Location

Dates

Guests

Vacation rentals in Pupukea, Hawaii, United States

Sunset Beach Lanai

Sunset Beach Lanai

Sunset Beach Lanai

Sunset Beach Lanai

Sunset Beach Lanai

Sunset Beach Lanai

2 bedrooms·1 bath

Pupukea • Hawaii

$1,305.83 USD total for 3 nights

Oct 22 – 25, 2026

Sunset Beach Cottage

Sunset Beach Cottage

Sunset Beach Cottage

Sunset Beach Cottage

Sunset Beach Cottage

1 bedroom·1 bath

Pupukea • Hawaii

4.9(89 reviews)

$1,780.68 USD total for 3 nights

Oct 22 – 25, 2026

View of the living room, kitchen and patio from the bedroom.

View of living room and bedroom with large sliding barn door for privacy.

North Shore Cottage Guest House | AirbnbOahu.com

North Shore Cottage Guest House | AirbnbOahu.com

Bedroom has a queen size bed, ceiling fan, mirror and closet.

North Shore Cottage Guest House | AirbnbOahu.com

1 bedroom·1 bath

Waialua • Hawaii

4.98(291 reviews)

$940.00 USD total for 3 nights

Oct 22 – 25, 2026

Enjoy Pacific Ocean views from your living room!

Amazing sunsets from the pool

Spacious North Shore Ranch House With Ocean Views image 3

Spacious North Shore Ranch House With Ocean Views image 4

Spacious North Shore Ranch House With Ocean Views image 5

Spacious North Shore Ranch House With Ocean Views

4 bedrooms·6 baths

Waialua • Hawaii

$14,790.00 USD total for 30 nights

Mar 6 – Apr 5, 2027

North Shore Retreat

North Shore Retreat

North Shore Retreat

North Shore Retreat

North Shore Retreat

North Shore Retreat

3 bedrooms·1 bath

Mokuleia • Hawaii

$12,105.00 USD total for 30 nights

Jan 11 – Feb 10, 2027

North Shore Bungalow

North Shore Bungalow

North Shore Bungalow

North Shore Bungalow

North Shore Bungalow

North Shore Bungalow

0 bedrooms·1 bath

Mokuleia • Hawaii

$10,248.75 USD total for 30 nights

Jan 11 – Feb 10, 2027

North Shore Studio

North Shore Studio

North Shore Studio

North Shore Studio

North Shore Studio

North Shore Studio

0 bedrooms·1 bath

Mokuleia • Hawaii

$7,425.00 USD total for 30 nights

Feb 24 – Mar 26, 2027

North Shore Palms

North Shore Palms

North Shore Palms

North Shore Palms

North Shore Palms

North Shore Palms

1 bedroom·1 bath

Mokuleia • Hawaii

$8,366.25 USD total for 30 nights

Mar 2 – Apr 1, 2027

Magic North Shore Beach House 30 Day Rental

Magic North Shore Beach House 30 Day Rental

Magic North Shore Beach House 30 Day Rental

Magic North Shore Beach House 30 Day Rental

Magic North Shore Beach House 30 Day Rental

Magic North Shore Beach House 30 Day Rental

4 bedrooms·2 baths

Hauula • Hawaii

$3,900.52 USD total for 3 nights

Nov 1 – 4, 2026

Morning Sunrise View

Relax, read a book , or simply enjoy a glass of Wine & let the view and sounds of the waves sooth your soul.

The Lana: Cuddle up, relax and enjoy the relaxing sounds of the beach and the amazing view.

Enjoy a great night sleep in this amazing oversized suite, designed and decorated with an elegant Coastal Decor theme to complete your Hawaiian Paradise experience. You'll love it all, from the cozy warm beams, to the custom designed feature wood w

Kitchen & Dining Bar Counter w/ seating for 4. Kitchen Stainless steel appliances include refrigerator, dishwasher, microwave, stove/range, coffee maker and toaster.

Beachfront Sunrise | Steps to Beach & Snorkeling !

1 bedroom·1 bath

Hauula • Hawaii

5(15 reviews)

$1,589.49 USD $1,462.05 USD total for 3 nights

Oct 22 – 25, 2026

Support Local Pool Spa Gym Top 5% Family Friendly image 1

Support Local Pool Spa Gym Top 5% Family Friendly image 2

Support Local Pool Spa Gym Top 5% Family Friendly image 3

Support Local Pool Spa Gym Top 5% Family Friendly image 4

Support Local Pool Spa Gym Top 5% Family Friendly image 5

Support Local Pool Spa Gym Top 5% Family Friendly

3 bedrooms·2½ baths

Makaha Valley • Hawaii

5(84 reviews)

$3,457.15 USD total for 3 nights

Oct 29 – Nov 1, 2026

PARADISE FOUND! Relax & enjoy a meal on our huge lanai. Walk out backyard gate & onto the beautiful Makaha Beach. Watch surfers & enjoy amazing nightly sunsets. Watch whales, dolphins & sea turtles play from our lanai & house. Whale season Nov-March

Beautiful uncrowded Makaha Beach is just out our back yard. Gorgeous sunsets, great snorkeling, surfing, swimming or just relaxing

Large backyard. Walk from the back yard onto beautiful Makaha Beach. Great place to snorkle, swim, surf, or scuba. Enjoy seeing whales from our yard November through April.

Beautiful oceanfront/beachfront home on large lot with huge lanai with large dining and seating area. Enjoy meals with friends and family at sunset.

Sit back and relax, take a nap or have a cocktail. Huge lanai is perfect for relaxing.

Flip Flop Hideaway Private Beachfront Surf Estate

6 bedrooms·5 baths

Waianae • Hawaii

4.78(60 reviews)

$9,775.00 USD $7,820.00 USD total for 10 nights

Oct 22 – Nov 1, 2026

Oasis in Paradise

Oasis in Paradise

Oasis in Paradise

Oasis in Paradise

Oasis in Paradise

1 bedroom·1 bath

Waianae • Hawaii

$4,023.25 USD $3,644.44 USD total for 29 nights

Oct 22 – Nov 20, 2026

UNBELIEVABLE VIEW OF OCEAN, BEACH, & SUNSETS GALORE!

GORGEOUS AND NEVER CROWDED BEACH! OUR CONDO IS IN TALLER BUILDING!

LivingRoom has been updated-kept photo showing beautiful ocean view-see
next pic

SUPER LOW RATE! 30 Nt Min. Stay! BEACHFRONT CONDO!FREE PKG,WiFi-POOL,HOT TUB,BBQ

1 bedroom·1 bath

Waianae • Hawaii

4.75(60 reviews)

$3,808.00 USD total for 30 nights

Oct 22 – Nov 21, 2026

UNBELIEVABLY BEAUTIFUL BEACH! GLORIOUS SUNSETS!

BEACHFRONT CONDO-LEGAL-GREAT VIEWS!-FREE PKG/WIFI-POOL, HOT TUB,TENNIS/PICKLE 2

1 bedroom·1 bath

Waianae • Hawaii

$1,285.25 USD total for 3 nights

Oct 22 – 25, 2026

Inquire for availability. Entire home in Paradise image 1

Inquire for availability. Entire home in Paradise image 2

Inquire for availability. Entire home in Paradise image 3

Inquire for availability. Entire home in Paradise image 4

Inquire for availability. Entire home in Paradise image 5

Inquire for availability. Entire home in Paradise

5 bedrooms·2 baths

Kapolei • Hawaii

4.78(9 reviews)

$2,004.71 USD total for 3 nights

Oct 22 – 25, 2026

Aloha Getaway

3 bedrooms·2½ baths

Kapolei • Hawaii

5(3 reviews)

$6,270.00 USD total for 30 nights

Oct 22 – Nov 21, 2026

Villa Ko Olina

3 bedrooms·3 baths

Kapolei • Hawaii

$13,230.00 USD total for 14 nights

Oct 22 – Nov 5, 2026

KoOlina Beach Villa 3Bed3Bath Amazing Ocean Views image 1

KoOlina Beach Villa 3Bed3Bath Amazing Ocean Views image 2

KoOlina Beach Villa 3Bed3Bath Amazing Ocean Views image 3

KoOlina Beach Villa 3Bed3Bath Amazing Ocean Views image 4

KoOlina Beach Villa 3Bed3Bath Amazing Ocean Views image 5

KoOlina Beach Villa 3Bed3Bath Amazing Ocean Views

3 bedrooms·3 baths

Kapolei • Hawaii

5(7 reviews)

$8,769.38 USD $7,960.02 USD total for 6 nights

Oct 22 – 28, 2026