Find Family-Friendly Vacation Rentals Near Wailea
About Wailea Family Rental on Vacation Cottage
Looking for a high-end yet affordable stay in or near Wailea? Look no further—we've got you covered with more than 1735 discount hotels, last-minute resorts, cheap holiday homes, villas, cottages, and condos available for booking in Wailea.
While Vacation Cottage is renowned for our top-notch cottage rentals, lake houses, and summer home resorts, we also offer premium stays at unbeatable prices. Our selection includes boutique hotels, inns, vacation homes, apartments, chalets, affordable penthouses, lakefront homes, beachfront resorts, villas, and more—all set in Wailea. Whether you're traveling with family or friends, planning a gathering, or hosting a cocktail party, we have the perfect discount luxury accommodations for your travel needs.
Frequently Asked Questions About Wailea Family Rentals
What are the top rated Family Rentals in Wailea?
There are a lot of options in Wailea. If you plan on staying in the Wailea area, consider making a reservation for a few nights at one of these properties as these have been rated the top Family Rentals in Wailea:
- Wailea Custom Home, Pool, Panoramic Ocean View, Waterfalls - Maui Ocean Palms
- Aloha Kai Suite at Wailea Beach Villas. Penthouse 205. Ocean View. 3 BR/3 BA
- 🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈
- Walk to Beach, Ocean Views, Relax by the Pool
- Featured on A&E's Vacation Rental Potential! Luxury Family Condo! AC and Pool!
- Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
- nNEW KITCHEN REMODEL! Amazing View!
- Very Best Deluxe Ocean View.Panoramic View.First Class!
- The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!
- Maui Breeze Retreat at Ho'olei available Feb 23-27,Apr 9-17,Apr 24-30! Book now!
How much does it cost to rent a family vacation rental in or near Wailea?
The average price per night for a family holiday rental in Wailea is $1,006. Check the list of kid-friendly accommodations in Wailea.
How many 2-bedroom apartment rentals are available to book in Wailea?
There are 1735 2-bedroom rental properties that are available in Wailea. You can book for your next trip with Vacation Cottage.
Do any family-friendly vacation rentals in Wailea have a pool?
Yes, here are some top-rated family vacation rentals in Wailea that have a private swimming pool:
- Maui Luxury with Island Serenity - Wailea Beach Villas Penthouse K107
- Ho'olei at Grand Wailea
- Luxurious Wailea Ocean Vistas
- Hoolei Residences 93-3 Luxurious 3BR Villa, Sleeps 8
Check all holiday rentals with a pool in Wailea on Vacation Cottage.
Can I find private owner rentals in Wailea?
Yes, We have 1735 direct by owner rentals in Wailea.
Do you have any luxury holiday rentals with a pool in or near Wailea?
Yes, Of course! There are many luxury rental properties in or near Wailea. Use our search filter to discover all of our luxury homes with your favorite amenities. Sorting by price is another way to find the luxury holiday rentals in Wailea, though more expensive is not always better.
