Holiday Homes in Wailea-Makena

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Featured Holiday Homes in Wailea-Makena

Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!

9.4 out of 10, Exceptional, (58)
"We had a wonderful stay. Loved the location and size of condo."
Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!

DISCOUNTED AUGUST SPECIAL Oceanfront Private Home

10.0 out of 10, Exceptional, (107)
"We had a wonderful week with our adult children and spouses/fiancée. The house perfect for our group of 7.Janna was a great host. Very responsive to our questions/texts.I recommend this house to anyone looking for a family vacation on Maui."
DISCOUNTED AUGUST SPECIAL Oceanfront Private Home

Luxurious Tropical Home with Heated Pool, 5min to Wailea Beach, Mini Split ACs!

10.0 out of 10, Exceptional, (62)
"Neat clean lots of amenities "
Luxurious Tropical Home with Heated Pool, 5min to Wailea Beach, Mini Split ACs!

Panoramic Views - Fourth Row Ho'olei - One of a Kind 112-4

10.0 out of 10, Exceptional, (27)
"The house is laid out very nicely. The views are spectacular."
Panoramic Views - Fourth Row Ho'olei - One of a Kind 112-4

Makena Oceanfront Home 3 Bedroom/3 Bath 1/2 Acre Lot On The Ocean

9.8 out of 10, Exceptional, (98)
"Comfortable beds, effective air conditioning and a great location a short walk from a sandy beach "
Makena Oceanfront Home 3 Bedroom/3 Bath 1/2 Acre Lot On The Ocean

Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center

9.8 out of 10, Exceptional, (100)
"Our extended family really enjoyed this condo. It is spacious for a large group. The location is very convenient to walk to the amenities -especially the beautiful pool area.It is also easy to drive to other areas of Maui.The property manager is very helpful- we enjoyed a number of the restaurant recommendations.We would love to return- thanks to all for making it a special stay."
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center

Maui Designer Beach Villa, Wailea, Ho'olei 39-2

9.8 out of 10, Exceptional, (25)
"Top notch location "
Maui Designer Beach Villa, Wailea, Ho'olei 39-2

Breath taking ocean and volcano views! Pool,Close to beaches and everything else

9.8 out of 10, Exceptional, (154)
"We had the best time at our VRBO. The house was beautiful. The host was so accommodating. They answer our text right away. The pool was amazing. We would definitely book here again."
Breath taking ocean and volcano views! Pool,Close to beaches and everything else

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

9.8 out of 10, Exceptional, (76)
"Great location for family gathering. Close to many amenities. "
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING

Very Best Deluxe Ocean View...Panoramic View....First Class!!

10.0 out of 10, Exceptional, (148)
"The home was amazing! Great view and quick access to the Grand Wailea and nearby shops. Will definitely stay here again!"
Very Best Deluxe Ocean View...Panoramic View....First Class!!

Kula Luxury Retreat With Stunning Ocean & Mountain Views!

10.0 out of 10, Exceptional, (72)
"We spent an amazing week here. If you are looking for peace and quiet with a stunning view and gracious hosts, this is the place! We will definitely stay here again!"
Kula Luxury Retreat With Stunning Ocean & Mountain Views!

Summer Deals Book now Island Retreat Spacious 3B 3B home.

10.0 out of 10, Exceptional, (141)
"There could not be a better house with a better view The yard itself is breathtaking The pictures are perfect on this site Martha was very attentive a came to our every need . Very clean place and kitchen has every appliance and utensils you could want. The concierge Martha referred us to was Dona and she booked everything for us. Thank you "
Summer Deals Book now Island Retreat Spacious 3B 3B home.

Ekahi Village 44C - Beautifully appointed Ocean View Condo mins from the beach

9.4 out of 10, Exceptional, (75)
"Excellent "
Ekahi Village 44C - Beautifully appointed Ocean View Condo mins from the beach

Exquisite Oceanview Villa: Gourmet Kitchen, Private Elevator and Pool Table

9.6 out of 10, Exceptional, (70)
"Will stay again"
Exquisite Oceanview Villa: Gourmet Kitchen, Private Elevator and Pool Table

Wailea Getaway - 2BD - steps to great pool & beach

9.0 out of 10, Wonderful, (2)
"We stayed for 8 days and everything was perfect! Condo is clean comfortable and fully stocked with everything you could need. Beach front pool is a must when in Maui as when the Trade Winds kick up you can retreat and enjoy the rest of the day at the pool while still enjoying the views and sounds of the beach. The pavilion and out door kitchen, ice-maker, refrigerators tables and chairs, allow every evening to be an ocean front dining experience. This is an amazing location second to none!!!! "
Wailea Getaway - 2BD - steps to great pool & beach

Hale Kamaole Condo w/ Shared Pool, Shared Outdoor Pool - Close to Beaches

9.0 out of 10, Wonderful, (30)
"This place had everything that was needed for a couple night stay. Nothing fancy, but comfortable."
Hale Kamaole Condo w/ Shared Pool, Shared Outdoor Pool - Close to Beaches

Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area

10.0 out of 10, Exceptional, (86)
"Great location, clean, comfortable and well maintained. The owner was easy to work with and truly provided everything that you need for a great vacation."
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area

Stunning views! Exclusive pool, spa and big private yard.

10.0 out of 10, Exceptional, (138)
"Lovely home with everything we would ever need. Wonderful hosts"
Stunning views! Exclusive pool, spa and big private yard.

One-of-a-Kind Maui Getaway!

10.0 out of 10, Exceptional, (109)
"The architecture and view were absolutely amazing and the house was perfect for our family. The outdoor spaces were ideal - loved the infinity pool! There were some minor issues during our stay, but the host was very attentive and quick to respond. I am confident that the owner has already handled the few remaining items. Our family is very excited to come back to this beautiful home. "
One-of-a-Kind Maui Getaway!

Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui

10.0 out of 10, Exceptional, (89)
"We had a fantastic time at this beautiful home that was fully equipped for our stay. Dan and Kelly are amazing hosts and we couldn’t have wished for a better place to be based for our Maui trip. Thank you so much!"
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
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 Wailea-Makena Hotel Reviews