FR Beach Rentals
Vacation Rental Managers Testimonials Manager Login
Book Direct & Save with a Vacation Rental Manager
Vacation Rental Managers Testimonials
BOOK DIRECT

Save on Fees and Experience Professional Service

WAILEA

IDEA DRIVEN VACATIONS

Search for Travel Guides, News, Events, Special Interests, and More!

  • Activities and Interests

    Uncover fun activities and special interests for your upcoming trip

  • Event Travel

    Plan your trip around concerts, festivals, and special events worth traveling for

  • Attractions

    Explore top landmarks, scenic spots, and can't-miss local highlights

  • Travel Guides

    Navigate each location like a local with our detailed travel guides

  • Travel News

    Stay updated with the latest travel trends and vacation rental tips

  • Trip Ideas

    Find inspiration for your next getaway with curated trip suggestions and themes

  • Travel Newsletter

    Join our newsletter for exclusive travel insights, featured destinations, and trip planning tips

TRENDING

Cape Coral Holiday Festival of Lights

Cape Coral Holiday Festival of Lights
December - Cape Coral Florida

Oceanside Vacation Rentals

Oceanside Vacation Rentals
by Find Rentals

Navarre Beach Florida Travel Guide

Navarre Beach Florida Travel Guide
Navarre Beach Florida

Things To Do Amelia Island Area Florida

Things To Do Amelia Island Area Florida
Amelia Island Area Florida Travel Guide

Norris Lake Tennessee Travel Guide

Norris Lake Tennessee Travel Guide
Norris Lake Area Tennessee

Wailea Travel Guide | Things to Do, Places to Eat, and Where to Stay

Things to do in Wailea Hawaii

Wailea Hawaii

Welcome to Wailea, a breathtaking resort community on the South Shore of Maui, Hawaii, where golden beaches, world-class resorts, high-end shopping, and laid-back Hawaiian beauty come together in one luxurious yet peaceful destination. Wailea may not shout for your attention but that’s its appeal. It’s the kind of place where you settle into the rhythm of the waves, where the dining is unpretentious but elevated, and where the days blur gently into each other under the sun. The glamour is there, but it doesn’t need to be chased. It finds you.

One of the most defining features of Wailea is its stunning beaches. Wailea Beach, Ulua Beach, Makena Beach, and Polo Beach are some of the best and most gorgeous stretches of sand that line the coast. Whether you're looking to soak up the sun, swim in the ocean, or try your hand at surfing or snorkeling, Wailea's beaches are a true paradise. Wailea is also a mecca for outdoor enthusiasts. With its warm climate and breathtaking scenery, Wailea offers endless opportunities for adventure. Take a whale watching tour, go kayaking, or hit the golf course for a round of 18. For those who love to hike, Wailea is home to a number of scenic trails that lead to hidden waterfalls, panoramic lookouts, and other natural wonders.

Wailea is not your typical tourist hub. It’s quieter than Lahaina or Ka’anapali and more upscale, with five-star resorts, immaculately manicured golf courses, and some of the best beaches in all of Hawaii. Think morning walks on the oceanfront Wailea Beach Path, evenings watching the sun sink into the Pacific, and days filled with snorkeling, spa visits, or mai tais by the pool. Wailea is polished, but never pretentious.

 

Book Direct to Save on Fees and Experience Professional Service with a Wailea Vacation Rental Management Company

Ali'i Resorts

Ali'i Resorts

Opening the Door to Maui's most Breathtaking, Awe-inspiring Oceanfront Vacation Rentals! We started Ali’i Resorts because vacation homes with..  learn more

View Profile
Browse 215 Vacation Rentals
AA Oceanfront Rentals and Sales

AA Oceanfront Rentals and Sales

AA Oceanfront Vacation Rentals and Sales provides property management services for long term sales, as well as, short term vacation lodging and real..  learn more

View Profile
Browse 95 Vacation Rentals
Vacation Maui

Vacation Maui

All Vacations-Maui condos and homes are set up to help create the ultimate Maui beach vacation experience. Our properties are all on or very close to..  learn more

View Profile
Browse 106 Vacation Rentals

 

 

Things to Do in Wailea, Hawaii

Beaches

Wailea Beach

This is the crown jewel. A wide, crescent-shaped stretch of soft sand fronting the Grand Wailea and Four Seasons resorts. Perfect for swimming, boogie boarding, or simply relaxing under an umbrella. Wailea Beach is technically public (all Hawaiian beaches are), but it feels like a private resort escape. Calm, clear waters and soft sand make it ideal for swimming or lounging, especially early in the day before the resort chairs fill the backdrop.

Makena Beach (Big Beach)

For something a bit more rugged, drive 10 minutes south to Makena State Park, home to Big Beach, a broad, golden stretch framed by black lava cliffs. This beach is gorgeous but watch for strong shore breaks. If you’re game for a short hike, climb over the rocks at the north end to reach Little Beach, an unofficial clothing-optional cove that has a countercultural reputation and sunset drum circles on Sunday evenings.
 

Polo Beach

Just south, Polo Beach is more low-key, framed by lava rock and fringed with naupaka shrubs. The snorkeling around the rocks is solid, especially if you go in the early morning when the water’s glassy and the fish are most active. Often overlooked, Polo Beach is a peaceful, family-friendly spot with tidepools, fewer crowds, and postcard views.
 

Ulua Beach

Calmer and quieter, especially in the morning. A favorite for snorkeling and spotting sea turtles near the reef just offshore. Good swimming, boogie boarding and excellent beginner to intermediate snorkeling around the rocky outcrop on the north end of the beach. There is also a good beginner level dive at the outer reef. Mokapu Beach is close to Ulua Beach and Keawakapu Beach is a quarter-mile stroll across Mokapu Beach as all three of these beaches connect.

 

Ulua Beach on the South Shore of Maui

 

Spas

Don’t miss out on a traditional Hawaiian lomi lomi massage. You can find them at the Willow Stream Spa (Fairmont Kea Lani), the Four Seasons Spa and more.
At the Kilolani Spa experience tranquility, peace, and harmony with the natural rhythms of the world. Honoring the Kilolani, the ancient Hawaiian stargazers who once navigated their journeys by the night sky.

The Shops at Wailea

High-end boutiques like Louis Vuitton and Tiffany & Co. sit alongside local shops, art galleries, and great restaurants. The Shops at Wailea offer local and high-end shopping, good food, live music, cultural performances, and family-friendly happenings that bring aloha spirit to life. 

 

The Shops at Wailea on the Island of Maui

 

Wailea Village

Wailea Village showcases boutique shopping, local eateries, and more. A vibrant hub nestled in the heart of Wailea with access to shopping, dining, services, and resort life. Wailea Village serves as the primary gateway into the resort community of Wailea–Makena. It features the first tee and pro shop for the iconic Wailea Blue Golf Course, which attracts golfers annually.

Wailea Beach Path

This scenic 1.5 mile coastal walk winds past beaches, tidepools, and resorts. This paved coastal walk threads past the backyards of Maui’s most luxurious resorts  such as the Four Seasons, the Grand Wailea, and Andaz Maui with cinematic views of the Pacific the whole way. Best done early in the morning or during the golden hour.

 

Wailea Beach Path along the Southwestern Coast of Maui

 

Golf

Wailea is a golfer’s dream with three championship courses: Gold, Emerald, and Blue. The Wailea Golf Club three courses each with wide ocean views and immaculate fairways.Views of the ocean from nearly every hole. The Emerald course is especially scenic, with its flower-lined holes and forgiving layout, perfect for vacation play.

Snorkeling & Boat Tours

Catch a snorkel tour to Molokini Crater, or try a kayak-and-snorkel trip launching right from Wailea’s beaches. Turtles are almost guaranteed, and in winter (December–April), you might even spot whales from shore. Molokini Crater is located about 3 miles off the southwestern coast of Maui, and boat tours to the crater often depart from Kihei, as well as, Ma'alaea Harbor and Lahaina

 

Molokini Crater Snorkel and Boating Tours

 

Places to Eat

Food lovers will be in heaven in Wailea, with its abundant seafood, exotic fruits, and other local specialties. From gourmet restaurants to bustling farmers' markets, Wailea offers a delicious taste of the Hawaiian Islands that will leave you wanting more. Whether you're in the mood for fresh poke, succulent seafood, or exotic local desserts, you'll find plenty of options to satisfy your cravings in Wailea.

For breakfast, Akami Bar & Grill inside Wailea Village is the kind of tucked-away spot that locals like to keep to themselves. Go for the miso-glazed avocado toast or the eggs with kalua pork and lomi tomato. Pair it with a coffee from Akamai Coffee Co., just next door they roast their own beans in small batches and serve the kind of cold brew that actually has backbone.
 
Monkeypod Kitchen by Merriman is the unofficial dining room of Wailea and it’s loud, fun, and the lilikoi foam mai tai is deservedly famous. Come during happy hour for half-priced pizzas (try the Hamakua mushroom and truffle oil) and live local music that somehow makes a Wednesday night feel like the weekend.
 
For something quieter and more refined, book dinner at Ka’ana Kitchen at the Andaz. Their open kitchen concept keeps things energized, but the food is the real event with dishes like Maui venison with ulu (breadfruit) purée or kampachi crudo with yuzu and chili water. The wine list leans biodynamic and global, with a sommelier who actually enjoys walking you through it.
 
One more worth mentioning: The Restaurant at Hotel Wailea, perched above the coast and adults-only, offers the kind of experience that’s designed to be slow. Request a table on the lanai at sunset and let the courses roll out ... local fish, Waipoli greens, and house-made sorbets from whatever fruit came in that morning. Here is a list of additional dining options.
Spago at the Four Seasons
Wolfgang Puck’s Hawaiian outpost. Upscale, innovative, and perfect for sunset dining.
 
Ka’ana Kitchen at Andaz Maui
A modern take on island cuisine with local ingredients and an open-air setting.
 
Nick’s Fishmarket
Romantic, high-end seafood at the Fairmont Kea Lani.
 
Monkeypod Kitchen
Farm-to-table Hawaiian comfort food with great happy hour and live music.
 
Lineage
Upscale local dishes with Filipino, Hawaiian, and Chinese influences.
 
Manoli’s Pizza Company

A casual, welcoming restaurant that blends island vibes with tasty Mediterranean-inspired fare.

Coconut’s Fish Café (in nearby Kihei)
Legendary fish tacos. Casual and delicious at Coconuts Fish Cafe.

 

Wailea Sunset along the South Shore of Maui

 

Where to Stay

Wailea Hawaii vacation rentals are some of the finest in the world, offering guests an unforgettable vacation experience. From spacious rooms with ocean views to expansive kitchens and family rooms for making great family memories.  Wailea vacation rentals through Find Rentals are perfect for helping  you escape the stresses of everyday life and indulge in the ultimate in luxury and relaxation.

Find Rentals vacation rental properties in Wailea, Hawaii provide travelers with the ultimate in luxury, comfort, and convenience. With spacious rooms and breathtaking views of the ocean and surrounding landscape, these properties are the perfect place to call home during your stay in Wailea. Whether you're traveling with a family, a group of friends, or simply seeking a romantic escape, Wailea Hawaii vacation rentals are the perfect choice for those looking for the ultimate comfort and relaxation in a picturesque destination.

Vacation Rental Stays

Bright and open living area
$370/night
Maui Kamaole F105
Condo in Kihei Hawaii
1 Bed • 2 Full Baths • Sleeps 4
AA Oceanfront Rentals and Sales
Living Room with a view
$550/night
Mana Kai 710C
Condo in Kihei Hawaii
2 Beds • 2 Full Baths • Sleeps 4
AA Oceanfront Rentals and Sales
Polo Beach - 2BR Oceanfront
Polo Beach - 2BR Oceanfront
Condo in Wailea Hawaii
2 Beds • 1 Full Bath • Sleeps 6
Hawaii Beachfront Condos

 

Best Time to Visit

Wailea is sunny almost year-round. Compared to the northern parts of Maui, it gets less rain and more blue sky beach days.

High Season

December–March (more whales, more expensive)

Best Balance

April–May and September–early November

Summer

Great for families, but warmer and more crowded

 

Best Way to Spend the Day or Week

Wailea moves at a slower, quieter rhythm, it is the kind of place where mornings stretch over long walks along the beach path, and evenings end with a mai tai in hand, watching the sky collapse into color. Here's how to do it right.
One of the easiest ways to orient yourself in Wailea is the Wailea Beach Path. A paved 1.5-mile coastal walk that threads past the backyards of Maui’s most luxurious resorts  such as the Four Seasons, the Grand Wailea, and Andaz Maui with cinematic views of the Pacific the whole way. Start early, just after sunrise, when the air is still cool and the paddleboarders are just heading out.
 
Book a morning snorkel trip with Kai Kanani Sailing, which launches directly from Maluaka Beach. Their catamaran cuts straight across to Molokini Crater, a volcanic atoll with exceptional visibility and schools of yellow tang that flit like confetti through the reef. They keep group sizes small, and their early-morning “Sunrise Deluxe” tour is as unhurried as it is well-catered with breakfast, mimosas, and hot coffee.
Inland, it’s worth carving out a morning for a guided walk through La Perouse Bay in the Ahihi-Kinau Natural Area Reserve. The trail winds through ancient lava flows and native kiawe trees, and if you’re lucky, you might spot spinner dolphins just offshore.
 
If you're more drawn to culture than sport, look into the Wednesday Art & Wine Night at The Shops at Wailea, where you’ll find local artists painting live outside the galleries and tastings from Hawaii vineyards and craft distillers. You can also catch a live slack-key guitar performance at The Fairmont Kea Lani’s Luana Lounge which is a quiet alternative to the larger luau crowds.

 

Getting There & Around

Wailea is about 30 minutes from Kahului Airport (OGG). You’ll want to rent a car to explore Maui beyond the resort bubble whether that’s driving to Haleakalā, the Road to Hana, or just heading to dinner in nearby Kihei.

 

Conclusion

Wailea, Hawaii is a truly special destination that offers visitors the perfect blend of beauty, luxury, and cultural richness. This tropical paradise offers visitors a chance to escape to a world of sun, surf, and relaxation. Wailea is like that luxurious Hawaiian dream you see in travel magazines but it's also surprisingly approachable. You can go full luxury with cabanas and spa treatments, or take it slow with beach walks, poke bowls, and turtle sightings. Whether you’re after romance, relaxation, or a taste of paradise, Wailea is easy to fall in love with and hard to leave.


Map of Wailea Hawaii on the Island of Maui

Additional Hawaiian Articles

Keawakapu Beach in Kihei Hawaii on the Island of Maui

Keawakapu Beach in Kihei Hawaii on the Island of Maui
Kihei Hawaii

Molokini Crater Off the Coast of Maui near Kihei

Molokini Crater Off the Coast of Maui near Kihei
Kihei Hawaii

Kihei Travel Guide | Things to Do, Places to Eat, and Stay

Kihei Travel Guide | Things to Do, Places to Eat, and Stay
Kihei Hawaii

Find a Manager for Your Rental Property
Find a Manager for Your Rental Property