Owner Direct Vacation Rentals in Island Harbor Beach

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  3.  Anguilla

  4.  Island Harbour
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119 Island Harbor Beach Vacation Homes From $100

Looking for the ideal vacation rental in Island Harbor Beach? Discover an extensive gallery of private rentals offering space, comfort, and authentic local character. Owner Direct simplifies your search by matching you with verified property options.

Oceanfront Villa with Pool, Jacuzzi and Kayaks on Anguilla Island
Oceanfront Villa with Pool, Jacuzzi and Kayaks on Anguilla Island
Villa
Island Harbour, Anguilla
0.3k from Island Harbor Beach center

Internet, Air Conditioner, Security/Safety, Guest Services, Pet Friendly, Child Friendly

6 Bedrooms5 Guests
New to Booking
$634
Average price / night
Check Availability
Maison HIBERNIA, An Artistic Villa Born from Anguilla’s Renowned  Restaurant
Maison HIBERNIA, An Artistic Villa Born from Anguilla’s Renowned Restaurant
House
Island Harbour, 2640, Anguilla
0.4k from Island Harbor Beach center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$442
Average price / night
Check Availability
Moonlight Cottage
Moonlight Cottage
Apartment
Island Harbor Beach, Island Harbour, Anguilla
0.7k from Island Harbor Beach center

Apartments, Cheap, Accommodations, Parking, Cottages, Lodgings, Vacation rentals, Places to stay, Self-catering

1 Bedroom2 Guests
10.0

Exceptional

8 reviews

$130
Average price / night
Check Availability
Spectacular Oceanview Luxury 5 Bdr Samaji Villa
Spectacular Oceanview Luxury 5 Bdr Samaji Villa
Villa
Island Harbour, AI-2640, Anguilla
0.5k from Island Harbor Beach center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Free Parking, Hot Tub, Internet, Kitchen

5 Bedrooms10 Guests
10.0

Exceptional

5 reviews

$2102
Average price / night
Check Availability
Elleamau
Elleamau
Apartment
Island Harbour, Anguilla
0.9k from Island Harbor Beach center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering, Accessible hotels

1 Bedroom2 Guests
9.8

Exceptional

10 reviews

$166
Average price / night
Check Availability
Ocean Front Villa In Island Harbour, Anguilla BWI
Ocean Front Villa In Island Harbour, Anguilla BWI
Villa
Island Harbour, AI-2640, Anguilla
0.5k from Island Harbor Beach center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

18 reviews

$695
Average price / night
Check Availability
The Hidden Cottage
The Hidden Cottage
Apartment
Welches Hill, Anguilla
2.1k from Island Harbor Beach center

Apartments, Cheap, Accommodations, Parking, Cottages, Lodgings, Vacation rentals, Places to stay, Family

3 Bedrooms6 Guests
9.7

Exceptional

25 reviews

$100
Average price / night
Check Availability
Upstairs 2 bedroom apartment- 5 mins from the beach
Upstairs 2 bedroom apartment- 5 mins from the beach
Apartment
The Valley, 2640, Anguilla
0.6k from Island Harbor Beach center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

8 reviews

$170
Average price / night
Check Availability
J's Place
J's Place
Apartment
East End Village, Anguilla
2.6k from Island Harbor Beach center

Pool, Parking, Air Conditioner, Pet Friendly, Security/Safety, Child Friendly

1 Bedroom4 Guests
New to Booking
$160
Average price / night
Check Availability
Caribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!
Caribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!
Villa
Island Harbour, AL 2640, Anguilla
0.9k from Island Harbor Beach center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry

4 Bedrooms14 Guests
10.0

Exceptional

8 reviews

$1177
Average price / night
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Cozy Coconut
Cozy Coconut
Apartment
East End Village, Anguilla
3.6k from Island Harbor Beach center

Apartments, Accommodations, Parking, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$125
Average price / night
Check Availability
1 Bedroom- 2 mins to Savannah Bay
1 Bedroom- 2 mins to Savannah Bay
Apartment
The Valley, 2640, Anguilla
1.0k from Island Harbor Beach center

Free Parking, Internet, Living Area

1 Bedroom4 Guests
New to Booking
$300
Average price / night
Check Availability
Barefoot Luxury Beach Villa
Barefoot Luxury Beach Villa
House
The Valley, Anguilla
3.6k from Island Harbor Beach center

Balcony/Terrace, Pool, Parking, Pet Friendly, Air Conditioner, Internet, Child Friendly

1 Bedroom4 Guests
New to Booking
$190
Average price / night
Check Availability
Clearview Villas (UPPER): Casual, Bright, Affordable, Perfect for Families
Clearview Villas (UPPER): Casual, Bright, Affordable, Perfect for Families
Villa
Island Harbour, Anguilla
1.0k from Island Harbor Beach center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
10.0

Exceptional

31 reviews

$437
Average price / night
Check Availability
Dolphin Villa
Dolphin Villa
Villa
Long Path, Anguilla
3.8k from Island Harbor Beach center

Air Conditioner, Parking, Internet, Pool, Balcony/Terrace, Child Friendly

4 Bedrooms8 Guests
New to Booking
$680
Average price / night
Check Availability
Very Private & Personal, Villa Hibernia,  Ocean Front Pool & Sea Gazebo,
Very Private & Personal, Villa Hibernia, Ocean Front Pool & Sea Gazebo,
Villa
island harbour, ai2640, Anguilla
1.0k from Island Harbor Beach center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

27 reviews

$970
Average price / night
Check Availability
Cozy one bedroom studio
Cozy one bedroom studio
House
The Valley, 2640, Anguilla
1.1k from Island Harbor Beach center

AC, Dryer, Internet, Kitchen, Laundry, Microwave, Washer

1 Bedroom2 Guests
9.8

Exceptional

9 reviews

$190
Average price / night
Check Availability
Clearview Villas (LOWER): Casual, Bright, Steps from Sea, Great for families!
Clearview Villas (LOWER): Casual, Bright, Steps from Sea, Great for families!
Villa
Island Harbour, Anguilla
1.1k from Island Harbor Beach center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.8

Exceptional

44 reviews

$211
Average price / night
Check Availability
4-bedroom house in charming quiet Harbour Ridge with AC, WiFi. Relax and unwind
4-bedroom house in charming quiet Harbour Ridge with AC, WiFi. Relax and unwind
House
Island Harbour, 2640, Anguilla
1.4k from Island Harbor Beach center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$1361
Average price / night
Check Availability
Ocean Front Secluded Villa, Pool/Jacuzzi, Tennis/Pickleball Court Stunning Views
Ocean Front Secluded Villa, Pool/Jacuzzi, Tennis/Pickleball Court Stunning Views
Villa
White Hill, 2640, Anguilla
1.6k from Island Harbor Beach center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Free Parking, Hot Tub, Internet, Kitchen

4 Bedrooms8 Guests
New to Booking
$1526
Average price / night
Check Availability
Harmony is perfect for family or groups! Lots of space with a breathtaking view!
Harmony is perfect for family or groups! Lots of space with a breathtaking view!
Villa
Shoal Bay, 2640, Anguilla
1.6k from Island Harbor Beach center

AC, Balcony, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Microwave

3 Bedrooms10 Guests
New to Booking
$593
Average price / night
Check Availability

Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Island Harbor Beach.

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Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Frequently Asked Questions

There are a lot of options in Island Harbor Beach. If you plan on staying in the Island Harbor Beach area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Island Harbor Beach

You can explore 119 verified vacation rentals in Island Harbor Beach. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Island Harbor Beach vary depending on the season, property size, and location. Rates typically start from around $100 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Island Harbor Beach include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Island Harbor Beach welcome pets. Currently, 22 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it's recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Island Harbor Beach often include amenities such as Balcony/Terrace, Kitchen, and Bedding/Linens. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.