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Wailea-Makena vacation rentals

Vacation rentals in Wailea-Makena by owner — compare homes, condos and cabins, message verified hosts, and book direct with no service fees.

Wailea-Makena, located on Maui, is known for its luxury resorts and beaches like Wailea Beach, Big Beach, Ahihi-Kina'u Natural Area Reserve, and the snorkeling hotspot of Molokini Crater. Visitors come here for top-tier golf courses, the Maui Film Festival, and dining at the Shops at Wailea. Houfy allows you to connect with local hosts in Wailea-Makena, offering a hassle-free booking experience. Browse stays ranging from upscale condos and beachfront homes to golf course villas in neighboring Kihei and Maalaea. Winter is popular for whale watching, while summer offers calm seas perfect for diving.

Top-Rated Vacation Homes in Wailea-Makena

Browse the highest rated vacation properties in Wailea-Makena.

Kihei Kai Nani, Sandy Beaches, Free Parking, Wi-Fi

1 bd·1 ba
5· 33

$737.62 USD total for 3 nights

Sep 29 – Oct 2, 2026

Wow!! Our best Airbnb experience, EVER!! We love traveling and often use Airbnb and DiAnne ‘s place was absolutely perfect! DiAnne is an outstanding host with excellent communication and attentiveness. Her condo was stocked with everything we could possibly need. The kitchen was outstanding and we were able to easily prepare our meals which saved money and helped us to stick with our healthy nutrition choices. DiAnne’s place was peaceful, very safe, cute, comfortable , conveniently located and an outstanding value. The staff and security team were friendly and very professional. The bed was very comfortable and all of the neighbors were respectful and quiet. We slept well. The pool was so nice and it was an easy, close walk to do laundry which saved us $120 because we didn’t need checked bags! The bus was easy to walk to and loved the Kihei which provides free transportation to and from the airport. The beach was so close! We were able to enjoy the sunset!
L. · Stay April 2024

Tranquil 1BD/2BA in South Kihei, Maui

1 bd·2 ba
5· 82

$2,341.32 USD total for 5 nights

Oct 29 – Nov 3, 2026

Home away from home
It was a nice treat after long hours of travel to let my hair down once we got to our room. The host was extremely prompt and detail oriented to assure we had a seamless check in and was thoughtful and provided ideas on how to spend our stay. I was happily surprised that our contribution went to helping rescue Maui marine wildlife. We will be staying here again.
J. R. · Stay March 2024

Comfortable 2BR/2BA in South Kihei, Maui

2 bd·2 ba
5· 44

$2,545.73 USD total for 4 nights

Oct 9 – 13, 2026

Probably the best outfitted rental I’ve ever have
Probably the best outfitted rental I’ve ever had, seriously, this condo had everything that you could need for a beach rental. Even things that are atypical were there like laundry soap, beach cart, snorkeling gear, and a cooler. The location was good. The pool is right outside of the unit, and one of the best beaches in the area was a 5 minute walk away. There were many affordable restaurant options in walkable distance, and just a few minutes in the car got you to many more. Would definitely stay again if we find ourselves vacationing in Maui.
T. A. · Stay July 2022

Oceanfront Maui Penthouse

3 bd·3 ba
5· 106

$8,512.71 USD total for 5 nights

Dec 11 – 16, 2026

Beautiful property, terrific owners
We've been to Maui numerous times and have generally stayed in high end hotels though we've done vacation rentals elsewhere. This location can't be beat and the condo is spectacular, exceptionally well outfitted for vacationers and professionally managed. The layout worked well for our family with older/adult children. It would also be excellent for couples vacationing together. We like to read, swim, walk, play games and we like to be next to the ocean - this place was ideal. The kitchen is surprisingly well outfitted and cooking together there was a joy. Easy access to Wailea restaurants and La Pelouse was also appreciated. We generally go to Big Beach but were so happy with the beach at Makena Surf that we barely got in the car. We found it so easy and pleasant to cook that we only ate out twice - at Migrant and Morimoto's, both of which we'd recommend for dinner. We also enjoyed hiking in the interior and lunch in Makawao where we'd gone for malasadas (but Komoda's was closed). The condo's lanais are lovely and a great place for morning coffee, reading and early evening cocktails. There were a few minor glitches with the condo but they were taken care of quickly and professionally. The owners have anticipated almost any question one could have in the form of a well thought out and well referenced notebook. We liked the views, the quiet and the cleanliness and comfort of this condo. The owners have outfitted it at a high level - nice sheets and towels, tasteful furniture, new carpeting, great kitchen and bath supplies. They have managed to make you feel like you're being welcomed into their home and like you're not imposing. Thank you for a wonderful stay. We can't wait to go back.
C. F. · Stay January 2016

Best Location! First Floor Family Friendly 2B/2B

2 bd·2 ba
5· 2

$2,093.98 USD total for 5 nights

Sep 29 – Oct 4, 2026

Kihei Akahi - Amazing Location

1 bd·1 ba
5· 13

$1,635.97 USD total for 4 nights

Sep 29 – Oct 3, 2026

Aloha Awesome and Paradise Perfect
What a fabulous condo Laurie and Jeff provide for your Maui island stay! As the saying goes, location, location, location! Not only does this condo provide you a luxuriously furnished place, it offers serenity and calm moments to soak up the aloha spirit in the morning breezes or sunset vibrant colors each evening. You will not be disappointed whatsoever! In fact, you’ll begin planning for a return visit before you leave. Laurie and Jeff are amazing owners and truly deliver 5-star service from beginning to end. You will find yourself in an island paradise location with one of two pools just steps away and one of several beaches a walk down the condo complex driveway. Laurie and Jeff have furnished this home with everything you can think of for your vacation needs (from beach gear, kitchen needs, bath/BR linens, electronic connections, etc). You can cook your own meals or explore the many wonderful restaurants within walking distance of a short drive away. Don’t forget to get your local Shave Ice treat too! You can immerse yourself in the many various island activities (snorkeling, paddle boarding, fishing, beach walking, swimming, mountain biking adventures on Mt. Haleakala as well trips to Lahaina, Upcountry and/or taking a cruise to Hana and exploring the waterfalls and delightful swimming spots along the way. OR, you can do everything that brings you rest, relaxation and rejuvenation of the body/spirit/soul. Enjoy the patio while listening to the soft songs of the island birds while breathing in the sweet scent of the plumeria tree or sit by the pool that’s just steps away or languish under a palm tree/umbrella on the beaches that are a short stroll from this condo. Give yourself and your family/friends the most enjoyable and memorable vacation at Kihei Hale O Maluhia. You’ll be on Maui time and living in the island spirit before you know it! Aloha!
G. · Stay June 2018

Wailea Surf Shack: Beaches, Shops & Golf!

1 bd·2 ba
5· 134

$1,401.99 USD total for 3 nights

Oct 10 – 13, 2026

This air bnb was by far the best we have ever stayed at! We stayed here for our honeymoon for a week, and Jes and Pete’s place is top notch. They were extremely thoughtful and had left cookies, macadamia nuts, fresh fruit, and a little surprise for us in the fridge! Also, Jes responded to any questions we had right away and was very friendly! I’ve never had such a responsive host. The place itself is absolutely gorgeous as it overlooks the golf course, the place was immaculate in terms of cleanliness and amenities! This air bnb had it all, and everything you could possibly need and more! They have plenty of beach chairs, boogie boards, a cooler, sunscreen, a variety of spices for cooking, and toiletry items! This condo is absolutely stunning with its open floor concept and is so peaceful. If you don’t want to stay at a resort but want to be in the heart of Wailea—stay here! We were able to walk or easily drive to everything. I absolutely loved this location, and the hosts are so kind!
G. · Stay July 2024

Ocean Views! Maui Vista - 180 steps to beach

2 bd·2 ba
5· 2

$1,538.20 USD total for 3 nights

Oct 17 – 20, 2026

Look no further!!!! If you are looking to book in Maui and you have 3-6 people then this is the spot for you. Located walking distance from the beach with plenty to do around. This hidden gem is equipped with the privacy for your family and recently renovated. I will book here again and every time I come to Maui. Captain Morgan’s is where you want to be.
C. · Stay March 2023

Recommended Homes in Wailea-Makena

Handpicked properties we think you'll love in Wailea-Makena.

Maui Banyan Studio T204A

0 bd·1 ba
4.72· 130

$566.03 USD $528.70 USD total for 3 nights

Oct 12 – 15, 2026

Kihei Akahi (2531 S. Kihei Road), #DG06

1 bd·1 ba
4.97· 120

$890.73 USD total for 3 nights

Sep 29 – Oct 2, 2026

Convenient 1BD/1BA in South Kihei, Maui

1 bd·1 ba
4.94· 79

$1,497.85 USD total for 5 nights

Oct 9 – 14, 2026

Cozy Studio in South Kihei, Maui

0 bd·1 ba
4.98· 95

$1,207.73 USD total for 4 nights

Oct 9 – 13, 2026

Maui Banyan T204

1 bd·1 ba
4.9· 105

$660.83 USD $599.51 USD total for 3 nights

Sep 29 – Oct 2, 2026

Wailea Grand Champions Villa

2 bd·2 ba
4.94· 145

$1,195.43 USD total for 3 nights

Sep 30 – Oct 3, 2026

Keawakapu Ocean View Condo

2 bd·1 ba
4.94· 149

$1,018.55 USD total for 4 nights

Sep 29 – Oct 3, 2026

South Kihei Guest Suite - Quiet Private Convenient

1 bd·1 ba
4.99· 151

$1,519.65 USD total for 6 nights

Oct 2 – 8, 2026

Pet friendly vacation rentals in Wailea-Makena

Bring your furry friend along! Browse pet-welcoming homes in Wailea-Makena.

$3,198.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

$2,336.50 USD total for 3 nights

Oct 2 – 5, 2026

Why visit Wailea-Makena

Discover what makes Wailea-Makena a perfect vacation rental destination.

Pristine Beaches

Wailea Makena is known for its stunning beaches.

Enjoy the golden sands of Wailea Beach, just 0.5 miles from the city center, ideal for sunbathing and snorkeling.

World-Class Golfing

Play at top-rated courses with ocean views.

Tee off at the Wailea Golf Club, 1 mile away, featuring three championship courses with scenic ocean vistas.

Cultural Experiences

Discover Hawaiian culture and history.

Visit the Keawala'i Congregational Church, just 4 miles away, for a glimpse into Maui's religious history and local culture.

Family-Friendly Activities

Entertain families with diverse activities.

The Maui Ocean Center, 10 miles from Wailea, offers interactive exhibits and the state's largest aquarium tank.

Where to stay in Wailea-Makena

The best areas and neighborhoods for your vacation rental in Wailea-Makena.

Wailea Resort

This area boasts luxury resorts, high-end shopping, and fine dining options along Wailea Alanui Drive.

Best for: luxury travelers, honeymooners, golfers

Makena

Known for its natural beauty, Makena is perfect for secluded beaches and tranquil surroundings.

Best for: nature lovers, tranquility seekers, beachgoers

Kihei

Located just north of Wailea, Kihei offers more budget-friendly accommodations and casual dining.

Best for: budget travelers, families, surfers

Maui Meadows

Situated on the slopes of Haleakalā, this residential area offers stunning views and easy access to parks.

Best for: nature enthusiasts, hikers, residential stay

Find Wailea-Makena vacation rentals that suit your style

Condos, vacation homes, apartments and more — pick the kind of Wailea-Makena vacation rental you want, then book it direct with the host.

Wailea-Makena vacation rentals with free WiFi, hot tub or air conditioning

Free WiFi, hot tub, air conditioning and more — every Wailea-Makena vacation rental here is listed by a verified host and bookable direct, with the price the host set.

Top attractions in Wailea-Makena

All within driving distance of Wailea-Makena vacation rentals.

Wailea Beach

Famous for its sparkling waters and golden sands, ideal for swimming and sunbathing. · 0.5 miles

Wailea Golf Club

Home to three premier golf courses offering ocean views. · 1 mile

Ahihi Kinau Natural Area Reserve

This protected area is a snorkeling paradise rich in marine life. · 5 miles

Keawala'i Congregational Church

A historic church offering insights into local Hawaiian culture. · 4 miles

Maui Ocean Center

Features Hawaii’s largest aquarium tank and marine exhibits. · 10 miles

The Shops at Wailea

An upscale shopping center with high-end retailers and dining. · 0.6 miles

Getting to and around Wailea-Makena

Getting around Wailea Makena is easiest by car, with nearby airports providing accessibility.

Airports
KAHULUI AIRPORT
Located 17 miles from Wailea, offering direct flights to major U.S. cities.
Driving
CAR RENTALS
Available at Kahului Airport and within Wailea for exploring the island at your own pace.

Similar vacation rentals near Wailea-Makena

Homes within 60 miles of Wailea-Makena, from verified hosts.

Molokai Island Retreat

1 bd·1 ba
4.98· 58

$621.02 USD total for 3 nights

Oct 25 – 28, 2026

Ocean Views- Beachfront- Steps to a Sandy Beach!

1 bd·1 ba
4.95· 151

$1,557.60 USD total for 3 nights

Oct 18 – 21, 2026

Maui Makai Condo

1 bd·1 ba
4.92· 114

$917.64 USD total for 3 nights

Sep 29 – Oct 2, 2026

Whaler 1063 on Ka'anapali Beach, Maui, Hawaii

1 bd·1 ba
4.98· 165

$1,406.74 USD total for 3 nights

Oct 5 – 8, 2026

Luxury Oceanfront Turtles Sunsets - Maui, Hawaii

1 bd·1 ba
4.9· 302

$1,256.76 USD total for 3 nights

Nov 11 – 14, 2026

Beachfront Guest Favorite | Turtles, Seals & Surf

1 bd·1 ba
5· 15

$828.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

Ocean Escape

0 bd·1 ba
5· 92

$933.93 USD total for 3 nights

Sep 29 – Oct 2, 2026

Tropical Hawaiian Oceanfront - Maui, Hawaii

1 bd·1 ba
4.85· 215

$882.32 USD total for 3 nights

Oct 24 – 27, 2026

Oceanfront Turtle Cove Maui Home - 5BR, 4BA, A/C

5 bd·4 ba
4.78· 148

$6,603.00 USD total for 3 nights

Oct 6 – 9, 2026

Amazing Sunsets Oceanfront Views - Maui, Hawaii

1 bd·1 ba
4.81· 194

$804.60 USD total for 3 nights

Sep 29 – Oct 2, 2026

Mahana 919

2 bd·2 ba
5· 193

$5,668.40 USD total for 5 nights

Oct 1 – 6, 2026

Kihei Garden Oasis

4 bd·2 ba
5· 161

$3,610.70 USD $2,958.95 USD total for 5 nights

Oct 1 – 6, 2026

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