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.

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Our top choices for Wailea-Makena hotels

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

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

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

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

1. Four Seasons Resort Maui at Wailea

Wailea

Quinn

26.522.900 ₫

33.175.310 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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

A balcony with a view of the ocean and sunset.

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

A resort pool area with lounge chairs, umbrellas, and palm trees.

2. Fairmont Kea Lani Maui

Wailea

Sonam

27.425.982 ₫

34.371.828 ₫ total

includes taxes & fees

24 Oct - 25 Oct

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

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

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 well-maintained golf course with a clear view of the ocean and a winding path.

3. Wailea Beach Resort - Marriott, Maui

Wailea

Rachel

14.749.320 ₫

19.321.350 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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

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

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

A spacious balcony with a view of a pool and palm trees, furnished with wicker chairs and a coffee table.

4. Grand Wailea Maui, A Waldorf Astoria Resort

Wailea

nicholas gaetano

17.812.521 ₫

22.824.435 ₫ total

includes taxes & fees

20 Nov - 21 Nov

A resort with multiple swimming pools, palm trees, and a view of the ocean.

A buffet with various food items including fruits, cheeses, and vegetables.

A circular fire pit with seating around it, outdoor umbrellas, and a view of the ocean at dusk.

A bar with a wooden sign, multiple bar stools, and a patterned wall.

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

Wailea

Alexander

20.519.668 ₫

26.171.663 ₫ total

includes taxes & fees

20 Nov - 21 Nov

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

A spacious indoor area with multiple tables and chairs, large windows offering views of the outdoors, and hanging pendant lights.

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

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.

6. Residence Inn by Marriott Maui Wailea

Wailea

Keala

11.851.208 ₫

14.068.806 ₫ total

includes taxes & fees

30 Oct - 31 Oct

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

Eshrar

11.618.324 ₫

14.560.345 ₫ total

includes taxes & fees

30 Oct - 31 Oct

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

A beach with a sunset, palm trees, and a rocky shoreline.

8. Days Inn by Wyndham Maui Oceanfront

South Kihei

Diane

5.340.806 ₫

6.340.178 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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

A resort with a pool, a covered outdoor area, and a stone wall.

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 Maui

Wailea

Maureen

23.262.524 ₫

29.151.406 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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".

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

10. Mana Kai Maui- Official Onsite Rental

South Kihei

Scott

8.668.460 ₫

12.135.115 ₫ total

includes taxes & fees

23 Oct - 24 Oct

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

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

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

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

11. Aston Maui Hill

South Kihei

Megan

7.549.323 ₫

8.961.951 ₫ total

includes taxes & fees

20 Nov - 21 Nov

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

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

A waterfall with moss-covered rocks, surrounded by tropical plants and palm trees.

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.

12. Grand Champions by KBM

Wailea

Sean

9.869.811 ₫

21.945.717 ₫ total

includes taxes & fees

19 Nov - 20 Nov

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

A living room with a sofa, a table, and a chair. There is a sliding glass door leading to an outdoor area with a table and chairs.

A tropical garden with a pond, palm trees, and a view of the ocean.

A beach with palm trees, a clear sky, and a pathway leading to the water.

13. Palms at Wailea 101 - 2BR Garden View Condo w/ A/C in Bedrooms & Spacious Lanais

Wailea

Joshua

10.025.139 ₫

24.157.494 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

14. Ho‘olei Villas at Grand Wailea

Wailea

Justin Robert

44.537.254 ₫

54.549.900 ₫ total

includes taxes & fees

19 Nov - 20 Nov

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

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

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.

15. Aston at the Maui Banyan

South Kihei

Perla

4.444.203 ₫

6.043.803 ₫ total

includes taxes & fees

21 Nov - 22 Nov

A kitchen with wooden cabinets, a granite countertop, a microwave, and a coffee maker.

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

An outdoor dining area with a table set for two, surrounded by lush tropical plants and a wooden fence.

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

16. Grand Champions

Wailea

Sophie

1.403.099 ₫

13.749.436 ₫ total

includes taxes & fees

6 Nov - 7 Nov

A covered outdoor area with a glass table and chairs, surrounded by lush greenery and a view of a mountain and buildings.

A living room with a glass-top table, wicker chairs, a ceiling fan, a flat-screen TV, and a sliding glass door leading to an outdoor area.

A stone planter with black and white pebbles, a wooden sculpture, and green foliage.

A cozy room with a bed, a sofa, a small table, and a fan. There is a window with blinds, a door, and a wall-mounted lamp.

17. Maui What A Wonderful World B and B Hawaii

South Kihei

Corentin

5.676.547 ₫

6.738.743 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A staircase with stone steps leading to a wooden deck, surrounded by lush green plants.

A wicker basket filled with bread, fruits, and packaged snacks, with a notice about a no check-in policy and contactless check-in instructions.

18. Guava Suite

South Kihei

Nancy

5.676.547 ₫

6.738.741 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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 modern living room with a dark sofa, a coffee table, and a view of a green landscape through large windows.

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

19. Signature Residences at Maui Banyan

South Kihei

Mai

2.279.024 ₫

15.630.268 ₫ total

includes taxes & fees

28 Oct - 29 Oct

A glass-top table with wooden chairs on a balcony with a view of a mountain and tropical vegetation.

A staircase with stone steps leading to a wooden door with a number plaque.

A kitchen with green cabinets, a dining table with wicker chairs, and a refrigerator.

A living room with a sofa, two side tables, a glass coffee table, and a painting on the wall.

20. Mango Suite

South Kihei

Randy

7.714.282 ₫

9.157.779 ₫ total

includes taxes & fees

26 Oct - 27 Oct

View all properties

Holiday Rentals in Wailea-Makena

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

"Loved it!"

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

"Absolutely loved our room. The kitchen was spacious and had all of the necessities. The best part was the lawn chairs, umbrella and tote bag provided in the room. Rooms large enough to relax and not feel so crowded."

Aparthotel

Aston Maui Hill

South Kihei

"Such a beautiful place, lots to do, close to local beaches, tons of yummy food nearby"

Condo

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 lush garden with palm trees, a bench, and a gazebo.

A hotel corridor with a concrete path, palm trees, and lush greenery.

Maui Banyan Vacation Club

South Kihei

"Its a nice hotel cause its in the middle of almost everything!"

Aparthotel

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

A modern open-plan living area with a kitchen, dining space, and a balcony with a view.

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

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

Palms at Wailea Maui

Wailea

"Great stay!"

Apartment

Grand Champions by KBM

Wailea

"Clean everything great time great location! "

Aparthotel

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

A beach with clear turquoise waters and a sandy shore.

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

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

The Residences at Kamaole Sands Resort

South Kihei

"Bonus was there were beach chairs, towels and an umbrella. We only used two chairs as our family were busy snorkeling or boarding away while 1-2 sat out and rested. Clean, right down from beach park 3...stocked pantry got some add-ons and pots and pans enough to allow us making most of our meals. Great times and great communication from host. Thanks! Lucas"

Condo

A resort with multiple buildings, palm trees, and well-maintained lawns.

A swimming pool surrounded by lounge chairs and palm trees, with a building in the background.

A spacious living room with a large flat-screen TV, a glass coffee table, and a comfortable sofa. A wooden staircase leads to an upper level with a balcony.

A balcony with a glass table and wicker chairs, overlooking a landscaped garden and hotel buildings.

Castle Kama'ole Sands

South Kihei

"We had everything we needed."

Apartment

A covered outdoor area with a dining table and chairs, a bar area, and a view of the ocean and palm trees.

A spacious kitchen with a large island, modern appliances, and a view of the ocean.

A kitchen with a granite countertop, stainless steel sink, wooden cabinets, and a view of the ocean through a large window.

A spacious living area with a kitchen, seating with blue cushions, and a large window with a view of palm trees.

Refined Resort Wailea Oceanview Vistas

Wailea

"Great well maintained property. Would recommend this property and will visit again when returning to Maui."

Condo

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

A modern living room with a dining area, kitchen, and a large mirror.

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

Wailea Grand Champions - CoralTree Residence Collection

Wailea

"Had a wonderful stay."

Condo

A modern kitchen with a large island, wooden cabinets, stainless steel appliances, and a bar area with stools.

A golf course with a well-maintained green, surrounded by palm trees and residential buildings with a hilly backdrop.

A spacious living room with a large sofa, a dining table, and a view of palm trees through large windows.

A swimming pool with lounge chairs and umbrellas, surrounded by tropical plants and trees.

Grand Champions by Maui Rental Group

Wailea

"Very nicely appointed and comfortable. Good beds. Plenty of room for two. Only suggestion is to make it easier to operate the TVs. "

Condo

A coastal landscape with palm trees, a rocky shoreline, and a clear blue sky.

A hotel with a landscaped garden, a waterfall, and palm trees.

An aerial view of a resort with multiple buildings, a swimming pool, and a beach area.

A modern kitchen with white cabinets, a dining area with wicker chairs, and a large window with a view of greenery.

Stunning Modern Beachfront Resort Vistas

South Kihei

"We had an absolutely amazing time during our stay. Our condo had an unexpected view of the ocean from the lanai and was a quick walk to the beach. There’s construction on the street out front so that main road was closed to through traffic which meant a slightly longer route to get places, but on the plus side, it meant no noise or street traffic. So we didn’t mind. The condo was really well stocked (a boogie board and sand toys would be a great addition if you’re thinking of adding items!) and...

Condo

A wooden table with a bottle, glasses, and snacks on a balcony overlooking a garden with palm trees and a building in the background.

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

A modern living room with a sofa, coffee table, and a dining area with chairs.

Kamaole Sands by Maui Rental Group

South Kihei

"It was clean Has a nice layout. Starter toiletries. Beach chairs and umbrella. Beach toys. We enjoyed our time there."

Condo

A balcony with a view of lush tropical plants and a distant mountain range.

A balcony with wicker chairs and a table, overlooking a lush green landscape with palm trees.

A hotel with multiple floors, a parking area, and a view of the ocean.

Maui Banyan by Maui Rental Group

South Kihei

"Too many speed bumps! Must be a problem with people not following the speed limit on the property. Other than that, we were very happy with the location of the property and having a beach just across the street was great!"

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Stay near popular Wailea-Makena attractions

A beach with palm trees, a row of beach umbrellas, and a green boat on the grass.

Wailea Beach

9.4/10 (4,138 reviews)

Nothing says holiday like spending a lazy day at Wailea Beach, a popular beach in Kihei. Wander the seaside or discover the beautiful sunsets in this romantic area.

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

Keawakapu Beach North

9.4/10 (804 reviews)

Why not spend a care-free afternoon at Keawakapu Beach North during your travels in Kihei? Stroll along the seaside or discover the area's sunsets.

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

Maluaka Beach

9.4/10 (731 reviews)

If a restful holiday is part of your travel plans, Maluaka Beach might be the perfect place to visit during your trip to Kihei. Discover the beautiful sunsets in this romantic area or enjoy its snorkelling spots.

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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.

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A coastal landscape with a sandy beach, turquoise waters, and a hill with dense vegetation.

Makena State Park Beach

9.4/10 (1,787 reviews)

If a restful holiday is part of your travel plans, Makena State Park Beach might be the perfect place to visit during your trip to Kihei. Stroll along the seaside in this relaxing area or seek out the snorkelling spots.

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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.

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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 romantic area.

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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.

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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 wooden sign for Keawa'i Church with a stone building and palm trees in the background.

Top Wailea-Makena Hotel Reviews

Wailea Beach Resort - Marriott, Maui

8/10 Good

"I wished there were more activities available or at least wished the activities were closer to the pool area. My kids wanted to do them, but the walk was too far since we settled into the pool area already. Everyone was so helpful and nice. This was our second time in Maui, and we brought our kids this time. They had an amazing time. The resort is well maintained and only a 5 min walk to a local market where we enjoyed many meals at. Shuttle service only goes in Wailea area. It was convenient that Enterprise rental was on site. We got our car quickly. The beach chairs and umbrellas were first come first serve. You are added to a waitlist by text. We got there right when it opened up at 8:00 am one day and got one right away; while on our last day, the wait was too long even at 8:00 am, but they provided us with a Tommy Bahama chair to sit on the beach still. Overall, our stay was wonderful. Beautiful property for families. Thank you for everything!"

Andaz Maui at Wailea Resort - a concept by Hyatt

10/10 Excellent

"Very nice way to end our stay in Maui. Great pool, easy beach access, and clean room."

Hotel Wailea Maui

10/10 Excellent

"Hotel Wailea was paradise! The grounds and the room were beautiful and clean. The customer service was EXCELLENT!!!! My husband and I didn’t want to leave. If you are looking for an adult only relaxing experience, I HIGHLY recommend Hotel Wailea. You will not be disappointed!"

Aston Maui Hill

10/10 Excellent

"Such a beautiful place, lots to do, close to local beaches, tons of yummy food nearby"

Four Seasons Resort Maui at Wailea

10/10 Excellent

"The Four Seasons Wailea is a truly exceptional property. The Amenities were all first class and service was in a class of its own. Our experience met and exceeded all expectations on all measures."

Maui Banyan Vacation Club

10/10 Excellent

"Good. Well equipped, microwave and kitchen. Standing shower. Clise to kamaole beaches"

Signature Residences at Maui Banyan

10/10 Excellent

Castle Kama'ole Sands

10/10 Excellent

"We had everything we needed."

Castle at Maui Banyan

8/10 Good

"Staff was very helpful and accommodating. Thoroughly enjoyed our stay."

More cheap stays in Wailea-Makena

Days Inn by Wyndham Maui Oceanfront

2980 S Kihei Road Kihei HI

5.340.806 ₫

6.340.178 ₫ total

28 Oct - 29 Oct

includes taxes & fees

Grand Champions

155 Wailea Ike Pl Kihei HI

1.403.099 ₫

13.749.436 ₫ total

6 Nov - 7 Nov

includes taxes & fees

9.2/10 Wonderful! (9 reviews)

AEI at Maui Banyan

2575 S Kihei Road Kihei HI

Get rates

Kihei Akahi - Maui Condo & Home

2531 S Kihei Rd Kihei HI

Get rates

7.8/10 Good! (232 reviews)

Kihei Akahi D-105 by Maui Rental Group

2531 South Kihei Rd. Kihei HI

Get rates

9.6/10 Exceptional! (5 reviews)

Kihei Kai Nani 238 - Garden View 1 Bedroom, Split AC, Steps to Kamaole II Beach!

2495 S Kihei Rd, Kihei, Hi Kihei HI

Get rates

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Book Hotels in Wailea-Makena on Expedia.com

Find hotels in Wailea-Makena, HI from 6.043.803 ₫

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. Four Seasons Resort Maui at Wailea

2. Fairmont Kea Lani Maui

3. Wailea Beach Resort - Marriott, Maui

4. Grand Wailea Maui, A Waldorf Astoria Resort

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

6. Residence Inn by Marriott Maui Wailea

7. AC Hotel by Marriott Maui Wailea

8. Days Inn by Wyndham Maui Oceanfront

9. Hotel Wailea Maui

10. Mana Kai Maui- Official Onsite Rental

11. Aston Maui Hill

12. Grand Champions by KBM

13. Palms at Wailea 101 - 2BR Garden View Condo w/ A/C in Bedrooms & Spacious Lanais

14. Ho‘olei Villas at Grand Wailea

15. Aston at the Maui Banyan

16. Grand Champions

17. Maui What A Wonderful World B and B Hawaii

18. Guava Suite

19. Signature Residences at Maui Banyan

20. Mango Suite

Holiday Rentals in Wailea-Makena

Wailea Ekahi - CoralTree Residence Collection

Kihei Akahi by Maui Rental Group

Signature Residences at Maui Banyan

Aston Maui Hill

Maui Banyan Vacation Club

Palms at Wailea Maui

Grand Champions by KBM

The Residences at Kamaole Sands Resort

Castle Kama'ole Sands

Refined Resort Wailea Oceanview Vistas

Wailea Grand Champions - CoralTree Residence Collection

Grand Champions by Maui Rental Group

Stunning Modern Beachfront Resort Vistas

Kamaole Sands by Maui Rental Group

Maui Banyan by Maui Rental Group

Stay near popular Wailea-Makena attractions

Wailea Beach

Keawakapu Beach North

Maluaka Beach

Kamaole Beach Park 3

Makena State Park Beach

Shops at Wailea

Polo Beach

Ulua Beach

Learn more about Wailea-Makena

Top Wailea-Makena Hotel Reviews

Wailea Beach Resort - Marriott, Maui

Andaz Maui at Wailea Resort - a concept by Hyatt

Hotel Wailea Maui

Aston Maui Hill

Four Seasons Resort Maui at Wailea

Maui Banyan Vacation Club

Signature Residences at Maui Banyan

Castle Kama'ole Sands

Castle at Maui Banyan

More cheap stays in Wailea-Makena

Days Inn by Wyndham Maui Oceanfront

Grand Champions

AEI at Maui Banyan

Kihei Akahi - Maui Condo & Home

Kihei Akahi D-105 by Maui Rental Group

Kihei Kai Nani 238 - Garden View 1 Bedroom, Split AC, Steps to Kamaole II Beach!

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