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

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.

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.

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.

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.

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.

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.

Luxury Vacationing Modern Condo Aug Specials $249

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.

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.