Kahoolawe Holiday Rentals, Hawaii: Private House Rentals

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Go beyond your typical stay in Kahoolawe

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Our top choices for Kahoolawe hotels

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.

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.

1. Grand Wailea Maui, A Waldorf Astoria Resort

Wailea

Mary Ann

19.698.036 ₫

25.069.514 ₫ 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.

A resort with a pool, beach, and mountain view.

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

2. Four Seasons Resort Maui at Wailea

Wailea

Quinn

26.629.500 ₫

33.308.646 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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.

3. Days Inn by Wyndham Maui Oceanfront

South Kihei

Diane

5.362.272 ₫

6.365.660 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A balcony with a view of the ocean and palm trees.

A beach with palm trees, umbrellas, and people.

A resort with a swimming pool, solar panels, and a view of the ocean.

A modern restaurant with a bar area, seating arrangements, and large windows providing views of the outdoors.

4. Maui Coast Hotel

South Kihei

Rachel

4.933.602 ₫

7.059.285 ₫ total

includes taxes & fees

2 Nov - 3 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 resort pool area with lounge chairs, umbrellas, and palm trees.

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

5. Fairmont Kea Lani Maui

Wailea

Mohammed

26.213.820 ₫

32.938.589 ₫ total

includes taxes & fees

12 Oct - 13 Oct

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

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

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

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

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

Wailea

Karolina

20.680.080 ₫

26.082.035 ₫ total

includes taxes & fees

8 Nov - 9 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 deck with two lounge chairs facing a scenic ocean view, a wooden floor, and a modern architectural design.

7. Wailea Beach Resort - Marriott, Maui

Wailea

Christina

15.250.260 ₫

19.923.527 ₫ total

includes taxes & fees

22 Oct - 23 Oct

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

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

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

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

8. AC Hotel by Marriott Maui Wailea

Wailea

Janice

11.019.417 ₫

13.852.456 ₫ total

includes taxes & fees

23 Oct - 24 Oct

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

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.

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

9. Residence Inn by Marriott Maui Wailea

Wailea

Keala

11.898.840 ₫

14.125.352 ₫ total

includes taxes & fees

22 Oct - 23 Oct

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

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

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

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

10. Hotel Wailea Maui

Wailea

Rashonner

22.057.020 ₫

27.726.503 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

11. Mana Kai Maui- Official Onsite Rental

South Kihei

Freddy

15.665.940 ₫

20.697.340 ₫ total

includes taxes & fees

9 Oct - 10 Oct

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

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

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

12. Aston Maui Hill

South Kihei

Michael

8.553.915 ₫

10.154.524 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

A multi-story hotel with balconies, a well-maintained lawn, and palm trees.

A stone wall with the text "MAUI BAY VILLAS" and "HILTON GRAND VACATIONS" indicating a hotel location.

A spacious lobby with a wooden ceiling, large windows, and a seating area with sofas and a coffee table.

13. Hilton Grand Vacations Club Maui Bay Villas

North Kihei

Ana

8.292.816 ₫

10.764.000 ₫ total

includes taxes & fees

17 Oct - 18 Oct

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

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

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.

14. Ho‘olei Villas at Grand Wailea

Wailea

Justin Robert

45.419.275 ₫

55.603.711 ₫ total

includes taxes & fees

22 Oct - 23 Oct

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 swimming pool and lush greenery, including palm trees.

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

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

15. Aston at the Maui Banyan

South Kihei

Perla

4.754.340 ₫

6.415.058 ₫ total

includes taxes & fees

6 Nov - 7 Nov

A terrace with wicker furniture, potted plants, and a view of the ocean.

A spacious living area with a wooden staircase, a dining table, and a sofa.

A kitchen with a large window, a dining area with chairs, and a view of palm trees.

A hotel with a lush garden, palm trees, and a red-roofed building.

16. Kohea Kai Hotel Maui

North Kihei

Koreta

3.358.824 ₫

4.758.363 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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.

17. Fairmont Kea Lani Maui Villa Experience

Wailea

Sze Wai

69.340.620 ₫

84.135.191 ₫ total

includes taxes & fees

31 Oct - 1 Nov

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

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

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.

18. Signature Residences at Maui Banyan

South Kihei

Roark

1.840.163 ₫

14.726.572 ₫ total

includes taxes & fees

12 Oct - 13 Oct

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 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

5.699.362 ₫

6.765.827 ₫ total

includes taxes & fees

12 Oct - 13 Oct

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 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.

20. Grand Champions by KBM

Wailea

Sean

11.056.808 ₫

25.870.111 ₫ total

includes taxes & fees

11 Oct - 12 Oct

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Top Kahoolawe Hotel Reviews

Days Inn by Wyndham Maui Oceanfront

10/10 Excellent

"Great value. Low price, clean, convenient property. Came with. Each chairs and beach towels to use."

Maui Coast Hotel

10/10 Excellent

"Greta place and cheap"

Aston Maui Hill

10/10 Excellent

"Way more than what we expected.. clean, well kept, extremely spacious and centrally located to shops, beaches and restaurants. Loved everything about the property"

Hilton Grand Vacations Club Maui Bay Villas

10/10 Excellent

"Great"

Wailea Beach Resort - Marriott, Maui

10/10 Excellent

"If you’re thinking of going to Maui for your honeymoon- think the Wailea Beach Resort by Marriott. You’ll be happy you did. Truly an amazing resort with unbeatable sunset and ocean views. Shay at the Adult Pool is absolutely amazing!!"

Four Seasons Resort Maui at Wailea

10/10 Excellent

"We were here with our adult children for a family trip and really enjoyed the pools, spa, Spago, the complementary car service and every employee we came in contact with! A great trip!"