Search Vacation Homes in Wailea-Makena

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Vacation Homes in Wailea-Makena

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

9.4 out of 10, Exceptional, (73)
"Excellent "
Ekahi Village 44C - Beautifully appointed Ocean View Condo mins from the beach

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

9.8 out of 10, Exceptional, (74)
"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

DISCOUNTED AUGUST SPECIAL Oceanfront Private Home

10.0 out of 10, Exceptional, (104)
"We had a wonderful time and the location can’t be beat!"
DISCOUNTED AUGUST SPECIAL Oceanfront Private Home

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

10.0 out of 10, Exceptional, (87)
"The location of the house is in a peaceful neighborhood just a short drive from the beach. It was great to be able to chill out after the day's adventure without being too close to the resorts and town. The house itself was spacious and had everything we meeded. The hosts were great and very responsive. Next time we're in Maui, we'll be back! "
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui

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

10.0 out of 10, Exceptional, (135)
"We had a great stay! The property is beautiful and close to beaches, restaurants, and groceries. It was exactly what our family of four was looking for."
Stunning views! Exclusive pool, spa and big private yard.

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

9.8 out of 10, Exceptional, (152)
"The experience couldn’t have been better! The house is lovely and was just what our family was looking for in being a home away from home in paradise. The house was full of useful amenities - kitchen is fully stocked; the laundry is great; and there is everything you need for the beach!The location is very close to town but far enough away to feel completely relaxed.Our family would absolutely stay here again!"
Breath taking ocean and volcano views! Pool,Close to beaches and everything else

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

9.8 out of 10, Exceptional, (96)
"Awesome stay! Very accommodating with everything you need in the kitchen! Great for family gatherings. Close to pool and beach! Beach gear to accommodate days on the sand! Definitely would stay again! "
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center

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

10.0 out of 10, Exceptional, (83)
"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

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

10.0 out of 10, Exceptional, (146)
"Everything was simply breathtaking!! What a beautiful condo and the location is second to none!!"
Very Best Deluxe Ocean View...Panoramic View....First Class!!

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

9.8 out of 10, Exceptional, (96)
"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

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

9.8 out of 10, Exceptional, (86)
"Wonderful home with nice amenities."
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach

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

10.0 out of 10, Exceptional, (141)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our fourth time staying here and it never disappoints. Lovely view, lovely home. Quiet neighborhood. Great location. We can't wait to come back."
Summer Deals Book now Island Retreat Spacious 3B 3B home.

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

9.6 out of 10, Exceptional, (69)
"Will stay again"
Exquisite Oceanview Villa: Gourmet Kitchen, Private Elevator and Pool Table

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

10.0 out of 10, Exceptional, (1)
"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

Ho'olei Ocean View 21-6 Newly Listed, Renovation May 2025

10.0 out of 10, Exceptional, (1)
"I would definitely stay here again! The condo was amazing and better than I expected. My only issues was having to try and track down the check in instructions at the last minute before we got there. Would have been nice to have some the instructions a little bit earlier. We would have ordered groceries earlier and used some of the other services offered but didn’t know about them until we checked in. I would still recommend this place. "
Ho'olei Ocean View 21-6 Newly Listed, Renovation May 2025

Top-tier getaway with pools, grill & hot tub - the waves await

9.4 out of 10, Exceptional, (21)
"Great property with wonderful views"
Top-tier getaway with pools, grill & hot tub - the waves await

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

10.0 out of 10, Exceptional, (60)
"Neat clean lots of amenities "
Luxurious Tropical Home with Heated Pool, 5min to Wailea Beach, Mini Split ACs!

One-of-a-Kind Maui Getaway!

10.0 out of 10, Exceptional, (108)
"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!

Exclusive Gated Paradise: Ho'olei Villa + Private Elevator and Resort Amenities!

9.6 out of 10, Exceptional, (82)
"Awesome place. Well appointed and in a great location."
Exclusive Gated Paradise: Ho'olei Villa + Private Elevator and Resort Amenities!

Maui Breeze Retreat at Ho'olei open Aug 27-Sep 14, Sep 25-Oct 11 & Oct 29-Nov 15

10.0 out of 10, Exceptional, (133)
"The property is clean and the property management response to several request was excellent."
Maui Breeze Retreat at Ho'olei open Aug 27-Sep 14, Sep 25-Oct 11 & Oct 29-Nov 15
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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