Discover Your Perfect Island Sails Vacation Homes

Best Vacation Homes in Island Sails

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10.0 (4 Reviews)
House
Hanalei Bay Villa 26
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10.0 (4 Reviews)
Apartment
Mauna Kai 5B
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  • Pool
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Why Choose Rent By Owner for your Island Sails Vacation Rental Homes?

What makes our Vacation 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.

Popular Areas for Island Sails Vacation Rentals

Where are the best neighborhoods to stay in Island Sails?

When selecting a neighborhood to stay in Island Sails, Princeville, Hawaii, you’ll find that the area offers a peaceful and scenic environment perfect for relaxing getaways. Surrounded by lush landscapes and stunning ocean views, this community provides easy access to the natural beauty of Princeville while maintaining a tranquil atmosphere. Whether you're seeking proximity to outdoor activities or simply want to enjoy the serene Hawaiian landscape, choosing a place within Island Sails ensures a convenient and comfortable base for your vacation experience. Discover the charm of staying in one of the most desirable neighborhoods in Princeville for an unforgettable Hawaiian escape.

Kaiulani

Located in the scenic Princeville area, Kaiulani offers a peaceful retreat with easy access to the region's lush landscapes and beautiful beaches. It's an ideal spot for those seeking a tranquil atmosphere while exploring what this part of Hawaii has to offer.

View 27+ Rentals in Kaiulani

Queen Emmas Bluffs

Perched overlooking stunning coastal views, Queen Emmas Bluffs provides a desirable setting for your stay in Princeville, blending natural beauty with convenient proximity to the area's premier attractions. Find your perfect getaway here to enjoy the serenity and scenic vistas of this destination.

View 2709+ Rentals in Queen Emmas Bluffs

Kawaihau

Nestled within the region near Kapaa, Kawaihau is known for its lush surroundings and peaceful ambiance, making it a great choice for travelers looking to immerse themselves in Hawaii’s natural charm. Here, you can enjoy the quiet beauty that defines this part of the island.

View 194+ Rentals in Kawaihau

Wailua Homesteads

Set in the scenic landscape of Kapaa, Wailua Homesteads offers a welcoming environment surrounded by verdant greenery and outdoor adventures. It’s a perfect base for exploring the region’s unique blend of culture and nature.

View 114+ Rentals in Wailua Homesteads

Hanalei Palms

Situated in the charming town of Hanalei, Hanalei Palms provides a comfortable retreat close to the region’s renowned beaches and lush scenery. This neighborhood is ideal for those wanting to experience the relaxed island lifestyle.

View 1942+ Rentals in Hanalei Palms

Kapahi

Located in the heart of Kapaa, Kapahi offers a convenient setting with easy access to local shops and the region's natural splendors. It’s an excellent choice for travelers seeking a balance of comfort and exploration in this tropical destination.

View 1383+ Rentals in Kapahi

Best Times to Visit Island Sails

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can significantly enhance your experience, as the best seasons for enjoying the region's beautiful climate and outdoor activities typically fall during specific months of the year.

Peak Season Highlights

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Winter (December to February)

During these months, you can enjoy the warm tropical climate of this Hawaiian region, making it an ideal time for outdoor activities and exploring the area's natural beauty.

Average Temperature Daytime: 75°F to 80°F - Nighttime: 65°F to 70°F
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Summer (June to August)

The summer months bring peak visitation due to sunny weather and optimal conditions for outdoor excursions, which are perfect for experiencing what the area has to offer.

Average Temperature Daytime: 85°F to 89°F - Nighttime: 70°F to 75°F

Off-Season Highlights

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Spring (March to May)

In spring, you’ll find fewer crowds and pleasant weather, offering a more relaxed experience when exploring the region’s scenic spots.

Average Temperature Daytime: 78°F to 82°F - Nighttime: 60°F to 65°F
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Fall (September to November)

Fall provides a quieter atmosphere with comfortable temperatures, making it an excellent time to enjoy the tranquility of this destination without the peak season crowds.

Average Temperature Daytime: 80°F to 85°F - Nighttime: 65°F to 70°F

Weekly Weather Forecast for Island Sails

How to Book Your Island Sails Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

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.

Explore and book the perfect rental in Island Sails

More Top-Rated Vacation Rentals in Island Sails Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

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

  • Access to lush outdoor gardens where you can enjoy the tropical scenery of this island destination.
  • Private or shared outdoor swimming pools perfect for relaxing under the Hawaii sun.
  • Well-maintained barbecue areas for hosting outdoor meals with picturesque views of the region.
  • Spacious patios or lanais ideal for lounging and taking in the warm island breezes.
  • Outdoor shower facilities that let you rinse off after a day at the nearby beaches.
  • Easy access to scenic walking trails or paths that showcase the natural beauty surrounding the area.
  • Outdoor recreational spaces such as tennis courts or playgrounds, suitable for family fun or active pursuits.

Top Attractions Around Island Sails

What attractions are nearby?

While staying here, you can explore nearby hiking trails and water activities that showcase the natural beauty of the region, making it easy to enjoy local adventures just minutes from your vacation rental in this idyllic Hawaiian destination.

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Family Activities

  • Na Pali Coast Snorkeling Tour: Immerse yourself in vibrant marine life as you explore the breathtaking cliffs and secluded beaches along the coast nearby.
  • Princeville Botanical Gardens: Discover the stunning variety of tropical plants and enjoy a family-friendly guided tour through lush, scenic landscapes.
  • Kilauea Point National Wildlife Refuge: Observe native seabirds and maybe even spotting some Hawaiian monk seals at this accessible wildlife refuge on the island’s northern tip.
  • Hanalei Bay Beach Activities: Relax on the soft sands and participate in safe, family-oriented water sports while taking in the picturesque views of the surrounding mountains.
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Adult Activities

  • Sailing Tours: Experience the stunning coastline on a sailing tour that offers breathtaking views and a chance to observe local marine life.
  • Golfing at Princeville Makai Golf Club: Tee off amidst lush landscapes and ocean vistas at one of the most scenic golf courses in the region, perfect for golf enthusiasts.
  • Snorkeling Adventures: Explore vibrant coral reefs and encounter colorful marine species just offshore here, ideal for underwater discovery.
  • Spa and Wellness Experiences: Unwind with luxurious spa treatments inspired by the natural beauty of the area, providing relaxation during your stay.

Island Sails Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local beaches: Take advantage of the nearby coastlines to enjoy sunbathing, swimming, or water activities in this beautiful region.
  • Visit scenic viewpoints: Enjoy breathtaking vistas from spots around here that highlight the natural beauty of the area’s lush landscapes and coastlines.
  • Experience local cuisine: Savor authentic flavors by dining at nearby restaurants that showcase the region’s fresh seafood and tropical ingredients.
  • Utilize outdoor activities: Make the most of opportunities for hiking, snorkeling, or other adventures right in the area’s scenic surroundings.

Transportation Options

  • Rental Car Services: You can easily explore the region by renting a car, offering flexibility and convenience to visit nearby beaches and attractions from Island Sails.
  • Public Transportation: Local buses provide an affordable way to navigate this destination, connecting you to key spots throughout the area without hassle.
  • Taxi and Ride-Sharing Options: Taxis and ride-sharing services are readily available, providing quick transportation for your trips around Princeville and beyond.
  • Bicycle Rentals: For a more eco-friendly option, consider renting a bicycle to enjoy scenic rides along the coastlines and within the local community here.

Local Customs Options

  • Respect for Aloha Spirit: When visiting, you are encouraged to embrace the Aloha Spirit, which emphasizes kindness, respect, and harmony with locals and visitors alike in this region.
  • Hula and Cultural Celebrations: Participating or observing traditional hula performances and local festivals gives you a deeper understanding of the area's rich cultural heritage.
  • Shell and Ocean Respect: Collecting shells or interacting with marine life should be done responsibly, as the ocean environment here is considered sacred and vital to the community.
  • Lei Giving Etiquette: Offering or accepting leis is a cherished custom that symbolizes greeting and respect in this destination, often seen during welcoming ceremonies or special occasions.

Frequently Asked Questions About Island Sails?

1. What are the top vacation rentals in Island Sails?

There are a lot of options in Island Sails. If you plan on staying in the Island Sails 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 Sails:

2. How many Rentbyowner vacation rentals are available in Island Sails?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 2774 in the Island Sails area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Island Sails. 

3. What is the cancellation policy for booking a vacation rental in Island Sails, Princeville?

The cancellation policy varies by property, so you should review the specific listing details or contact the owner directly to understand the terms and potential refunds related to your stay.

4. How do I confirm the availability of a vacation rental in Island Sails, Princeville?

Availability is updated regularly on the listing. You can check real-time availability when you search, or reach out to the property owner for confirmation if needed.

5. Are there any additional fees I should be aware of when booking a vacation rental in Island Sails?

Additional fees such as cleaning charges, security deposits, or service fees may apply. These details are listed in the property description, or you can ask the owner for clarification before confirming your reservation.

6. What amenities are typically included in vacation rentals here?

Most properties offer amenities like Wi-Fi, fully equipped kitchens, and laundry facilities. To see what's available at a particular rental, please review the listing details or contact the owner directly.

7. What steps should I take if I need to modify or cancel my reservation in Island Sails, Princeville?

You should review the property's cancellation and modification policies listed on the booking platform, and contact the owner if necessary for assistance with changes to your reservation.

Best Vacation Homes in Island Sails