
Vacation rentals in Wailea
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Quick stats about vacation rentals in Wailea

Total vacation rentals
Explore 1,930 vacation rentals in Wailea

Nightly prices starting at
Wailea vacation rentals start at G$16,719 GYD per night before taxes and fees

Verified guest reviews
Over 55,460 verified reviews to help you choose

Family-friendly vacation rentals
1,140 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
1,840 properties feature pools

Rentals with dedicated workspaces
1,120 properties have a dedicated workspace

Wi-Fi availability
1,930 of Wailea vacation rentals include wi-fi access

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Wailea rentals

4.8 Average rating
Wailea stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated vacation rentals in Wailea
Guests agree: these stays are highly rated for location, cleanliness, and more.

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

A.R.A Retreats: The Molokini
FULLY Renovated Summer 2023! Nicknamed “Molokini” this condo has stunning ocean view front and center of Molokini, you can witness multiple humpbacks jumping and playing during whale season from the comfort of your own private lanai. This condo is located in Wailea Ekolu in the well-known luxury resort community of Wailea. It offers a beautiful space for you to unwind after you spend all day taking in the sunshine around the island. Sit and enjoy your coffee whilst taking in our amazing views

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC
Wailea Ekahi is a luxurious resort fronting onto beautiful Keawakapu Beach with acres of tropical grounds and 4 pools. Unit 16B is a mid property, renovated ground floor ocean view studio unit (500 sq feet) with a King sized bed, walk in shower and full kitchen. Enjoy your morning coffee and meals from the peaceful, shaded lanai which opens onto the lush greenspace and gardens while enjoying ocean views. A short walk to the beach, pools, luxury shopping, highend dining and golf courses.

Romantic, Luxury Retreat w/Ocean View-Couples Only
Luxury accommodations in the heart of Wailea, Maui. Our condo has lovely ocean views, views of the lush tropical gardens and the pool. Sunset views from the lanai are stunning. Gourmet kitchen. 2 HD TVs, Bose sound system, AC, washer/dryer in unit, complimentary assigned parking. If our condo is not available during the days of your travel, please check availability at our other Wailea Palms condo at https://www.airbnb.com/rooms/1728525 Our condo is not suitable for children or infants.

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.

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.

OCEANFRONT Luxury Condo *180° SWEEPING Ocean Views
*Please note, The MAXIMUM OCCUPANCY of this 2-bedroom unit is 6 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 ground floor, oceanfront, luxury 806 square foot unit opens up onto your very own private patio and grassy lawn. Complete with lounge chairs and outdoor seating, just steps from the turquoise waters of the Pacific Ocean, your paradise awaits.

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.

Ekahi Ocean Studio: Wailea Paradise by the 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.

Luxurious Wailea Ocean Vistas
Completely remodeled. Our new Wailea luxury condo is immaculate and offers direct ocean views. Airy, comfortable, and with stylish decor, every amenity a Maui visitor could hope for is provided. Guests will fall in love with Wailea's beautiful lushness while enjoying a charming well-designed hideaway. We have considered every detail to provide the most effortlessly luxurious stay possible. With beaches nearby and two pools onsite, this island paradise has everything and more.

Ocean/Golf Course Views, Tropical Resort in Wailea
Breathe in and exhale slowly while gazing at the beautiful ocean, serene greenery and misty mountaintops. Make the most of a country-club setting by lounging on sun decks and swimming in heated pools. Retreat to an updated condo to unwind and fall asleep in a comfy bed. (This unit is suitable for a maximum of four (4) guests. Infants of any age are counted as guests.)

Luxury Vacationing Modern Condo Sept Specials $299
JUST RENOVATED THIS BEAUTIFUL CONDO IS BORDERING KIHEI AND WAILEA. THE CONDO BOASTS 17 FT CEILINGS, 1025 sq ft, 4 FRENCH DOORS THAT OPEN OUT TO A DOUBLE BALCONY WITH INCREDIBLE VIEWS OF THE OCEAN AND VOLCANO. TENNIS COURTS, SWIMMING POOL, BOCCE BALL, SHUFFLE BOARD,PUTTING GREEN AND ACROSS THE STREET FROM KEAWAKAPU BEACH. PERFECT FOR A FAMILY VACATION.
Popular amenities for Wailea, Wailea-Makena vacation rentals
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Gorgeous Condo in Wailea Ekahi Village!

Wailea Hidden Gem

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- Maui
- Kaanapali Beach
- Lahaina Beach
- Whalers Village
- Wailea Beach
- Maui Vista Condominium
- Polo Beach
- Honolua Bay
- Kapalua Bay Beach
- Big Beach
- Black Rock Beach
- Black Sand Beach
- Haleakala National Park
- Old Lahaina Luau
- Ka'anapali Golf Courses
- Kihei Kai Nani
- KOA Resort
- Kamaole Beach Park II
- Aston Mahana at Kaanapali
- Maui Ocean Center
- Maui Arts & Cultural Center
- PacWhale Eco-Adventures
- Hāmoa Beach
- Kahana Beach





