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 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.

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

1. Four Seasons Resort Maui at Wailea

Wailea

Quinn

26.532.125 ₫

33.186.847 ₫ total

includes taxes & fees

7 Nov - 8 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.

2. Grand Wailea Maui, A Waldorf Astoria Resort

Wailea

nicholas gaetano

19.626.007 ₫

24.977.844 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

3. Fairmont Kea Lani Maui

Wailea

Sonam

27.671.065 ₫

34.661.861 ₫ 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 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.

4. Wailea Beach Resort - Marriott, Maui

Wailea

Christina

14.754.450 ₫

19.328.070 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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

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.

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.

5. Days Inn by Wyndham Maui Oceanfront

South Kihei

Diane

5.342.664 ₫

6.342.382 ₫ total

includes taxes & fees

26 Oct - 27 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 hotel with a large entrance, palm trees, and a sign indicating it is the Maui Coast Hotel.

6. Maui Coast Hotel

South Kihei

Scott

5.567.863 ₫

7.807.939 ₫ total

includes taxes & fees

23 Oct - 24 Oct

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

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

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

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

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

Wailea

Karolina

20.449.150 ₫

26.088.581 ₫ total

includes taxes & fees

17 Nov - 18 Nov

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

8. Residence Inn by Marriott Maui Wailea

Wailea

Keala

11.855.330 ₫

14.073.699 ₫ total

includes taxes & fees

26 Oct - 27 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.

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

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

9. AC Hotel by Marriott Maui Wailea

Wailea

Eshrar

11.622.365 ₫

14.565.408 ₫ total

includes taxes & fees

26 Oct - 27 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.

10. Hotel Wailea Maui

Wailea

Maureen

23.270.615 ₫

29.161.548 ₫ total

includes taxes & fees

31 Oct - 1 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 hotel room with a balcony, a bed, a sofa, a TV, and a ceiling fan.

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

11. Mana Kai Maui- Official Onsite Rental

South Kihei

Baijumon

8.671.475 ₫

12.139.332 ₫ total

includes taxes & fees

20 Oct - 21 Oct

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

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

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.

12. Ho‘olei Villas at Grand Wailea

Wailea

Justin Robert

44.552.744 ₫

54.568.873 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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

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

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.

13. Hilton Grand Vacations Club Maui Bay Villas

North Kihei

Allison

8.262.492 ₫

10.724.639 ₫ total

includes taxes & fees

25 Oct - 26 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 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.

14. Aston at the Maui Banyan

South Kihei

Perla

4.736.955 ₫

6.391.601 ₫ total

includes taxes & fees

18 Nov - 19 Nov

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

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.

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

15. Aston Maui Hill

South Kihei

Megan

8.134.361 ₫

9.656.463 ₫ total

includes taxes & fees

17 Nov - 18 Nov

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

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

A spacious living area with a kitchen, dining area, and a balcony with a view of palm trees.

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

16. Kohea Kai Hotel Maui

North Kihei

Lingxi

3.346.542 ₫

4.740.962 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

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.

17. Maui What A Wonderful World B and B Hawaii

South Kihei

Corentin

5.678.522 ₫

6.741.088 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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

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

18. Signature Residences at Maui Banyan

South Kihei

Mai

2.369.823 ₫

15.818.887 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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.

19. Guava Suite

South Kihei

Nancy

5.678.522 ₫

6.741.087 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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

20. Grand Champions by KBM

Wailea

Sean

10.471.995 ₫

22.664.139 ₫ total

includes taxes & fees

19 Nov - 20 Nov

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Top Kahoolawe Hotel Reviews

Maui Coast Hotel

10/10 Excellent

"It was well worth the cost places to eat bar by the pool beach is literally 3 minutes away walking abc store near by."

Maui Beach Vacation Club

10/10 Excellent

"EVERYTHING ABOUT THE PROPERTY AND THE ROOM WAS SUPERB."

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!"

Wailea Beach Resort - Marriott, Maui

10/10 Excellent

"Not sure if you can beat the pools, value, location, views, snorkel, and staff on the island! Loved our stay!"

Aston Maui Hill

10/10 Excellent

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

Maui Sunset

8/10 Good

"I personally like Maui Sunset. The condo unit has been updated nicely and cleaned. The staff is very helpful when needed assistance. The landscapes have been well maintained for every guest to enjoy and it is right on the beach. Swimming pool and hot tub are clean and well-maintained daily. I definitely will book and stay at Maui Sunset again next time visit Maui."

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."