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House vacation rentals in Wailea, Wailea-Makena

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Popular amenities for Wailea, Wailea-Makena house rentals

House rentals with a pool

Top guest favorite
A serene sandy beach is shown with gentle waves lapping against the shore. Sunbathers are positioned leisurely on the sand, and a few umbrellas provide shade nearby. Lush palm trees line the back of the beach, creating a tranquil atmosphere under a clear blue sky.
Home in Lahaina
5 out of 5 average rating, 21 reviews

Newly Remodeled Cottage

SusanRating, 5 stars1 week ago
Look no more!! Vans place is absolutely stunning. We stayed here with our four kids & we cannot wait to return. The location is so peaceful and extremely spacious. Thank you Van for hosting our stay. We look forward to staying here again.
Superhost
Home in Lahaina
4.93 out of 5 average rating, 30 reviews

ICC 20 Remodeled 2BD Hawaiian Cottage w Pool AC

NeekaRating, 5 stars4 months ago
Beautiful property with a great deck. Was perfect for a family vacation. So close to all the resorts and the beach. Great location to get around Maui. Would highly recommend!
Guest favorite
A private balcony features a wooden table surrounded by four chairs, with a serene view of lush greenery and palm trees. Bright sky and the distant buildings of the resort can be seen, suggesting a peaceful outdoor setting.
Home in Kihei
4.95 out of 5 average rating, 22 reviews

Luana Kai C209

ShriyaRating, 5 stars6 months ago
Beautiful condo in Kihei with every possible amenity to make you feel right at home. Private and peaceful with a pool, beach access. Perfect for getting around to snorkeling which was nearby. Access to stores too. Great place from which to visit Haleakala as well!
Superhost
A refreshing pool is surrounded by palm trees, with the ocean visible in the background. Several lounge chairs are positioned near the poolside for relaxation. The clear blue water reflects the bright sky, creating a vibrant outdoor space.
Home in Kihei
4.9 out of 5 average rating, 82 reviews

Maui Sunset Resort A102 - Aloha Mai, Remodel, Grou

KaiaRating, 5 stars1 month ago
Gary was proactive with communications and his place was perfect for our needs! The amenities were great! the beach is a quick walk to the other end of the property and perfect for viewing the sunset!
Guest favorite
A spacious living area features comfortable seating arranged around a glass-top coffee table. Light-colored walls and tropical decor create a calming ambiance. The kitchen and dining area are visible in the background, showcasing modern appliances and a dining table for shared meals.
Home in Lahaina
5 out of 5 average rating, 9 reviews

Your Beachfront Island Home Awaits! #1A2

MiraRating, 5 stars3 weeks ago
This place is terrific! It's clean, very comfortable, nicely laid out. The rooms are spacious and all have AC units and ceiling fans - and an AC unit in the main living/eating area. The linens and towels are high quality. There is a wonderful deck that overlooks the pool and the ocean with easy access to a small grassy area and beach. The house has lots of amenities for guests' use incl boogie boards, snorkel equipment, sand toys for kids. There are also a lot of spices and other items in the pantry which is always nice when you cook in. The hosts are responsive and friendly. The only downside is the condo sits on a pretty high traffic road and it can be noisy. You can walk to some restaurants but a car is a must. I would come back here for sure.
Top guest favorite
A refreshing swimming pool is surrounded by lounge chairs, set among tropical palm trees. The water's surface reflects the nearby buildings and sky, creating a serene atmosphere. The pool area is designed for relaxation and enjoyment.
Home in Kihei
4.98 out of 5 average rating, 52 reviews

Centrally located and steps to the beach!

LukeRating, 5 stars2 weeks ago
No detail is forgotten! This is the best accessorized and appointed home away from home we have ever experienced. It is a great location, and we like the Lanai that rolls out onto the lawn. We love the short 1/2 block walk to the beach. it is wonderful to have air conditioning and fans. The kitchen is well stocked for any cooking activity and we especially appreciate it that snacks and coffee were waiting for us. We loved the gift of chocolate covered macadamias. We appreciate the superlative attention to detail and the efficient accessibility of the hosts. Mahalo Ashley and Mike!!
Superhost
A panoramic view of a sandy beach is offered, with gentle waves lapping at the shore. Clear turquoise waters meet a bright blue sky, dotted with fluffy white clouds. Lush greenery fringes the beach, enhancing the natural beauty of the idyllic setting.
Home in Kaanapali
4.89 out of 5 average rating, 108 reviews

#1 Kaanapali Beach Modern Condo C101 Maui Eldorado

JesseRating, 5 stars7 months ago
Very beautiful location to stay at in Kaanapali! Has a gym with just enough equipment, grills and pools, and an included private golf cart upon request to the beautiful Kaanapali beaches. Also towel service available until 5:30pm! So wonderful! AC and other amenities were great, did not have a single issue or complaint my entire stay here. Had a great time here, will hopefully be back!!!
Guest favorite
A private lanai is featured, providing comfortable seating with colorful pillows and a round table set for dining. Lush greenery surrounds the space, with stunning ocean views visible beyond a railing. Clear skies and soft clouds complement the serene seaside atmosphere.
Home in Lahaina
4.89 out of 5 average rating, 19 reviews

Oceanfront 2BR Condo w/ Pool Access & Sunset Views

KurtisRating, 5 stars2 weeks ago
Very highly recommend this listing! the views were stunning and with obstruction. The suite feels very private and the lanai is ideal for anyone looking to relax while looking out and watching the ocean. The unit is also very near attractions and beaches on West Maui with great parking access (included which is rare) and calm roads. Even during higher surf days, the sound proofing in the suite didn't disturb our sleep. we had a very enjoyable time!

Weekly house rentals

Guest favorite
A spacious living room is presented, featuring a large, comfortable sofa and two accent chairs with vibrant patterns. A coffee table with a glass top sits centrally, and a television is mounted on the wall. Natural light fills the area, creating an inviting space.
Home in Lahaina
4.97 out of 5 average rating, 33 reviews

Mahalo Pono @ Ka 'anapali Royal

JohnRating, 5 stars3 weeks ago
We absolutely loved Jay and Amy’s place. It had everything we needed and more. The location was perfect ( 5 minute walk to the shopping center), restaurants and beach were also a short drive away. The house was pristine. It’s better in person than in the pictures to be honest. Amy was very helpful and super responsive with any questions we had. We truly felt at home. Would definitely stay here again. Thank you, Jay and Amy for your hospitality. You truly made our vacation very special.
Superhost
A spacious lanai overlooks the ocean, furnished with a circular dining table and several chairs. Comfortable seating is arranged against the railing, providing a view of the pool and beach. Palm trees and the blue sky complete the serene coastal setting.
Home in Lahaina
New place to stay

Island-Inspired 2BD Oceanfront ~ Quam Properties

LynnRating, 5 stars3 weeks ago
We stayed in two units at Hololani. This one was my fav. More spacious. Wonderful lanai. Unit is comfortable and we felt at home. Made some great dinners and enjoyed the view. This is a neighborhood condo not the high end resort. Pool amazing. 90 degrees! We loved our stay! Note units are Not air conditioned. Fans adequate. A couple of big box fans would have gone a long way to making us more comfortable.
Top guest favorite
The cottage exterior features a light green facade and a welcoming porch. Lush greenery surrounds the property, providing privacy. Large windows allow natural light to enter. The roof is gently sloped, complemented by charming architectural elements that enhance the cottage's charm.
Home in Haiku-Pauwela
4.99 out of 5 average rating, 71 reviews

Hunter Hales KALA cottage Haiku Maui

ForrestRating, 5 stars2 weeks ago
Mike's place was very clean and it's location is hard to beat—it's a short walk from Haiku Market for food and supplies, and also just a short walk from multiple restaurants. This was my fourth trip to the Haiku area, and this was honestly the nicest and cleanest AirBnB I've stayed at there!
Guest favorite
The exterior of the cozy O'hana home is surrounded by lush tropical vegetation, featuring vibrant flowers and dense greenery. Stairs lead to the covered porch, highlighting the traditional architecture. Overhead, a bright blue sky and scattered clouds create a welcoming atmosphere.
Home in Wailuku
4.92 out of 5 average rating, 144 reviews

Gratitude Bed and Breakfast BBWK2022/0001

EliseRating, 5 stars3 months ago
We arrived at Rhonda’s on Christmas Eve and she was there to greet us and show us around the space - she had a little tree with lights set up and a lovely wreathe on the door. There was also delicious banana bread and her homegrown lilikoi waiting for us inside. The space is so comfortable and well decorated- we felt immediately at home. Very convenient to walk to a few restaurants as well. Even though the house isn’t on a main street at all, if you keep the windows open (and why wouldn’t you!) you may experience a good bit of noise in the early morning (roosters, garbage truck, general people sounds). We had a lovely time enjoying breakfast on the porch and would happily stay at the Gratitude BnB again!
Superhost
An open-concept living area is designed with high vaulted ceilings and large windows, allowing natural light to brighten the space. A comfortable sectional sofa faces a stylish coffee table, while the kitchen island offers seating with sleek barstools. Tropical wallpaper adds a pop of color.
Home in Lahaina
4.85 out of 5 average rating, 39 reviews

3-bed 2-bath Beach Bungalow w/ Bikes & Pickleball!

JessicaRating, 5 stars1 week ago
Clean and exactly like the pictures. Parking is easy and the place is charming.
A comfortable living area features a sectional sofa with decorative cushions and an armchair. Soft lighting is provided by a floor lamp, and draped curtains frame the windows, enhancing the cozy ambiance. The flooring is tiled, creating an open and inviting space.
Home in Paia
4.77 out of 5 average rating, 102 reviews

Charming 2bd/1ba downstairs Unit with AC

MackenzieRating, 5 stars7 months ago
Rina’s place was great for us. It had all the basic amenities that we needed. The place is a quick walk to the town of Paia and a few local beaches. All the food in the town is great and the beaches were awesome. It was a good place to rest after a long day of being out and about. No complaints here.

Private house rentals

A modern kitchen area features sleek stainless steel appliances and a large waterfall island with bar seating. The open layout connects to a dining area with a long wooden table, while floor-to-ceiling sliding doors provide views of the outdoor space.
Home in Wailea-Makena
New place to stay

Luxury Oceanview Wailea Retreat | Hōkū Hale

NicoleRating, 5 stars5 days ago
Absolutely EXCEPTIONAL stay. I mean it when I say photos do not do this place an ounce of justice. Upon arrival, I was greeted with spectacular views, impeccable decor, and a spotlessly clean and comfortable spot for a large group in what is easily the best location in Maui. Watching the sunset from the lanai was breathtaking and perhaps my favorite part of the whole trip. I’ve stayed at a lot of places on Maui over the years, and this is one place I can say for certain I will be coming back to. Oh - and the guidebook was a great touch for local tips!
Guest favorite
A serene view of the ocean pool area is framed by lush palm trees. The azure water reflects the afternoon sky, while a rainbow arches over the horizon. Comfortable lounge chairs surround the pool, creating an inviting space for relaxation.
Home in Lahaina
4.85 out of 5 average rating, 92 reviews

Clean, Ocean Front, Big 1 Bd, 1st Fl, Royal Kahana

NickRating, 5 stars1 week ago
First time in Maui was a success. Only thing we would change is the length of stay. Recommend 10 days minimum. Will definitely be looking to stay here again.
A private patio area features colorful lounge chairs, inviting relaxation under the shade of palm trees. A sparkling pool is centered within the space, enclosed by a fence, while the charming home is visible in the background, framed by the lush garden.
Home in Kihei
5 out of 5 average rating, 3 reviews

Hale Luana 4B House pool/spa/AC, STKM2023/00001

LauraRating, 5 stars2 weeks ago
Five stars with a big caveat about the AC- see below. The many pluses: Very good value for highly walkable neighborhood, especially for families: well-locked pool, awesome playground at the end of the block, and lots of kids toys for pool and beach. Very comfortable layout with 4th bedroom garage conversion that feels like its own suite. Robyn lives in the front house and was so helpful with local recommendations and even lent some additional beach gear. For those who are more heat sensitive like us: Listing is vague about AC settings: lowest allowed temp in the main house is 73 and in the 4th bedroom, window AC goes to 72 but only can be turned on 7p-7a. These are reasonable ways to balance electricity use, but hopefully hosts will be more transparent in the listing (and include what cost would be for lower settings, which we didn’t end up asking about because we squeaked by.) It would have been nice to have option for a cooler temp at night ideally.
Guest favorite
A spacious living area is highlighted by high wooden beams and large windows, inviting natural light. Comfortable seating arrangements include a mix of couches and chairs in tropical patterns. A dining area is visible in the background, along with an open kitchen equipped with modern appliances.
Home in Kihei
4.89 out of 5 average rating, 44 reviews

3 Bedroom Private House Kihei /Wailea Maui

AbhilashRating, 5 stars2 months ago
The coconut cottage is an ideal base for Maui adventures! Large, spacious property to easily accommodate up to 6-8 people - with a full functioning kitchen, 2.5 baths, large backyard and a lovely front-facing deck. We had the most luxurious and comfy stay, and lots of fun family memories in the main living area. The property is located in Kihei, with quick access to the beach, shopping and local markets. Marc is the most gracious host, and was incredibly accommodating, easily accessible and super kind. 10/10 recommend!!!! Would love to come back at some stage :)
Guest favorite
An outdoor lanai features a wooden deck with a table and four chairs, surrounded by vibrant tropical plants and blooming bougainvillea. Sunlight filters through the greenery, creating a welcoming space for relaxation or dining outdoors.
Home in Kihei
4.9 out of 5 average rating, 86 reviews

One Block to the Beach! Cozy Beach House in Kihei

AlisaRating, 5 stars18 months ago
Thank you for this amazing stay Leanne! We had such a great time and enjoyed the close beach at sunset, went snorkeling during the day and even saw turtles just 5min away (by car). All rooms have air condition which we enjoyed during the night. It’s a pretty quiet neighborhood so this will be a really relaxing holiday. Perfect area to explore the island. If Germany wouldn’t be as far away, we would love to come back!
An open-concept living area features a wooden dining table surrounded by upholstered chairs, alongside a light-furnished seating arrangement. A fan hangs from the ceiling, and a decorative shelf showcases glassware and plants, contributing to a bright and airy ambiance.
Home in Lahaina
5 out of 5 average rating, 4 reviews

Come Back to Puamana Nani

NicoleRating, 5 stars2 months ago
Annie is a great host, the home was clean and comfortable. The beach a minute or two walk. The pool is close to the condo, about a minute too. We slept peacefully in the comfortable beds, the kitchen was well stocked, and the place is beautiful and comforting. We sat outside to drink coffee in the mornings and it felt like home, but better.
The exterior of a two-story cottage is presented, showcasing a blend of dark wooden siding and light-colored accents. Surrounded by lush greenery, a paved pathway leads to the entrance. A sign indicating the property name is visible near the driveway.
Home in Kihei
4.97 out of 5 average rating, 67 reviews

Exclusive Beachfront Cottage, Ocean Views, WiFi/AC

MariRating, 5 stars10 months ago
Absolutely perfect! Beautiful beach access with great walkability to local restaurants and shops. This place was peaceful and quiet! Great sunset view from the balcony. The space was clean and very easy to find. The beach made for great turtle watching.

Quick stats about house rentals in Wailea, Wailea-Makena

  • Total rentals

    50 properties

  • Nightly prices starting at

    $70 before taxes and fees

  • Total number of reviews

    2.3K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Rentals with a pool

    30 properties have a pool

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

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  4. Maui County
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