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Holiday rentals in Island Harbour

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Top-rated holiday rentals in Island Harbour

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

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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.

30 Jun – 7 Jul

$700 SGD per night

Guest favourite

Flat in The Quarter

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.

11–18 Jun

$170 SGD per night

Guest favourite

Flat in Shoal Bay, Anguilla

4.95 out of 5 average rating, 19 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.

28 Feb – 7 Mar

$279 SGD per night

Guest favourite

Flat in East End Village, Anguilla

5.0 out of 5 average rating, 26 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"

28 Sep – 5 Oct

$130 SGD per night

Guest favourite

Flat in Mount Fortune

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.

6–13 Jul

$181 SGD per night

Guest favourite

Cottage in Cul-de-Sac, St. Martin

4.98 out of 5 average rating, 101 reviews

VILLA JADE 2: WATERFRONT/ POOL

VILLA JADE is a complex of 3 villas located in the CUL DE SAC Bay and its islets ... VILLA JADE 2 is a spacious suite /sea view for 2 people on the waterfront, with private pool. The 3 villas are adjoining but very quiet and intimate. Your only view is the sea... Direct access to the sea by a pontoon, and kayaks at your disposal.

25 Mar – 1 Apr

$482 SGD per night

Guest favourite

Villa in Philipsburg, Sint Maarten

4.99 out of 5 average rating, 224 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.

18–25 Oct

$624 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.

3–10 May

$161 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).

13–20 Oct

$375 SGD per night

Guest favourite

Guest suite in The Valley

4.91 out of 5 average rating, 23 reviews

Hidden Treasure

Hidden Treasure is a unique place with a style of its own. Everything comes to life when contrasted against its hues of green and brings a sense of home that is difficult to escape. From the centrality of location to the variety of amenities offered within, this is a definite win!

19–26 Jul

$112 SGD per night

Guest favourite

Flat in The Valley

4.95 out of 5 average rating, 41 reviews

Fully Equipped Island Apartment with Fruit Garden

Live out your island adventures at this cozy apartment. Unwind at this comfortable one bedroom. Enjoy the privacy of this home with the convenience of being located just 7-minute walk from local supermarket, Ashley and sons. The area feels peaceful and secluded.

22–29 Oct

$112 SGD per night

Flat in Island Harbour, Anguilla

4.92 out of 5 average rating, 12 reviews

Oceanfront Panoramic Suite - Arawak Beach Club

Stay in one of our most popular suites with panoramic island harbor views. Luxurious California king bed, fiber-optic Internet. Full kitchen, kayaks, paddleboards available. Common areas for relaxation. Welcome to Arawak Beach Club!

7–14 Jun

$232 SGD per night

Holiday rentals for every style

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Popular amenities for Island Harbour holiday rentals

Free parking on premises

Air conditioning

Other great holiday rentals in Island Harbour

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

14–21 Nov

$469 SGD per night

Guest favourite

Guest suite in West End, Anguilla

4.94 out of 5 average rating, 50 reviews

Hummingbird, Charming Garden Studio, West End

24–31 Mar

$246 SGD per night

Guest favourite

Apartment in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 56 reviews

Beach front luxury! Huge 2BR that has it all! 😍🤩😍

24–31 Aug

$938 SGD per night

Guest favourite

Home in North Side, Anguilla

5.0 out of 5 average rating, 14 reviews

Beautiful newly built one bedroom entire house

24 Nov – 1 Dec

$207 SGD per night

Flat in North Side, Anguilla

4.88 out of 5 average rating, 33 reviews

KC Corner House

3–10 Nov

$123 SGD per night

Guest favourite

Home in Cul de Sac, St. Martin

5.0 out of 5 average rating, 48 reviews

villa koala saint martin un petit coin de paradis

16–23 May

$555 SGD per night

Flat in AI, Anguilla

4.83 out of 5 average rating, 36 reviews

Bow of The Ship Penthouse - Arawak Beach Club

13–20 Oct

$257 SGD per night

Guest favourite

Home in Island Harbour, Anguilla

5.0 out of 5 average rating, 5 reviews

Oceanfront Villa With Pool Jacuzzi Near Shoal Bay

11–18 Oct

$535 SGD per night

Destinations to explore