1. USA
  2. Hawaii
  3. Princeville
  4. Island Sails
  5. Rentals by Owner

Island Sails Rentals by Owner

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7.8 (471 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
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10.0 (4 Reviews)
House
  • Parking
  • Security/Safety
  • Sports/Activities
10.0 (4 Reviews)
Apartment
  • Parking
  • Pool
  • Security/Safety

Why Choose Rent By Owner for your Island Sails vacation rental?

What makes our Rentals by Owner 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 Sails

When should you plan your Rentals by Owner stay?

Determining the ideal time to visit can enhance your experience here, as understanding seasonal trends and weather patterns in this region helps you select the perfect moment to enjoy your rental by owner in Island Sails, Princeville, Hawaii.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, the area experiences its peak season with warm temperatures and vibrant scenery, making it an ideal time for enjoying outdoor activities.

Average Temperature Daytime: 78°F - Nighttime: 65°F
summer
Summer (June to August)

The summer season attracts visitors seeking sunny weather and longer daylight hours, perfect for exploring this island paradise.

Average Temperature Daytime: 85°F - Nighttime: 70°F

Off-Season Highlights

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Spring (March to May)

In spring, fewer travelers arrive, offering you a quieter experience while still enjoying pleasant weather and beautiful landscapes.

Average Temperature Daytime: 77°F - Nighttime: 60°F
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Fall (September to November)

During fall, the region sees a dip in visitors, providing a more relaxed atmosphere and excellent opportunities for exploring at your own pace.

Average Temperature Daytime: 80°F - Nighttime: 62°F

Weekly Weather Forecast for Island Sails

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

  • Access to scenic outdoor swimming pools, perfect for relaxing under the Hawaiian sun.
  • Beautifully maintained landscaped gardens and pathways for leisurely strolls in the fresh air.
  • Private or shared outdoor barbecue grills to enjoy al fresco dining with friends and family.
  • Well-equipped outdoor lounge areas where you can unwind while taking in the tropical surroundings.
  • Direct access to nearby beaches or oceanfront views to enhance your seaside experience.
  • Community tennis courts or other outdoor sports facilities to stay active during your stay.
  • Outdoor showers or rinse stations to keep your gear clean after a day on the beaches.
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Family Activities

  • Hanalei Bay Beach: Enjoy a family day at this scenic beach, perfect for swimming, picnicking, and building sandcastles while taking in stunning mountain views.
  • Kilauea Point National Wildlife Refuge: Explore the refuge to observe native seabirds and possibly spot Hawaiian sea turtles along the rugged coastline.
  • Princeville Botanical Gardens: Discover this lush garden with guided tours that introduce your family to Hawaii’s vibrant flora and tropical plants.
  • Queen’s Bath: Experience a natural ocean pool carved into volcanic rock, ideal for adventurous families willing to explore safely during calm conditions.
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Adult Activities

  • Golfing at Princeville Golf Course: Enjoy a day on the lush greens with stunning ocean views that perfectly complement your game here in this scenic region.
  • Spa and Wellness Treatments: Indulge in rejuvenating spa services designed to relax and revitalize you amidst the tranquil atmosphere of the area.
  • Hiking Hanalei Bay Trail: Explore the natural beauty of the region on a scenic hike along the coastal trail with breathtaking views of the ocean and lush surroundings.
  • Water Activities at Hanalei Bay: Engage in kayaking, paddleboarding, or snorkeling in the clear waters of the bay, offering an authentic experience of this island haven.

Island Sails Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining options: Take advantage of the region’s renowned cuisine by visiting nearby eateries that showcase authentic Hawaiian flavors.
  • Plan outdoor activities early in the day: Maximize your time by scheduling outdoor adventures to enjoy the pleasant climate and scenic views here.
  • Utilize available amenities: Make full use of the condo's amenities, such as private patios or pools, to enhance your relaxing stay in this tropical destination.
  • Respect the natural environment: Help preserve the area's beauty by following eco-friendly practices during your visit to this idyllic part of Hawaii.

Transportation Options

  • Rental Car Services: Renting a car gives you the flexibility to explore the scenic beauty of this area at your own pace, with several providers conveniently located nearby.
  • Public Transportation: The region is served by local buses that offer an affordable and eco-friendly way to get around and reach popular destinations within the island’s northern coast.
  • Taxi and Rideshare Options: Taxis and rideshare services like Uber and Lyft provide quick, reliable transportation for door-to-door convenience here in this tropical destination.
  • Bicycle Rentals: Biking is a great way to enjoy the fresh air and stunning scenery, with several rental shops offering bikes suitable for all ages along the coast.

Local Customs Options

  • Respect for Aloha Spirit: Embracing the local customs in this area means honoring the Aloha Spirit, which emphasizes kindness, respect, and genuine hospitality towards all visitors and residents alike.
  • Traditional Hawaiian Gift-Giving: When visiting here, it’s customary to exchange small tokens or gifts as a sign of goodwill and connection with the community.
  • Observance of Cultural Protocols: You should be mindful of local practices such as removing shoes before entering homes and respecting sacred sites during your stay in this region.
  • Celebration of Local Festivals: Participating in or observing regional events and festivals offers a meaningful way to connect with the area's rich cultural heritage and community spirit.

Frequently Asked Questions About Island Sails Rentals by Owner

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 1270 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 a rental by owner in Island Sails?

The cancellation policy varies depending on the individual listing. You should review the specific rental's terms on the listing page or contact the owner directly to understand the applicable cancellation rules and any associated fees.

4. How do I ensure my reservation is secure when booking in this region?

Reservations are typically secured through the Rent By Owner platform, which offers secure payment options and verified listings. For additional peace of mind, confirm the host’s credentials and read reviews from previous guests before finalizing your booking.

5. Are there any additional fees I should be aware of when staying at a rental by owner here?

Additional fees such as cleaning charges, security deposits, or service fees may apply. These details are usually specified on the listing or during the booking process, so it’s advisable to review the full fee breakdown before confirming your reservation.

6. What amenities can I expect when renting a property by owner in this area?

Most rentals feature amenities tailored to guests’ comfort, such as fully equipped kitchens, Wi-Fi, and laundry facilities. The exact amenities are listed on each property’s page, so be sure to check the details to ensure they meet your needs.

7. How do I contact the property owner if I have questions about my stay?

You can reach out to the owner directly through the messaging system provided on the Rent By Owner platform. It’s recommended to clarify any questions about the property, local regulations, or special requests before completing your booking.

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