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Compare Vacation Homes in Kalaupapa with updated reviews, rates, and availability.

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

9.8 out of 10, Exceptional, (65)
"This place is STUNNING! The location, the views, the rooms, the beach, the private pool. "
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

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

10.0 out of 10, Exceptional, (7)
"Great spaces to accommodate a large family including a large kitchen, multiple bedrooms and bathrooms, lanai dinning"
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!

Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana

10.0 out of 10, Exceptional, (63)
"We stayed in Kahana with our children and their families. Six adults and three kids under 6 in this beautifully styled, waterfront property. The condo was beautifully and thoughtfully appointed with everything we needed. Clean, quiet and modern unit situated on a beautiful property. Pool and grounds are spotless and offer magnificent views of the islands, whale spouts and swimming sea turtles. Our hosts were helpful, considerate and easy to communicate with. Thank you Tracy and Steve for a...
Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana

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

10.0 out of 10, Exceptional, (88)
"This house is beautiful, layout was perfect for our family of 17. Short walk to one of the best beaches in Maui, cute coffee shops, restaurants and beach rentals. Communication was great with property management. House was very well organized and one of the best features was the laundry room with 3 washers and 3 dryers! Will definitely be one of our best memories "
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!

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

10.0 out of 10, Exceptional, (4)
"Great stay! Had everything we needed for 8 adults. Close to ocean and groceries….wish we didn’t have to leave!"
Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!

Secluded Ocean View Napili Home - Sleeps 14

10.0 out of 10, Exceptional, (57)
"House was great for extended family trip."
Secluded Ocean View Napili Home - Sleeps 14

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

10.0 out of 10, Exceptional, (57)
"The property is everything and then some. Gorgeous sunset views, ample outdoor space and plenty of places to sit eat or play outdoor games. The house is very well equipped. All of the rooms are very generously sized and having incredible ocean views. Our house could not have been nicer and responded to everything almost immediately. We can’t wait to come back!"
Private gated home with 300 Foot private beach front, beach toys and much more!

Kapalua Golf Villas by KBM Resorts

3.5 star property
10.0 out of 10, Exceptional, (3)
"Privacy was very important to me. "
The price is SAR 3,383
SAR 6,057 total
includes taxes & fees
3 Feb - 4 Feb
Kapalua Golf Villas by KBM Resorts

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

9.4 out of 10, Exceptional, (78)
"We had a great time. Everyone enjoyed the house, the pool, the hot tub and the games. It was great that all the rooms had their own AC and it was very comfortable for our family."
Spectacular Ocean View. Close to Beaches & Shopping Plaza. Large Pool & Spa

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

10.0 out of 10, Exceptional, (67)
"The house was perfect for our family of eight (including a two year old). Everyone loved the pool, privacy and beautifully landscaped grounds. Being literally three minutes from the beach was such a plus. We walked down every morning and evening for the sunrises/sunsets. I highly recommend this property ! It made our stay and we thoroughly enjoyed Maui!"
NEW Construction! Just Steps from Maui's Best Beach!

Beautiful oceanfront condo with lanai, pool, beach access, & washer/dryer

9.6 out of 10, Exceptional, (24)
"We enjoyed the rental very much. It is far from town but we rented a car and got our groceries and supplies. We did end up buying to much so it’s donation to the cleaners. The views and walk to the beach are fabulous. The only thing is the red sand/ dirt. Trying to keep our feet and shoes clean. Some of the cooking supplies were broken or unusable. We did buy new and left them for the next guest. "
Beautiful oceanfront condo with lanai, pool, beach access, & washer/dryer

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

9.8 out of 10, Exceptional, (214)
"Host was easy to communicate with. Place was clean and as described. Check-out process was super easy. "
The Best of the Best JUST GOT BETTER with 3rd Remodel

Two-story, oceanfront condo with pool, water Views, & balcony

9.4 out of 10, Exceptional, (18)
"Perfect property "
Two-story, oceanfront condo with pool, water Views, & balcony

Remodeled, Ground floor studio

9.8 out of 10, Exceptional, (42)
"Great view and unit. All amenities were nice and complete. Perfect patio with a great view. "
Remodeled, Ground floor studio

Lovely 2 bdr 2 bath condo in prestigious Paniolo Hale, 4min walk to Kepuhi Beach

9.4 out of 10, Exceptional, (54)
"Laura’s beautiful home was the best place that we have stayed at during our 15-nights, 3-islands visits. Laura puts a lot of love into the house - it is beautifully decorated, richly equipped, and highly maintained. We felt so blessed to be able to stay at her magnificent home. Thank you Laura for sharing your piece of heaven with us. We hope to come back again."
Lovely 2 bdr 2 bath condo in prestigious Paniolo Hale, 4min walk to Kepuhi Beach

Remote Island Retreat: Ocean Views & Pool

2.0 star property
10.0 out of 10, Exceptional, (2)
"Clean, conveniently located, had everything we needed."
The price is SAR 784
SAR 2,183 total
includes taxes & fees
5 Feb - 6 Feb
Remote Island Retreat: Ocean Views & Pool

Awesome Beach - Elegant Villa - Tropical Oasis

10.0 out of 10, Exceptional, (41)
"Great location for our family. You could walk across the street to Napili bay or take 7 minute walk to Kapalua bay. We had 6 adults and everyone was very comfortable. The vrbo was very well equipped for a beach day with beach chairs, towels, and umbrellas. Everything was clean and has great space for our family vacation."
Awesome Beach - Elegant Villa - Tropical Oasis

Laid back Molokai beach-hideaway

10.0 out of 10, Exceptional, (51)
"The grounds are beautiful and well tended. The condo is very comfortable with screened verandas. Molokai is hawaii at a slower pace. "
Laid back Molokai beach-hideaway

Oceanfront All-Suite Escape with AC & Pool | Steps to Sand | Walk to Dining

8.8 out of 10, Excellent, (11)
"My family was super excited about the place and location of the Condo but when we arrived at the property the dishwasher and ice machine in the fridge did not work and when we contacted Vacasa they said it was an owner issue. The plates and mugs and silverware were not clean from the outset so we hand washed every item before using it. We then hand washed after every meal. ( There were 6 of us so a ridiculous amount of vacation time was spent at the sink!) The condo is in an amazing location but...
Oceanfront All-Suite Escape with AC & Pool | Steps to Sand | Walk to Dining

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

9.6 out of 10, Exceptional, (20)
"Here with our family fir a 30th bday"
Maui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House)
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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Other property types in Kalaupapa

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3444)
"Nice area and walkable to grocery and food trucks.."
The price is SAR 1,459
SAR 1,832 total
includes taxes & fees
27 Feb - 28 Feb
Aston Kaanapali Shores

Napili Shores Maui by OUTRIGGER

3.0 star property
8.8 out of 10, Excellent, (1551)
"On property restaurant was great. Front desk personnel very welcoming."
Napili Shores Maui by OUTRIGGER

Kahana Falls Maui by VRI Americas

3.5 star property
8.0 out of 10, Very Good, (837)
"we enjoyed sitting out on the deck mornings and evenings sheets on the sofa bed seemed a bit soiled when we arrived didn't like the amount of light shining through the adjoining door - made sleep more difficult"
Kahana Falls Maui by VRI Americas
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.