- USA
- Hawaii
- Princeville
- Island Sails
- Rentals by Owner
Discover Your Perfect Island Sails Rental by Owner in Princeville, Hawaii for an Authentic Hawaiian Getaway
Discover Your Perfect Island Sails Rentals by Owner
-
Rentals by Owner
-
Luxury Vacation Rentals
-
Pet Friendly Vacation Rentals
-
Unique Vacation Rentals
-
Cabin Rentals
-
Cottage Rentals
-
Ski Chalet Rentals
-
Timeshares
-
Villa Rentals
-
Hotels with Suites
-
Resort Rentals
-
Family Vacation Rentals
-
Vacation Rentals with Pools
-
Oceanfront Vacation Rentals
-
Beach House Rentals
-
Summer Vacation Rentals
-
Winter Vacation Rentals
-
Short Term Rentals
-
Corporate Accommodation
-
Large Group Vacation Rentals
-
Sustainable Travel
Island Sails Rentals by Owner
- Parking
- TV
- Security/Safety
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
- Parking
- Security/Safety
- Sports/Activities
- Air Conditioner
- Parking
- TV
- Parking
- Pool
- Security/Safety
- Security/Safety
- Bedding/Linens
- Wellness Facilities
- Parking
- Pool
- View
- Security/Safety
- Bedding/Linens
- Wellness Facilities
- Parking
- Pool
- Security/Safety
- Security/Safety
- Bedding/Linens
- Wellness Facilities
Why Choose Rent By Owner for your Island Sails vacation rental?
What makes our Rentals by Owner special?
Popular Areas for Island Sails Rentals by Owner
Where are the best neighborhoods to stay in Island Sails?
When choosing a place to stay in Island Sails, Princeville, Hawaii, you’ll find that the neighborhood offers a tranquil and scenic setting perfect for relaxing and exploring. Known for its lush landscapes and stunning ocean views, this area provides easy access to some of the most beautiful beachfronts on the island. Whether you prefer a quiet retreat or a lively community atmosphere, staying in Island Sails ensures you experience the natural beauty and laid-back charm that make Princeville a sought-after destination. Booking your vacation rental by owner through Rent By Owner guarantees a trustworthy, seamless experience as you enjoy all that this exceptional Hawaiian neighborhood has to offer.
Kaiulani
Located in the scenic region of Princeville, Kaiulani offers a peaceful retreat surrounded by lush landscapes and easy access to local amenities. This neighborhood is ideal for visitors seeking a serene stay with convenient proximity to the area's natural beauty.
View 27+ Rentals in KaiulaniQueen Emmas Bluffs
Perched overlooking stunning vistas, Queen Emmas Bluffs provides a unique vantage point within the region, perfect for those wanting breathtaking views during their stay. The area’s tranquil atmosphere complements its scenic surroundings, making it a desirable location for relaxation.
View 2709+ Rentals in Queen Emmas BluffsKawaihau
Situated in the heart of the region, Kawaihau connects you to the vibrant local culture and outdoor adventures that Hawaii is known for. Staying here means enjoying an authentic Hawaiian experience just moments from nature and community attractions.
View 194+ Rentals in KawaihauWailua Homesteads
This welcoming neighborhood offers a blend of tranquility and accessibility, providing a perfect base for exploring the natural wonders nearby. Here, you can enjoy a peaceful environment while remaining close to the area's popular outdoor activities.
View 114+ Rentals in Wailua HomesteadsHanalei Palms
Nestled near the charming town of Hanalei, Hanalei Palms delivers a laid-back atmosphere paired with lush surroundings. It's an excellent choice for those looking to immerse themselves in the relaxed island lifestyle.
View 1942+ Rentals in Hanalei PalmsKapahi
Located in close proximity to Kapaa's vibrant scene, Kapahi offers easy access to local shops, dining, and outdoor recreation. This area is perfect for travelers who want a comfortable home base with convenient connections to the area's highlights.
View 1383+ Rentals in KapahiBest 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 (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.
Summer (June to August)
The summer season attracts visitors seeking sunny weather and longer daylight hours, perfect for exploring this island paradise.
Off-Season Highlights
Spring (March to May)
In spring, fewer travelers arrive, offering you a quieter experience while still enjoying pleasant weather and beautiful landscapes.
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.
Weekly Weather Forecast for Island Sails
How to Book Your Island Sails vacation rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Island Sails
Common Rentals by Owner Amenities
What amenities can you expect?
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.
Top Attractions Around Island Sails
What attractions are nearby?
In the area surrounding Island Sails, Princeville, you can enjoy a variety of outdoor activities such as scenic hiking trails, relaxing beach outings, and exploring lush natural landscapes, making it an ideal destination for adventure seekers and relaxation lovers alike.

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.
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
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:
- Mid-century Remodeled Spectacular Ocean Views! 10% Discount for Week+ Stays!
- Hanalei Bay Villas - Spectacular Views and Walk to Beaches/Snorkeling!
- Convenience & Comfort, A minute walk to Hanalei bay and short stroll to town!
- KAUAI GOOD VIBES 3BD, Air Conditioning, 2 baths, Outdoor shower, beach trail
- Luxury Home With Spectacular 180 Degree White Water Views & Infinity Edge Pool
- The Perfect Relaxation & Beach Destination
- Nalu Hanalei, Stunning Hanalei home right by the beach! TVR#5123
- Private pool and jacuzzi oasis; walk to the beach, golf, restaurants, shopping
- Just steps to Hanalei Bay. A Peaceful Getaway TVR4188 W31871267
- Large Island-Style Family Home with Wheelchair Accessibility
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?
4. How do I ensure my reservation is secure when booking in this region?
5. Are there any additional fees I should be aware of when staying at a rental by owner here?
6. What amenities can I expect when renting a property by owner in this area?
7. How do I contact the property owner if I have questions about my stay?
More Rentals You May Like Near Island Sails
- Air Conditioner
- Parking
- Pool
- Parking
- TV
- View
- Parking
- TV
- View
- Parking
- TV
- View
- Parking
- TV
- View
- Air Conditioner
- Parking
- Pool
- Parking
- TV
- View
- Parking
- TV
- View
- Air Conditioner
- Parking
- Pool
- Parking
- TV
- View
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pool