Holiday rentals in Wailea-Makena

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Top-rated holiday rentals in Wailea-Makena

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

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Superhost

Apartment

4.83 out of 5 average rating, 143 reviews

Palms At Wailea #608-2 BR/2 BA. Nov/Dec. Special

Beautiful Palms At Wailea Condo, located in the heart of Wailea, surrounded by $mil.homes. 5* location. Vinyl wood flooring & Split Air-Cond. system in hallway & in master-B/R. Fans through-out. Immaculately clean & comfortable. Walking distance to shops, hotels, restaurants, beaches.1200 sq. ft., 2BR/2Ba, wide open floor plan ,2nd. fl.unit. Low rise complex. Very private. Large lanai . Barbecue grills located near entryway of complex. Views from the Club House & Pool.The best place to stay!

Guest favourite

Apartment

4.98 out of 5 average rating, 102 reviews

Spectacular Ocean Views, 1st Class, Luxury Condo

🌈Unrivaled Views, Sunsets, Whales, Rainbows 🌈 Nestled on beautiful Kahana Beach, our resort boasts stunning views of Molokai and Lanai. Experience the perfect blend of serenity and convenience, walking distance to charming restaurants & shops. Just a short drive to Kaanapali with its array of dining and shopping options. Centrally positioned between Kaanapali Beach and Kapalua with immediate access to some of the world's most exquisite beaches and the Pacific's most spectacular golf courses.

Guest favourite

Rental unit

4.86 out of 5 average rating, 159 reviews

Whale Season! Great Ocean view! Family Fave!

Experience island living from our top floor ocean-view condo. Awaken to the gentle sounds of birds and waves, and enjoy stunning views of the Pacific. This condo features modern amenities and stylish decor, providing the perfect blend of comfort and elegance. Unwind on the private balcony, where you can witness whales breaching and the sun setting over the horizon. Offering unparalleled vistas and comfortable accommodations, our condo is the ideal setting for an unforgettable Hawaiian getaway.

Guest favourite

Cottage

4.91 out of 5 average rating, 211 reviews

Ualani Retreat. Private Ocean View Cottage.

GREAT SPECIALS THRU October Private Detached stand alone cottage home on 3 acre retreat. Beautiful ocean and mountain views. Lush Haven surrounded by fruit trees and bamboo groves. Nicely equipped kitchen. Laundry room. Cable TV. Wi-Fi. Delightful Island Home. Very Comfortable. Hot Tub. Close to enjoy some of Maui's best attractions - Haleakala Volcano, Road to Hana, Waterfalls & Baldwin Beach. Locally Owned & Occupied B&B PERMIT : BBPH 2012/0002 SUP2 2012/0001

Guest favourite

Apartment

4.88 out of 5 average rating, 145 reviews

*** Beautiful Oceanfront Maui Condo ***

🌴☀️🌴 TOURISM WELCOME! We are a fully legal Short Term Vacation Rental (STVR) condo and have been Superhosts on Airbnb for 10+ years. While Lahaina town is closed, the rest of the island (including areas of West Maui) is open, and visitors are welcome. Respectful tourism is highly encouraged. Please feel free to book any open dates on our calendar and Mahalo for helping to support Maui. 🌴☀️🌴 Come explore Maui from our beautiful centrally located Oceanfront Condo right on Sugar Beach!

Guest favourite

Rental unit

4.95 out of 5 average rating, 119 reviews

Wailea Couples Retreat, 300 FT To Keawakapu Beach

Ekahi Ocean Studio is perfectly located in the lower village of Wailea Ekahi (ground floor), a lush-landscaped paradise, just steps from the oceanfront pool and to world-renowned Keawakapu beach. This studio is perfect for couples seeking a peaceful, romantic retreat. You can spend your days lounging at the beach or oceanfront pool, running along the nearby beachfront pathway, exploring nearby Wailea restaurants and resorts or enjoying our cook's kitchen and your private Lanai.

Superhost

Apartment

4.71 out of 5 average rating, 167 reviews

*VEHICLE INCLUDED! Wavecrest Resort EAST MOLOKAI

TA-075-407-5648-01 THIS UNIT COMES WITH THE ABILITY TO USE OF AN SUV...... UPDATE!!!! We now have dedicated internet!!!!No more bad resort Wi-Fi!!! This unit is located on the island of Molokai. After years as a long term rental, my cozy,semi-private location at Wavecrest Resort is a vacation rental again. Often described as a home away from home this unit will bring a warm feeling to your heart and soul.

Guest favourite

Guest suite

4.95 out of 5 average rating, 320 reviews

Guest House Near Maui’s Best Beaches

Come visit our beautifully remodeled attached guest cottage. Your home away from home. New air conditioning keeps you cool after a warm beach day. The location is within a mile of some of the best beaches on the island (and probably the world!!) We are very close to grocery stores, shopping, restaurants, beautiful Wailea, and the kihei boat ramp for catching a boat for a whale watch or snorkel adventure.

Superhost

Apartment

4.88 out of 5 average rating, 99 reviews

Top Floor Stunner! Highly Upgraded! Feb Open! #414

"The Kaleialoha" #414 Maui is open and ready for your arrival! Please come help us rebuild our community! This TOP FLOOR unit has unobstructed Ocean and outer island Views! This beautiful completely remodeled unit will take your breath away! New AC unit in living area! New High end sofa sleeper in living room! Cal King Bed and second TV in bedroom. Bosch Washer and dryer in unit.

Superhost

Apartment

4.82 out of 5 average rating, 169 reviews

Spectacular Direct Ocean Front location!

Spectacular oceanfront location only steps away from the beach! This stunning space provides everything a Maui vacation should offer. Positioned right on the water, this quaint condo offers direct ocean views and access along with a dreamy sight of the West Maui mountains. Wake up in paradise to the sound of the ocean waves crashing right outside your door!

Superhost

Townhouse

4.88 out of 5 average rating, 136 reviews

Luxurious Hawaiiana Home in Napili with Hot Tub

Follow us on Insta: @alohastays Elegant 3 Bedroom 3 bath home 2 min walk from Napili Bay Solar Panels & Tesla Batteries power this home. Relax in your own private hot tub or lounge in the hammock on the back lanai.The Napili Bay Villa is the best in accommodating your group right in the heart of the Napili & Kapalua area.

Guest favourite

Rental unit

4.79 out of 5 average rating, 156 reviews

Summer Special! Remodel Great Value Book Now!

This beautiful remodeled Two-bedroom/One bath condo is only 126 steps from the beach!! Enjoy beautiful sunsets and long walks on miles of beautiful beach! Watch the whales in the bay and enjoy snorkeling, swimming and boarding. This spot is a well kept secret - close to shopping and dining spots!