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Island Sails Vacation Packages

Island Sails Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Plantation Hale Suites

Plantation Hale Suites

3 out of 5
Save 100% on your flight
per person
Dec 18 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Lihue (LIH)
Book a stay at this business-friendly aparthotel in Kapaa. Enjoy 3 outdoor pools, 2 spa tubs, and WiFi (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Coconut Marketplace and Waipouli Beach are located nearby.
Hanalei Bay Resort

Hanalei Bay Resort

3 out of 5
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Lihue (LIH)
Stay at this 3-star condo in Princeville. Enjoy free WiFi, 2 outdoor pools, and a free beach shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Hanalei Bay and Princeville Golf Club Prince Course are located nearby.
Makai Club Resort

Makai Club Resort

3.5 out of 5
per person
Jan 3 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Lihue (LIH)
Stay at this 3.5-star golf condo in Princeville. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions Hanalei Bay and Princeville Makai Golf Club are located nearby.
Tip Top Motel Cafe & Bakery

Tip Top Motel Cafe & Bakery

2 out of 5
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Lihue (LIH)
Stay at this motel in Lihue. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Nawiliwili Harbor and Nawiliwili Bay are located nearby.
OUTRIGGER Kauaʻi Beach Resort & Spa

OUTRIGGER Kauaʻi Beach Resort & Spa

4 out of 5
Save 100% on your flight
per person
Dec 19 - Dec 27
found 6 hours ago
Roundtrip flight included
Appleton (ATW) to Lihue (LIH)
Stay at this 4-star beach resort in Lihue. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Nawiliwili Harbor and Nawiliwili Bay are located nearby.
Grand Hyatt Kauai Resort and Spa

Grand Hyatt Kauai Resort and Spa

4.5 out of 5
Save 100% on your flight
per person
Dec 18 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Lihue (LIH)
Stay at this 4.5-star luxury hotel in Koloa. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Poipu Beach and Lawai Beach are located nearby.
Kiahuna Plantation Resort Kauai by OUTRIGGER

Kiahuna Plantation Resort Kauai by OUTRIGGER

3 out of 5
Save 100% on your flight
per person
Dec 18 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Lihue (LIH)
Book a stay at this beach aparthotel in Koloa. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Poipu Beach and Lawai Beach are located nearby.
1 Hotel Hanalei Bay

1 Hotel Hanalei Bay

5 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 4
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Lihue (LIH)
Book a stay at this luxury resort in Princeville. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Hanalei Bay and Puupoa Beach are located nearby.
Kamahana 16 - up

Kamahana 16 - up

2 out of 5
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Lihue (LIH)
Stay at this condo in Princeville. Enjoy balconies, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Hanalei Bay and Island Sails are located nearby.
2417 at Lihue Oceanfront Resort

2417 at Lihue Oceanfront Resort

3.5 out of 5
per person
Jan 3 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Lihue (LIH)
Stay at this 3.5-star beach resort in Lihue. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Popular attractions Nawiliwili Harbor and Nawiliwili Bay are located nearby.
Waipouli Beach Resorts & Spa Kauai by OUTRIGGER

Waipouli Beach Resorts & Spa Kauai by OUTRIGGER

4 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 4
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Lihue (LIH)
Stay at this 4-star beach hotel in Kapaa. Enjoy free parking, a beach locale, and 3 spa tubs. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Fuji Beach and Coconut Marketplace are located nearby.
Koloa Landing Resort at Poipu, Autograph Collection

Koloa Landing Resort at Poipu, Autograph Collection

4.5 out of 5
Save 100% on your flight
per person
Dec 18 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Lihue (LIH)
Stay at this 4.5-star luxury hotel in Koloa. Enjoy free WiFi, 3 outdoor pools, and 5 spa tubs. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lawai Beach and Poipu Beach are located nearby.

3-4 Night Vacations in Island Sails

Price found within the past 48 hours. Click for updated prices.
Plantation Hale Suites

Plantation Hale Suites

3 out of 5
per person
Jan 6 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Lihue (LIH)
Hanalei Bay Resort

Hanalei Bay Resort

3 out of 5
Save 100% on your flight
per person
Jan 6 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Lihue (LIH)
OUTRIGGER Kauaʻi Beach Resort & Spa

OUTRIGGER Kauaʻi Beach Resort & Spa

4 out of 5
Save 100% on your flight
per person
Jan 6 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Lihue (LIH)
1 Hotel Hanalei Bay

1 Hotel Hanalei Bay

5 out of 5
Save 100% on your flight
per person
Dec 21 - Dec 25
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Lihue (LIH)

5-7 Night Vacations in Island Sails

Price found within the past 48 hours. Click for updated prices.
Makai Club Resort

Makai Club Resort

3.5 out of 5
per person
Jan 3 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Lihue (LIH)
OUTRIGGER Kauaʻi Beach Resort & Spa

OUTRIGGER Kauaʻi Beach Resort & Spa

4 out of 5
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Lihue (LIH)
Hanalei Bay Resort

Hanalei Bay Resort

3 out of 5
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Lihue (LIH)
Aston Islander on the Beach

Aston Islander on the Beach

3 out of 5
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Lihue (LIH)

Island Sails Last Minute Hotel Deals

1 Hotel Hanalei Bay
1 Hotel Hanalei Bay
5 out of 5
5520 Ka Haku Road, Princeville, HI
Book a stay at this luxury resort in Princeville. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
1 Hotel Hanalei Bay
Club Wyndham Bali Hai Villas
Club Wyndham Bali Hai Villas
3 out of 5
4970 Pepelani Loop, Princeville, HI
Stay at this 3-star eco-certified hotel in Princeville. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the property ...
Club Wyndham Bali Hai Villas
The Cliffs at Princeville
The Cliffs at Princeville
3.5 out of 5
3811 Edward Road, Princeville, HI
Stay at this 3.5-star golf aparthotel in Princeville. Enjoy free WiFi, 2 outdoor pools, and 2 spa tubs. Our guests praise the helpful staff in our reviews. Popular ...
The Cliffs at Princeville
Club Wyndham Ka ‘Eo Kai
Club Wyndham Ka ‘Eo Kai
3 out of 5
3970 Wyllie Rd., Kauai, Princeville, HI
Stay at this 3-star golf hotel in Princeville. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
Club Wyndham Ka ‘Eo Kai
The Westin Princeville Ocean Resort Villas
The Westin Princeville Ocean Resort Villas
4 out of 5
3838 Wyllie Rd, Princeville, HI
Stay at this 4-star eco-certified hotel in Princeville. Enjoy free WiFi, 4 outdoor pools, and breakfast (surcharge). Our guests praise the helpful staff and ...
The Westin Princeville Ocean Resort Villas
Makai Club Resort
Makai Club Resort
3.5 out of 5
4180 Lei O Papa Road, Princeville, HI
Stay at this 3.5-star golf condo in Princeville. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff in our reviews. Popular ...
Makai Club Resort
Club Wyndham Bali Hai Villas
Club Wyndham Bali Hai Villas
2 out of 5
Princeville
Stay at this hotel in Princeville. Enjoy a garden. Popular attractions Hanalei Bay and Island Sails are located nearby.
Club Wyndham Bali Hai Villas
See all 2,072 properties in Island Sails
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Hawaiian Airlines
Thu, Dec 12 - Wed, Dec 25
SAN
San Diego Intl.
LIH
Lihue
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Select Hawaiian Airlines flight, departing Thu, Dec 12 from San Diego Intl. to Lihue, returning Wed, Dec 25, priced at $237 found 3 days ago
Delta
Mon, Dec 9 - Mon, Dec 16
PDX
Portland Intl.
LIH
Lihue
$246 Roundtrip, found 2 days ago
$246
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Dec 9 from Portland Intl. to Lihue, returning Mon, Dec 16, priced at $246 found 2 days ago
Hawaiian Airlines
Fri, Nov 29 - Thu, Dec 5
OAK
Oakland Intl.
LIH
Lihue
$265 Roundtrip, found 5 days ago
$265
Roundtrip
found 5 days ago
Select Hawaiian Airlines flight, departing Fri, Nov 29 from Oakland Intl. to Lihue, returning Thu, Dec 5, priced at $265 found 5 days ago
United
Tue, Dec 31 - Tue, Jan 14
SEA
Seattle - Tacoma Intl.
LIH
Lihue
$280 Roundtrip, found 4 days ago
$280
Roundtrip
found 4 days ago
Select United flight, departing Tue, Dec 31 from Seattle - Tacoma Intl. to Lihue, returning Tue, Jan 14, priced at $280 found 4 days ago

Book the perfect getaway to Island Sails

With Hotwire, booking your next trip to Princeville is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Island Sails while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Island Sails flight and hotel package for as low as $902.

Living it up in Princeville means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Island Sails, Princeville vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Island Sails for some of the best accommodations and flight deals.

FAQs about cheap Island Sails packages:

How to get cheap vacation deals to Island Sails?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $353.

How much are Island Sails packages?

Vacation packages to Island Sails vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $902.

How to find cheap car rentals near Island Sails?

Hotwire partners with some of the most reliable car rental companies in Princeville to bring you the best car rental deals in Island Sails for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Island Sails now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Island Sails right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.