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

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.

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.

Luxurious Condo in South Kihei

Beautiful fully renovated condo. Located in Maui Kamaole, the best resort complex in South Kihei. Walking distance to the beach, shops, restaurants and bars. This condo has everything a renter needs during vacation. Full kitchen, washer and dryer, beach gear, towels, bedding and more. The complex has two swimming pools, barbecues, tennis courts and outdoor picnic areas. This location is next to fun activities such as swimming, snorkeling, diving, surfing, kayaking, fishing, and more.

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront condo DIRECTLY ON Keawakapu beach! Mana Kai is a hotel zoned resort in the ideal location, on the border of Wailea and Kihei. Our condo is designed with a modern surf feel in mind, welcome to the beach! If you enjoy Wailea's 5 star resorts right down the beach, but crave a kitchen, less fees, better views, or don't want to cross the street to get to the beach, stay with us! We have the best PM in Maui, Tracy O'Reilly to take amazing care of you!

MAUI BLISS! RARE Wailea 3-bedroom...sleeps 10!

This is the one you've been waiting for! Perfect for families, couples, or anyone who loves to spread out, this 1700 sq ft Grand Champions 3 bedroom has been painstakingly remodeled with luxury finishes throughout. Two kings, two pull-out queens, plus...bunk beds! Nestled in the most peaceful corner of the resort, boasting stunning ocean views from the lanai, and minutes away from Wailea beaches, restaurants, and shopping, this is truly what Maui vacation dreams are made of!

Wailea Ekolu Village 2/2 with stunning ocean view!

Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and surrounded by brilliant, lush, flowery grounds. Super-close to dining, golf, shopping, and only a short stroll to award-winning Wailea and Ulua beaches! Please note that this Wailea Resort condo has received government approval to operate as a vacation rental for the next 5 years.

*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

Grand Champions - King Bed - Close to Wailea Beach

We are located in the heart of Wailea at the Grand Champions Villas, close to Maui's best beaches and within walking distance to great restaurants, the Shops of Wailea and surrounded by Championship Golf Courses. Grand Champions is a serene 12-acre park-like resort next to the Wailea Tennis Club and Wailea Blue Golf Course. Have fun with the whole family at this stylish place.

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.)

Maui Wailea Brand New Modern Spacious Condo

Beautifully designed, modern, and brand new vacation condo is situated on the Wailea Blue golf course and the Wailea tennis club. Walk to Shops at Wailea and 3 min drive to Keawakapu Beach. Brand new kitchen, spa like bathroom with walk in shower, in-unit laundry. Relax with friends and families at this peaceful place to stay. Book your vacation today : )

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

Experience the best of Wailea from this rare 3BR/2BA luxury villa, featuring breathtaking views of the Pacific Ocean, Wailea Blue Golf Course and majestic Haleakalā. Spacious enough for families or groups, this exceptional retreat offers all the comforts of home—just a short walk from world-famous beaches, luxury resorts, fine dining and premier shopping.