Island Harbour Holiday Rentals

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Our top choices for Island Harbour holiday rentals

Cozy one bedroom studio

Cozy one bedroom studio
Sea Rocks
9.8 out of 10, Exceptional, (6)
"Hostess and host with the most! Amazing property, Indira and George couldn’t have been more accommodating! "
United States
Tracy
The price is NZ$330
includes taxes & fees
7 Jan - 8 Jan 2026
Cozy one bedroom studio

Cozy 1-bedroom fully furnished apartment located in Island Harbour, Anguilla.

Cozy 1-bedroom fully furnished apartment located in Island Harbour, Anguilla.
The Valley
The price is NZ$337
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy 1-bedroom fully furnished apartment located in Island Harbour, Anguilla.

Lovely 6-bedroom Villa with Pool

Lovely 6-bedroom Villa with Pool
Island Harbour
The price is NZ$6,914
includes taxes & fees
1 Jan - 2 Jan 2026
Lovely 6-bedroom Villa with Pool

Fountain Anguilla

Fountain Anguilla
3.5 star property
Shoal Bay
9.0 out of 10, Wonderful, (62)
"It was very nice property to stay it "
United States
Felicia
The price is NZ$1,093
includes taxes & fees
10 Jan - 11 Jan 2026
Fountain Anguilla

Turtles Nest Beach Resort 

Turtles Nest Beach Resort 
3.0 star property
West End Village
9.4 out of 10, Exceptional, (167)
"Great place on one of the best beaches in Anguilla."
Canada
John
The price is NZ$833
includes taxes & fees
30 Jan - 31 Jan 2026
Turtles Nest Beach Resort 

AIR Residence relax in your home away from home centrally located on Anguilla

AIR Residence relax in your home away from home centrally located on Anguilla
The Valley
9.6 out of 10, Exceptional, (4)
"Quiet place. Great host. Highly recommend. "
United States
Daniel M.
AIR Residence relax in your home away from home centrally located on Anguilla

Fortune Estate East (Rental Car Available)

Fortune Estate East (Rental Car Available)
Alabama
10.0 out of 10, Exceptional, (1)
"The apartment was very modern and well kept. Home away from home. Very comfortable. TV in the bedroom and livingroom. AC in the bedroom and livingroom area to keep cool. The staff were extremely hospitable."
United States
bianca
The price is NZ$375
includes taxes & fees
9 Jan - 10 Jan 2026
Fortune Estate East (Rental Car Available)

Modern Smart Suite w/ free fast WIFI & 5 min beach access

Modern Smart Suite w/ free fast WIFI & 5 min beach access
George Hill
9.8 out of 10, Exceptional, (7)
"Perfect and comfy get away spot! "
United States
iesha
The price is NZ$276
includes taxes & fees
30 Jan - 31 Jan 2026
Modern Smart Suite w/ free fast WIFI & 5 min beach access

Stunning Seaside Beach, Breeze, Cozy, Studio Condo on Sandy Hill Beach

Stunning Seaside Beach, Breeze, Cozy, Studio Condo on Sandy Hill Beach
The Valley
10.0 out of 10, Exceptional, (1)
"Second stay in this location. Love it!"
United States
Vicki
The price is NZ$454
includes taxes & fees
12 Jan - 13 Jan 2026
Stunning Seaside Beach, Breeze, Cozy, Studio Condo on Sandy Hill Beach

Charming 1-bedroom apartment with AC, WiFi in wonderful Tackling

Charming 1-bedroom apartment with AC, WiFi in wonderful Tackling
North Side
8.0 out of 10, Very good, (1)
The price is NZ$296
includes taxes & fees
31 Jan - 1 Feb 2026
Charming 1-bedroom apartment with AC, WiFi in wonderful Tackling

Clean & comfy spacious-1 Bdrm condo w/free fast WIFI & 5 mins to beach

Clean & comfy spacious-1 Bdrm condo w/free fast WIFI & 5 mins to beach
The Valley
9.0 out of 10, Wonderful, (2)
"Every think was good. Suggest better indication for arriving at house. There isn't the civic number, so it's quite difficult guess the right house"
Italy
YLENIA
The price is NZ$336
includes taxes & fees
31 Jan - 1 Feb 2026
Clean & comfy spacious-1 Bdrm condo w/free fast WIFI & 5 mins to beach

Anguilla Vacation Rental Short Term / Long Term

Anguilla Vacation Rental Short Term / Long Term
Mount Fortune
9.4 out of 10, Exceptional, (21)
"The owner went above and beyond to ensure anything that we needed was supplied. Internet was a little slow but I felt that was typical of the area. I hope to go back and visit again in the future. Easy to get around from the property. Everything was great! I even saw the neighbours parrot on the roof one afternoon...how cool is that! I felt well looked after."
United States
Teresa C.
The price is NZ$434
includes taxes & fees
5 Jan - 6 Jan 2026
Anguilla Vacation Rental Short Term / Long Term

Anguilla -James Place Apartments Short Term/ Long Term Lease

Anguilla -James Place Apartments Short Term/ Long Term Lease
Mount Fortune
9.8 out of 10, Exceptional, (6)
"Anguilla is an island of beautiful beaches and people. You need a car to visit the beaches and great restaurants so James Place Apartments is a comfortable, quiet base from which to explore. Its spacious accommodations include a fully equipped kitchen so you don’t have to eat all your meals out. Everything is fresh and clean. The bed is comfortable and the bedroom has AC. We loved our stay!"
United States
Kathy H.
The price is NZ$427
includes taxes & fees
5 Jan - 6 Jan 2026
Anguilla -James Place Apartments Short Term/ Long Term Lease

Deany's UpTop Luxury Suite

Deany's UpTop Luxury Suite
The Valley
Deany's UpTop Luxury Suite

OUR STUDIO APARTMENTS COMES EQUIPPED WITH ALL ESSENTIAL NEED

OUR STUDIO APARTMENTS COMES EQUIPPED WITH ALL ESSENTIAL NEED
THE VALLEY
8.6 out of 10, Excellent, (4)
"The property is great for a quiet getaway, as the area is very secluded and safe . All essentials were in the room ."
United States
Sheena C.
The price is NZ$241
includes taxes & fees
9 Jan - 10 Jan 2026
OUR STUDIO APARTMENTS COMES EQUIPPED WITH ALL ESSENTIAL NEED

Dream Weaver Villa in RendezVous Bay

Dream Weaver Villa in RendezVous Bay
RendezVous Bay
10.0 out of 10, Exceptional, (1)
"It’s a beautiful house with large rooms. The host and his daughter are so helpful. Whatever you need they will accomadate. We arrived late and they arranged to have food for us at the house. Just a beautiful house with comfortable beds. We were very happy and would go back anytime."
United States
Bert V.
The price is NZ$1,867
includes taxes & fees
2 Jan - 3 Jan 2026
Dream Weaver Villa in RendezVous Bay

Lovely studio apartment Beachfront/swimming pool

Lovely studio apartment Beachfront/swimming pool
Seafeathers
The price is NZ$308
includes taxes & fees
3 Jan - 4 Jan 2026
Lovely studio apartment Beachfront/swimming pool

Sheriva Luxury Villas and Suites

Sheriva Luxury Villas and Suites
4.0 star property
West End Village
Sheriva Luxury Villas and Suites

Home away from home in paradise

Home away from home in paradise
Anguilla
2.0 out of 10, (1)
"leaves much to be desired in both offering and services"
United States
Marlyn L.
The price is NZ$316
includes taxes & fees
1 Jan - 2 Jan 2026
Home away from home in paradise
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Island Harbour Hotel Reviews

Find out more about Island Harbour

Everything you need to know about Island Harbour holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Island Harbour holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Island Harbour holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Island Harbour holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Island Harbour. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Island Harbour holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Island Harbour holiday rentals we have selected for you start as low as NZ$331 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Island Harbour rentals

At Expedia, we put the best Island Harbour holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Island Harbour rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Island Harbour holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Island Harbour. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Island Harbour?

Yes, there are holiday rentals close to the most popular sights in Island Harbour, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Island Harbour. Make sure you have time to check out the parks and waterfront during your trip.

What are some of the best holiday rentals that Island Harbour has to offer?

Zen is Private, Tranquil, and Perfectly Located near Shoal Bay Beach!: This highly rated holiday home rental in Island Harbour offers a balcony, 1 hot tub and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Some other homes for rent in Island Harbour include Cozy one bedroom studio and 4-bedroom house in charming quiet Harbour Ridge with AC, WiFi. Relax and unwind.

How many holiday rentals will I find in Island Harbour?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Island Harbour stay.

What can I see and do in Island Harbour?

Island Harbor Beach and Scilly Cay are a couple of lovely local spots to get outside and enjoy nature. Captain's Bay Beach and Maho Beach are a couple of places you'll find in the wider area.

What are holiday rentals like in Island Harbour?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Island Harbour. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a small group gathering.