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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Go beyond your typical stay in Wailea-Makena

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Our top choices for Wailea-Makena hotels

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

A restaurant with outdoor seating overlooking a scenic view, featuring modern furniture and a glass-enclosed dining area.

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

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

1. AC Hotel by Marriott Maui Wailea

Wailea

Janice

฿15,072

฿18,888 total

includes taxes & fees

21 Oct - 22 Oct

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

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.

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

2. Residence Inn by Marriott Maui Wailea

Wailea

Keala

฿15,374

฿18,250 total

includes taxes & fees

23 Oct - 24 Oct

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 balcony with a view of the ocean and sunset.

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

3. Fairmont Kea Lani Maui

Wailea

James

฿35,956

฿45,040 total

includes taxes & fees

25 Oct - 26 Oct

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.

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

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

4. Four Seasons Resort Maui at Wailea

Wailea

Quinn

฿34,476

฿43,123 total

includes taxes & fees

21 Oct - 22 Oct

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

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

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

Wailea

Karolina

฿26,572

฿33,900 total

includes taxes & fees

15 Nov - 16 Nov

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

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

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

6. Wailea Beach Resort - Marriott, Maui

Wailea

Christina

฿19,172

฿25,115 total

includes taxes & fees

15 Nov - 16 Nov

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 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.

7. Grand Wailea Maui, A Waldorf Astoria Resort

Wailea

nicholas gaetano

฿25,451

฿32,391 total

includes taxes & fees

30 Oct - 31 Oct

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

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

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

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

8. Hotel Wailea Maui

Wailea

Rashonner

฿30,238

฿37,893 total

includes taxes & fees

31 Oct - 1 Nov

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

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

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.

9. Days Inn by Wyndham Maui Oceanfront

South Kihei

Diane

฿6,928

฿8,225 total

includes taxes & fees

19 Oct - 20 Oct

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 hotel with a modern architectural design, featuring a prominent building with multiple floors and a flat roof.

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

Baijumon

฿11,268

฿15,774 total

includes taxes & fees

17 Oct - 18 Oct

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

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.

A tennis court surrounded by palm trees and buildings with red roofs.

11. Aston Maui Hill

South Kihei

Kifaya

฿9,813

฿11,649 total

includes taxes & fees

15 Nov - 16 Nov

A resort pool area with a hot tub, lounge chairs, and palm trees.

A golf course with a water body, trees, and a distant mountain.

A wooden bridge over a pond, a well-maintained lawn, and a building with a balcony.

A resort with a swimming pool, palm trees, and a mountainous backdrop.

12. Villa, Garden View, 2-bedroom

Wailea

฿30,786

฿52,798 total

includes taxes & fees

19 Oct - 20 Oct

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.

13. Fairmont Kea Lani Maui Villa Experience

Wailea

Sze Wai

฿87,754

฿106,530 total

includes taxes & fees

24 Oct - 25 Oct

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

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

A tropical garden with a pond, 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.

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

Wailea

Joshua

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

A beach with clear skies and calm waters.

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.

15. Grand Champions

Wailea

Sophie

฿1,065

฿16,251 total

includes taxes & fees

16 Oct - 17 Oct

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

A modern hotel with a central pathway, surrounded by lush greenery and palm trees.

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

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

16. Aston at the Maui Banyan

South Kihei

Perla

฿5,777

฿7,856 total

includes taxes & fees

14 Nov - 15 Nov

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

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

A multi-level hotel atrium with a central bar, outdoor seating, and multiple balconies.

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

17. Ho‘olei Villas at Grand Wailea

Wailea

Justin Robert

฿57,892

฿70,907 total

includes taxes & fees

10 Nov - 11 Nov

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

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

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

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.

18. Guava Suite

South Kihei

Nancy

฿7,379

฿8,759 total

includes taxes & fees

18 Oct - 19 Oct

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

A bathroom with a large, round, terracotta sink, a mirror, and a tiled countertop.

19. Maui What A Wonderful World B and B Hawaii

South Kihei

Corentin

฿7,379

฿8,759 total

includes taxes & fees

18 Oct - 19 Oct

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

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

20. Signature Residences at Maui Banyan

South Kihei

Mai

฿1,065

฿16,251 total

includes taxes & fees

16 Oct - 17 Oct

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Holiday Rentals in Wailea-Makena

Condo

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

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.

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

Wailea Grand Champions - CoralTree Residence Collection

Wailea

"Had a wonderful stay."

Apartment

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

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

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

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

Grand Champions by KBM

Wailea

"Clean everything great time great location! "

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 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

"Nice location. Very hospitable and Kind staff. Would stay here again"

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 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!"

Condo

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

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

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

Apartment

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

A living room with a sofa, coffee table, TV, and artwork on the wall.

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

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

Refined Resort Wailea Oceanview Vistas

Wailea

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

Apartment

A beach with a clear view of the ocean, a sandy area with some greenery, and a few people in the distance.

A balcony with wicker furniture and a view of lush greenery.

A modern kitchen with a large window, a wooden cabinet, and a countertop with a bowl.

A spacious living area with a sofa, a table, and a bar area with stools.

Beautiful Kihei Condo - Walk to the Beach!

South Kihei

"Property management was extremely accommodating to our early check in needs to drop our stuff off. Huge patio to enjoy your morning coffee and book, close to the beach, and great staff. I would stay here again in a heartbeat!"

Condo

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

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 spacious living area with a dining table, sofa, and a ceiling fan.

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

Castle Kama'ole Sands

South Kihei

"We had everything we needed."

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 coastal view with palm trees and a building with a sloped roof.

Wailea Ekahi - CoralTree Residence Collection

Wailea

"Loved it!"

Condo

A balcony with a table and chairs, overlooking a tennis court and a house with a garden.

A modern kitchen with a large island, wooden cabinets, and pendant lighting.

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

A spacious living area with a large sofa, a dining table, and a kitchen in the background.

Grand Champions by Maui Rental Group

Wailea

"Loved our stay !!! Great spot and close to everything !!"

Condo

A clear view of a swimming pool surrounded by palm trees and lush greenery, with lounge chairs and a covered seating area.

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

A tropical garden with palm trees and a variety of plants.

Maui Kamaole by Maui Rental Group

South Kihei

"All of it was great. Great location and beautiful grounds"

Apartment

A dining table with chairs and a glass of water, overlooking a beach with palm trees and the ocean.

A modern kitchen with a large island, dark cabinetry, and a view of the ocean.

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

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

Polo Beach - CoralTree Residence Collection

Wailea

"Everything about this stay was amazing. Such a beautiful and spacious condo. Pools and easy access to the beach. We are very happy with the stay and are already looking to come back again soon. "

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

A modern kitchen with a central island, stainless steel refrigerator, and wooden cabinets.

A kitchen with a granite countertop, stainless steel appliances, and wooden cabinets.

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."

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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)

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.

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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.

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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 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.

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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)

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

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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.

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

Top Wailea-Makena Hotel Reviews

Mana Kai Maui- Official Onsite Rental

8/10 Good

"Older property with beautiful views and location, but room furniture needs updating in a desperate way. The views and location do not match the furnishings of what is offered. Staff is amazing, so friendly and treat you like family. Had the most memorable trip ever, everyday melted my stress away. Thank you for your kindness and flexibility so very much deserved."

Fairmont Kea Lani Maui

10/10 Excellent

"Perfect stay for our honeymoon and babymoon. Absolute paradise, great location and beautiful hotel."

AC Hotel by Marriott Maui Wailea

10/10 Excellent

"Everything"

Wailea Beach Resort - Marriott, Maui

10/10 Excellent

"Loved the check in process with Judy, she’s fantastic!! Ate at one of the on site restaurants food and service was amazing. Did not like the $61 a night valet parking fee"

Days Inn by Wyndham Maui Oceanfront

8/10 Good

"Our room was clean. The front desk staff were all very friendly and helpful. Centrally located and a good value for the price."