Default HTG hotel image

Search Hotels with Pool in Kaanapali Hillside

  • 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

Check availability on Kaanapali Hillside Hotels with Pool

Tonight
3 Oct - 4 Oct
Tomorrow
4 Oct - 5 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

Our top choices for Kaanapali Hillside hotels with a pool

A resort with a large pool, palm trees, and a view of the ocean.
A resort with multiple swimming pools, palm trees, and a beach view.
A woman in a swimsuit standing by a pool with a view of the ocean and palm trees.
A gazebo with white columns and a metal roof, surrounded by lush tropical plants and a small water feature.

1. The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali
Kannapali Beach Area
  • Splash into holiday bliss at this luxury resort with three sparkling pools and a thrilling waterslide.
฿20,203
฿25,922 total
includes taxes & fees
30 Oct - 31 Oct
The Westin Maui Resort & Spa, Ka'anapali
A resort with multiple swimming pools, a beach, and a mountain in the background.
A balcony with two rocking chairs and a small table, overlooking a pool and a beach with palm trees and a sunset view.
A resort with multiple buildings, a beach, and a pool area.
A spacious indoor area with a large wooden table, comfortable seating, and large windows offering a view of the ocean.

2. Sheraton Maui Resort & Spa

Sheraton Maui Resort & Spa
Kannapali Beach Area
  • Dive into pool paradise at this Maui resort with a waterslide, lazy river, and poolside bar service.
฿11,041
฿15,298 total
includes taxes & fees
7 Oct - 8 Oct
Sheraton Maui Resort & Spa
A resort with a large pool, palm trees, and a view of the ocean.
A resort with a large pool, beachfront, and a mountain backdrop.
View from room
View from room

3. Hilton Vacation Club Ka'anapali Beach Maui

Hilton Vacation Club Ka'anapali Beach Maui
Kaanapali
  • Sparkling blue pool sanctuary awaits with family fun, scenic lounging, and poolside cocktail service.
฿8,239
฿10,976 total
includes taxes & fees
23 Oct - 24 Oct
Hilton Vacation Club Ka'anapali Beach Maui
A pool area with a bridge, surrounded by lush greenery and a view of the sea.
A beach view with palm trees, a clear sky, and a calm sea.
A room with two beds, a bathtub, and a large window with a view of the sea.
An outdoor dining area with tables set for a meal, overlooking a body of water.

4. Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa
Kannapali Beach Area
  • Discover 6 inviting pools with cabanas, waterslides, and a poolside bar, creating an aquatic paradise at this Maui resort.
฿14,739
฿19,609 total
includes taxes & fees
30 Oct - 31 Oct
Hyatt Regency Maui Resort & Spa
A resort with a swimming pool, palm trees, and a view of the ocean.
A resort with a pool, palm trees, and a view of the ocean.
An aerial view of a resort with a swimming pool, palm trees, and a beach.
A balcony with a view of a beach and palm trees.

5. OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort
Kannapali Beach Area
  • Discover a poolside paradise with stunning ocean views and luxury cabanas at this beachfront oasis.
฿9,027
฿12,509 total
includes taxes & fees
28 Oct - 29 Oct
OUTRIGGER Kaanapali Beach Resort
A swimming pool with a curved design, surrounded by palm trees and lounge chairs, with a building in the background.
A spacious living area with a white sofa, red patterned rug, and a wooden coffee table. There are potted plants, a guitar, and a view of the ocean through large windows.
A beach with sun loungers, clear turquoise water, and a sailboat in the distance.
A lobby with wicker furniture, a large mirror, and a view of the outdoors.

6. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
Kannapali Beach Area
  • Swim into paradise with multiple pools, hot tubs, and a beach steps away at this serene Hawaiian retreat with vibrant marine life.
฿7,400
฿11,772 total
includes taxes & fees
1 Nov - 2 Nov
Aston Maui Kaanapali Villas
An aerial view of a resort with a central swimming pool surrounded by lounge chairs and palm trees.
View from room
A resort with multiple buildings, a swimming pool, and a beach.
Room

7. Aston Kaanapali Shores

Aston Kaanapali Shores
Lahaina
  • Refreshing lagoon escape with two tropical pools and poolside bar service perfect for soaking in the warm Hawaiian sun.
฿8,027
฿10,525 total
includes taxes & fees
10 Oct - 11 Oct
Aston Kaanapali Shores
Restaurant
A balcony with a view of the ocean and a sailboat.
A resort with a beach, pool, and ocean view.
A beach view with palm trees, a clear sky, and a distant mountain.

8. Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows
Kannapali Beach Area
  • Two blissful outdoor pools await at this Kaanapali Beach resort with tennis courts and spa amenities.
฿7,400
฿10,577 total
includes taxes & fees
3 Nov - 4 Nov
Royal Lahaina Resort & Bungalows
A resort with a large pool, palm trees, and a view of the ocean at sunset.
A resort with a pool, palm trees, a waterfall, and a view of the ocean.
A resort with a large pool, palm trees, and a view of the ocean.
A fire pit surrounded by stone seating and palm trees against a sunset sky.

9. The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas
Kannapali Beach Area
  • Tropical paradise beckons with 2 pools, lazy river, and waterslide for endless fun.
฿16,612
฿19,720 total
includes taxes & fees
13 Oct - 14 Oct
The Westin Ka'anapali Ocean Resort Villas
A pool area with lounge chairs and umbrellas, a sign reading "The Whaler," and a view of the ocean and a mountain in the background.
Terrace/patio
A hotel room with a large bed, a balcony with a view of the ocean, a television, and a wooden dresser.
A resort with a swimming pool, beach, and palm trees.

10. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
Kannapali Beach Area
  • Serene beachfront pool and tennis oasis steps from Kaanapali Beach's pristine shores.
฿8,235
฿22,038 total
includes taxes & fees
7 Oct - 8 Oct
The Whaler Resort Kaanapali Beach
View all properties

Choose what matters most at hotels with a pool in Kaanapali Hillside

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Kaanapali Hillside Hotel Reviews

Aston Kaanapali Shores

Aston Kaanapali Shores

10/10 Excellent
"Very beautiful property, friendly staff. We had a wonderful experience and we will return to the property on our next Maui visit"
David 3-night trip
Posted 5 hours ago
Aston Kaanapali Shores
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

10/10 Excellent
"My FIRST time ever to Hawaii! I had to see this place not just for its location on Kaanapali Beach, but that it was recommended by Great Value Vacations. Quite the drive from the airport, and it was tricky to park as the garage has narrow spaces, but I loved my first hotel in the Aloha State! The food, the beach, the staff, the sunsets, and the rooms lived up to all my expectations."
Jared 2-night trip
Posted 15 hours ago
OUTRIGGER Kaanapali Beach Resort
Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER

10/10 Excellent
"Clean room"
JOEL 4-night trip
Posted 15 hours ago
Napili Shores Maui by OUTRIGGER
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

10/10 Excellent
"The room was clean, and I loved the mature, relaxing atmosphere of the property. The bell desk and restaurant staff were excellent. They were all friendly, attentive, and welcoming. The morning yoga class was amazing, with a wonderful instructor who made the experience really enjoyable. I also loved the live music every evening. It added such a nice touch to the atmosphere. The only small negative was the check in and check out experience at the front desk. One of the staff members didn’t seem particularly enthusiastic about her job, which felt a little different from the otherwise warm and welcoming service throughout the hotel. Overall, we really enjoyed our stay and especially appreciated the beautiful atmosphere, yoga, live music, and excellent service from most of the staff."
Yoshika 2-night trip
Posted 18 hours ago
Royal Lahaina Resort & Bungalows
Hilton Vacation Club Ka'anapali Beach Maui

Hilton Vacation Club Ka'anapali Beach Maui

10/10 Excellent
"We loved our 10 day stay at the Hilton Vacation Club. Would highly recommend! We especially enjoyed the location and the excellent nearby beaches for snorkeling, the pool area, the room with a lovely bathroom, comfy bed, kitchen supplies, the friendly, helpful staff, mini golf course on site, supermarket across the road, and a nice church and restaurants within walking distance. Just a great spot!"
Joseph 10-night trip
Posted 1 day ago
Hilton Vacation Club Ka'anapali Beach Maui
Sheraton Maui Resort & Spa

Sheraton Maui Resort & Spa

10/10 Excellent
"Clean"
suzanna 3-night trip
Posted 3 days ago
Sheraton Maui Resort & Spa
Aston at Papakea Resort

Aston at Papakea Resort

10/10 Excellent
"Great resort and we'd definitely stay again!"
Elizabeth 7-night trip
Posted 5 days ago
Aston at Papakea Resort
OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa

10/10 Excellent
"Awesome experience"
Anibal 4-night trip
Posted 6 days ago
OUTRIGGER Honua Kai Resort & Spa

Frequently asked questions

What are some accommodation options with pools in Kaanapali Hillside?
Royal Lahaina Resort & Bungalows: Hotel, 8-minute walk from Kaanapali Beach. Features a full-service spa, 2 outdoor swimming pools and 2 bars. The Westin Maui Resort & Spa, Ka'anapali: Hotel steps from Whalers Village. Offers 2 restaurants, 3 outdoor swimming pools and a full-service spa. Aston Kaanapali Shores: Aparthotel located near Kaanapali Beach. Provides a full-service spa, 2 outdoor swimming pools and 2 hot tubs. OUTRIGGER Kaanapali Beach Resort: Resort, 1-minute walk from Kaanapali Beach. Features cabanas (surcharge), an outdoor pool and sunloungers. Maui Seaside Hotel: Offers complimentary wireless Internet access, an outdoor pool and flat-screen televisions.
What is there to see and do in Kaanapali Hillside?
Explore places such as Kaanapali Beach and Whalers Village while you're in the area. Make a point to visit attractions such as Kahekili Beach and Maui Nui Botanical Gardens.
When is the best time to book a hotel with a pool in Kaanapali Hillside?
Taking the local weather in Kaanapali Hillside into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually September and August, with an average temperature of 25°C, while the coldest months are February and March, with an average of 23°C. Average annual precipitation for Kaanapali Hillside is 224 mm.

Explore a world of travel with Expedia