
Holiday houses in Wailea
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Quick stats about holiday rentals in Wailea

Total holiday rentals
Explore 1,930 holiday rentals in Wailea

Nightly prices starting at
Wailea holiday rentals start at $114 AUD per night before taxes and fees

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

Family-friendly holiday rentals
1,140 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday 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 holiday 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 holiday rentals in Wailea
Guests agree: these stays are highly rated for location, cleanliness and more.

Beach Front Luxury in Makena
Only steps away from the beach, our newly remodeled 1600 sq/ft condo is tucked away in the coveted South Maui oceanfront resort of Makena Surf. Enjoy the exceptional view of islands Lanai, Molokini & Kahoolawe from our comfortable lanai. Dining, shopping & golfing are just minutes away. The condo is loaded with premium & luxury features. Two bedrooms, two bathrooms, and a gourmet kitchen. The resort has two pool, tennis courts and private beach access. Perfect for a family of 4 or 5 persons.

StunningReno*Palms in Wailea Condo-Beach*Golf*Pool
New 160K Renovation+Redecoration for a Hawaiian Beach Vibe.Wailea is one of the most sought after resort on Maui. Here you can relax in luxury of the beautiful grounds + refreshing swimming pool and spa. World Class Golf+Shopping. Ground floor condo with private lanai that overlooks the grass. King Master Bed with private bath,2 Uber deluxe pull out Queen bed couches.Short stroll to Keawakapu Beach from condo where you can snorkel+take long beach walks. EverythingProvidedBeach items+Yeti+ more

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.

Wailea Beauty - walk to the beach & shops
Our locally-owned, newly redesigned 2BD/2BA modern Maui condo is located on the award-winning Wailea Blue Golf Course at The Grand Champions Villas. The Villas are nestled in the heart of tropical Wailea; minutes from shopping, tennis, restaurants and pristine beaches. Stroll to upscale boutiques and restaurants, or take a short walk to some of the most beautiful beaches in the world. Our condo features local Hawaii art and is your perfect home away from home on the beautiful island of Maui.

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.

Maui Kamaole in Kihei | Ocean View, Pool, Hot Tub
Welcome! This is Maui Kamaole, perfectly located on Maui’s sun-soaked south shore! Highlights: - 2 Sparkling pools (one heated), 2 hot tubs, sauna and BBQ area on the property - Modern renovated ground floor unit for easy access—be on the beach in moments! -Stunning ocean views from your spacious private lanai (with glorious sunsets) -Tennis courts -Near golf, snorkeling, shopping, dining and luaus -15 minutes from Ma'alaea Harbor: sunset, snorkel and scuba trips, and whale watching!

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.

Modern Renovated Palms at Wailea Condo!
MODERN CONDO WITH ATTENTION TO DETAIL! Our bright, modern island condo awaits you! Breathe easy knowing that you have everything at your fingertips. Enjoy your morning coffee on the large lanai. Pack a beach bag and head to one of the best beaches just a 10 minute walk away. Explore the Shops at Wailea. You will feel right at home cooking in our fully equipped kitchen. Close out your day by watching the sunset from the pool area and then stargazing on the lanai. Then repeat!

Upscale and Elegant Vistas
Spacious and elegant condo in the much sought after Wailea area. Fantastic unobstructed ocean and sunset views. Completely remodeled and freshly outfitted. No expense was spared to create our ocean view oasis. This one-bedroom, two-bathroom condo features thoughtful luxurious finishes throughout. Located in sunny and luxurious Wailea, with all of Maui is within reach. Beach chairs, umbrellas, luxury beach towels and a cooler are all provided to enjoy a day at the beach nearby.

Ocean/Golf Course Views, Tropical Resort in Wailea
Breathe in and exhale slowly while gazing at 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.)

Wailea Surf Shack: Beaches, Shops & Golf!
Welcome to Wailea Surf Shack, a beautifully renovated Maui retreat in the heart of Wailea. Book with confidence knowing that we live on the island, personally manage and care for the condo, and truly treat our guests like family. We go above and beyond to make sure your stay is comfortable, relaxing, and filled with wonderful Maui memories.
Popular amenities for Wailea holiday rentals
Other great holiday rentals in Wailea

Beach Front Wailea, Full Ocean View A/C, ELUA102

Gem near Keawakapu Beach - Privacy and Ocean Views

Stunning Wailea 2/2, AC, Upper Fl, walk to beach

Wailea Elua 401 | Ocean Views | Pool | Hot Tub

Gorgeous Condo in Wailea Ekahi Village!

Wailea Elua condo - Ocean Views | Gym | Pickleball

Wailea Hidden Gem

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





