / 13
    8 Bedrooms, 10 Bathrooms, Sleeps 16 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Satellite TV
    • Hot Tub
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Island Harbour, Anguilla
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    1 / 25
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • DVD Player
    • Patio
    • Grill
    • Waterfront
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • DVD Player
    • Internet Access
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Island Harbour, Anguilla
    1 / 39
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Satellite TV
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Island Harbour, Anguilla
    1 / 24
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Internet Access
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Island Harbour, Anguilla
    1 / 22
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor...
    • Wi-Fi
    • Washer
    • Patio
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Grill
    Suitability
    • 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
    1 / 7
    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Balcony
    • Air Conditioning
    • Parking
    • DVD Player
    • Private Outdoor...
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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 stars 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...
    See all reviews
    1 / 8
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Hot Tub
    • Private Outdoor...
    • Satellite TV
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-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... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 27
    8 Bedrooms, 10 Bathrooms, Sleeps 16 | Quick View
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • Satellite TV
    • Wi-Fi
    • Washer
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-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... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
    1 / 21
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Construction Note: Please note that there is construction next door to this villa until further notice. Beachcourt Villa will experience noise, depending on what work is being done at the time. Please enquire with one of our Villa Specialists for further details. Built on a hill forty feet above... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
    1 / 21
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Construction Note: Please note that there is construction next door to this villa until further notice. Beachcourt Villa will experience noise, depending on what work is being done at the time. Please enquire with one of our Villa Specialists for further details. Built on a hill forty feet above... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
    Get the List
    1 / 21
    4 Bedrooms, 8 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Construction Note: Please note that there is construction next door to this villa until further notice. Beachcourt Villa will experience noise, depending on what work is being done at the time. Please enquire with one of our Villa Specialists for further details. Built on a hill forty feet above... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
    1 / 21
    7 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Construction Note: Please note that there is construction next door to this villa until further notice. Beachcourt Villa will experience noise, depending on what work is being done at the time. Please enquire with one of our Villa Specialists for further details. Built on a hill forty feet above... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
    1 / 21
    2 Bedrooms, 8 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Construction Note: Please note that there is construction next door to this villa until further notice. Beachcourt Villa will experience noise, depending on what work is being done at the time. Please enquire with one of our Villa Specialists for further details. Built on a hill forty feet above... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
    1 / 32
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Parking
    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 / 32
    3 Bedrooms, 6 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Parking
    • Air Conditioning
    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 / 21
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Private Outdoor...
    • Air Conditioning
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Located just west of Shoal Bay East the views from the pool deck and upper balcony are panoramic and dramatic. Special touches throughout this lovely villa reflect the extensive efforts to make this villa comfortable and relaxing for guests. The home has four bedrooms, five bathrooms and has... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 29
    5 Bedrooms, 7 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Island Harbour, Anguilla AI 2640
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Housekeeping...
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Island Harbour, Anguilla XXXXXX
    1 / 31
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Patio
    • Washer
    • Hot Tub
    • Internet Access
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • 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