Family-friendly holiday rentals in Wailea

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

Family · Kitchen · Walkability

Go Golfing from a Peaceful Apartment in a Beach Community

Unit #903 – Key Features Garden views, ground floor A/C (3 zones) Lanai seating Quiet Updated appliances; washer/dryer Primary: king bed Second: twins (convert to king) Sleeper sofa Kitchen TV, Wi-Fi Free U.S./Canada calls Amenities Beach chairs, umbrella, boards, cooler, towels Baby gear: Pack ’n Play Pool, hot tubs Location Wailea—near beaches, golf, shops, dining. Keawakapu Beach is a short walk. Guest Support On-island contact after booking. Parking Dedicated space + guest parking.

Indoor spaces · Family · Bathroom

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

Kitchen · Family · Value

Sale! Gorgeous 3BR/2BA with Ocean & Sunset views

Location and views are everything when it comes to this home. Nestled in the heart of Wailea, most consider the beautiful area of Maui. This RARE 3br/2ba villa has enough space for a large family or a group of good friends. Just a short walk to some of the most beautiful beaches in the world, World class shopping mall and 5 star resorts. Enjoy all the comforts of home while taking in breath taking Grand views of the Deep Blue Pacific, Hole 2 of the Blue Wailea Golf Course and Mount Haleakala.

Indoor spaces · Family · Breakfast

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.

Family · Kitchen · Outdoor spaces

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.

Kitchen · Indoor spaces · View

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.

Kitchen · Family · Hospitality

Luxury Condo in Wailea Ekahi w/Direct Beach Access

Do you want direct and private access to probably the best beach (i.e. Keawakapu) on Maui? Then look no further than our unit in the Wailea Ekahi complex! This quiet and spacious condo has every amenity you could want to make your Maui vacation truly unforgettable. You are also in walking distance to the stores and restaurants at the Shops at Wailea and also the Wailea Beach Path. This condo has everything you need to make your Maui experience memorable, luxurious, and convenient.

Kitchen · Family · Comfort

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.

Kitchen · Indoor spaces · Cleanliness

Stunning ocean view Villa, Heated pool, Wailea

Legendary Maui sunsets from your private lanai. Whales splashing offshore in season. A heated pool all your own, tucked into over half an acre of tropical gardens. This artist-designed Victorian-style villa is 5 minutes from Keawakapu Beach and the Shops at Wailea, and made for families, with shallow-end pool steps, a gated lanai, and baby gear ready on arrival. Boutique hotel attention, complete privacy. Your view retreat awaits.

Kitchen · Indoor spaces · Accuracy

*Fully Remodeled* Modern Island Style*

I am looking forward to hosting you at the Palms at Wailea 606 and making your vacation fun and enjoyable. The Palms is an upscale community that offers you great shopping, dining, golfing, world-class resorts, and beaches all within a few minutes. I offer you a clean, comfortable and memorable stay on the island. I want to make your Maui dreams come true! Mahalo and looking forward to seeing you! -Aini

Kitchen · Family · Nearby

South Maui Guesthouse

This air conditioned very exclusive, private 2-bedroom Guest House is surrounded with lush gardens on a ½ acre property, off the street located in an upscale very private neighborhood (Maui Meadows, above Wailea), yet minutes from the best beaches Maui has to offer. A real Hawaiiian retreat, where you wake up to the sound of birds, not traffic. Permit Number BBKM2018/xxx3 GETxxxxxxxx2801

Family · Indoor spaces · Breakfast