Book a Place to Stay in Wailea for Your Summer Getaway
About Wailea Summer Rental on Vacation Cottage
Elevate your summer travels with 1799 top-notch stay to make the most of your summer adventures? Consider a summer resort or villa rental in or near Wailea. Choosing the perfect holiday rental for your upcoming summer getaway on Vacation Cottage is a breeze. Whether you're traveling with family, friends, or a group to Wailea or its surrounding areas, Vacation Cottage offers a plethora of luxury summer accommodations to select from. Many of these accommodations boast top-notch amenities such as private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxurious bedrooms, bathtubs, and pet-friendly environments.
Searching for a tranquil retreat in Wailea for an unforgettable summer holiday? Vacation Cottage's summer rental homes are ready to provide you with the utmost comfort you deserve. Whether you're in need of a premium summer condo, luxury flat, resort, villa, bungalow, cozy cabin, RV, or cottage in Wailea, Vacation Cottage has you covered for your next summer escapade.
Frequently Asked Questions About Wailea Luxury Rentals
What are the top rated Summer 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 Summer Rentals in Wailea:
- Aloha Kai Suite at Wailea Beach Villas. Penthouse 205. Ocean View. 3 BR/3 BA
- Very Best Deluxe Ocean View.Panoramic View.First Class!
- Private S. Maui home w/ocean views, pool, hot tub
- Wailea Ekahi 40A - 5-Star South Maui Oasis
- Amazing view, Close to the beach, Wailea Ekahi Unit 20i
- 1br/1ba Condo Steps From The Pavilion pool, Mokapu Beach with beautiful views.
- Luxe Oceanview Hideaway on Wailea Old Blue Golf Course
- DIRECT BEACHFRONT 4Bd 3BA 3892 s.f. WAILEA PANORAMIC OCEAN & OUTER ISLAND VIEWS
- 14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!
- 5D - 2 Minute Walk to the beach/main pool, well-equipped, see reviews!
How many summer rentals are available around Wailea, HI?
In 2026, Vacation Cottage offers 1799 summer rentals in or around Wailea. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
How much does it cost to rent a summer rental in Wailea?
The average price per night for a summer rental in Wailea is $1,003. Check the full list of summer accommodations in Wailea.
How many summer rentals are available to book in Wailea?
There are 1799 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Vacation Cottage.
Do any summer rentals in Wailea have a private pool?
Yes, here are some popular summer holiday rentals in Wailea that have a private or indoor pool:
- Lavish Premier Beachfront Townhouse W/Unrivaled Views Wailea Elua 1305
- Ho'olei at Grand Wailea
- Luxurious Wailea Ocean Vistas
- Luxurious Beachfront Condo with Modern Amenities - Makena Surf Resort #E-203
Check all holiday rentals with a pool in Wailea on Vacation Cottage.
Can I rent pet-friendly summer rentals in Wailea?
Yes, We have 1799 summer rental homes in Wailea and types of place to stay in Wailea include:
- Vacation Homes: 1799 available for rent
- Villas: 1799 Rentals available for rent
- Holiday Apartments: 1799 Rentals available for rent
- Hotels with Suites: 1799 Rentals available for book
Do you have a luxury summer rental with a pool in Wailea?
Yes, of course! There are many luxury summer rental properties in Wailea. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Wailea.
