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Compare 82 Vacation Homes in Kalaupapa with updated reviews, rates, and availability.

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

9.8 out of 10, Exceptional, (67)
"We had a fantastic time! Everything was even better than we expected. We only wish we’d had a little more sunshine"
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, (89)
"We had a great stay! It started with a walkthrough of the house to understand how to work everything and learn where everything was. Any time we needed help the communication was prompt and very easy. Any small issues were immediately remedied. The beds were fairly comfortable and the house was very aesthetically pleasing. The view from the roof was nice and the pool was very clean. We would definitely rent from them again!"
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, (6)
"A "great room" inside for a large group and lots of lovely outdoor space around the pool makes for a perfect spot to bring your family. I had 11 and the five grandkids - ages 25-16 in one big room and all the adults in nice rooms for each couple. Just a short walk to the beach and a great little coffee shop. Kids are asking to come again! Thanks for making a memory for all of us."
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, (59)
"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!

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 AED 2,673
AED 5,177 total
includes taxes & fees
18 Mar - 19 Mar
Kapalua Golf Villas by KBM Resorts

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

9.4 out of 10, Exceptional, (79)
"Great location, well maintained property. Really comfortable beds. Centrally located with short drives to great beaches, shopping and dining. Only bummer is the pool was cold and hot tub did not work. That needs to be on and working."
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)
"The resort is its own oasis, from playing in the sand to swimming in the pool. The room had everything we needed, you know when you say, I wonder if they gave this or that...the answer was yes. The resort has activities each day, a Mai Tai hour. We had all the ammenities we needed. We arrived late so lots closed but we were prepared. You dont get a lot of noise from neighbors, the staff are super nice and helpful. 10 out of 10 stay! "
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; Inquire about specials from 4/24 - 7/16

9.8 out of 10, Exceptional, (43)
"Clean, quiet, as advertised. "
The price is AED 1,341
AED 2,734 total
includes taxes & fees
8 Mar - 9 Mar
Remodeled, Ground floor studio; Inquire about specials from 4/24 - 7/16

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

9.4 out of 10, Exceptional, (55)
"Absolutely terrific condo in one of the best areas to stay on Molokai. Comfortable. Lots of places to sit and relax. Great internet. Well stocked kitchen with all the appliances you need to cook anything. Terrific bed and pillows. Good shower with lots of hot water. Awesome ventilation and shade from large trees so it was never hot. And...that deck/patio. Wow. It's a wrap-around and *huge*. It's like you are sitting in the trees. Perfect for morning coffee, dinners while spying on the wild...
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, (3)
"We stayed at this property for six nights. Accurate description, lots of room, clean and comfortable. Quiet area with short walk to beaches and hiking. Pool was nice too. Beware of deer running across roads at all hours. "
The price is AED 723
AED 2,066 total
includes taxes & fees
17 Mar - 18 Mar
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, (52)
"Everything about this property was just right for us. Spending a week on Molokai was the best part of our trip to Hawaii. It is a long way from home, but I would be delighted to return to this lovely, quiet little island, especially if it includes another stay at this property. "
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, (3461)
"Great views. Pleasant staff"
The price is AED 1,286
AED 1,625 total
includes taxes & fees
2 Mar - 3 Mar
Aston Kaanapali Shores

Kahana Falls Maui by VRI Americas

3.5 star property
8.0 out of 10, Very Good, (847)
"We loved this place and will stay again for sure! The ONLY complaint we had was the door to our room. The lock seemed to malfunction daily, sometime twice daily. Quite a few trips back to the lobby to get a new key. Room 302B We will be back next year!!"
Kahana Falls Maui by VRI Americas

Kahana Villa

3.0 star property
8.0 out of 10, Very Good, (313)
"Clean, cozy, comfortable!"
Kahana Villa
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.