
Cottage holiday rentals in Kaanapali
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Top-rated cottage rentals in Kaanapali
Guests agree: These cottages are highly rated for location, cleanliness and more.

OCEAN VIEW Kaanapali Cottage ICC 24
OCEAN VIEW top of the property adjacent to the 12th fairway of the Royal Kaanapali Golf Course. This Kaanapali Cottage with 2 beautiful swimming pools is a mere 5 minute walk from the local favorite "Airport Beach", featuring world-class snorkeling & miles of pristine white sand beach's. There is a beachfront boardwalk & paths for walking, exercising in both directions accessing shopping (Whalers Village) & restaurants. ITS A PERFECT PLACE FOR ANYONE WANTING TO GET AWAY WEEKLY DISCOUNT

Oceanview Cottage away from heat! w/ County Permit
Closest Airbnb to Haleakala National Park & Road To Hana. Away from 100 degree heat & traffic & yet still close to food & market! Private Cottage on 2acres of orchard on Haleakala, w/ endless pano Bi-Coastal View (Double Ocean View that no other islands have) & night city view! Stunning sunset & starry nights. Two master suites with ensuite Full Baths. For past guests whom love this home, this AirBnB ends on 12/31/26. Hawaii Supreme Court ruled no more short term rental in agriculture lands.

LunaHouse In The Heart of Paia
Thoughtfully refurbished / modernized c.1934 plantation cottage in central Paia Town. Steps away from beach, restaurants, bars, grocery, boutiques. 832 SF; Amenities including: Ceiling Fans; A/C; Outdoor shower, Large 26cf fridge w/ ice-maker, Micro-hood, Dishwasher, oven and induction cooking pads, LG laundry; Wifi Internet: 200mbs; Max occupancy is 4 Guests (Including children & infants). Office room w/ desk, ergonomic chair. BBQ area w/ sink; Fridge, Propane grill. Maui Permit: BBPH

Kaanapali Cottage ICC 29 Indoor/Outdoor Living
International Colony Club’s cottage 29 is located in the world-famous Kaanapali Beach area, and a five minute walk from one of Maui’s best beaches. Built in 1964, this community affords a spacious and mature landscape between 44 private cottages spread over 10 acres. Our Hawaiian plantation style cottage is reminiscent of homes built during the plantation era and conveniently located close to beaches, shopping and restaurants, but is secluded from the hustle and bustle of the big resorts.

Romantic and Private Cottage and Gazebo for two!
Romantic, Private, a Sanctuary, beautifully decorated, local charm and sleeping to the sounds of Wailuku River are a few things our guests say about our Inn. An American Whirlpool hottub is our newest feature amenity along with the air conditioning, washer/dryer, full kitchen and a large shower in your private bathroom. A king Size bed, Wifi, barbeque grill, television, fans beach towels are standard amenities. The detached Gazebo is perfect for reading, meditating, or just doing nothing!

Romantic Suite | Tropical Escape | BBQ & Hot Tub
• Perfect for couples—Queen bed and romantic ambiance • Outdoor hot tub, BBQ, and tropical vibes • Prime location in Kihei—just minutes from restaurants, bars, coffee shops, and groceries • Quick access to top spots: 15 mins to Wailea, 1 hr to Haleakalā, 2 hrs to Hana Sleep on Maui Cottage: 1 Bed Honeymoon Jacuzzi Penthouse • Backyard amenities shared with our Sleep on Maui House. Contact us to discuss rates and options for groups up to 8!

North Shore Ocean View Cottage
This recently built comfortable cottage is located on the north shore of the island of Maui, tucked away in the quiet countryside of Haiku but relatively close to major attractions! Enjoy a relaxing vacation in a rich tropical setting with spectacular ocean views! Please Note: State of Hawaii Maui County adds 17.96% tax to your guest fees. TA-060-126-6176-01 GE-060-126-6176-01 BBPH 2016/0001 SUP 2 2015/0008

One Block to the Beach! Cozy Beach Cottage Kihei
Welcome to Chez Maui! This cozy 2-bedroom, 1-bathroom cottage is just one block from the beach, offering a peaceful and private retreat. Perfect for your vacation or for remote workers, traveling healthcare professionals, snowbirds or those in transition to longer-term accommodation. The cottage comfortably hosts up to 4 guests maximum and has been recently renovated. *Make sure to turn on your notifications for Airbnb Messaging.*

Charming Kaanapali cottage with ocean view
A charming "Old Hawaii" bungalow on lush landscaped tropical grounds, only a ten minute walk from Kaanapali Beach, the best beach in West Maui. Close to numerous restaurants and shops in the Kaanapali area. But so beguiling is the view of Lanai and Molokai islands as you drink your morning coffee, so inspiring the sunsets as you sip your cocktail in the late afternoon--you may never leave the lanai!

Rustic Upcountry retreat with breathtaking views!
Maui County Permits BBMP2019/0006 & SUP2 2019/0003 This is a BnB not a STRH Owners live on property At this time we are hosting to guests 12 or older. This property is terraced so not optimal for young children. This is a non smoking property. No smoking is allowed. Use of the pool, hot tub and dry sauna are private when reserved with our private calendar. Mahalo!

Great Location, 1 BR Beachy, VERY CLEAN Cottage
COUNTY PERMITTED - This home holds legal Maui Permit STPH2015/0006. Amazing Haiku location, Very Clean, Cute Beachy-style, 1BR/1BA cottage home. 1 Queen bed very comfortable, quick walk to Haiku Grocery, Haiku Cannery, Nuka Sushi, Haiku Mangala Yoga, Colleen's, Short 4 mile drive to Ho'okipa, (sleeps 1-2) well equipped kitchen & new appliances

Private Country Cottage, Ocean View, A/C, Hana Hwy
Relax & enjoy the peace & quiet, coastal ocean views lush tropical setting & complete privacy at your modern cottage with private lanai. Palm Cottage is ideal for a quiet vacation, honeymoon or just a peaceful getaway. Come to quiet, rural Maui to get away from the crowds; yet only a few minutes drive from shops, restaurants & beaches.
Popular amenities for Kaanapali cottage rentals
Cottage rentals with a hot tub

Privacy, Luxury, Ocean View Cottage, HotTub, K-Bed

Romantic and Private Cottage and Gazebo for two!

Leilani's "Leimomi" Cottage - County Licensed

Luxury Cottage,Saltwater Spa-Close to Beach,Dining

Romantic Suite | Tropical Escape | BBQ & Hot Tub

Rustic Upcountry retreat with breathtaking views!
Private cottage rentals

Walk to small beach, charming cottage

Maui Meadows Ocean View Cottage

Cute Plantation Cottage; Walk into Wailuku Town!

Beautiful Cottage 5 Minutes From Beach

3B/2B FamilyVacationComfort HawaiianaCharm Central

Renovated Plantation Home; Walk into Wailuku Town!

Grateful Casita

Remodeled 2BR | Deck | Washer/Dryer
Luxury cottage rentals

Ho'okipa Rose - Peace and Serenity

Pono Plantation Maui-3 Bedroom Cottage

Charming Cottage in Kuau near Mama’s Beach

Private 2 bedroom cottage with pool

Haiku Nani, County Licensed

CLASSIC HAWAIIAN COTTAGE

NEW 2/2 Beautiful Modern beach Chic Oasis with AC

Lani Paradise Oceanfront Cottage
Quick stats about cottage rentals in Kaanapali

Nightly prices starting at
Kaanapali holiday rentals start at $397 NZD per night before taxes and fees

Verified guest reviews
Over 540 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Kaanapali rentals

4.8 Average rating
Kaanapali stays are highly rated by guests—averaging 4.8 out of 5!
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