Family-friendly vacation rentals in Wailea

Ekahi 22C Toes in the Sand in Under 2 Minutes

Ideal location in Wailea's Ekahi Village. Less than 2 minutes till your toes are in the sand of south Maui's best beach. Private partial ocean view 2 bedroom, 2 bath 1,505 sf recently updated condo. Ground floor unit, main lanai spills onto green belt. Ekahi's amenities of pools, pickleball, and pavilion are mere steps away. Fully equipped kitchen, 3 HDTVs, & 3-zone AC. Beach chairs, cooler, and beach towels provided. Easy access with zero steps from parking lot to unit. Owned by Ekahi 22C, LLC.

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

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.

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 Villa with Oceanfront Pool

Aloha, if you are looking for the perfect place to call home in Maui, you just found it! Our Wailea Ekahi Villa is a spacious and private home away from home that makes you feel far from it all yet is still close to everything! Wailea Ekahi is like your own private oasis w/ 35 acres of open grassy spaces, private walk paths and the most AMAZING oceanfront pool to relax in and melt all your worries away! NOTE - main pool closed Aug 10 to Oct 15 - discount included in price.

*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

Last Minute Deal! Wailea Condo Oceanfront Complex

Step into your own private tropical oasis in this fabulous Wailea condo! This adorable 792 square foot, ground floor unit is walking distance to one of the most incredible beaches on Maui with tantalizing turquoise blue waters of the Pacific! This lavish condo boasts an open and airy living space you will love with AC throughout. Relax on the remarkable lanais with a table with seating for four.

Wailea Gem-Remodeled Ocean View

Beautiful, fully remodeled Wailea Jewel! Peaceful and private location with expansive ocean views. Our newly renovated, one bedroom, 2 bathroom condo has everything you need to enjoy your Maui getaway. Located a short drive from the airport and just minutes away from some of the best beaches and dining in Hawaii. You will truly feel like you're in paradise during your stay.

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.