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8 Aug - 10 Aug
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29 Aug - 31 Aug
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26 Sep - 28 Sep

Vacation Homes in Kalaupapa

Remodeled, Ground floor studio at The Mahana #102
Outdoor pool

Remodeled, Ground floor studio at The Mahana #102

9.8 out of 10, Exceptional, (52)
"Clean, quiet, as advertised. "
Remodeled, Ground floor studio at The Mahana #102
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
On the beach, sun loungers, beach towels

Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!

10.0 out of 10, Exceptional, (18)
"We loved our four days at this home. It was beautiful and so close to a lovely beach. Just wish we could have stayed longer!!"
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
Maui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House)
Property grounds

Maui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House)

9.6 out of 10, Exceptional, (24)
"Here with our family fir a 30th bday"
Maui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House)
Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!
Outdoor pool

Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!

10.0 out of 10, Exceptional, (16)
"Property was in great location and very clean. Property manager was very nice and very accommodating."
Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach! Pickle Ball Ct!
Outdoor pool

The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach! Pickle Ball Ct!

10.0 out of 10, Exceptional, (96)
"This home is absolutely beautiful and accommodated our family of 25 well! It’s a block from the beach and has a great pool for kids of all ages! We loved our stay! "
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach! Pickle Ball Ct!
Private gated home with 300 Foot private beach front, beach toys and much more!
Terrace/patio

Private gated home with 300 Foot private beach front, beach toys and much more!

10.0 out of 10, Exceptional, (65)
"Beautiful location - we felt like we were staying in an ocean front resort."
Private gated home with 300 Foot private beach front, beach toys and much more!
Luxury Maui Vacation Property | Near Napili Beach | 3 Bedrooms
Terrace/patio

Luxury Maui Vacation Property | Near Napili Beach | 3 Bedrooms

10.0 out of 10, Exceptional, (174)
"We loved the condo - it's a 2 minute walk to Napili Beach and has a private and lovely back deck for grilling and hanging out."
Luxury Maui Vacation Property | Near Napili Beach | 3 Bedrooms
Spacious 2bedroom/2bath Beach Front Condo
Outdoor pool

Spacious 2bedroom/2bath Beach Front Condo

10.0 out of 10, Exceptional, (13)
"Everything was great! Very spacious. We had everything that we needed. "
Spacious 2bedroom/2bath Beach Front Condo
Kapalua Golf Villas by KBM Resorts
On the beach

Kapalua Golf Villas by KBM Resorts

4.0 star property
10.0 out of 10, Exceptional, (7)
"We loved our stay in this villa! We will be back for years to come! "
Kapalua Golf Villas by KBM Resorts
NEW Construction! Just Steps from Maui's Best Beach!
Beach nearby, sun loungers, beach towels

NEW Construction! Just Steps from Maui's Best Beach!

10.0 out of 10, Exceptional, (70)
"We thought this house was perfect for our group. "
NEW Construction! Just Steps from Maui's Best Beach!
Lower Nightly Rates Aug-Oct!! Oceanview in Napili - 5 Bedroom w/spa, Sleeps 14
Outdoor spa tub

Lower Nightly Rates Aug-Oct!! Oceanview in Napili - 5 Bedroom w/spa, Sleeps 14

10.0 out of 10, Exceptional, (62)
"Very nice place, great location. The accommodations made for a very fun and relaxing trip."
Lower Nightly Rates Aug-Oct!! Oceanview in Napili - 5 Bedroom w/spa, Sleeps 14
Aloha Getaway: Luxe Beachfront 3bdm/2bth house - best Molokai white sand beaches
On the beach, sun loungers, beach towels

Aloha Getaway: Luxe Beachfront 3bdm/2bth house - best Molokai white sand beaches

10.0 out of 10, Exceptional, (18)
"Location of property on the island was very good. Having the pool and the barbecue a few steps away was a plus. Parking readily available close to entry. Host was very responsive and timely."
Aloha Getaway: Luxe Beachfront 3bdm/2bth house - best Molokai white sand beaches
The Best of the Best JUST GOT BETTER with 3rd Remodel
Property grounds

The Best of the Best JUST GOT BETTER with 3rd Remodel

9.8 out of 10, Exceptional, (224)
"Great location, clean, and accommodating! They had tons of beach accessories for the whole family. Would stay here again!"
The Best of the Best JUST GOT BETTER with 3rd Remodel
Resort Townhome w/ Pool - Walk to Pohaku Beach
Interior

Resort Townhome w/ Pool - Walk to Pohaku Beach

9.4 out of 10, Exceptional, (27)
"Had a great stay. Great communication prior to check in. Easy to get keys, wifi, etc."
Resort Townhome w/ Pool - Walk to Pohaku Beach
Golf Villa! Sweeping Ocean Sunset Views!
Pool

Golf Villa! Sweeping Ocean Sunset Views!

9.6 out of 10, Exceptional, (85)
"Property and location were amazing."
Golf Villa! Sweeping Ocean Sunset Views!
Ocean front | Snorkel with turtles!
Pool

Ocean front | Snorkel with turtles!

10.0 out of 10, Exceptional, (13)
"Great stay. We will return. "
Ocean front | Snorkel with turtles!
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Interior

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

9.8 out of 10, Exceptional, (73)
"All in all just a perfect location to host and relax."
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Spectacular Ocean View. Close to Beaches & Shopping Plaza. Large Pool & Spa
Beach

Spectacular Ocean View. Close to Beaches & Shopping Plaza. Large Pool & Spa

9.6 out of 10, Exceptional, (84)
"The size of the property is much larger than what is pictured. Large bedrooms, spacious property, great pool. The owners do a great job in getting the groundskeepers to come routinely to maintain the pool and keep it clean. Would highly recommend."
Spectacular Ocean View. Close to Beaches & Shopping Plaza. Large Pool & Spa
Discounted for summer 2025! Laid back Molokai beach-hideaway
On the beach, sun loungers, beach towels

Discounted for summer 2025! Laid back Molokai beach-hideaway

10.0 out of 10, Exceptional, (58)
"Great property, lots of space and large lanai, well equipped, close to several beautiful beaches. Very quiet and relaxing. Bit of a drive to any amenities. "
Discounted for summer 2025! Laid back Molokai beach-hideaway
3BD NEW! Luxurious, Newly Remodeled, Walk to beach
Interior

3BD NEW! Luxurious, Newly Remodeled, Walk to beach

10.0 out of 10, Exceptional, (57)
"Great property, excellent location, very easy to work with mgmnt"
3BD NEW! Luxurious, Newly Remodeled, Walk to beach
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.
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Top Kalaupapa Hotel Reviews

Aston Kaanapali Shores

Aston Kaanapali Shores

10/10 Excellent
"Close to ocean, lots of places to eat within 5-10 minutes "
Stacy 7-night trip
Posted 1 day ago
Aston Kaanapali Shores