Book Holiday Homes in Island Harbour

Start date: Check-in selected.
To Date
End date: Check-out

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Island Harbour

Paradise in Anguilla

Paradise in Anguilla

Sandy Hill
Book a stay at this beach vacation home in The Valley. Enjoy a beach locale, a garden, and laundry facilities. Popular attractions Sandy Hill Bay and Sandy Hill ...
Opens in a new windowParadise in Anguilla
White Sands Anguilla

White Sands Anguilla

3.5 out of 5
Cul De Sac Road, Blowing Point
Stay at this 3.5-star business-friendly vacation home in Blowing Point. Enjoy free WiFi, free parking, and a garden. Popular attractions Grand Case Beach and ...
Opens in a new windowWhite Sands Anguilla
Dream Weaver Villa in RendezVous Bay

Dream Weaver Villa in RendezVous Bay

RendezVous Bay
The price is NZ$1,851 per night from 2 Dec to 3 Dec
NZ$1,851
2 Dec - 3 Dec
includes taxes & fees
Stay at this vacation home in Rendezvous Bay. Enjoy a garden, laundry facilities, and balconies. Popular attractions Rendezvous Bay Beach and Aurora International ...
Opens in a new windowDream Weaver Villa in RendezVous Bay
Save an average of 15% on thousands of hotels when you're signed in
Anguilla's "place to be" spacious 5-bedroom villa on upscale Meads Bay beach

Anguilla's "place to be" spacious 5-bedroom villa on upscale Meads Bay beach

2 out of 5
West End
Stay at this vacation home in West End Village. Enjoy laundry facilities and air conditioning. Popular attractions Meads Bay Beach and Meads Bay are located ...
Opens in a new windowAnguilla's "place to be" spacious 5-bedroom villa on upscale Meads Bay beach
Your Dream Home Awaits: 3-Bedroom Retreat, Close to Everything

Your Dream Home Awaits: 3-Bedroom Retreat, Close to Everything

Cauls Bottom
Stay at this vacation home in The Valley. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Stone Cellar Art Gallery and Scrub Island are ...
Opens in a new windowYour Dream Home Awaits: 3-Bedroom Retreat, Close to Everything
DragonFly Studio, a charming place dedicated to relaxation

DragonFly Studio, a charming place dedicated to relaxation

The Valley
Stay at this vacation home in The Valley. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Scrub Island and Stone Cellar Art Gallery ...
Opens in a new windowDragonFly Studio, a charming place dedicated to relaxation
Cozy one bedroom studio

Cozy one bedroom studio

The Valley
The price is NZ$333 per night from 3 Dec to 4 Dec
NZ$333
3 Dec - 4 Dec
includes taxes & fees
Stay at this vacation home in Island Harbour. Enjoy laundry facilities and air conditioning. Popular attractions Island Harbor Beach and Scilly Cay are located ...
Opens in a new windowCozy one bedroom studio
Sienna is Private, Tranquil,  and Perfectly Located near Shoal Bay Beach!

Sienna is Private, Tranquil, and Perfectly Located near Shoal Bay Beach!

Shoal Bay
Stay at this vacation home in Island Harbour. Enjoy laundry facilities, balconies, and an in-room coffeemaker. Popular attractions Shoal Bay Beach and Island ...
Opens in a new windowSienna is Private, Tranquil, and Perfectly Located near Shoal Bay Beach!
The Little Villa (Newly Renovated)

The Little Villa (Newly Renovated)

anguilla
Stay at this vacation home in The Valley. Enjoy a garden, laundry facilities, and patios. Popular attractions Grand Case Beach and Elsie Bay are located ...
Opens in a new windowThe Little Villa (Newly Renovated)
Don't see what you're looking for?
See all available properties in Island Harbour
View all properties
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.

Island Harbour Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Island Harbour vacation homes are the perfect way for you to wing it.

Holiday houses in Island Harbour let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Island Harbour in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Island Harbour adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Island Harbour with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Island Harbour vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Island Harbour Holiday Homes essential information

Accommodation
43 Holiday Homes
Lowest Price
NZ$333
Highest Price
NZ$1,851
Popular accommodation
Paradise in Anguilla, White Sands Anguilla, Dream Weaver Villa in RendezVous Bay, Anguilla's "place to be" spacious 5-bedroom villa on upscale Meads Bay beach , Your Dream Home Awaits: 3-Bedroom Retreat, Close to Everything , DragonFly Studio, a charming place dedicated to relaxation, Cozy one bedroom studio, Sienna is Private, Tranquil, and Perfectly Located near Shoal Bay Beach!, The Little Villa (Newly Renovated)

Top trending hotels in Island Harbour

Clearview Villas (UPPER): Casual, Bright, Affordable, Perfect for Families

Clearview Villas (UPPER): Casual, Bright, Affordable, Perfect for Families

Island Harbour
Stay at this villa in Island Harbour. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Scilly Cay and Island Harbor Beach ...
Opens in a new windowClearview Villas (UPPER): Casual, Bright, Affordable, Perfect for Families
Caribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!

Caribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!

Island Harbour
Book a stay at this family-friendly villa in Island Harbour. Enjoy private pools, laundry facilities, and balconies. Popular attractions Scilly Cay and Island ...
Opens in a new windowCaribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!
Clearview Villas (LOWER): Casual, Bright, Steps from Sea, Great for families!

Clearview Villas (LOWER): Casual, Bright, Steps from Sea, Great for families!

Island Harbour
Stay at this villa in Island Harbour. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Scilly Cay and Island Harbor Beach ...
Opens in a new windowClearview Villas (LOWER): Casual, Bright, Steps from Sea, Great for families!
Save an average of 15% on thousands of hotels when you're signed in
Beautiful 2000 sq. ft Sunrise & Sunset Penthouse near Shoal Bay Beach, Anguilla

Beautiful 2000 sq. ft Sunrise & Sunset Penthouse near Shoal Bay Beach, Anguilla

Canifest
Stay at this condo in Island Harbour. Enjoy free WiFi, breakfast (surcharge), and laundry facilities. Popular attractions Shoal Bay Beach and Island Harbor Beach ...
Opens in a new windowBeautiful 2000 sq. ft Sunrise & Sunset Penthouse near Shoal Bay Beach, Anguilla
Don't see what you're looking for?
See all available properties in Island Harbour
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.