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Compare 109 Vacation Homes in Kahoolawe with updated reviews, rates, and availability.

Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A

9.6 out of 10, Exceptional, (93)
"Had a wonderful 7 days in Kihei - this place was great. Loved that you could walk the beautiful beach, the grounds were very well maintained, the pool was delightful and my husband was able to walk to the city park and play pickleball every morning. "
Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A

272-1 Large oceanfront home- fully air conditioned, 25 feet from the water

9.0 out of 10, Wonderful, (40)
"Pumana was a beautiful area. We arrived just before a huge storm and the 2nd night of our stay there was a leak in the ceiling from the heavy rain fall. We got in touch with the property manager and he helped us move to a different property. We were thankful for his help and kindness. We were extremely happy with our stay. "
272-1 Large oceanfront home- fully air conditioned, 25 feet from the water

Spacious Family Beach House with Large Heated Pool; walk to Beach 🏖

10.0 out of 10, Exceptional, (127)
"Very spacious house with a delightful pool. Walk to a nice beach good for kids. Convenient location. Loved it!"
Spacious Family Beach House with Large Heated Pool; walk to Beach 🏖

Stunning Beachfront Private Home! Perfect for Families, Great Location!

9.8 out of 10, Exceptional, (93)
"11 family members stayed at this property. Beautiful yard, view of ocean, access to beach, great location."
Stunning Beachfront Private Home! Perfect for Families, Great Location!

Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

9.8 out of 10, Exceptional, (193)
"If you are looking for a group gathering, this is the place. Location, and all other desires were right there.We were there during the last storm (Jan 2025), and did have some leaks and flooding, but that doesn't change how we felt about staying there. No one can predict the weather!I want to thank the property owner for offering such a beautiful place to vacation!!LB"
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

Island Retreat Spacious 3B/3B Wailea Home Ocean View Private Pool & Hot Tub!

9.8 out of 10, Exceptional, (138)
"We had an amazing time at this vacation rental! Right from the start, we were blown away by how clean, spacious, and well-equipped the house was. It looked just like the photos and description on VRBO. The kitchen had everything we needed to whip up our meals, and the living areas were perfect for the whole family. The deck with the hot tub was a fantastic way to unwind after a long day at the beach, and the sunset views were just incredible. We even caught some fireworks from the Grand Wailea...
Island Retreat Spacious 3B/3B Wailea Home Ocean View Private Pool & Hot Tub!

Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach

9.8 out of 10, Exceptional, (80)
"Our family of five adults just finished a 10 day Stay here. Looks just like the pictures. The view is amazing!!!! The house is a great size for families with plenty of room to spread out and have your own space with tons of outdoor seating and areas. We enjoyed the pool and the hot tub every day and the beach is a pretty close drive. You can walk to the beach, however it is all downhill for a long way so unless you’re very fit, I wouldn’t recommend it, as you’d be going entirely uphill in the...
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach

105-1 Puamana Spacious Townhome Near Ocean.

9.4 out of 10, Exceptional, (52)
"We checked out of this beautiful condo three days before the Maui fires. It was one of those places where we for sure will come back to. As far as I can tell, it is still standing, but the clubhouse and some surrounding buildings did burn. This is the most amazing location on the island. Will definitely be back hopefully to help rebuild, and for sure to enjoy the beauty."
105-1 Puamana Spacious Townhome Near Ocean.

272-2 Oceanfront Magic

10.0 out of 10, Exceptional, (1)
"We had a great time. The house is on the waterfront which is good for beginner surfers (like us). We took some of the best pictures of the entire vacation. The management was extremely responsive, kind, and very professional. We'll be back soon."
272-2 Oceanfront Magic

4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea Beach

10.0 out of 10, Exceptional, (57)
"This was our first trip to Maui. Linda was very attentive and sent us multiple recommendations so that we could have an idea of things we wanted to do prior to our stay. Having access to the pool was very nice as well for the evenings we wanted to continue relaxing in the water without the beach. We highly recommend this property and would love to rent it again in the future!! "
4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea Beach

Spacious Maui Beach House, Private Pool, AC, Sleeps 6

10.0 out of 10, Exceptional, (46)
"We arrived shortly after a substantial rain storm that flooded the area. Amber and her family worked hard to clean up and by the time we arrived we could barely notice the area was recently flooded. The house was great, but the pool area was the highlight. Amazing to have a private pool area like that steps from the beach. Our family spent hours in it every day. Thanks for the great stay and we hope to return ."
Spacious Maui Beach House, Private Pool, AC, Sleeps 6

PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING

9.8 out of 10, Exceptional, (70)
"Home exceeded our expectations. Private beautiful backyard and clean home. Quick access to everywhere we needed to go and had chairs and towels for the beach. Highly recommend this property! "
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING

PRIVATE HOME-NEWLY REMODELED-AC-HOT TUB-METICULOUS CLEANING

9.8 out of 10, Exceptional, (58)
"The house was perfect, plenty of space, very nice amenities. Thank you very much!"
PRIVATE HOME-NEWLY REMODELED-AC-HOT TUB-METICULOUS CLEANING

Sugar Beach Resort condo with ocean view, AC - surf, bike & golf

8.8 out of 10, Excellent, (48)
"Beautiful sunsets, beach just off patio, and easy parking by door. Furniture needs updating and could be a little cleaner but rarely inside anyway. Small price to pay for view and price. Full kitchen and bath adequate. Towels, cooler, and beach chair available for use. Washer and dryer in room. Patio seats 4. Great place for breakfast. You can rent snorkel equip and life vests at shop on site. Gift bag upon arrival."
Sugar Beach Resort condo with ocean view, AC - surf, bike & golf

BEACHFRONT HOUSE KIHEI, MAUI..TRUE HAWAIIAN HOME 1960's

9.8 out of 10, Exceptional, (97)
"We truly enjoyed the beach house! The sunsets were amazing! "
BEACHFRONT HOUSE KIHEI, MAUI..TRUE HAWAIIAN HOME 1960's

Location, Location.... Just Steps Away from the Ocean!

9.6 out of 10, Exceptional, (134)
"This was an amazing location, so close to Lahaina & easy to get throughout the island. The condo supplies in the kitchen were great. We found this to be a great stay. If I were to be very nitpicking, the bathroom fan was very dusty & got me thinking maybe what else was dirty, however I saw nothing else. The pools need a bit of love that are in the complex, but the oceanside one was so amazing that the love that is needed to it does not even matter. I would say this is one of the best pools I...
Location, Location.... Just Steps Away from the Ocean!

Stunning Beach Front Townhouse

10.0 out of 10, Exceptional, (87)
"Stunning is the right word for the location and view. The evening sunsets were beautiful.The condo has everything you need for a week of staying in or going out. Kitchen is well equipped, plenty of towels, and lots of beach gear.Couldn't ask for a better spot. We would definitley stay again!"
Stunning Beach Front Townhouse

BEACHFRONT MAUI KIHEI HOUSE

9.8 out of 10, Exceptional, (156)
"We were a multigenerational family with ages from 5 to 76 spending quality time together from 2 different parts of Canada. The house more than adequately suited our needs..the lanai was great for dinners, the yard was great for games, the beach was great for watching beautiful sunsets. Our host, Brian, was most accommodating and responded to our needs quickly. I would not hesitate to recommend this house for your family gathering…you will not regret it. Thank you, Brian, for sharing your...
BEACHFRONT MAUI KIHEI HOUSE

Spacious Hawaiian home 50 steps from Sugar Beach!

8.8 out of 10, Excellent, (66)
"It was a great location and convenient to lots of things. More neighborhood and not resorty."
Spacious Hawaiian home 50 steps from Sugar Beach!

Charming 3 BR Puamana Oceanfront in private gated community

9.6 out of 10, Exceptional, (105)
"Comfy beds, lots bathrooms, well stocked kitchen in a georgous location. Paradise! "
Charming 3 BR Puamana Oceanfront in private gated community
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 Kahoolawe

Aston Maui Hill

3.0 star property
9.0 out of 10, Wonderful, (779)
"Property was lovely and we especially appreciated the surprise welcome gift that was waiting for us. Pool was well maintained. It felt a little small for the number of units but we never had a problem finding lounges to sit in. "
Aston Maui Hill

Wailea Ekahi - CoralTree Residence Collection

3.0 star property
9.2 out of 10, Wonderful, (510)
"Perfect location, comfortable apartment and great view. Coral tree was very responsive to all my needs. "
Wailea Ekahi - CoralTree Residence Collection

Wailea Grand Champions - CoralTree Residence Collection

3.0 star property
9.0 out of 10, Wonderful, (694)
"Great location, remodeled and clean. "
Wailea Grand Champions - CoralTree Residence Collection
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.