We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Holiday rentals in Island Harbour

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Island Harbour

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Home in Shoal Bay Village, Anguilla

4.92 out of 5 average rating, 13 reviews

Shoal Bay Coastal Sanctuary, Anguilla

Shoal Bay Coastal Sanctuary is located directly on the coast with beautiful unobstructed views of the sea. It's a gracious two story home of 3 bedrooms and 3 full bathrooms--the lower level is comprised of 2 bedrooms on either side of an open plan "kitchen / dining room / living room" with the penthouse bedroom on the upper level. All rooms face onto the Caribbean and overlook the freshwater pool--every room is fully screened and air conditioned and graciously decorated in a Caribbean motif.

11–18 Jul

$709 SGD per night

Guest favourite

Villa in Cul-de-Sac, St. Martin

4.99 out of 5 average rating, 116 reviews

VILLA JADE 1: WATERFRONT SUITE/ POOL

VILLA JADE est située dans la baie de "FRENCH CUL DE SAC". C'est un complexe en bord de mer composé de 3 villas privées. VILLA JADE 1 est une suite pour 2 personnes avec piscine privée. Les villas sont calmes et intimes...votre unique vue est la mer. La baie de "FRENCH CUL DE SAC" est à 5 minutes de ORIENT BAY, touristique avec restaurants, bars, activités nautiques, mais aussi à quelques minutes de GRAND CASE, notre petit village typique avec restaurants gastronomiques en bord de mer....

13–20 Aug

$406 SGD per night

Guest favourite

Flat in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 172 reviews

The Beach House Apartment

A stylishly modern one bedroom apartment directly located on the beautiful white sand beach of Simpson Bay. Enjoy the crystal clear waters by day and explore the Caribbean charm of our bustling nightlife. Our island getaway provides you with the full relaxation experience complete with beach chairs, umbrellas, outdoor shower, snorkel gear and paddle boards to complete beach side experience Amenities include free WIFI, kitchen, king size bed, beach chairs, umbrella's and much more

4–11 Oct

$426 SGD per night

Guest favourite

Flat in The Quarter, Anguilla

5.0 out of 5 average rating, 22 reviews

Thrush Nest View Studio Apartment

Forget your worries in this spacious and serene studio apartment designed for relaxation after a long day at the beach . Kick your feet up while enjoying a cup of coffee to the sunrise or a glass of wine to the sunset as this space provides panoramic views from every angle. Located in the centre of the island this vacation apartment is the ideal platform for exploring beaches, island tours and extraordinary dinning. Contemporary decor with modern amenities all can enjoy.

22–29 Jun

$172 SGD per night

Guest favourite

Flat in Shoal Bay, Anguilla

4.95 out of 5 average rating, 21 reviews

Azure at Bayview Homes

Azure, our 1 bedroom home, is one of Anguilla's best kept secrets. Azure is fully equipped and features a living room, dining room, spacious bedroom with air-conditioning and king bed, 1 bathroom, walk in closet, linen closet with extra linens, fully equipped kitchen, large outdoor space, wifi, smart TV, washing machine, dryer and parking. Two barstools are provided for use at the kitchen bar with the living and dining areas comfortably entertaining up to 4 persons each.

23–30 Jun

$279 SGD per night

Guest favourite

Flat in East End Village, Anguilla

5.0 out of 5 average rating, 27 reviews

C&J Apartments overlooking Mimi Bay Beach (Apt 2)

Enjoy Anguilla while staying in a spacious 2 bedroom unit, which is apart of a 2 bedroom 4 unit apartment complex. It was designed and is maintained by the hosts. Each room is tastefully decorated to ensure a calming experience. Pictures add to the decor some featuring the work of the talented artist, Canita Ruan, the hosts' daughter. Ceiling fans are in each room, but you may not need them as the area is pretty cool. The area is very quiet. "Your Home Away From Home"

9–16 Oct

$132 SGD per night

Flat in AI, Anguilla

4.84 out of 5 average rating, 38 reviews

Bow of The Ship Penthouse - Arawak Beach Club

Awake to stunning Caribbean vistas in our favorite suite, 'The Bow Of The Ship,' at Arawak Beach Club. Luxuriate in a California king bed, private balcony, and easy beach bar access. Explore nearby restaurants and grocery stores. Shoal Bay is just a 10-minute drive away. Enjoy Fiber Internet, Smart TV, ocean breezes, and on-site amenities including an oceanfront pool, paddle boards, glass bottom kayaks, and optional rental car.

22–29 Aug

$255 SGD per night

Guest favourite

Flat in Mount Fortune, Anguilla

5.0 out of 5 average rating, 45 reviews

Fortune Estate (Car rental available)

Newly built modern cozy apartment with remote gate access, back up generator and perimeter security camera system located in Mount Fortune on the eastern end of the island. Five minutes driving access to grocery stores, Island Harbour beach and the restaurants thereon like Falcon Nest. 10 minutes drive from the famous Shoal Bay beach.

8–15 Sep

$184 SGD per night

Guest favourite

Villa in Shoal Bay Village, Anguilla

5.0 out of 5 average rating, 15 reviews

BellamareVilla Oceanfront, Pool

Bellamare Villa is located on the edge of Shoal Bay's 1 mile of powdery, white sand beach. We offer uninterrupted ocean views with over 6000 Sq.Ft living space, porches, decks and private pool all on ground level. We are ideal for couples, families, Retirees and Groups. With a charming setting, come enjoy privacy and comfort.

24–31 Oct

$1,503 SGD per night

Guest favourite

Villa in Philipsburg, Sint Maarten

4.99 out of 5 average rating, 226 reviews

Villa Dream View Belair Sint Maarten SXM

Embrace the tranquility in a friendly tropical caribbean modern designed private villa with spacious rooms that are sure to keep you comfortable and feeling at home. Enjoy the sunny day with infinity pool overlooking caribbean sea or enjoy the sea view while watching the sailing huge cruise ships.

15–22 Oct

$632 SGD per night

Flat in Bad Cox Pond, Anguilla

4.88 out of 5 average rating, 17 reviews

The Studio at AXA Farmhouse

Welcome to your tranquil retreat at AXA Farmhouse. This private studio offers a serene getaway, complete with a fully equipped kitchen, a spa-inspired bathroom, and a separate entrance for your convenience. Rest easy on a plush bed, and enjoy the comfort of air conditioning throughout your stay.

2–9 Sep

$156 SGD per night

Guest favourite

Villa in Island Harbour, Anguilla

5.0 out of 5 average rating, 19 reviews

Villa Romantica Overlooking the Ocean

My place is close to family-friendly activities, nightlife, beaches, restaurants. You’ll love my place because of the views, the people, the location, the outdoors space, and the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids).

10–17 Sep

$380 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Island Harbour holiday rentals

Free parking on premises

Air conditioning

Other great holiday rentals in Island Harbour

Guest favourite

Guest suite in The Valley, Anguilla

4.92 out of 5 average rating, 24 reviews

Hidden Treasure

17–24 Jul

$114 SGD per night

Guest favourite

Villa in Upper Prince's Quarter, Sint Maarten

5.0 out of 5 average rating, 36 reviews

EXQUISITE 5-STAR BEACHFRONT VILLA

14–21 Sep

$1,254 SGD per night

Guest favourite

Home in North Side, Anguilla

5.0 out of 5 average rating, 15 reviews

Beautiful newly built one bedroom entire house

19–26 Sep

$205 SGD per night

Guest favourite

Villa in Oyster Pond , Sint Maarten

5.0 out of 5 average rating, 32 reviews

Ultra Modern Tropical Villa w. stunning sea views

30 Nov – 7 Dec

$1,415 SGD per night

Guest favourite

Flat in Grand-Case, St. Martin

5.0 out of 5 average rating, 10 reviews

Charming appartment on the beach, 1 or 2 bedrooms

20–27 Oct

$553 SGD per night

Guest favourite

Guest suite in West End, Anguilla

4.94 out of 5 average rating, 51 reviews

Hummingbird, Charming Garden Studio, West End

27 Mar – 3 Apr

$249 SGD per night

Guest favourite

Flat in Island Harbour, Anguilla

5.0 out of 5 average rating, 7 reviews

Cozy one bedroom studio apartment

3–10 Nov

$156 SGD per night

Guest favourite

Home in Island Harbour, Anguilla

5.0 out of 5 average rating, 6 reviews

Oceanfront Villa With Pool Jacuzzi Near Shoal Bay

26 Sep – 3 Oct

$607 SGD per night

Destinations to explore