1. Anguilla
  2. Island Harbour
  3. Cottage Rentals

Island Harbour Cottage Rentals

10.0
Exceptional
(11 Reviews)
2 Guests 1 Bedroom 1 Bathroom
Family Friendly Cottage
  • Balcony/Terrace
  • Kitchen
  • Parking
AU $447/Night For 7 Nights AU $3,128
10.0
Exceptional
(8 Reviews)
2 Guests 1 Bedroom 1 Bathroom
Apartment
  • Balcony/Terrace
  • View
  • Parking
AU $182/Night For 7 Nights AU $1,276
8.8
Fabulous
(6 Reviews)
1200 ft² 2 Guests 2 Bedrooms 1 Bathroom
Ocean View Cottage
  • Oceanfront
  • Ocean View
  • Balcony/Terrace
AU $495/Night For 7 Nights AU $3,462
9.5
Exceptional
(29 Reviews)
566.9 ft² 6 Guests 3 Bedrooms 3 Bathrooms
Free Cancellation Apartment
  • View
  • Parking
  • Air Conditioner
AU $201/Night For 7 Nights AU $1,407
10.0
Exceptional
(51 Reviews)
5000 ft² 10 Guests 4 Bedrooms 3 Bathrooms
Ocean View Villa
  • Private Pool
  • Pool
  • Ocean View
AU $1,741/Night For 7 Nights AU $12,183
10.0
Exceptional
(1 Review)
8 Guests 4 Bedrooms 4 Bathrooms
Free Cancellation Apartment
  • Pet Friendly
  • Parking
  • Air Conditioner
AU $238/Night For 7 Nights AU $1,669
9.0
Exceptional
(65 Reviews)
2 Guests 1 Bedroom 1 Bathroom
Ocean View Condo
  • Oceanfront
  • Pool
  • Ocean View
AU $1,023/Night For 7 Nights AU $7,165
10.0
Exceptional
(31 Reviews)
3500 ft² 8 Guests 4 Bedrooms 4 Bathrooms
Ocean View Villa
  • Ocean View
  • Balcony/Terrace
  • View
AU $629/Night For 7 Nights AU $4,404
9.8
Exceptional
(10 Reviews)
13993.08 ft² 2 Guests 1 Bedroom 1 Bathroom
Ocean View Apartment
  • Oceanfront
  • Ocean View
  • Balcony/Terrace
AU $233/Night For 7 Nights AU $1,630
10.0
Exceptional
(26 Reviews)
3240 ft² 4 Guests 2 Bedrooms 2 Bathrooms
Ocean View Villa
  • Private Pool
  • Pool
  • Ocean View
AU $1,144/Night For 7 Nights AU $8,009
9.2
Exceptional
(7 Reviews)
4 Guests 2 Bedrooms 4 Bathrooms
Apartment
  • Balcony/Terrace
  • View
  • Parking
AU $269/Night For 7 Nights AU $1,885
10.0
Exceptional
(26 Reviews)
2 Guests 1 Bedroom 1 Bathroom
Ocean View Villa
  • Oceanfront
  • Ocean View
  • Balcony/Terrace
AU $716/Night For 7 Nights AU $5,012

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Why Choose Rent By Owner for your Island Harbour Cottage Rentals?

What makes our Cottage Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Island Harbour

When should you plan your Cottage Rentals stay?

Choosing the optimal time to visit here can enhance your experience, as the best seasons often depend on weather patterns and local events that influence availability at cottages in this charming destination.

Peak Season Highlights

spring
December to April

During this period, you can enjoy warm and sunny weather with minimal rainfall, making it ideal for exploring the region's natural beauty and relaxing at your cottage by the water.

Average Temperature Daytime: 27-30°C - Nighttime: 21-24°C
spring
Late July to September

This peak season offers a lively atmosphere with optimal beach conditions, perfect for those seeking vibrant local events and clear, calm seas around the area.

Average Temperature Daytime: 29-31°C - Nighttime: 24-26°C

Off-Season Highlights

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May to June

In these months, you’ll find fewer visitors and more tranquil surroundings, providing an excellent opportunity for peaceful stays in this destination’s cozy cottages.

Average Temperature Daytime: 28-30°C - Nighttime: 22-24°C
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October to November

As the weather begins to cool slightly, the area remains a serene retreat with fewer crowds, making it an ideal time to unwind comfortably in your cottage rental.

Average Temperature Daytime: 26-28°C - Nighttime: 21-23°C

Weekly Weather Forecast for Island Harbour

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy spacious outdoor dining areas perfect for meals with a view of the surrounding waters.
  • Relax on private balconies or terraces that overlook the scenic landscape of the area.
  • Take advantage of well-maintained outdoor pools to cool off and unwind in the warm climate.
  • Make use of outdoor grilling facilities to prepare homemade meals with fresh local ingredients.
  • Benefit from lush gardens or landscaped yards that offer peaceful spots for reading or lounging.
  • Utilize direct access to nearby beaches or waterfront areas for sunbathing and water activities.
  • Participate in outdoor activities such as kayaking, paddleboarding, or boating right from your doorstep.
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Family Activities

  • Island Harbour Kayaking Tours Explore the calm waters and scenic coastline by kayak, offering a family-friendly way to enjoy the area's natural beauty.
  • Local Fishing Experiences Engage in beginner-friendly fishing excursions that introduce your family to Anguilla’s vibrant marine life along the tranquil shores.
  • Beach Picnics at Island Harbour Spend a relaxing day with a picnic on the beach, where you can unwind and enjoy the stunning ocean views with your loved ones.
  • Nature Walks and Bird Watching Discover the local flora and fauna through guided walks, perfect for family members of all ages interested in wildlife and nature.
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Adult Activities

  • Sailing and Boating: Spend your day exploring the serene waters with local boat rentals, offering a unique perspective of this destination’s maritime beauty.
  • Fishing Excursions: Enjoy tranquil fishing trips where you can unwind and potentially catch some of the region’s abundant marine life.
  • Water Sports: Engage in exhilarating water activities like kayaking or paddleboarding, perfect for a fun and active experience here.
  • Dining by the Waterfront: Indulge in the area’s fresh seafood and local cuisine at waterfront restaurants, immersing yourself in the regional flavors.

Other Places to Stay in Island Harbour

Island Harbor Beach
Captain's Bay Beach

Island Harbour Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities in Advance: Research and organize local experiences and natural attractions to make the most of your time here, ensuring you reserve the best cottages close to your preferred destinations.
  • Explore Coastal Dining Options: Take advantage of the region’s fresh seafood and waterfront eateries by planning visits around your cottage stay, enhancing your overall experience.
  • Engage with Local Culture: Immerse yourself in the area's vibrant community by participating in local events or markets, which can be conveniently accessed from well-located cottages.
  • Choose a Cottage in a Prime Location: Select accommodations that offer easy access to both the serene waters and the lively spots nearby, allowing you to enjoy this destination fully without long commutes.

Transportation Options

  • Car Rentals: Renting a car offers the most flexibility when exploring this destination, allowing you to easily access local sights and activities from your cottage.
  • Taxis: Taxis provide convenient and reliable transportation for quick trips around the area without the need for personal vehicle ownership.
  • Public Buses: Public buses are an economical choice for getting around here, connecting key points of interest in the region efficiently.
  • Shuttle Services: Shuttle services operate between popular locations and your cottage, offering a comfortable and stress-free travel option here.

Local Customs Options

  • Respectful Greetings When visiting local communities, it is customary to greet others with warmth and friendliness, reflecting the welcoming spirit of this Caribbean destination.
  • Celebrating Local Festivals Engaging in traditional festivals often involves lively music, dance, and vibrant attire, offering a unique glimpse into the area's rich cultural heritage.
  • Traditional Cuisine Etiquette It is common to share meals communally and show appreciation for local dishes, which are an integral part of the island’s hospitality and customs.
  • Environmental Respect Visitors are encouraged to respect the natural surroundings by minimizing waste and avoiding harm to coastal and marine ecosystems here in this tranquil region.

Frequently Asked Questions About Island Harbour Rental Cottages

2. How many Cottages are available in Island Harbour?

Currently, the total number of properties listed by RBO in 2026 is over 4 in the Island Harbour area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Island Harbour. 

3. What is the cancellation policy for cottages in this area?

Cancellation policies vary depending on the individual listing. It is recommended to review the specific cancellation terms listed for each cottage before booking or contact the property owner directly for detailed information.

4. Are there any additional fees I should be aware of when booking a cottage here?

Additional fees such as cleaning charges, service fees, or taxes may apply and are usually detailed in the listing. To ensure transparency, please read the full description or reach out to the owner for clarification.

5. What amenities are typically included with cottages in this destination?

Most cottages offer essential amenities like Wi-Fi, air conditioning, kitchen facilities, and outdoor spaces. For a complete list of available amenities, refer to the individual property listing or contact the owner directly.

6. How do I ensure my booking in this region is secure and reliable?

Booking through verified listings ensures a secure process. Each cottage listing is managed by the owner or an authorized agent, providing you with confidence in your reservation. For further assurance, contact the host directly to confirm details before booking.

7. Is there a specific check-in and check-out procedure I should follow during my stay?

Check-in and check-out procedures are outlined in each listing and may vary between properties. It is advisable to review the instructions provided or contact the owner directly to coordinate your arrival and departure times.

More Rentals You May Like Near Island Harbour

9.0
Exceptional
(3 Reviews)
193.75 ft² 2 Guests 1 Bedroom 1 Bathroom
Family Friendly Bed & Breakfast
  • Hot Tub
  • Balcony/Terrace
  • Parking
AU $132/Night For 7 Nights AU $923
10.0
Exceptional
(24 Reviews)
4 Guests 2 Bedrooms 2 Bathrooms
Ocean View Condo
  • Oceanfront
  • Pool
  • Ocean View
AU $777/Night For 7 Nights AU $5,437
New
8 Guests 4 Bedrooms 4 Bathrooms
Free Cancellation Villa
  • Pool
  • Balcony/Terrace
  • Parking
AU $954/Night For 7 Nights AU $6,676
10.0
Exceptional
(18 Reviews)
4000 ft² 6 Guests 3 Bedrooms 3 Bathrooms
Ocean View Villa
  • Private Pool
  • Fireplace/Heating
  • Pool
AU $943/Night For 7 Nights AU $6,604
New
2497.23 ft² 6 Guests 1 Bedroom 3 Bathrooms
Free Cancellation House
  • Balcony/Terrace
  • Pet Friendly
  • Parking
AU $421/Night For 7 Nights AU $2,945
10.0
Exceptional
(13 Reviews)
5000 ft² 12 Guests 5 Bedrooms 5 Bathrooms
Ocean View Villa
  • Private Pool
  • Oceanfront
  • Hot Tub
AU $2,158/Night For 7 Nights AU $15,109
10.0
Exceptional
(12 Reviews)
5 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Villa
  • Balcony/Terrace
  • Kitchen
  • Parking
AU $619/Night For 7 Nights AU $4,335
10.0
Exceptional
(12 Reviews)
6 Guests 2 Bedrooms 2 Bathrooms
Family Friendly House
  • Kitchen
  • Parking
  • Internet
AU $276/Night For 7 Nights AU $1,931
10.0
Exceptional
(9 Reviews)
10 Guests 4 Bedrooms 3 Bathrooms
Ocean View House
  • Private Pool
  • Pool
  • Ocean View
AU $2,830/Night For 7 Nights AU $19,813
10.0
Exceptional
(8 Reviews)
4 Guests 2 Bedrooms 1 Bathroom
Ocean View Apartment
  • Ocean View
  • Balcony/Terrace
  • View
AU $194/Night For 7 Nights AU $1,358
10.0
Exceptional
(6 Reviews)
5100 ft² 14 Guests 4 Bedrooms 4 Bathrooms
Ocean View Villa
  • Private Pool
  • Pool
  • Ocean View
AU $1,552/Night For 7 Nights AU $10,865
10.0
Exceptional
(5 Reviews)
10 Guests 5 Bedrooms 3 Bathrooms
Ocean View Villa
  • Private Pool
  • Oceanfront
  • Hot Tub
AU $2,575/Night For 7 Nights AU $18,024

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