
Family-friendly holiday rentals in Wailea
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Wailea
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Romantic, Luxury Retreat w/Ocean View-Couples Only
Luxury 1 bedroom 2 bath condo which has been fully renovated. Our condo has lovely ocean views as well as views of the lush tropical gardens and the pool. It has a fully stocked gourmet kitchen with high end appliances, assorted spices, coffee and tea. Sunset views from the lanai are stunning. 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 Not suitable for children or infants.

Spacious garden oasis near Maui's best beaches!
Aloha! Welcome to our beautiful home at Maui Kamaole, an upscale complex located next to Keawakapu Beach and minutes to Wailea. Our condo is perfectly suited for couples and small families wanting space with stylish comfort in a prime location. Relax on a luxurious king-sized bed, sectional sofa w/ a pull-out sleeper, and a pack and play for toddlers! Enjoy the essentials of modern connectivity, a fully stocked kitchen, with two full bathrooms. Soak in paradise on two lush garden patios!

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.

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!

A.R.A Retreats: Garden Oasis
Nicknamed “Garden Oasis” for its beautiful little garden walk out off the Lanai onto a beautiful field. While it also has a amazing view of the pacific ocean the beautiful private walkout really set the tone for a relaxing and private oasis. Wailea Ekolu Village is a three-minute drive or 18 minute walk to the beautiful golden sands of Wailea Beach. The Shops at Wailea, Monkeypod Kitchen and so much more just a short walk away!

Stunning ocean view, heated pool at home by Wailea
Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

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

130K Hawaiian Reno on Wailea Blue Golf *Ocean View
BRAND NEW 130K Renovation+BRAND NEW Hawaiian Styled Contemporary Decor. Located right on Wailea Blue Golf course in the Grand Champions at Wailea with incredible ocean views from the patio.We are perfectly located just down from Money Pod+up from The Shops of WaileaCheck out our other property #201 VRBO (2050379)+#1905 VRBO(1222713) in The Palms we are Super Host with 5 STAR reviews)!! BOOK UP TO 365 DAYS.

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.

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 : )

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.)
Popular amenities for Wailea family-friendly rentals
Family-friendly home rentals with a hot tub

Tropical Escape to Wailea with Stunning Oceanview

Very Comfortable Kamaole Sands Condo Sleeps 4

Luxury Vacationing Modern Condo June Special $379

Elua 1310 Oceanfront -Family Managed-Remodeled9/25

21A Grand Champions 1 Bed - Ulua & Mokapu beaches

Grand Champions 169 Beautiful 3 BR on the Fairway!

Romantic One BR Condo (Remodeled)

Beautiful Ocean Views In Maui Kamaole.
Family- and pet-friendly home rentals

Maui Meadows Ocean View Cottage

Oceanview, Banana Bread, Hot Tub & Sauna near OGG

The Lava Shack

Cozy Cute Condo | Maui Vista | Walk to The Beach

Mermaid Bungalow, cozy and ready for action.

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

Sugar Beach Bliss 503 - Best Oceanfront Vacay!

Kamaole Ocean View 7bd 3bth Beach Full AC HOT TUB
Family-friendly home rentals with a pool

Luxury Oceanview Wailea Retreat with Sunset Views

Wailea Escape/Golf Views, Beaches & Family Comfort

Beachfront 2BR w/ ocean views and pool access

Fabulous Ocean Views at Ho'okipa at Wailea Ekolu!

Wailea Ekahi Getaway•Walk to Keawakapu beach

Endless Ocean Views - 1bd/2 bath

Ekahi 22C Toes in the Sand in Under 2 Minutes

Luxe 2bed Wailea, 5-min walk to beach, ocean view,
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £342 | £357 | £324 | £298 | £267 | £275 | £266 | £246 | £235 | £247 | £280 | £360 |
| Avg. temp | 16°C | 16°C | 16°C | 17°C | 18°C | 18°C | 19°C | 20°C | 19°C | 19°C | 18°C | 17°C |
Quick stats about holiday rentals that are family-friendly in Wailea

Total holiday rentals
Explore 1,100 holiday rentals in Wailea

Nightly prices starting at
Wailea holiday rentals start at £104 per night before taxes and fees

Verified guest reviews
Over 28,820 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Holiday rentals with a pool
1,050 properties feature pools

Rentals with dedicated workspaces
690 properties have a dedicated workspace

Wifi availability
1,100 of Wailea holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Wailea rentals

4.8 Average rating
Wailea stays are highly rated by guests – averaging 4.8 out of 5!
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- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Wailea Beach
- Honolua Bay
- Polo Beach
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- Old Lahaina Luau
- Whalers Village
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- Maui Ocean Center
- Kihei Kai Nani
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- Maui Arts & Cultural Center
- Haleakala National Park
- KOA Resort
- PacWhale Eco-Adventures
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