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Compare 83 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

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

8.8 out of 10, Excellent, (12)
"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

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

10.0 out of 10, Exceptional, (9)
"Loved the home, and location and it was perfect for our family. We will be back!"
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!

Kapalua Golf Villas by KBM Resorts

4.0 star property
10.0 out of 10, Exceptional, (3)
"Privacy was very important to me. "
The price is SAR 3,032
SAR 5,643 total
includes taxes & fees
18 Mar - 19 Mar
Kapalua Golf Villas by KBM Resorts

Laid back Molokai beach-hideaway

10.0 out of 10, Exceptional, (54)
"We had a wonderful time staying at Poniolo Hale. The unit was very well stocked with kitchen appliances and nice furnishings. The screened in porch and large lanai added some much appreciated, very comfortable living space. The beaches within walking distance were very enjoyable and relaxing. Overall, this unit is one of the best condos we have had the pleasure of staying at in Hawaii. "
Laid back Molokai beach-hideaway

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

9.8 out of 10, Exceptional, (215)
"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

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

10.0 out of 10, Exceptional, (52)
"Clean, well appointed, safe, and an easy walk to a beautiful beach. Home was as advertised. Excellent communication. Highly recommend. "
3BD NEW! Luxurious, Newly Remodeled, Walk to beach

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

10.0 out of 10, Exceptional, (7)
"Everything was as advertised. The house was absolutely spotless when we arrived. The yard was so much fun for adults and kids. The owner and property manager were both very responsive to all questions and concerns.I highly recommend this property."
Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!

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

9.4 out of 10, Exceptional, (80)
"My family and I truly embraced our stay at the property. The seamless check-in and the pristine, inviting atmosphere made for a delightful experience. The property manager's swift responses to our few inquiries were a testament to exceptional service. Highly recommend."
Spectacular Ocean View. Close to Beaches & Shopping Plaza. Large Pool & Spa

Private 4bd Home, Walk to Beach

10.0 out of 10, Exceptional, (94)
"Property had, as expected, just the right number of bedrooms, beds (which were really comfy) and bathrooms. The back deck was wonderful, only drawback was the road traffic noise, but it wasn't constant. Rooms wete spacious and kutchen had everything we needed"
Private 4bd Home, Walk to Beach

Stunning Gated Home, Private Pool & Spa

10.0 out of 10, Exceptional, (81)
"Amazing! Property as advertised. Extremely clean. Plentiful amenities. Lauren and Michael were friendly and most helpful. Beautiful views inside and out. Would definitely stay again."
Stunning Gated Home, Private Pool & Spa

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

Book Spring Deals and Save! Residences 8 3B/2.5B, Slps 8, AC, Walk to Napili Bay

9.0 out of 10, Wonderful, (35)
"Property was safe, clean and it had all the things we needed for daily use and beach use. Felt just like home and cannot wait to come back again in the future. Thank you for your help and speedy response to inquiries. "
Book Spring Deals and Save! Residences 8 3B/2.5B, Slps 8, AC, Walk to Napili Bay

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

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! Pickle Ball Ct!

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!

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

10.0 out of 10, Exceptional, (61)
"The house was perfect, it checked all of the boxes; right on the ocean with beach access, location was great, everyone in our group had access to large bed with private bath. The panoramic view was wonderful, don’t miss a sunset here. Floor plan was great for a group of eight. "
Private gated home with 300 Foot private beach front, beach toys and much more!

Spacious 4BR Kapalua Villa Best Views in Golf Villas

2.0 star property
10.0 out of 10, Exceptional, (1)
"Our group of friends needed a place to stay for a wedding. This location was perfect and would definitely book again!"
Spacious 4BR Kapalua Villa Best Views in Golf Villas

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

9.6 out of 10, Exceptional, (21)
"Overall terrific. I didn’t give 5 stars because the property was a bit janky (one slider was broken, the kitchen screen door barely could move so we left it open all day), TV remotes didn’t work (buttons to change channels would toggle)….but really - very minor gripes when considering how easy everything was and communication with the property management. We were happy to stay here and truly enjoyed our time! It was comfy and clean! (No dead cockroaches!!) "
Maui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House)

Coastal Paradise 🏝️ Private 3 Bedroom - AC, Pool, Spa, Beach, WFH

10.0 out of 10, Exceptional, (1)
"We loved this home. It was beautiful and had everything one needs in a holiday home. Our family of six did not feel crowded at all. It is within walking distance to a good beach and within 10 minutes to Fleming or Slaughterhouse beaches. There is also the Whaler's Village with shops, good dining and beaches about 15 minutes driving away. The host was very responsive. My only suggestion is that the VRBO place coordinates for the property in the directions. GPS took us to the property next door....
Coastal Paradise 🏝️ Private 3 Bedroom - AC, Pool, Spa, Beach, WFH

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
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, (3482)
"Our upgraded room was large with a full kitchen. I loved sitting on the balcony and looking at the ocean and he beautiful garden area. "
Aston Kaanapali Shores

Napili Shores Maui by OUTRIGGER

3.0 star property
8.8 out of 10, Excellent, (1574)
"Absolutely amazing!"
Napili Shores Maui by OUTRIGGER

Kahana Beach Vacation Club

3.0 star property
8.4 out of 10, Very Good, (647)
"Being right on the beach was great. The pool, hot tub and seating area outside were excellent. The staff were very friendly and helpful. I would highly recommend it to anyone that is looking for a relaxing vacation."
Kahana Beach Vacation Club
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.