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Vacation rentals in Kaanapali

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Top-rated vacation rentals in Kaanapali

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A light-filled living area showcases a beige couch and two patterned chairs, positioned around a wooden coffee table. Floor-to-ceiling windows reveal expansive ocean views, allowing natural light to enhance the space. A ceiling fan adds to the comfort, while a mounted TV is visible on the sideboard.
Condo in Lahaina
4.96 out of 5 average rating, 157 reviews

Whales Watch: Luxe Beachfront-180° Ocean views/AC!

Watch Whales breach during migration & sea turtles and sail boats sailing by while snuggled up in your dreamy, oceanfront kingsize bed with luxurious 600 count cotton sheets! If you love swimming with the turtles and the sound of the ocean, then this is the place for you. Luxuriously remodeled, very secluded corner unit, your Maui hideaway is just 15 feet from the ocean with unbeatable, 180 degrees ocean views. Located on the 5th floor of Valley Isle Resort in Kahana (Within the Hotel Zone).

Top guest favorite
A charming cottage is nestled among tropical greenery, featuring lush palms and vibrant plants. The entrance is highlighted by a welcoming staircase leading up to a covered porch. A scenic landscape can be observed in the background, showcasing the natural beauty of the surroundings.
Home in Makawao
4.99 out of 5 average rating, 159 reviews

Private Luxurious Cottage

This marvelous accommodation is for the nature-lover who enjoys luxury. It boasts a lovely deck which looks out onto majestic tall trees and lush green foliage with a romantic soaking tub for two. Centered in the room is a custom-made king-size bed fashioned from cherry wood and adorned with luxurious bedding. There is full kitchen and dining area with views for a tranquil place to share a meal. This is true Hawaiian style where you can enjoy comfortable, elegant and laid-back island living.

Top guest favorite
A lush outdoor garden area is visible, featuring vibrant green grass and tropical plants. A seating arrangement with a table and chairs can be seen under an overhang, framed by a flowering tree. The ocean glistens in the distance beneath a clear blue sky.
Townhouse in Kapalua
4.96 out of 5 average rating, 181 reviews

Amazing Kapalua ,Stay 7 nights, only pay for 6 !

Our place is close to 3 beautiful beaches, 2 spectacular golf courses, tennis garden, hiking trails, whales, zip line, shops, restaurants, pools, barbecue, and spas. You’ll love our place because of the incredible views from the outdoor garden. It is huge and we call it our living room on the lawn. You'll love the ambiance, neighborhood, people. You will love everything about the Ridge at Kapalua. Our place is good for couples, solo adventurers, business travelers, not suitable for children.

Top guest favorite
An inviting outdoor living area features wooden seating arrangements adorned with plush cushions. Lush greenery surrounds the space, and decorative string lights create a warm ambiance overhead. A shaded daybed offers a comfortable spot for relaxation amid the tropical landscape.
Cottage in Kaanapali
4.93 out of 5 average rating, 149 reviews

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.

Top guest favorite
The open-concept living space features a modern kitchen with sleek cabinetry and a bar top overlooking a sunlit living area. Floor-to-ceiling windows reveal panoramic ocean views and access to a comfortable seating area, inviting relaxation in a coastal setting.
Condo in Kaanapali
4.99 out of 5 average rating, 151 reviews

Luxury Mahana 1bd/2ba-Great Views-Free Park/WiFi

Locally Owned and Operated 1BD/2BA condo with the best direct beachfront location, panoramic Ocean views, sunsets, and seasonal whale watching. The owner’s spared no expense in renovating this unit making it hand’s down one of the nicest units in all of the Mahana. Wake up to the cool tropical breeze and sounds of the shoreline just 50 feet away. Floor to ceiling windows in the living area and bedroom bring the stunning views and warm Maui sun inside while central AC keeps you cool inside.

Guest favorite
A dining table is set with plates and utensils, positioned on a lush green lawn. Palm trees surround the area, offering a tropical ambiance with the ocean visible in the background under a partly cloudy sky.
Condo in Napili-Honokowai
4.92 out of 5 average rating, 159 reviews

OCEAN FRONT Condo at Napili Bay, Near Kapalua!

Thank you for checking out my OCEAN FRONT condo located at the Charming Napili Shores resort. This recently renovated condo is in the high demand I building, which is the closest to the ocean in the complex. Imagine every morning you enjoy the brunch ordered from the famous Gazebo restaurant at your own Lanai right beside the ocean; Soak up the sunshine on the Napili beach steps away from the resort during the day, and come back in the evening to watch the stunning sunset in your room!

Top guest favorite
Farm stay in Haiku-Pauwela
4.93 out of 5 average rating, 675 reviews

Adorable Gingerbread House Farm Stay, Makawao

This LEGALLY PERMITTED Farm Stay has the lush beauty and privacy,, without the drive to Hana! Only 15-20 minutes to the airport, 10 minutes to beaches, 2 minutes to restaurants and shops...on a private gated property with organic nursery. Seasonal stream in the back yard. Simply BEAUTIFUL! We gave 8.5 acres of diversified farm-fruit, water lilies, 10,000 sq ft greenhouse) Comes with a FREE FARM TOUR and/or LABYRINTH WALK with every booking! Permit Number STMP 2015 / 0001 SUP2 2013 / 0013

Top guest favorite
A light-filled living room features a designer sectional sofa and a wooden coffee table. Floor-to-ceiling glass doors offer unobstructed views of the ocean and balcony. A modern TV is positioned on a wooden console, enhancing the contemporary aesthetic of the space.
Condo in Kihei
4.99 out of 5 average rating, 264 reviews

Luxury condo • 180° Ocean Views • Steps to Beach

Enjoy panoramic ocean, mountain, beach & sunset views year round at Hale Meli (short for "Hale Mahina Meli" or “Honeymoon House” in Hawaiian), a top floor condo with exquisite designer interiors and high-end amenities. Ideally located in Kihei, the condo is right across the street from one of the best beaches on Maui and is walking distance to restaurants, shops and grocery stores. It is also your perfect home base for exploring the rest of Maui, being centrally located on the island.

Top guest favorite
An aerial view captures the lush green landscaping surrounding the property, featuring palm trees and well-maintained rolling lawns. The ocean sparkles in various shades of blue, while nearby buildings with solar panels are visible, creating a serene atmosphere just steps from the beach.
Condo in Napili-Honokowai
4.98 out of 5 average rating, 102 reviews

Napili Bay Oceanview Hideaway

Welcome to Napili Bay, Maui's hidden gem, and a favorite spot for some of the best snorkeling on Maui. Relax in the ocean breeze from your private lanai. Enjoy ocean views throughout the condo. Lush tropical landscaping, plumerias, monkeypods, and many more plant varieties throughout the property. 2nd floor studio condo, beautiful vaulted ceilings, low density property, old school Hawaiian resort. Easy access to world-class beaches, restaurants, shopping and golfing.

Top guest favorite
A spacious bedroom is equipped with a large bed adorned with colorful pillows. Two patterned armchairs are positioned beside a small table, creating a cozy seating area. A glass sliding door provides natural light and offers a view of the outdoor greenery.
Condo in Napili-Honokowai
4.98 out of 5 average rating, 112 reviews

Your Oasis by the Sea, stay at B103!

Step off your lanai, & enjoy the pristine ocean, pool, or hot tub. Snorkel with sea turtles & colorful fish. Walk to Kaanapali Beach & boardwalk for casual dining or groceries. Additional shops & restaurants minutes away at Whaler's Village & downtown Lahaina. NO RESORT FEES!!! Resort amenities include parking, pools & spas, tennis courts, putting greens, internet, shuffleboard, & concierge services for booking island excursions.

Top guest favorite
Condo in Kaanapali
4.98 out of 5 average rating, 202 reviews

Kaanapali Shores - SUPER CLEAN! OceanView 1bd/1ba

A legal short term rental! 1 bedroom, 1 bath with open floor plan. This condominium has a comfortable Cal-King bed in the bedroom and sofa sleeper in the living-room. **Central A/C*Fully equipped kitchen w/ granite counters*refrigerator*stove top + oven*coffee maker* microwave* dishwasher* washer/dryer* Free in room WiFi** Onsite gym is managed by an outside contractor and charges $9/day for useage.

Top guest favorite
A scenic view captures the sunset over a lush landscape, with a pool reflecting the colorful sky. Tall trees frame the scene, and the distant ocean is visible beneath the dramatic clouds. The vibrant greens of the surrounding vegetation provide a serene backdrop.
Cottage in Makawao
4.99 out of 5 average rating, 237 reviews

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!

Popular amenities for Kaanapali vacation rentals

When is the best time to visit Kaanapali?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$104,387 GYDG$102,086 GYDG$104,387 GYDG$93,300 GYDG$83,677 GYDG$105,015 GYDG$108,781 GYDG$105,643 GYDG$82,631 GYDG$79,075 GYDG$84,096 GYDG$99,994 GYD
Avg. temp23°C23°C23°C24°C25°C26°C27°C27°C27°C26°C25°C24°C

Frequently Asked Questions

  • What are the best places to stay in Kaanapali?

    Kaanapali has beachfront resorts and vacation rentals set along its scenic coastline and near lively open-air shopping and dining areas. Many guests also choose stays near golf courses or within landscaped neighborhoods for a relaxed island atmosphere.

  • What are the best things to do in Kaanapali with kids?

    Families can explore the sandy beaches, swim in gentle waves, or try paddleboarding together. The area often features snorkeling spots, cultural performances, and interactive programs that highlight local traditions and marine life.

  • What are some of the best things to do in Kaanapali?

    Kaanapali has a lively beachfront, snorkeling near vibrant reefs, and rounds of golf amid ocean views. Exploring Whalers Village, watching traditional ceremonies, or taking part in a sunset cruise are frequently suggested experiences.

  • How is the weather in Kaanapali?

    Kaanapali experiences warm temperatures year-round, ranging from 64–90°F (18–32°C), with drier, sunnier months in late spring through early fall. Occasional showers are more common in winter, but even then, the area often sees plenty of sunshine.

  • What are the best places to visit in Kaanapali?

    Popular spots include Kaanapali Beach, Whalers Village, and Black Rock, which is known for snorkeling and daily cliff diving ceremonies. The lush beachfront path and landscaped gardens create relaxed spaces to wander and take in island views.

  • What are some hiking trails in Kaanapali?

    Trails near Kaanapali range from coastal boardwalk paths lined with native plants to lush areas just outside the resort zone. Nearby, visitors can often explore gentle walks or venture to forested routes with volcanic views.

  • What are some family activities we can do in Kaanapali?

    Families often enjoy swimming and snorkeling at Kaanapali Beach, exploring Whalers Village’s hands-on exhibits, or participating in lei-making workshops. Boat tours and wildlife watching trips help introduce younger travelers to local nature.

  • What are some of the best day trip ideas from Kaanapali?

    Travelers often take day trips to explore lush upcountry towns, scenic coastal areas, or the historic center of Lahaina. Journeys to volcanic landscapes or traditional communities introduce rich history, art studios, and farm experiences.

  • Are there any pet friendly accommodations available in Kaanapali?

    Many vacation rentals and some resort areas in Kaanapali have pet-friendly options, often including nearby green spaces and walking paths. It is helpful to check each listing’s amenities for current pet policies and facilities.

  • What are some local tips for visiting Kaanapali?

    Bring reef-safe sunscreen, as local waters and coral are sensitive to chemicals. Early mornings are often quieter for popular spots, and learning a few Hawaiian phrases helps connect with the community.

  • What is Kaanapali known for?

    Kaanapali is known for its sweeping beach, clear waters, and lively mix of outdoor recreation and island culture. Cliff diving ceremonies at Black Rock and beachfront pathways draw travelers seeking both relaxation and local traditions.

  • What are the best hidden gems to explore in Kaanapali?

    Around Kaanapali, seek out quiet garden pathways, tucked-away coves, or small art galleries featuring local creators. Seasonal pop-up markets and shell-strewn stretches of beach often reward curious explorers.

  • What are the best foods to try in Kaanapali?

    Sample fresh poke bowls, grilled fish with local spices, and tropical fruit desserts like haupia or shave ice. Many eateries also feature plate lunches and Japanese, Filipino, or Hawaiian-influenced dishes.

  • What should I bring for a trip to Kaanapali?

    Pack lightweight clothing, sandals, a hat, and reef-safe sunscreen for sunny days, plus a light jacket for occasional evening breezes. Snorkel gear and a reusable water bottle can be handy for outdoor excursions.

  • What is the nightlife in Kaanapali like?

    Nightlife in Kaanapali has relaxed beachfront bars, live music venues, and hula performances. Many evenings also feature sunset gatherings, open-air lounges, and opportunities to sample local craft cocktails.

  • What are the most popular events or festivals in Kaanapali?

    Kaanapali frequently hosts hula celebrations, culinary festivals, and cultural events tied to traditional Hawaiian music and dance throughout the year. Whale season, often marked by educational activities, draws many visitors between late fall and early spring.

  • Are there family friendly vacation rentals in Kaanapali?

    Kaanapali has a variety of family-friendly vacation rentals, including spacious condos, beachfront apartments, and homes with shared pools and outdoor areas. Search for listings featuring kid-friendly amenities like full kitchens or gathering spaces.

  • When is the best time to visit Kaanapali?

    Late spring through early fall is often recommended for clearer skies and minimal rainfall, with temperatures that typically range from 68–90°F (20–32°C). Winter visits offer a chance to experience cultural events and humpback whale sightings along the coast.

All about Kaanapali

There aren’t many beaches in the world associated with royalty, but Kaanapali’s three miles of white sand beaches were once the official playground of the Hawaiian royal family. In this storied section of Maui, royalty surfed, swam, and relaxed. Today Kaanapali remains popular for all of those aforementioned activities, but is perhaps most renowned for its cliff divers. These brave souls hurtle toward the waters below dramatically illuminated by torchlight, a reenactment of ancestral courage. While Kaanapali’s coastline is dominated by a series of resorts and two enormous championship golf courses — the intentional outcome of Hawaii’s first planned resort development — its beaches are an inviting destination for sunbathing. Here the shoreline gently fades into shallow crystalline waters where sea turtles are regularly spotted gently floating with the tide, and the songs of migrating whales miles away can be heard echoing under the surface.

What are the top things to do in Kaanapali?

Take an Electric-Powered Submarine

Many visitors may boast of snorkeling or even diving beneath Maui’s vibrant waters, but how many can claim they took an undersea adventure inside a submarine? Atlantis Submarine’s small fleet of battery-powered craft delivers up to 48 passengers down to a depth of 100 feet to safely peer at the seascape and underwater wildlife populating installed artificial reefs, all from the comforts of an air-conditioned vessel.

Black Rock (Pu’u Keka’a)

Located at the furthest northern end of Ka’anapali Beach, this old lava flow is Kaanapali’s most iconic landmark and legendary for its cliff divers. Traditionally believed to be the spot where the dead would leap to enter the afterlife, these days local kids and visitors still test their wits by jumping from Black Rock (and snorkeling underneath). A ceremonial leap is also staged nightly, accompanied with lit torches and a blow of a conch shell to honor the memory of King Kahekili, Maui's last independent king.

Hidden Coral Reefs

If snorkeling among tropical fish and sea turtles rates high on your list, you’ll want to seek the hidden coral reefs located between Kaanapali and Lahaina, just north of Wahikuli Beach – a “secret” spot where crowds are few, but the sea turtles are numerous.

Quick stats about vacation rentals in Kaanapali

  • Total vacation rentals

    Explore 4,790 vacation rentals in Kaanapali

  • Nightly prices starting at

    Kaanapali vacation rentals start at G$2,092 GYD per night before taxes and fees

  • Verified guest reviews

    Over 46,520 verified reviews to help you choose

  • Family-friendly vacation rentals

    2,470 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    4,510 properties feature pools

  • Rentals with dedicated workspaces

    3,150 properties have a dedicated workspace

  • Wi-Fi availability

    4,780 of Kaanapali vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Beachfront, Self check-in, and Gym across Kaanapali rentals

  • 4.8 Average rating

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

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