House vacation rentals in Wailea, Wailea-Makena

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Popular amenities for Wailea, Wailea-Makena house rentals

House rentals with a pool

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 showcases a blue sectional sofa adorned with colorful cushions. Two ceiling fans circulate air over the room, which is illuminated by natural light. A coffee table rests in front of the sofa, and art pieces decorate the walls.
Home in Wailuku
4.96 out of 5 average rating, 24 reviews

Maalaea Kai 307 - Maui Prime Oceanfront

ChrisRating, 5 stars4 days ago
This was a fantastic place to spend our week in Maui. The condo was amazing and spacious with all the amenities you would need to enjoy your time. The location is perfect, relatively close to the airport and well situated next to route 30 so you could go everywhere on the island quite easily. The view from the condo is second to none, from the patio you can easily see the Haleakalā mountain and from the front door is a great sight of the western Maui mountains. And on top of everything this condo was much more peaceful than the huge resort areas. There were not too many people around, and even when we did go to the beach we were able to find a spot easily. I’d recommend this condo for anyone who wants to spend a week or a few days in Maui - the price is quite good compared to the normal resorts, you get a great view and anything you don’t pick up on your way from the airport you can grab on a 20 minute drive to Kihei. This place was perfect for us.
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!!
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.
Top guest favorite
Home in Wailea
4.76 out of 5 average rating, 25 reviews

The Palms 1202 - The most expansive ocean views

GregRating, 5 stars13 months ago
Andre was a tremendous host. He was promptly responsive to our questions and requests. His condo is beautiful and well-equipped. The view from the lanai and every room was spectacular. My wife and I would love to stay here again.
Superhost
A private pool is surrounded by lush tropical vegetation, creating a serene outdoor space. Bright green lounge chairs are positioned nearby, inviting relaxation under clear blue skies. Sunlight reflects off the water's surface, enhancing the tranquil ambiance.
Home in Kihei
4.83 out of 5 average rating, 6 reviews

CLOUD 9 BEACH HOUSE - pool, walk to beach, legal

StaceyRating, 5 stars1 month ago
We are a family of 7. 6 adults and one teenager. Tamara's home has a Homey feeling. We felt right at home. She provided so many amenities. She was extremely friendly and responsive as if she was part of your family. Beds were very comfortable, and she supplied many daily used items. Don't just take my word. Book her home and see for yourself. We will definitely book with her again in the near future.

Weekly house rentals

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 :)
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, 72 reviews

Hunter Hales KALA cottage Haiku Maui

JenniferRating, 5 stars1 day ago
We had a fantastic stay! The property is clean and comfortable with tons of natural light. Great local setting-around the corner from a great coffee shop and one of the best restaurants on the island. We’ve stayed at a number of properties on the island - we plan to return to this one. Highly recommend.
Superhost
A private lanai features a dining table surrounded by four chairs, offering views of swaying palm trees and the ocean beyond. The serene landscape showcases a clear blue sky and gentle waves.
Home in Kihei
4.77 out of 5 average rating, 30 reviews

Oceanfront Koa Lagoon Condo w/ Sunset Views

KarenRating, 5 stars3 days ago
The condo was perfect! Very quiet property and the water view was wonderful. Unfortunately, we just missed whale season but still enjoyed watching the kayakers going by. The kitchen had every item we needed and the washer/dryer was so appreciated. The elevator in the building is very efficient and parking was no problem at all. The location is excellent…not in a busy area and very easy to get to everything on the island. We will be back!
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, 145 reviews

Gratitude Bed and Breakfast BBWK2022/0001

ConnieRating, 5 stars2 days 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.
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.
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.
A spacious living area features a comfortable arrangement of green seating with orange accent pillows. Large windows allow natural light to flood the space, framing views of the outdoors. A wooden coffee table sits centrally, complemented by a rug, while a wall-mounted television is visible.
Home in Paia
4.81 out of 5 average rating, 114 reviews

Beautiful ocean view home with central A/C

MarcusRating, 5 stars1 month ago
Had a great 1 night stay here. Slept 6 comfortably and was an easy walk into town. No complaints!!
Top guest favorite
A modern, two-bedroom home is showcased, featuring a covered lanai with a dining area for six. Large windows provide views of the surroundings, while the exterior combines wood and blue siding against a bright sky and greenery.
Home in Haiku-Pauwela
4.98 out of 5 average rating, 121 reviews

Peaceful and Spacious; North Shore Maui

Mitchell AlanRating, 5 stars5 days ago
Great place, having a home cooked meal in this deck with some evening sun was amazing. I would recommend staying here!

Private house rentals

An open living area is highlighted by a comfortable white sofa and a wooden coffee table. A flat-screen TV is mounted on the wall, while natural light floods the space through large sliding doors that open to a scenic patio view. Stylish decor elements enhance the ambiance.
Home in Kihei
4.43 out of 5 average rating, 7 reviews

Kihei 533 Ocean View Condo

TravisRating, 5 stars2 weeks ago
Beautiful little condo with a great view. Check in was hassle free, the place was clean, and it was exactly as described. The host was very responsive answered all my questions along with giving clear and concise instructions. The area is great with plenty of amenities around and there is a nice beach right by. Overall, I would highly recommend booking a stay here.
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!
A spacious oceanfront lanai offers views of the crystal-clear water and gentle waves. Comfortable seating arrangements include soft cushions. Lush greenery frames the scene, enhancing the natural beauty of the beach and ocean beyond, inviting relaxation and enjoyment of coastal breezes.
Home in Wailuku
4.65 out of 5 average rating, 229 reviews

Charming Direct Oceanfront North Shore Beach House

LaurenRating, 5 stars2 weeks ago
Amazing house in a beautiful location. The beach is rocky but you can walk up to a sandy area easily. There is a super gorgeous tree swing in the park nextdoor that our kids loved walking to. We loved the neighborhood cat, Buddy, and watching the locals fishing out front.
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!
Top guest favorite
A cozy living area features a light-colored sofa adorned with blue and white cushions. Two patterned armchairs complement the space, while a round wooden dining table sits nearby. Natural light enters through sheer curtains, and a colorful wall art piece adds visual interest.
Home in Paia
4.92 out of 5 average rating, 204 reviews

Paia cottage walk to town and beach

NadyaRating, 5 stars3 weeks ago
This is a great find. Everything was as described. Very good location. Nice clean cottage that is equipped with everything we needed for 8 days stay. I would highly recommend.
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 stars1 month 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
A stunning coastal view showcases gently swaying palm trees along the shoreline. The clear blue waters reflect the sky, while a sandy beach extends in the distance, leading to lush green landscapes. Soft clouds float overhead, adding to the serene atmosphere.
Home in Kihei
4.63 out of 5 average rating, 8 reviews

Sandy Paradise Royal Mauian-503

DavidRating, 5 stars2 months ago
This home and its location is a very good value. The home was very comfortable. It was perfect for 4 adults with 2 king beds, 2 private baths, and A/C in every room. It should be noted the condo is advertised for up to 6 people but any additional people in the condo would have felt very crowded in the 803 sq ft space. The location is amazing with immaculate grounds and public beaches on each side of the property and a number of restaurants and shops across the street. It's in an excellent location and walking friendly. The view from the balcony was amazing. The pictures were very accurate in showing it. We went hoping to see some whales from the balcony and we were not disappointed. Whales appeared often and between 100 to 200 yards from shore and were easily seen with the naked eye. Binoculars were an added bonus for closer viewing. This property is a wonderful value when you consider the location, the view, and the quality of the property. We'll book again.

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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