Holiday Homes in Kaanapali

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Top-rated Holiday Homes in Kaanapali

Guests agree: These holiday homes are highly rated for location, cleanliness and more.

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Holiday home in Lahaina

Westin Kaanapali Ocean Resort Villas Studio King

Your family will be close to everything when you stay at this centrally-located place. King bed studio with kitchen, dining area, balcony, in-unit laundry, pull-out sofa bed for 2 kids. 2 big pools with plenty of ocean access. Tons of activities available from snorkel, to zip line, to hiking, to canoe, all within a minute walk or several minute drive. You will make magical family memories here. We only have Sat July 30-Sat Aug 6 available. There is no particular view guaranteed for this Villa.

Guest favourite
Holiday home in Lahaina
4.95 out of 5 average rating, 43 reviews

Napili Bay Perfection at its Best, Specials!

We invite you to stay at what is considered by many, the best spot on Napili Bay. This upgraded condo is a top floor, corner unit with the beach and inviting waters of Napili Bay, right outside your door. If you are looking for a Maui beach vacation away from the hotel scene, then search no further. Come enjoy our dream spot and see why we have fallen in love with Maui and all that Napili Bay has to offer. No expense was spared with bedding and electronics to help you relax in style.

Guest favourite
Holiday home in Wailea
4.95 out of 5 average rating, 62 reviews

Beautiful beaches for swimming and sunsets!

Beautifully updated 1BR/2BA condo across from the white sands of Kamaole Beach #3, one of the nicest beaches on the island, and minutes from other world renown beaches in Kihei, Wailea and Makena. This beautiful resort also features a gorgeous swimming pool, two jacuzzis, children's wading pool, four tennis courts, Hawaiian-style grounds and tropical ambience, all located minutes from world-class golf courses in Wailea and Makena. Kamaole Sands Resort #3-207, in preferred BUILDING #3

Guest favourite
Holiday home in Haiku
5 out of 5 average rating, 52 reviews

Hā'iku Hale - 3 Bedroom Maui Getaway!

The Ha’iku Hale is taken care of by a local family that seeks to uphold the values of Hawai’i’s culture. Designed to be a sanctuary in the middle of paradise to retreat & rejuvenate. With 3 Bedrooms and 2 Baths the Hale comfortably sleeps up to 6 people. The Hale Master Bedroom has a plush king size bed, A/C, and a private bathroom. Located within walking distance of the Ha’iku Cannery Center so you’ll be able to dine and shop easily! 10 Mins from Ho'okipa, perfect for surfers!

Holiday home in Lahaina

Amazing Oceanview & Amenities - 1 Bedroom Studio

Your family will be close to everything when you stay at this centrally-located place. Great snorkeling right in front! **You will be notified via email within 24 hours whether the dates you have chosen are available. ** STUDIO PREMIUM VILLA SLEEPS UP TO 4 ADULTS The villa comfortably sleeps up to four adults and features well equipped kitchen includes glass cooktop, microwave oven, full-size refrigerator, dishwasher, coffee maker, toaster, blender, dinnerware, washer and dryer

Holiday home in Lahaina

Ocean View! 1-bedroom villa on resort property

Relax with the whole family at this peaceful place to stay, or escape with a loved one for a romantic getaway. Located in The Westin Ka'anapali Ocean Resort Villas, this 900 sq foot villa sleeps up to 4 adults comfortably. Master bedroom with king-sized bed Large shower, separate whirlpool tub and two vanities Living area with sofa bed 2 Flat-panel TVs, DVD player and Bose® radio Dining area Fully equipped kitchen Washer and dryer Private lanai with outdoor furniture Free Wi-fi

Holiday home in Lahaina
5 out of 5 average rating, 3 reviews

The Westin Kaanapali Ocean Resort Villas

Studio Premium Villa - timeshare condo Situated on Ka'anapali Beach on the west coast of Maui, this resort offers a host of amenities and it's great location has access to a number of fun activities, places to eat, etc. Once booked my wife and I would be happy to provide recommendations. The Studio premium villa offers the balance of convenience and tranquility you need to help you rejuvenate. Comfortably sleeps up to 4 (if 2 are willing to sleep on a pull-out sofa).

Holiday home in Lahaina

2 BR Maui Ocean View Villa Christmas Week!

2 bedroom / 2 bath en suite ocean view villa at Westin Kaanapali Ocean Resort Villas North. Beautifully appointed two bedroom en suite villa with fully furnished kitchen, bathrooms with separate whirlpool baths and showers, in-room washer/dryer and everything you need for a fabulous vacation. Property has 5 pools and hot tubs, kid's club, waterslide, tennis courts, ping pong, barbeque area, restaurants, shuttles to shopping and more.

Holiday home in Wailea
4.83 out of 5 average rating, 6 reviews

Dreamy Kihei Condo, Steps From The Beach (335-12)

This cozy condo is located at Kihei Kai Nani Resort. Walking distance to: The beach ( Kamaole II Beach ) Groceries ( Hawaiian Moons ) Coffee shops (Cinnamon Roll Place) Restaurants ( Café ole, 808 Deli, Maui Fish and Chips, South-shore Grindz and more! ) Park ( Kamaole Beach Park ) There are lots of activities near by as well. Feel free to ask for recommendation's on anything from surf lessons to the best snorkel spots.

Superhost
Holiday home in Kihei
4.5 out of 5 average rating, 6 reviews

WorldMark Kihei, 2br Condo Near the Beach

A family friendly resort, WorldMark Kihei is directly across from lovely Kameole beach and located in south Maui. King in Master, 2 Twin Beds or Queen in second bedroom, and Queen Murphy Bed in living area. Condos have full kitchens and two full bathrooms The resort fee for WiFi is $9.95 per day or $49.95 for 10 days for 3 devices (rates subject to change)

Top Guest favourite
Holiday home in Lahaina
4.98 out of 5 average rating, 107 reviews

Oceanfront Paradise! Sea Turtle Cove C24 Napili Pt

Spectacular Ocean & Outer Island views from your Air Conditioned condo! Enjoy snorkeling with Sea Turtles in your backyard, seasonal Whale Watching from your kitchen, and breathtaking Sunsets... Welcome to Paradise! Traveling with family or friends? Please see our other listing just few doors down: Oceanfront Oasis! Sea Turtle Cove B17 Napili Point

Guest favourite
Holiday home in Paia
5 out of 5 average rating, 15 reviews

North Shore Maui. Kuau Studio by the beach

Forget your worries in this spacious and serene space. You can't beat the location: Kuau Makai Studio is just a few steps away from Mama's Beach in a quaint and quiet neighborhood where it is still a pleasure to walk about. *NOTICE: OUR NIGHTLY RATE INCLUDES A MANDATORY HAWAII STATE OF 18.712% ON ALL RENT, starting January 1st, 2026.

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