Oceanfront Rentals in Island Sails, HI: Compare 10+ Sites & Save

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  3.  USA

  4.  Hawaii

  5.  Princeville
  6.  Island Sails

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1009 Best Oceanfront Rentals in Island Sails (Starting from $206)

1Br Princeville Sands Condo with Pool and Hot Tub (137-A)
1Br Princeville Sands Condo with Pool and Hot Tub (137-A)
House
HI, USA
0.1k from Island Sails center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$206
Average price / night
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Nihilani 34C - Beautiful Hawaiian Townhouse
Nihilani 34C - Beautiful Hawaiian Townhouse
Condo
Princeville, HI, 96722, United States
0.1k from Island Sails center

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

3 Bedrooms6 Guests
10.0

Exceptional

88 reviews

$618
Average price / night
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Pualani Villa
Pualani Villa
Apartment
Princeville, HI, USA
0.1k from Island Sails center

Apartments, Accommodations, Pools, Parking, Spa, Lodgings, Hot tubs, Places to stay

1 Bedroom8 Guests
New to Booking
$918
Average price / night
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NEW Premium 2BD + Bonus Rm | A/C | Epic Pool & Spa
NEW Premium 2BD + Bonus Rm | A/C | Epic Pool & Spa
Condo
Princeville, HI, 96722, United States
0.1k from Island Sails center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
New to Booking
$700
Average price / night
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3BR Nihilani Condo with AC, Pool & Close to Shops 8C
3BR Nihilani Condo with AC, Pool & Close to Shops 8C
House
Princeville, HI, USA
0.2k from Island Sails center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

3 Bedrooms6 Guests
10.0

Exceptional

8 reviews

$477
Average price / night
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Stunning home with multiple lanais, private gym, lush green space & fruit trees
Stunning home with multiple lanais, private gym, lush green space & fruit trees
House
Princeville, HI, 96722, United States
0.1k from Island Sails center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Kitchen, Laundry, Living Area

6 Bedrooms12 Guests
9.2

Superb

5 reviews

$1713
Average price / night
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Hale Terra 3br 2ba Beautiful Nihilani Condo, Central AC, Pool, Hot Tub
Hale Terra 3br 2ba Beautiful Nihilani Condo, Central AC, Pool, Hot Tub
House
Princeville, HI, USA
0.2k from Island Sails center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

3 Bedrooms7 Guests
9.7

Exceptional

3 reviews

$918
Average price / night
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Pualani Villa by Gather: Luxe Princeville Retreat w/ Pool & Hot Tub
Pualani Villa by Gather: Luxe Princeville Retreat w/ Pool & Hot Tub
Condo
Princeville, HI, 96722, United States
0.1k from Island Sails center

AC, Crib, Dryer, Free Parking, Heater, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$757
Average price / night
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Princeville Condo with AC, Pool, Garage, Beach Gear 27B
Princeville Condo with AC, Pool, Garage, Beach Gear 27B
House
Princeville, HI, USA
0.2k from Island Sails center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

3 Bedrooms6 Guests
9.5

Superb

10 reviews

$638
Average price / night
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Ohana Kai, Luxe Princeville home w/ AC
Ohana Kai, Luxe Princeville home w/ AC
House
Princeville, HI, 96722, United States
0.1k from Island Sails center

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

4 Bedrooms10 Guests
New to Booking
$967
Average price / night
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Casa Makara
Casa Makara
Apartment
Princeville, HI, USA
0.2k from Island Sails center

Apartments, Accommodations, Parking, Spa, Lodgings, Places to stay

1 Bedroom8 Guests
New to Booking
$416
Average price / night
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Pili Aloha
Pili Aloha
House
Princeville, HI, USA
0.2k from Island Sails center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Hot tubs, Places to stay

1 Bedroom6 Guests
New to Booking
$742
Average price / night
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Beautifully Furnished-Great for families 3 Bed, 2 1/2 Bath Nihilani, Princeville
Beautifully Furnished-Great for families 3 Bed, 2 1/2 Bath Nihilani, Princeville
Condo
Princeville, HI, 96722, United States
0.1k from Island Sails center

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

3 Bedrooms6 Guests
10.0

Exceptional

161 reviews

$594
Average price / night
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Upgraded Condo in North Shore Hanalei/ Princeville Kauai
Upgraded Condo in North Shore Hanalei/ Princeville Kauai
Condo
Princeville, HI, 96722, United States
0.1k from Island Sails center

AC, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
9.8

Exceptional

67 reviews

$486
Average price / night
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Nihilani 32B
Nihilani 32B
Apartment
Island Sails, Princeville, Hawaii, USA
0.2k from Island Sails center

Apartments, Accommodations, Pools, Lodgings, Beach, Hot tubs, Places to stay

2 Bedrooms6 Guests
8.0

Good

2 reviews

$449
Average price / night
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Large Island-Style Family Home with Wheelchair Accessibility
Large Island-Style Family Home with Wheelchair Accessibility
House
Princeville, HI, 96722, United States
0.1k from Island Sails center

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

3 Bedrooms8 Guests
10.0

Exceptional

159 reviews

$414
Average price / night
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Leilani Villa
Leilani Villa
Apartment
Princeville, HI, USA
0.2k from Island Sails center

Apartments, Cheap, Accommodations, Pools, Parking, Spa, Lodgings, Vacation rentals, Hot tubs

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$734
Average price / night
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Mauna Lanai Princeville Condo, 3BR/3BA, Central AC, Pool-View Lanai
Mauna Lanai Princeville Condo, 3BR/3BA, Central AC, Pool-View Lanai
Condo
Princeville, HI, 96722, United States
0.1k from Island Sails center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Hot Tub, Internet, Kitchen

3 Bedrooms7 Guests
10.0

Exceptional

64 reviews

$546
Average price / night
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Alii Kai 7201
Alii Kai 7201
Apartment
Princeville, HI, USA
0.3k from Island Sails center

Apartments, Accommodations, Pools, Parking, Spa, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$348
Average price / night
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Beautiful, Airy 1 Br 1.5 Ba Condo Golf Course View, Pool, Hot tub (209A)
Beautiful, Airy 1 Br 1.5 Ba Condo Golf Course View, Pool, Hot tub (209A)
Condo
Princeville, HI, 96722, United States
0.1k from Island Sails center

Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

1 Bedroom4 Guests
9.0

Fabulous

24 reviews

$354
Average price / night
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Tropical Princeville Condo with Private Lanai
Tropical Princeville Condo with Private Lanai
Apartment
Princeville, HI, USA
0.3k from Island Sails center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Jacuzzis, Places to stay, Family

2 Bedrooms6 Guests
9.0

Fabulous

3 reviews

$440
Average price / night
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Best Pool & Hot Tub In Princeville! Tropical 2 Bedroom Sleeps 6 w/ Central A/C!
Best Pool & Hot Tub In Princeville! Tropical 2 Bedroom Sleeps 6 w/ Central A/C!
Condo
Princeville, HI, 96722, United States
0.1k from Island Sails center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
9.4

Superb

23 reviews

$537
Average price / night
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Condo in Princeville
Condo in Princeville
Condo
Princeville, HI, 96722, United States
0.2k from Island Sails center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub

2 Bedrooms6 Guests
New to Booking
$577
Average price / night
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Tropical Princeville Condo w/ Private Lanai!
Tropical Princeville Condo w/ Private Lanai!
Condo
Princeveille, HI, 96722, United States
0.2k from Island Sails center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

12 reviews

$545
Average price / night
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New Listing! Lovely North Shore Gem in Princeville
New Listing! Lovely North Shore Gem in Princeville
Condo
Princeville, HI, 96722, United States
0.2k from Island Sails center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

6 reviews

$641
Average price / night
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Island Cottage A/C-Pool-BBQ
Island Cottage A/C-Pool-BBQ
Cottage
Princeville, HI, 96722, United States
0.2k from Island Sails center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$582
Average price / night
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Nihilani 18C Newly renovated plantation style home
Nihilani 18C Newly renovated plantation style home
Condo
Princeville, HI, 96722, United States
0.2k from Island Sails center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

4 reviews

$493
Average price / night
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Pro Tip:
VacationByOwnerRentals 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 Oceanfront Rentals in Island Sails.

Where to stay in Island Sails? Best neighborhoods & areas

Island Sails Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 1009 verified oceanfront rentals in Island Sails. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Island Sails vary depending on the property size, exact beachfront location, and season. Rates typically start from around $206 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Island Sails offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Island Sails welcome pets. Currently, 1 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Island Sails often include features designed for a comfortable coastal stay, such as View, Oceanfront, and Ocean View. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.