Wailea-Makena Holiday Rentals, Hawaii: Private House Rentals

A coastal landscape with rocky cliffs, a body of water, and a distant mountain range under a cloudy sky.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Wailea-Makena

Pet friendly

Apartment

Apart hotel

Spa

Pool

Resort

Condo

Hot tub

Family friendly

Waterpark

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Wailea-Makena hotels

A staircase with a view of a garden, palm trees, and a bridge.

A resort with a large swimming pool, palm trees, and a view of the ocean.

A spacious lobby with a curved wooden arch, seating areas, and a bar.

A balcony with a view of the ocean and sunset.

1. Fairmont Kea Lani Maui

Wailea

Brian

฿37,382

฿46,696 total

includes taxes & fees

31 Aug - 1 Sept

A pool with a waterfall feature, surrounded by palm trees and a stone structure.

An aerial view of a beach resort with rows of sun loungers, palm trees, and a view of the ocean.

A resort with multiple buildings, a beach, and a mountainous backdrop.

A resort with a pond, a wooden bridge, and lush greenery.

2. Grand Wailea Maui, A Waldorf Astoria Resort

Wailea

Katelyn

฿24,219

฿30,899 total

includes taxes & fees

12 Sept - 13 Sept

A resort pool area with a central fountain, surrounded by lounge chairs and palm trees, leading to the ocean.

A balcony with wicker furniture, a view of the ocean, palm trees, and a mountain in the distance.

A bar area with a curved counter, multiple bar stools, and a view of palm trees and the ocean at dusk.

An aerial view of a resort with multiple pools, palm trees, and lounge areas.

3. Four Seasons Resort Maui at Wailea

Wailea

You Jin

฿27,317

฿34,590 total

includes taxes & fees

1 Sept - 2 Sept

A modern bar area with a long counter, multiple stools, and a large TV screen displaying a scenic view.

A resort pool area with sun loungers and umbrellas, surrounded by lush greenery and overlooking a body of water with a sunset in the background.

An outdoor seating area with wicker chairs and orange cushions, a fire feature, and a view of the hotel building in the background.

A multi-story hotel with a central courtyard, balconies, and a view of the ocean.

4. Residence Inn by Marriott Maui Wailea

Wailea

Keala

฿14,635

฿17,374 total

includes taxes & fees

5 Sept - 6 Sept

A water park with multiple slides and a pool area surrounded by lush greenery and palm trees.

A serene outdoor seating area with two tables covered in white tablecloths and wooden stools, overlooking a coastal view with the ocean and a distant island.

A deck with two lounge chairs facing a scenic ocean view, a wooden floor, and a modern architectural design.

A spa setting with a bathtub, candles, flowers, and a champagne bottle.

5. Wailea Beach Resort - Marriott, Maui

Wailea

Michal

฿19,105

฿24,999 total

includes taxes & fees

12 Sept - 13 Sept

A bedroom with a wooden bed, white bedding, a beach-themed picture on the wall, and a ceiling fan.

A living room with a sofa, ottoman, and chairs, a table with a lamp, and a view of the beach through a sliding glass door.

A hotel with a sign for Days Inn by Wyndham, surrounded by palm trees and a well-maintained lawn.

A balcony with a view of a beach, outdoor furniture, and a clear sky.

6. Days Inn by Wyndham Maui Oceanfront

South Kihei

Susana lago

฿6,834

฿8,113 total

includes taxes & fees

1 Sept - 2 Sept

A poolside lounge area with outdoor seating, a fire feature, and umbrellas providing shade.

An outdoor lounge area with a thatched roof, fire pit, and multiple seating arrangements.

A spacious lounge area with a modern design, featuring a large sofa, a coffee table, and a seating area with thatched umbrellas.

A modern living area with a wooden bar, seating, and a large TV.

7. AC Hotel by Marriott Maui Wailea

Wailea

Janice

฿14,867

฿18,631 total

includes taxes & fees

6 Sept - 7 Sept

A resort with a pool, palm trees, and a view of the ocean.

A corridor with wooden columns and a marble floor, leading to a dark area with trees.

A spacious lobby with a high ceiling, wooden columns, and a marble floor.

A spacious lobby with high ceilings, modern furniture, and large windows offering a view of the ocean.

8. Andaz Maui at Wailea Resort - a concept by Hyatt

Wailea

"This, our second time staying at this resort, was even better than the first, mostly due to the outstanding hospitality across every staff person we encountered during our stay. Exceptional service consistently, from the valet team to the breakfast servers and beach shack attendants etc. The food, including the breakfast buffet and beach bar should also get top marks. With rising costs of vacations, these are the things that make a difference and deliver value for dollar."

Genhee

฿26,456

฿33,359 total

includes taxes & fees

27 Sept - 28 Sept

A poolside area with a fire pit, lounge chairs, and umbrellas.

A spacious indoor area with a high ceiling, large windows, and a view of the ocean.

A bar area with a view of palm trees and the ocean at sunset.

A room with a view of the ocean and lush greenery.

9. Hotel Wailea, Relais & Chateaux - Adults Only

Wailea

Rashonner

฿26,456

฿33,372 total

includes taxes & fees

31 Aug - 1 Sept

A beach with palm trees, a clear sky, and a view of the ocean.

A lobby with a stone wall, a large blue mural of a turtle, and seating areas with a stone floor.

A hotel room with a balcony, a bed, a sofa, a TV, and a ceiling fan.

A pool area with palm trees, a beach view, and a building with a sign reading "Five Palms Beach Grill".

10. Mana Kai Maui- Official Onsite Rental

South Kihei

Baijumon

฿19,966

฿26,378 total

includes taxes & fees

31 Aug - 1 Sept

A hotel lobby with a large arched window overlooking a beach, several wooden chairs, and ambient lighting.

A resort with multiple buildings, a swimming pool, and a view of the ocean.

A spacious outdoor lounge area with multiple seating options, including sofas and chairs, surrounded by lush greenery and architectural features like arches and a pergola.

11. Fairmont Kea Lani Maui Villa Experience

Wailea

Sze Wai

฿104,929

฿126,882 total

includes taxes & fees

24 Sept - 25 Sept

A resort with a swimming pool, palm trees, and ocean views.

A spacious living room with a sofa, a coffee table, and a television. There are large windows and a balcony visible.

A hotel with a pool, outdoor seating, and a view of the ocean.

An aerial view of a resort with multiple buildings, a swimming pool, and a view of the ocean.

12. Aston Maui Hill

South Kihei

Arleen

฿8,667

฿10,289 total

includes taxes & fees

30 Sept - 1 Oct

A room with a large window overlooking the ocean, wicker furniture, a sofa, and a table with a lamp.

A modern living room with a glass table, wicker chairs, and a view of the ocean.

A spacious living room with a large window offering a view of the ocean and mountains. There is a seating area with a sofa and chairs, a coffee table with a decorative piece, and a kitchen area visible in the background.

A modern kitchen with a large window overlooking a scenic ocean view.

13. Makena Surf - CoralTree Residence Collection

Wailea

Vesselina

฿26,446

฿40,082 total

includes taxes & fees

2 Sept - 3 Sept

A resort with thatched-roof structures, a pool with a waterfall, and wooden railings.

A spacious kitchen with a large island, wooden cabinets, and a view of the ocean.

A golf course with a pond, trees, and a view of the ocean.

A pool with a waterfall feature, lounge chairs, and palm trees under a sunset sky.

14. Ho‘olei Villas at Grand Wailea

Wailea

Justin Robert

฿56,990

฿69,802 total

includes taxes & fees

15 Sept - 16 Sept

A balcony with wicker furniture, a wooden table, and a view of a lush landscape and distant buildings.

A modern living room with a blue sofa, a dining area with white chairs, a kitchen with stainless steel appliances, and a large 'ALOHA' sign above the kitchen.

A sunset beach scene with a wooden walkway and palm trees.

A two-story building with a white exterior and a covered outdoor area.

15. Grand Champions by KBM

Wailea

Sean

฿43,431

฿73,294 total

includes taxes & fees

31 Aug - 1 Sept

A beach with clear turquoise water, a sandy shore, and a backdrop of a resort area with buildings and trees.

A resort with a pool, lush greenery, and a view of the ocean.

A balcony with a view of a swimming pool and lush greenery, including palm trees.

A balcony with a view of a landscaped area, palm trees, and a building with multiple floors.

16. Aston at the Maui Banyan

South Kihei

Boris

฿5,687

฿7,734 total

includes taxes & fees

28 Sept - 29 Sept

A tropical garden with a waterfall, palm trees, and a house.

A two-story building with a balcony on the upper floor, surrounded by lush tropical vegetation.

A swimming pool area with lounge chairs and umbrellas, surrounded by lush greenery and palm trees.

A beach with clear skies and calm waters.

17. Grand Champions

Wailea

Sophie

฿2,438

฿18,966 total

includes taxes & fees

1 Sept - 2 Sept

A pool area with lounge chairs and palm trees.

18. Maui Kamaole B106 1 Bedroom Apts

South Kihei

฿5,942

฿27,482 total

includes taxes & fees

15 Sept - 16 Sept

A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

A breakfast table with various fruits, pastries, and beverages in a bright room with a view of the sea.

A hotel room with two beds, a ceiling fan, a large window with a view of the beach, a desk with a chair, and a TV on the wall.

A breakfast table set on a balcony with a view of a tropical landscape.

19. Signature Residences at Maui Banyan

South Kihei

Julie

฿1,573

฿17,118 total

includes taxes & fees

31 Aug - 1 Sept

A balcony with a table set for breakfast, overlooking a residential area with palm trees and modern buildings.

A swimming pool with lounge chairs and palm trees.

A beach with clear turquoise waters and a sandy shore.

A modern living room with a dining area, a TV, and a large window.

20. The Residences at Kamaole Sands Resort

South Kihei

Sophie

฿3,065

฿20,306 total

includes taxes & fees

31 Aug - 1 Sept

View all properties

Holiday Rentals in Wailea-Makena

Aparthotel

Aston Maui Hill

South Kihei

"Dennis and the entire staff made our trip so enjoyable. We will forever have a special place in our hearts for this place. Celebrated our 10 year wedding anniversary here!"

Condo

A balcony with a glass table, chairs, and a sofa.

A kitchen with a large window overlooking the ocean, a coffee maker, and a vase with flowers on the counter.

A modern kitchen with wooden cabinets, a large island, and a view of the ocean.

Wailea Ekahi - CoralTree Residence Collection

Wailea

"Very nice condo and conveniently located to beach and dining options."

Condo

A balcony with a table set for two, featuring a bottle and two wine glasses, with a view of a building and greenery in the background.

A house with a sloped roof and two skylights, surrounded by palm trees and a view of the ocean.

A coastal view with tall palm trees and a clear blue sky.

A spacious kitchen with wooden cabinets, a built-in island, and a dishwasher.

Kihei Akahi by Maui Rental Group

Wailea

"It was nice for the price, bedroom does not have AC though, only the living room"

Condo

Signature Residences at Maui Banyan

South Kihei

"Thank you for hosting us! The place was very clean and the location was fantastic, close to the beach, shops and restaurants!"

Condo

A balcony with white chairs, a glass door, and a view of palm trees and a clear blue sky.

A swimming pool with lounge chairs and a hot tub, surrounded by palm trees and a hotel building.

A modern hotel with multiple buildings, a parking lot, and a tennis court.

A resort with multiple buildings, a swimming pool, and a view of the ocean and mountains.

Maui Banyan Vacation Club

South Kihei

"Its near everything"

Aparthotel

The Residences at Kamaole Sands Resort

South Kihei

Aparthotel

A resort pool area with a hot tub, palm trees, and a building with balconies.

A modern kitchen with grey cabinetry, stainless steel appliances, and a large window offering a view of palm trees.

A balcony with a glass door leading to a patio area, furnished with striped chairs and a small table.

A resort with a pool, palm trees, and a building with multiple balconies.

Palms at Wailea Maui

Wailea

"We had an amazing time. We were close to the shops and beaches. The kids loved the pool and we had a beautiful view of the ocean. We would definitely stay there again."

Condo

A resort with a swimming pool surrounded by palm trees and a view of the ocean.

A resort with a pool, palm trees, and a small waterfall.

A modern kitchen with a built-in stove, a sink, and a window with a view of palm trees.

A resort with a pool surrounded by rocks and lily pads, palm trees, and a well-maintained lawn.

Palms at Wailea Two Bedrooms - Partial Ocean View by Coldwell Banker Island Vacations

Wailea

"The Palms at Wailea is a favorite vacation property. It is beautifully maintained, and is located in a very nice area."

Apartment

Grand Champions by KBM

Wailea

"Clean everything great time great location! "

Apartment

A hotel room with a large bed, a TV, and a balcony with a view of the ocean and palm trees.

A beach with a mountain in the background, umbrellas, and people.

A pool area with a clear view of the ocean, surrounded by palm trees and a well-maintained garden.

A modern kitchen with wooden cabinets, a stainless steel dishwasher, and a large window overlooking a balcony with tropical plants.

Modern & Central Oceanview Vistas

South Kihei

"Planning on staying again excellent property 🌺"

Condo

A modern living room with a TV, wooden coffee table, sofa, and a balcony with a view of greenery.

A sandy beach with palm trees, umbrellas, and people.

A sign for Kihei Kai Nani Vacation Resort with a clear view of the building and surrounding greenery.

A modern kitchen with white cabinets, a dining area with a wooden table and chairs, a gray sofa, and a ceiling fan.

Kihei Kai Nani Beachside Resort Vistas

South Kihei

"Great location close to shops and restaurants right across the street from the beach. Will definitely stay again. Would recommend for anybody. the bed was extremely comfortable."

Condo

A modern living room with a large TV, comfortable seating, and a view of a residential area.

A modern kitchen with white cabinetry, a large island, and a view of the outdoor patio.

A spacious living room with a grey sofa, a coffee table, and a TV mounted on the wall. There is a ceiling fan, a large window with a view of a green landscape, and a wooden side table.

A modern dining area with a glass table, wicker chairs, and a view of a coastal landscape through large windows.

Wailea Grand Champions - CoralTree Residence Collection

Wailea

"This was a great stay for my husband and I. It was right on the golf course with views of the ocean. The staff were super helpful and communicated with us daily. The unit was updated and had new appliances. We will definitely be coming back next year."

Condo

A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

An outdoor kitchen with a stone countertop, a built-in grill, and a view of the ocean and palm trees.

A hotel room with a dining table, chairs, a vase of flowers, a view of palm trees and mountains, and framed artwork on the wall.

A tropical resort with palm trees, a pool, and a view of the ocean.

Wailea Ekahi by Maui Rental Group

Wailea

"It was clean and had nice view"

Condo

A modern kitchen with a large island, a dining area with a round table and chairs, and a view of the outdoors through large windows.

A spacious living area with a large sliding glass door leading to a balcony with a view of the ocean. There is a dining area with wicker furniture and a kitchen with modern appliances.

A modern kitchen with white cabinets, a large island, and a view to the outside.

A room with two patterned armchairs, a small wooden table, a painting, and a view of the sunset through a glass door.

Upscale and Elegant Vistas

Wailea

"Stunning ocean view, beautiful updated condo that had everything we needed right down to beach chairs. Beaches, restaurants, shopping all so convenient. We had a wonderful stay!"

Condo

A living room with a TV, a wooden table, a sofa, and a view of the ocean through large glass doors.

A modern kitchen with grey cabinets, a central island, and a dining area with a glass table and chairs.

A spacious living area with a round coffee table, a sofa, and a dining set.

A modern kitchen with a central island, built-in appliances, and a staircase leading to an upper level.

Luxurious & Spacious Ocean Vistas

South Kihei

"Super cute and clean! Way bigger than we needed, but very comfortable !"

See all holiday rentals

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Wailea-Makena attractions

A tropical beach with palm trees, a sandy shore, and the ocean.

Wailea Beach

9.4/10 (4,138 reviews)

This stretch of powdery sand is part of an upscale resort community and is an ideal place to sunbathe, snorkel, and dive with Hawaiian green turtles and manta rays.

See properties

A beach with palm trees, a hotel, and the ocean.

Keawakapu Beach North

9.4/10 (804 reviews)

Enjoy the peace and quiet at one of Maui’s less crowded and wider beaches, where kids can wander around the rock pools, and divers can explore the artificial reef.

See properties

A beach with clear blue water, a sandy shore, and a mountain in the background.

Kamaole Beach Park 3

9.2/10 (1,660 reviews)

During your trip to Kihei, enjoy the surf and sand at Kamaole Beach Park 3 along with the snorkelling. Wander the seaside or discover the beautiful sunsets in this romantic area.

See properties

A beach with clear turquoise water, a person in the water, and a mountain in the background.

Maluaka Beach

9.4/10 (731 reviews)

This is part of Maui’s so-called “Turtle Town,” a prime spot for sighting the inquisitive Hawaiian green turtles that are very common here.

See properties

A sandy beach with a large tree and a clear blue sky.

Makena State Park Beach

9.4/10 (1,787 reviews)

Three distinct, undeveloped beaches and a dormant volcano crater form this scenic southern region of Maui.

See properties

A dessert on a white plate with a strawberry and mint garnish.

Shops at Wailea

9.2/10 (381 reviews)

You can enjoy retail therapy at Shops at Wailea during your stay in Kihei. Wander the beautiful beaches or discover the beautiful sunsets in this romantic area.

See properties

A beach with lush greenery, palm trees, and a clear blue ocean.

Polo Beach

9.2/10 (186 reviews)

If a restful holiday is part of your travel plans, Polo Beach might be the perfect place to visit during your trip to Kihei. Wander the seaside or discover the beautiful sunsets in this relaxing area.

See properties

A calm sea with a rainbow, palm trees, and a cloudy sky.

Ulua Beach

8.8/10 (53 reviews)

Why not spend a care-free afternoon at Ulua Beach during your travels in Kihei? Discover the beautiful sunsets in this romantic area or enjoy its snorkelling spots.

See properties

Learn more about Wailea-Makena

Discover things to see and do in Wailea-Makena as you venture to popular sights like Wailea Beach.

See all hotels in Wailea-Makena

A beach with clear turquoise water, people sunbathing and swimming, and a mountain in the background.

Top Wailea-Makena Hotel Reviews

Andaz Maui at Wailea Resort - a concept by Hyatt

10/10 Excellent

Mana Kai Maui- Official Onsite Rental

8/10 Good

"I liked how this was on the beach. I felt safe here. The only reason why I don’t give it five stars is because the waves at this beach were to strong for me. I did like the fact that housekeeping doesn’t come every day so I didn’t feel the pressure to have to be up by a certain time."

Four Seasons Resort Maui at Wailea

10/10 Excellent

"Loved every moment we spent there! Best decision to stay at Four Seasons for our honeymoon trip :)"

Ho‘olei Villas at Grand Wailea

10/10 Excellent

"Amazing property with an incredible staff. A+++ all the way around!"

Wailea Elua- CoralTree Residence Collection

10/10 Excellent

"Great condo on an absolutely stunning property. The landscaping was superb- everywhere I looked there was beautiful scenery. Great ocean view and easy walk to the beach. We enjoyed the coastal walk to visit other nearby properties as well. The pools on site were quiet and peaceful. We would love to come back again!"

Castle Kama'ole Sands

10/10 Excellent

"We had a wonderful view with great accommodations. Only strange feature was a timer on the air conditioning that could only be set for 6 hours, so you would wake up in the early morning to a hot room. It was very nice for the price."

Wailea Ekahi - CoralTree Residence Collection

10/10 Excellent

"Very nice condo and conveniently located to beach and dining options."

More cheap stays in Wailea-Makena

Days Inn by Wyndham Maui Oceanfront

2980 S Kihei Road Kihei HI

฿6,834

฿8,113 total

1 Sept - 2 Sept

includes taxes & fees

Grand Champions

155 Wailea Ike Pl Kihei HI

฿2,438

฿18,966 total

1 Sept - 2 Sept

includes taxes & fees

9.4/10 Exceptional! (6 reviews)

AEI at Maui Banyan

2575 S Kihei Road Kihei HI

Get rates

Kihei Akahi D-105 by Maui Rental Group

2531 South Kihei Rd. Kihei HI

Get rates

9.6/10 Exceptional! (5 reviews)

Aston Maui Hill

2881 S Kihei Road Kihei HI

Get rates

8/10 Very good! (3 reviews)

Maui Parkshore - Maui Condo & Home

2653 S Kihei Rd Kihei HI

Get rates

8/10 Very good! (109 reviews)

Explore a world of travel with Expedia

More ways to book

Book Hotels in Wailea-Makena on Expedia.com

Find hotels in Wailea-Makena, HI from ฿7,734

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Wailea-Makena

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Wailea-Makena hotels

1. Fairmont Kea Lani Maui

2. Grand Wailea Maui, A Waldorf Astoria Resort

3. Four Seasons Resort Maui at Wailea

4. Residence Inn by Marriott Maui Wailea

5. Wailea Beach Resort - Marriott, Maui

6. Days Inn by Wyndham Maui Oceanfront

7. AC Hotel by Marriott Maui Wailea

8. Andaz Maui at Wailea Resort - a concept by Hyatt

9. Hotel Wailea, Relais & Chateaux - Adults Only

10. Mana Kai Maui- Official Onsite Rental

11. Fairmont Kea Lani Maui Villa Experience

12. Aston Maui Hill

13. Makena Surf - CoralTree Residence Collection

14. Ho‘olei Villas at Grand Wailea

15. Grand Champions by KBM

16. Aston at the Maui Banyan

17. Grand Champions

18. Maui Kamaole B106 1 Bedroom Apts

19. Signature Residences at Maui Banyan

20. The Residences at Kamaole Sands Resort

Holiday Rentals in Wailea-Makena

Aston Maui Hill

Wailea Ekahi - CoralTree Residence Collection

Kihei Akahi by Maui Rental Group

Signature Residences at Maui Banyan

Maui Banyan Vacation Club

The Residences at Kamaole Sands Resort

Palms at Wailea Maui

Palms at Wailea Two Bedrooms - Partial Ocean View by Coldwell Banker Island Vacations

Grand Champions by KBM

Modern & Central Oceanview Vistas

Kihei Kai Nani Beachside Resort Vistas

Wailea Grand Champions - CoralTree Residence Collection

Wailea Ekahi by Maui Rental Group

Upscale and Elegant Vistas

Luxurious & Spacious Ocean Vistas

Stay near popular Wailea-Makena attractions

Wailea Beach

Keawakapu Beach North

Kamaole Beach Park 3

Maluaka Beach

Makena State Park Beach

Shops at Wailea

Polo Beach

Ulua Beach

Learn more about Wailea-Makena

Top Wailea-Makena Hotel Reviews

Andaz Maui at Wailea Resort - a concept by Hyatt

Mana Kai Maui- Official Onsite Rental

Four Seasons Resort Maui at Wailea

Ho‘olei Villas at Grand Wailea

Wailea Elua- CoralTree Residence Collection

Castle Kama'ole Sands

Wailea Ekahi - CoralTree Residence Collection

More cheap stays in Wailea-Makena

Days Inn by Wyndham Maui Oceanfront

Grand Champions

AEI at Maui Banyan

Kihei Akahi D-105 by Maui Rental Group

Aston Maui Hill

Maui Parkshore - Maui Condo & Home

Explore a world of travel with Expedia

Go further with the Expedia app