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Vacation rentals in Kihei

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Quick stats about vacation rentals in Kihei

  • Total vacation rentals

    Explore 3,200 vacation rentals in Kihei

  • Verified guest reviews

    Over 161,440 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,320 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Vacation rentals with a pool

    2,970 properties feature pools

  • Rentals with dedicated workspaces

    1,360 properties have a dedicated workspace

  • Wi-Fi availability

    3,150 of Kihei vacation rentals include wi-fi access

  • Popular amenities for guests

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

  • 4.8 Average rating

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

Top-rated vacation rentals in Kihei

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

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Top guest favorite
A picturesque view captures a beach at sunset with vibrant orange and purple hues in the sky. Swaying palm trees line the shoreline, where beachgoers can be seen enjoying the golden sand and gently lapping waves. The grassy area near the beach is dotted with lounge chairs.
Condo in Wailea

Mana Kai Palms Oceanfront Condo: Keawakapu Beach

Welcome to Mana Kai Palms Our luxurious, newly renovated condominium is located on Keawakapu Beach, named Maui's best for its pristine sand, clear waters, and abundant marine life. The Mana Kai Resort offers a wide range of amenities and with only 100 units, provides a warm, family feel. We are conveniently located minutes from all South Maui has to offer. Hosted by Tracy O'Reilly, a Superhost and #1 rated rental agent on Maui. Do as much as you want or as little as you desire at Mana Kai Palms

FamilyLocationAir conditioning

4.97 out of 5 average rating, 108 reviews
Top guest favorite
Apartment in Kihei

Family Oceanview | North Kihei Beach Access + Pool

Make family memories in this top-floor ocean-view condo in Kihei. Enjoy Pacific views, ocean breezes, year-round sunsets, and seasonal whale watching from the private lanai. Just steps away, the beach across the street is ideal for morning walks, beachcombing, dipping your feet in the water, and sunset strolls. The shallow, rocky shoreline is not ideal for swimming, but some of South Maui’s favorite swimming beaches are just a short drive away. A comfortable home base for Maui adventures nearby.

FamilyLocationView

4.89 out of 5 average rating, 216 reviews
Guest favorite
Condo in Kihei

Ocean Bliss - Walk to Everything + Strong AC

Maui Surf Condo ~ Amazing Ocean View Designer Condo - Fronting world’s best beaches. Full kitchen, Remodeled, Luxury King bed, Huge Ocean Views, huge balcony. If you found us on socials Maui Surf Condo, message us for discount airbnb. Walk to everything (no car needed!) – food, drinks, surf/sup, dive, beach, snorkeling, skating, playground, volleyball, tennis, basketball and more! Views of the islands, whales! Fastest internet speed. Construction is completed. Please note our signed rent

LocationValueTV

4.86 out of 5 average rating, 248 reviews
Superhost
An inviting private balcony features comfortable seating, including a round, woven chair and rattan seats with cushions. A telescope is positioned for views of the ocean and adjacent landscaped garden, showcasing palm trees swaying in the breeze and a glimpse of the heated pool.
Apartment in Kihei

The Whale Watch 208-Oceanfront Kihei

HOTEL ZONED, NOT affected by new Hawai’i legislation banning 1/2 of Maui’s Airbnbs Next to Pacific Whale Sanctuary, this newly renovated 2bed, 2bath is a modern oceanfront oasis. On the 2nd floor, overlooking a heated pool with sweeping ocean, sunset, and mountain views. Steps away to a protected ancient Hawaiian beach perfect for snorkeling, viewing sea turtles and whales shopping, dining and sightseeing just moments away. Sip cocktails or grill out on the rooftop deck with 360* views of Maui.

ValueFamilyGrill

4.88 out of 5 average rating, 142 reviews
Top guest favorite
A spacious living area features a light grey sofa and a wooden coffee table positioned on a natural fiber rug. Large glass doors open to a patio with ocean views, while a flat-screen TV sits atop a console. Neutral curtains frame the windows, creating an airy atmosphere.
Condo in Maalaea

Coastal Dream Oceanfront Condo!

Take a moment to unwind and appreciate the stunning views from the patio, where you can spot whales from Nov-April and catch a glimpse of surfers riding the "Freight Train" during mid-summer. Venture out for a leisurely walk to Maalaea Harbor Shops and the Maui Ocean Center, or explore with a drive to Lahaina (West), Hana (East), or Wailea (South tip). Enjoy delightful amenities including Heated Pool, Oceanfront BBQ station, and Lounge area on the lawn. Designated parking right out front.

LocationFamilyBeach

4.98 out of 5 average rating, 128 reviews
Top guest favorite
An expansive covered lanai features comfortable seating with plush cushions, accented by a decorative table. String lights adorn the ceiling, and panoramic ocean views showcase a vibrant sunset over palm trees and neighboring properties.
Guest suite in Wailea

Sweeping Panoramic Ocean Views - Private Ohana

Live like a local at the Ocean Blue Ohana - the private first floor of this amazing Hawaiian pole home on a half acre property in South Maui. As you enter the space, you will be drawn to the sweeping panoramic ocean views. You are sky-high, perched 500 feet above sea level, looking at the most glorious views of the neighboring islands, mountains, coastline, and Maui's amazing skyline. To top it off, you are 5 minutes from the Wailea Resorts and beautiful golden sand, crystal clear beaches.

FamilyLocationBeach

4.99 out of 5 average rating, 146 reviews
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

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.

ValueLocationNearby

4.99 out of 5 average rating, 285 reviews
Top guest favorite
The living area features a light-toned sofa adorned with decorative pillows, accompanied by a round coffee table. A view of the ocean is visible through floor-to-ceiling sliding glass doors, with tropical greenery framing the scene. A ceiling fan enhances the airy feel of the space.
Condo in Kihei

Stunning Ocean Views

Welcome to our slice of paradise in Maui! Enjoy breathtaking 180° ocean views just steps from the sandy shores of Kamaole I Beach and a short stroll to restaurants, shops and bars. Our newly remodeled coastal-modern condo features A/C throughout, a luxurious Cal King bed, private lanai, fully equipped kitchen, ultra-fast Wi-Fi, in-unit washer/dryer and beach gear. Relax by the pool, enjoy rooftop BBQs with ocean views, or unwind on your lanai with an unforgettable Maui sunset.

ValueFamilyAir conditioning

4.97 out of 5 average rating, 181 reviews
Guest favorite
A comfortable living area features a light-colored sofa and two patterned chairs around a round coffee table. A large window allows natural light, while air conditioning is available on the wall. Decorative elements include artwork and a textured area rug.
Condo in Kihei

Ocean View 2 bdrm with AC & pool., include all tax

Newly renovated! Appliances, hardwood and tile floor, light fixtures, granite countertop, furniture... all brand new! A short drive to downtown Kihei, this gem of a condo is still far enough away that you can relax in peace and quiet with the beach across the street and a pool and BBQ area in the resort. A spacious living area complement the 2 bedrooms, kitchen, bathroom, and large and private lanai with the ocean within view. The host guarantees his utmost attention.

LocationValueGetting around

4.82 out of 5 average rating, 119 reviews
Superhost
Condo in Kihei

Kihei Condo: Steps from Beach & Yummy Eats!

✨ Your Maui Escape Awaits! 🌺 Nestled in the heart of Kihei, our condo is just steps from Kamaole Beach Park—famous for golden sands, calm waters, and stunning sunsets. Stroll to local shops, food trucks, and restaurants, or unwind on your private lanai in true island comfort. With a central location near Haleakalā, the Road to Hana, and Twin Falls (waterfalls), this tranquil retreat is the perfect home base to savor all of Maui’s beauty, flavor, and adventure. 🌴☀️

FamilyValueLong stay

4.85 out of 5 average rating, 155 reviews
Guest favorite
A scenic view reveals the ocean with soft waves meeting sandy shores, framed by palm trees. In the foreground, tennis courts are visible against a backdrop of rolling hills, showcasing lush greenery under a clear blue sky.
Condo in Kihei

Maui is Open - Come Support the Locals

This beautifully upgraded penthouse condo, with stunning ocean and majestic mountain views, is centrally located in Kihei, which is widely considered to have the best beaches and weather on Maui. World-class restaurants, trendy food truck parks, and favorite local haunts are just a stone's throw away. Do you take advantage of the unlimited number of close-by activities, or just relax on the lanai and enjoy the view? It's your call!

ValueLocationKitchen

4.97 out of 5 average rating, 121 reviews
Guest favorite
An oceanfront view from the private lanai showcases turquoise waters and palm trees. A comfortable bed with ocean-themed decor invites relaxation, while a bright living area features tasteful furnishings amidst airy blue walls. The pool area is surrounded by lounge chairs, with lush greenery accentuating the scenery.
Condo in Kihei

FULLY REMODELED*LUXURY*OCEANFRONT*Beaches*Sunset!

*The MAXIMUM OCCUPANCY of this 1-bedroom unit is 4 people at all times. This includes adults, children, infants, and overnight guests. Between the white sand beaches of Kamaole I and II, lies the oasis that is the Royal Mauian. This fourth floor, oceanfront, luxury 610 square foot unit opens up onto your very own private lanai with FULL ocean views.

FamilyValueWalkability

4.97 out of 5 average rating, 134 reviews

Popular amenities for Kihei vacation rentals

Self check-inBeachfrontGymBBQ grillLaptop-friendly workspace

Stay near Kihei's top sights

Kamaole Sands

4 locals recommend

Sugar Beach

4 locals recommend

Kamaole Beach Park III

341 locals recommend

Mana Kai Maui

12 locals recommend

Charley Young Beach

129 locals recommend

Keawakapu Beach

130 locals recommend

Kihei beach vacation rentals

Top guest favorite
A serene lanai is equipped with two sleek swivel chairs and a small dining table. The view beyond showcases a vibrant landscape of lush greenery and ocean hues, visible between the palm trees under a clear sky.
Condo in Kihei

NEW Ocean View 1 Bedroom Condo with Common Hot Tub

LocationValueSleep quality

4.96 out of 5 average rating, 157 reviews
Top guest favorite
An outdoor dining area features a glass table and white chairs, situated on a balcony with a view of the ocean. Palm trees frame the scene, and distant mountains can be seen across the water, creating a serene coastal atmosphere.
Condo in Kihei

Full Ocean- Full Sunsets- Beaches at Royal Mauiian

LocationFamilyLong stay

4.91 out of 5 average rating, 151 reviews
Guest favorite
A private lanai features a table set for two with chairs, overlooking landscaped grounds and palm trees. The Pacific Ocean is visible in the distance, along with a glimpse of the resort building.
Condo in Kihei

Sugar Beach Renovated 10% Discnt on 7 days Booking

FamilyLocationNearby

4.9 out of 5 average rating, 125 reviews
Top guest favorite
Condo in Kihei

Across Beach! Ground Floor 2 bed 2 bath, sleeps 6

LocationValuePool

4.89 out of 5 average rating, 289 reviews
Guest favorite
An oceanfront view is captured from the lanai, showcasing gentle waves lapping at a sandy beach below. Lush palm trees line the shore, swaying in the breeze under a bright blue sky with scattered clouds.
Apartment in Kihei

Ocean Front With Ocean View! AC, King Bed, 2 Bath!

LocationFamilyAmenities

4.93 out of 5 average rating, 164 reviews
Guest favorite
A private lanai features a round table with two high-backed chairs, offering panoramic views of the ocean and surrounding coastline. Lush palm trees and sandy beach are visible below, under a bright blue sky with scattered clouds.
Condo in Wailea

Oceanfront Mana Kai Penthouse..Heaven meets Earth!

FamilyLocationCheckout

4.96 out of 5 average rating, 145 reviews
Top guest favorite
A covered lanai is furnished with a round wooden table and two chairs, overlooking the ocean. The vibrant sunset casts warm hues across the sky and water, while palm trees frame the scene, enhancing the coastal ambiance.
Condo in Kihei

“Paradise Views” Menehune Shores, Kihei, Maui

ValueFamilyDecor

4.99 out of 5 average rating, 241 reviews
Top guest favorite
A vibrant sunset casts shades of orange and pink across the sky, reflecting upon the ocean. Silhouetted palm trees gently sway in the foreground, while lounge chairs are positioned on the beachside terrace, creating a serene coastal atmosphere.
Condo in Kihei

Escape to Sugar Beach / Ocean Views

ValueFamilyAccess

4.99 out of 5 average rating, 122 reviews

Kihei home rentals

Top guest favorite
The kitchen features light-colored cabinetry paired with granite countertops and stainless steel appliances. A large refrigerator and microwave are visible, along with an oven and stove. A central island with a wooden top provides additional workspace. Soft lighting enhances the functional layout.
Home in Kihei

12 Minute Walk Kamaole Beach II-Quiet Private Easy

LocationValueQuiet

4.98 out of 5 average rating, 161 reviews
Guest favorite
A spacious single-story home is surrounded by lush palm trees and vibrant tropical plants. The well-maintained lawn features a mix of greenery, with the house's exterior displaying a neutral tone under a bright blue sky.
Home in Kihei

Cajudoy's Hale - STKM 2O13-OO18/TA-081-709-8752-01

FamilyLocationCheck-in

4.86 out of 5 average rating, 175 reviews
Top guest favorite
A charming guest house is presented with a wraparound deck, framed by palm trees and lush greenery. The exterior features light-colored siding and a sloped roof, with windows allowing natural light. A clear blue sky enhances the inviting setting of this private retreat.
Home in Wailea

South Maui Guesthouse

LocationFamilyComfort

4.97 out of 5 average rating, 319 reviews
Guest favorite
The covered private lanai is depicted, featuring seating areas with outdoor couches and ceiling fans. A well-maintained lawn leads up to the entrance. Bright blue skies and soft clouds frame the space, creating a serene outdoor environment for relaxation.
Home in Kihei

Modern Family Kihei Home by the Beach

FamilyLocationLayout

4.84 out of 5 average rating, 116 reviews
Guest favorite
A cozy outdoor deck is showcased, featuring two wicker chairs and a small table, inviting relaxation. The inviting turquoise door stands adjacent to a wall with the word 'Aloha' elegantly displayed. String lights add a warm touch above, surrounded by tropical greenery.
Home in Kihei

Enjoy paradise living at the THERE Maui House!

ValueFamilyView

4.91 out of 5 average rating, 149 reviews
Guest favorite
The spacious backyard features a resort-style pool complemented by a waterfall and grotto. Surrounding palm trees and tropical landscaping enhance the serene atmosphere, while lounge chairs and a shaded sitting area with an umbrella are positioned nearby. Soft lighting highlights the tranquil setting as dusk approaches.
Home in Wailea

Maui Meadows Retreat B&B-3 BR-Ocean Views-AC-Pool

FamilyLocationQuiet

4.91 out of 5 average rating, 117 reviews
Superhost
A spacious living area features comfortable seating arrangements with a sectional sofa and wicker chairs. A large mirror enhances the sense of openness. Two televisions are positioned on opposite walls, and the tiled floor is complemented by natural lighting from multiple windows.
Home in Wailea

Condo in Kihei 2 BR - 2 bath Condo

ValueLocationHospitality

4.88 out of 5 average rating, 119 reviews
Top guest favorite
Home in Wailea

Stunning ocean view Villa, Heated pool, Wailea

LocationValueHospitality

4.96 out of 5 average rating, 472 reviews

Kihei condo rentals

Top guest favorite
Ocean views are framed by large glass doors, inviting sunlight to illuminate the airy space. Palm trees sway gently outside, enhancing the tropical ambiance. A modern ceiling fan is visible, facilitating airflow while complementing the relaxed atmosphere.
Condo in Kihei

Oceanfront Views in the heart of Kihei

ValueLocationNearby

4.94 out of 5 average rating, 165 reviews
Guest favorite
A vintage toy van is positioned on a sandy beach, facing a vibrant sunset over the ocean. Warm golden light reflects off the waves, creating a serene scene. The gentle surf adds a sense of calm to the atmosphere, with small ripples lapping at the shore.
Condo in Wailea

Groovy bright condo 2 bed / 2 bath South Kihei

ValueFamilyKitchen

4.93 out of 5 average rating, 207 reviews
Top guest favorite
An aerial view showcases Kihei Garden Estates, highlighting its proximity to the beach, restaurants, and shopping areas. Lush greenery surrounds the complex, with the ocean visible in the background. Clear directional arrows indicate nearby amenities, enhancing the understanding of the location.
Condo in Kihei

Close to the beach-2Bd/1Bath Condo-Great Location!

ValueFamilyQuiet

4.95 out of 5 average rating, 182 reviews
Guest favorite
The living area features a comfortable sofa accompanied by a coffee table and woven armchair. A large television is mounted on a decorative wall with tropical artwork. Floor-to-ceiling windows invite natural light and provide a view of the private lanai and surrounding plants.
Condo in Kihei

Newly remodeled unit near the best beach in Kihei.

LocationValueWifi

4.97 out of 5 average rating, 305 reviews
Top guest favorite
An updated kitchen features wooden cabinets and a polished granite countertop. Stainless steel appliances, including a refrigerator, microwave, and oven, blend seamlessly. A double sink and coffee maker are visible, with a backsplash of small, iridescent tiles adding texture.
Condo in Kihei

'E Komo Mai' ! 1 Bed/1 Bath in Tropical Gardens

LocationFamilyIndoor spaces

4.97 out of 5 average rating, 182 reviews
Guest favorite
An aerial view captures the coastal layout of Kihei, showcasing the vibrant blue ocean alongside lush greenery and developed areas. The landscape reveals a mix of residential and commercial structures, with the distant outline of mountains framing the horizon.
Condo in Kihei

2BR Condo Across from Famous South Maui Beaches

FamilyValueWalkability

4.87 out of 5 average rating, 169 reviews
Top guest favorite
Condo in Wailea

Luxury Vacationing Modern Condo October Spec. $325

ValueFamilyWalkability

4.96 out of 5 average rating, 186 reviews
Top guest favorite
An expansive view of Kamaole Beach is visible from the lanai, framed by swaying palm trees. The vibrant blue ocean meets the sandy shoreline, with people enjoying the beach below. The lush green landscape adds a tranquil touch to this coastal scene.
Condo in Kihei

200 Steps from the Beach | Sunset views!

LocationFamilyNearby

4.97 out of 5 average rating, 304 reviews

When is the best time to visit Kihei?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 4,137 ZARR 4,352 ZARR 3,905 ZARR 3,492 ZARR 3,293 ZARR 3,310 ZARR 3,161 ZARR 2,962 ZARR 2,879 ZARR 2,979 ZARR 3,277 ZARR 3,889 ZAR
Avg. temp16°C16°C16°C17°C18°C18°C19°C20°C19°C19°C18°C17°C

Frequently Asked Questions

  • What are the best places to stay in Kihei?

    Kihei has a range of vacation rentals, condos, and locally owned guesthouses across beachfront and residential neighborhoods. Many visitors look for stays near the coastline to enjoy ocean access, while others explore quieter areas inland for a relaxed atmosphere.

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

    Explore sandy beaches for swimming or snorkeling, visit local parks with playgrounds, and check out marine life at the Hawaiian Islands Humpback Whale National Marine Sanctuary. Family-friendly food trucks and small shops create a relaxed, welcoming environment.

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

    Enjoy snorkeling and paddleboarding along the coastline, explore traditional Hawaiian markets, or visit the Hawaiian Islands Humpback Whale National Marine Sanctuary. Sunset strolls on local beaches and sampling regional cuisine are frequently suggested activities.

  • How is the weather in Kihei?

    Kihei has warm, breezy days year-round, with temperatures typically between 53–76°F (12–24°C). Drier months fall in late spring and summer, while winter brings occasional showers and slightly cooler evenings.

  • When is the best time to visit Kihei?

    Late spring and summer are often recommended for clearer skies and drier weather, making beach and outdoor activities popular. Winter brings mild temperatures, more frequent rain, and seasonal whale watching opportunities.

  • What are the best places to visit in Kihei?

    Many visitors explore the Hawaiian Islands Humpback Whale National Marine Sanctuary, Kihei Regional Park, and colorful farmers markets. Local beaches, with calm waters and golden sand, are also frequently suggested.

  • What are some hiking trails in Kihei?

    Kihei has coastal paths along beachfronts, native plant trails in regional parks, and routes where you might spot local wildlife. Nearby areas feature volcanic landscapes and scenic overlooks for those seeking more adventurous hikes.

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

    Families often spend time at local parks, swim and snorkel at calm beaches, or take educational tours at the Hawaiian Islands Humpback Whale National Marine Sanctuary. Local gelato shops and oceanfront playgrounds add to the welcoming atmosphere.

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

    Around Kihei, you can explore upcountry farms, stroll local botanical gardens, or discover small towns known for art and history. Haleakalā National Park is frequently suggested for sunrise experiences and sweeping volcanic views.

  • Are there any pet friendly accommodations available in Kihei?

    Many vacation rentals and condos in Kihei welcome pets, especially in residential neighborhoods near parks and coastal paths. Local beaches and open spaces offer plenty of opportunities for outdoor activities with your dog.

  • What are some local tips for visiting Kihei?

    Pack reef-safe sunscreen, respect traditional Hawaiian customs, and rinse off before entering the ocean to help preserve marine life. Early mornings are often quieter on the beaches, and food trucks can be a good place to try locally rooted flavors.

  • What is Kihei known for?

    Kihei is known for its sunny coastline, frequent whale sightings during certain months, and relaxed beach town ambiance. Locally rooted markets and Hawaiian cultural sites add to its distinct character.

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

    Discover peaceful neighborhood beaches, small-batch gelato spots, and community-run farmers markets with regional produce. Shaded walking trails near ponds are occasionally mentioned by returning visitors.

  • What are the best foods to try in Kihei?

    Sample poke bowls, fresh-caught fish plates, and shave ice topped with island flavors. Food trucks serve traditional Hawaiian lunches alongside Asian and Pacific-inspired dishes.

  • What should I bring for a trip to Kihei?

    Bring lightweight clothing, sun protection, and sandals for the beach. Reef-safe sunscreen, a reusable water bottle, and a light rain jacket are also useful for changing weather and outdoor activities.

  • What is the nightlife in Kihei like?

    Kihei has a welcoming nightlife with open-air bars, casual music venues, and local restaurants offering evening entertainment. Many spots highlight live Hawaiian music, relaxed social scenes, and coastal views.

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

    Kihei celebrates Hawaiian arts festivals, seasonal farmers markets, and community oceanfront gatherings throughout the year. During winter, events often center on whale watching and local environmental awareness.

  • Are there family friendly vacation rentals in Kihei?

    Many vacation rentals in Kihei are suitable for families, with options that include multiple bedrooms, kitchen facilities, and access to pools or outdoor spaces. Neighborhoods near beaches or parks are often selected by traveling families.

All about Kihei

Blessed with six miles of coastline, the beachfront town of Kihei is located in one of the driest and sunniest sections of Maui. It’s a beach lovers’ destination where once-in-a-lifetime sunsets seem to happen daily, affordable shopping and dining options are numerous, and condo rentals are near safe, swimmable beaches like Kamaole Beach Park III that invite underwater exploration with just a mask and snorkel. Kihei is also central to many of the island’s more popular destinations, such as ʻIao Valley, Lahaina, and Maui’s North Shore. Unlike the highly developed and resort-laden Kāʻanapali, Kihei retains a laid-back dose of local flavor, including roadside food stands, farmers’ markets, and families selling homemade wares.

What are the top things to do in Kihei?

Road to Hana

If you’re a fan of scenic road trips, this winding 10-hour, 64-mile journey defines “unforgettable,” delivering around 600 hairpin turns, 60 bridges (many one-way), and countless waterfalls along the way. Most visitors will stop in the quaint town of Hana before turning back, but if weather permits, you can take the road less traveled for another 44 miles to complete the entire loop, where the Pools at 'Ohe'o in Haleakalā National Park and the young lava fields of Haleakalā await.

Humpback Whale Watching

If you’re planning to visit Maui between November and May, there’s a good chance you’ll spot North Pacific humpback whales migrating offshore. Whale-watching tours depart from the harbors of Lahaina and Maʻalaea. Those who prefer to stay on land can watch the whales from Maʻalaea Bay. Just remember to bring binoculars for optimal viewing.

Haleakalā Crater

Even if you don’t wake up early enough to watch the sunrise from this spectacular 1 million-year-old, 10,000-foot summit, the 2-hour drive up the mountain from the base of Haleakalā National Park can offer a dramatic four-seasons-in-one-day adventure. Just be sure to bring a jacket or sweatshirt, as high winds and 40-degree Fahrenheit temperatures are not uncommon.

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