Wailea Summer Rentals, Cottages & Cabins
Book a Place to Stay in Wailea for Your Summer Getaway
About Wailea Summer Rental on Hawaii.Villas
Discover 1774 summer rentals in or around Wailea, finding the perfect rental home for your upcoming summer retreat on HawaiiVillas is effortless. Whether you're traveling with family, friends, or a group to Wailea or nearby areas, HawaiiVillas offers a variety of summer accommodations to choose from, many featuring premium amenities like private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxurious bedrooms, bathtubs, and pet-friendly environments.
Searching for a serene place to stay in Wailea for an unforgettable summer vacation? HawaiiVillas' summer rental properties are here to ensure you enjoy the utmost comfort you deserve. Whether you prefer a stylish condo, luxurious resort, villas, bungalow, cozy cabin, RV, or cottage in Wailea, HawaiiVillas has everything you need for your next summer getaway.
Summer Rental: Explore Top Destinations
- Summer Rental in Acadia
- Summer Rental in Anna
- Summer Rental in Anna Maria Island
- Summer Rental in Avalon
- Bar Harbor Summer Rental
- Belmar Summer Rental
- Berkeley Springs Summer Rental
- Berkshire Summer Rental
- Big Bear Lake Summer Rental
- Block Island Summer Rental
- Brigantine Summer Rental
- California Summer Rental
- Canyon Lake Summer Rental
- Cape Cod Summer Rental
- Cape May Summer Rental
Explore More
- Beach Home Rentals
- Business Travel
- Cabin Rentals
- Cottage Rentals
- Cheap Hotels
- Family Rentals
- Group Travel
- Holiday Home Rentals
- Hotels with Suites
- Luxury Rentals
- Monthly Stays
- Oceanfront Vacation Rentals
- Pet Friendly Vacation Rentals
- Vacation Rentals with Pools
- Resort Rentals in Wailea
- Short Term Stays
- Ski Chalet Rentals
- Sustainable Travel
- Timeshare Rentals
- Unique Vacation Rentals
- Vacation Rentals
- Villa Rentals
- Winter Rentals
Frequently Asked Questions About Wailea Luxury Rentals
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 Summer Rentals in Wailea:
- Romantic, Luxury, Sensual Retreat - Couples Only
- Aloha Kai Suite at Wailea Beach Villas. Penthouse 205. Ocean View. 3 BR/3 BA
- Owner Direct - Check our 160 Reviews! - Elua Village 701, Luxury 2BR, Ocean View
- LOWEST Rates in Wailea right now! Spacious 5-STAR Wailea Retreat🏝Corner unit
- Very Best Deluxe Ocean View.Panoramic View.First Class!
- 125+ 5 STAR REVIEWS SAYS IT ALL! Upgraded thru/vaulted ceil/Golf & Ocean view!
- Private S. Maui home w/ocean views, pool, hot tub
- Wailea Ekahi 40A - 5-Star South Maui Oasis
- 1br/1ba Condo Steps From The Pavilion pool, Mokapu Beach with beautiful views.
- Maui Luxury with Island Serenity - Wailea Beach Villas Penthouse K107
Yes, here are some popular summer holiday rentals in Wailea that have a private or indoor pool:
- Hawaiian Cottage and Personal Paradise/BBKM 2013/0004
- Ho'olei at Grand Wailea
- Luxurious Wailea Ocean Vistas
- Wailea Custom Home, Pool, Panoramic Ocean View, Waterfalls - Maui Ocean Palms
Check all holiday rentals with a pool in Wailea on Hawaii.Villas.
Yes, We have 1774 summer rental homes in Wailea and types of place to stay in Wailea include:
- Vacation Homes: 1774 available for rent
- Villas: 1774 Rentals available for rent
- Holiday Apartments: 1774 Rentals available for rent
- Hotels with Suites: 1774 Rentals available for book


















