Holiday Homes in Wailea-Makena

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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec

Featured Holiday Homes in Wailea-Makena and around

Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (86)
"Maui Meadows Guesthouse is spectacular. The private pool and spa with waterfall are its own little paradise. The location is in a quiet neighborhood with quick access to beaches, restaurants and island activities. Andrew our host is helpful, quick to respond and meticulous. From the backyard porch swing for Grandpa to the toy drawer for our Grandson, this house provides comfort and relaxation for all. We hope you enjoy your stay as much as we have."
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center
A heated pool

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

9.8 out of 10, Exceptional, (103)
"Beautiful property"
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center
Beautiful Oceanfront Views! Enjoy Hotub, Grill & 3 Lanais!
Property grounds

Beautiful Oceanfront Views! Enjoy Hotub, Grill & 3 Lanais!

9.8 out of 10, Exceptional, (78)
"Perfect location, well equipped unit, outstanding water front property"
Beautiful Oceanfront Views! Enjoy Hotub, Grill & 3 Lanais!
Gorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View
Beach nearby, sun-loungers, beach towels

Gorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View

10.0 out of 10, Exceptional, (68)
"stayed for one week with family and enjoyed the place very much. The host is very attentive and quick to respond to all questions/requests. We will come back."
Gorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View
Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!
Beach

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

9.4 out of 10, Exceptional, (58)
"Everything you need in the condo and enough beaches to try one every day!"
Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!
Ground-floor condo steps from pool - hot tub, tennis, beach access
Pool

Ground-floor condo steps from pool - hot tub, tennis, beach access

9.4 out of 10, Exceptional, (24)
"We were v"
Ground-floor condo steps from pool - hot tub, tennis, beach access
Very Best Deluxe Ocean View...Panoramic View....First Class!!
Pool

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

10.0 out of 10, Exceptional, (149)
"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!!
Maui Breeze Retreat at Ho'olei! Open Sep 25-Oct 14, Oct 26-Nov 7 & Nov 26-Dec 10
Sun-loungers

Maui Breeze Retreat at Ho'olei! Open Sep 25-Oct 14, Oct 26-Nov 7 & Nov 26-Dec 10

10.0 out of 10, Exceptional, (140)
"Beautiful property in a great location. "
Maui Breeze Retreat at Ho'olei! Open Sep 25-Oct 14, Oct 26-Nov 7 & Nov 26-Dec 10
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach
Property grounds

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

9.8 out of 10, Exceptional, (88)
"This was a great home as well as nicely stocked home for our vacation. "
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach
Kihei Akahi A108: Kamaole Beach II Ocean View Town House directly across street.
Property grounds

Kihei Akahi A108: Kamaole Beach II Ocean View Town House directly across street.

9.2 out of 10, Wonderful, (55)
"This condo was in the perfect spot near shopping right across from the ocean. The only complaint was there were little bugs in the kitchen that got into food that I had to throw away. And I feel the cleaning could have been better. I will say it has everything that you need while you were there overall we were fine with the exception of those couple of things"
Kihei Akahi A108: Kamaole Beach II Ocean View Town House directly across street.
Sleeps 10, Family Favorite, Fully Upgraded Modern Renovated & Decorated Remodel
A heated pool

Sleeps 10, Family Favorite, Fully Upgraded Modern Renovated & Decorated Remodel

10.0 out of 10, Exceptional, (32)
"Comfortable and spacious, but it was the peacefulness, comfort and view from the lanai that drew us outdoors while we were staying. Easy walk to the fabulous pool area, and very easy access to many beautiful beaches. We would absolutely stay here again."
Sleeps 10, Family Favorite, Fully Upgraded Modern Renovated & Decorated Remodel
Exquisite Oceanview Villa: Gourmet Kitchen, Private Elevator and Pool Table
Pool

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
Beautiful Home! 4 Adults 4 Minors w/Stunning Ocean Views!
Beach

Beautiful Home! 4 Adults 4 Minors w/Stunning Ocean Views!

10.0 out of 10, Exceptional, (49)
"This place was perfect for our stay with 4 adults and 4 kids. The lanai has a wonderul view. The place was clean and in a great location."
Beautiful Home! 4 Adults 4 Minors w/Stunning Ocean Views!
NEW LISTING Private Home across from Keawakapu Beach Tennis Pickleball Court!
Beach

NEW LISTING Private Home across from Keawakapu Beach Tennis Pickleball Court!

9.8 out of 10, Exceptional, (8)
"Wonderful property across the street from beach! For us it was fantastic!! Mahalo"
NEW LISTING Private Home across from Keawakapu Beach Tennis Pickleball Court!
Panoramic Ocean View Condo on Golf Course close to Beaches
Interior

Panoramic Ocean View Condo on Golf Course close to Beaches

10.0 out of 10, Exceptional, (15)
"We absolutely loved our stay at this beautiful vacation home, with amazing views, and great access to beaches, restaurants and shops. We would come back in a heartbeat "
Panoramic Ocean View Condo on Golf Course close to Beaches
Exclusive Gated Paradise Ho'olei Villa and Private Elevator w/ Resort Amenities!
Pool

Exclusive Gated Paradise Ho'olei Villa and Private Elevator w/ Resort Amenities!

10.0 out of 10, Exceptional, (44)
"Top notch place to stay! Great location even better view! "
Exclusive Gated Paradise Ho'olei Villa and Private Elevator w/ Resort Amenities!
PRIVATE HOUSE ON MAUI / 3 BEDROOMS / 5MIN TO BEACH /UPGRADED WAILEA / KIHEI HI.
Exterior

PRIVATE HOUSE ON MAUI / 3 BEDROOMS / 5MIN TO BEACH /UPGRADED WAILEA / KIHEI HI.

9.8 out of 10, Exceptional, (39)
"Huge home and very nice location. Marc was quick with communication. Thank you!"
PRIVATE HOUSE ON MAUI / 3 BEDROOMS / 5MIN TO BEACH /UPGRADED WAILEA / KIHEI HI.
DISCOUNTED OCTOBER Special - Oceanfront Private Home
Outdoor dining

DISCOUNTED OCTOBER Special - Oceanfront Private Home

10.0 out of 10, Exceptional, (108)
"The house is awesome and would definitely stay there again. Janna and her team are great. "
DISCOUNTED OCTOBER Special - Oceanfront Private Home
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
Beach nearby, beach towels

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

10.0 out of 10, Exceptional, (91)
"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
Breath taking ocean and volcano views! Pool,Close to beaches and everything else
Outdoor pool

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

9.8 out of 10, Exceptional, (157)
"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
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

Days Inn by Wyndham Maui Oceanfront

Days Inn by Wyndham Maui Oceanfront

10/10 Excellent
" ,,,"
George 4-night trip
Posted 20 hours ago
Days Inn by Wyndham Maui Oceanfront

Find out more about Wailea-Makena

Find out more about Wailea-Makena

Wailea-Makena Holiday Homes information

Number of reviews
1,149
Accommodation
82 Holiday Homes
Lowest Price
Highest Price

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