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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

Superhost
Home in Kihei
5 out of 5 average rating, 3 reviews

Aloha Aku CoCoPalm Suite – Experience Tropical Bli

AshleyRating, 5 stars74 months ago
We had the most amazing time. All of the small touches were there, and we were constantly surprised by the high level of service and pride in the property. You cannot beat the view, and the hot tub is awesome! The unit was stocked with the nessesities, as well as delightful extras. The bed was incredibly comfortable, and the cherry on top was the ducks!! So charming. We cannot wait to come back!
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, 22 reviews

Newly Remodeled Cottage

SusanRating, 5 stars2 weeks 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
4.96 out of 5 average rating, 23 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!
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, 53 reviews

Centrally located and steps to the beach!

AmyRating, 5 stars2 weeks ago
Mike and Ashley’s place was perfect for our little getaway. It was one of our birthdays and they had a little balloon and card for us. They were very responsive when we needed a couple of things and I 10/10 recommend to stay here!
Guest favorite
Home in Lahaina
5 out of 5 average rating, 9 reviews

3BR/3BA Pualei Beach House

CourtneyRating, 5 stars1 week ago
Ryan's place was exactly as pictured. The neighborhood and townhouse was very quiet and family friendly. Ryan was very responsive to the small things that can sometimes come up when traveling. Lahaina is still in process of rebuilding but even so there was more than enough to stay busy. Would highly recommend.
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
4.88 out of 5 average rating, 109 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 stars3 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, 34 reviews

Mahalo Pono @ Ka 'anapali Royal

MattRating, 5 stars3 weeks ago
We throughly enjoyed our stay and the place was super nice! Nice of them to let us use their beach chairs, towels and boogie board. Owners accommodating to let us check in a little early. Little bit of a walk to beaches but we’re walkers and really enjoyed it. Pretty centralized and beach accessible.
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, 73 reviews

Hunter Hales KALA cottage Haiku Maui

SarahRating, 5 stars6 days ago
Mikes spot was amazing! Spotlessly clean, had anything you can think of (from glass food containers, cooking supplies, filtered water, everything…) and was perfectly located to hop on the road to Hana. It’s walkable to a few cafes but is very private and secluded from the road. We loved hearing the sounds of the toads at night as well as the rooster saying hello in the morning. A perfect place to relax 😎
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, 146 reviews

Gratitude Bed and Breakfast BBWK2022/0001

ConnieRating, 5 stars1 week ago
We had such a lovely week long stay here!This house is peaceful, quiet, clean, and very comfortable- a hidden gem for sure. It truly felt like a home away from home and the perfect place for us to relax, unwind and enjoy. The house was furnished with all the amenities that we needed and is walkable to restaurants and shops. Rhonda was so welcoming and was always available if we had questions or needed anything. We would happily stay at the Gratitude Bed and Breakfast 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, 40 reviews

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

CodyRating, 5 stars5 days ago
Dan & Steph’s place was the perfect getaway location for me! It was so close to amazing beaches and restaurants, and the seemingly remote nature or the house made it seem I returned to a private island when I returned!
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 stars1 week 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!
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 stars3 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, 87 reviews

One Block to the Beach! Cozy Beach House in Kihei

VikRating, 5 stars1 week ago
Wonderful to stay at Leanne’s place! Great spot to work remotely while enjoying Maui. And such a responsive and helpful host! Strongly recommend!
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 living area is designed with a spacious layout, featuring a comfortable sectional sofa adorned with bright cushions. A coffee table sits in the center, and a television is placed against a wall, providing a focal point. Large sliding glass doors open to the outdoor lanai, revealing vibrant greenery.
Home in Haiku-Pauwela
4.55 out of 5 average rating, 44 reviews

Sweeping Ocean View Modern Stylish Monthly avail

DonnaRating, 5 stars2 months ago
This was mine and my families first trip to Maui. The location of Holly’s house was perfect just right down the street from the market and good restaurants. The house was equipped with everything we needed and more. Never had to even bother Holly with questions she left a paper with the keys covering anything we needed to know. The location was just a short drive from beautiful beaches and great shopping . I would recommend staying at holly’s for a carefree, relaxing time. Maui was more beautiful than I had imagined we are planning on making this a yearly trip now. Thank you Holly and Airbnb. Donna S. Atlanta,GA

Quick stats about house rentals in Wailea, Wailea-Makena

  • Total rentals

    50 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 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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