Explore Wailea Vacation Rentals
About Wailea Vacation Rentals
Explore more than 1847 vacation rentals available in Wailea. These accommodations, including vacation homes and HawaiiVillas properties, boast excellent amenities and exceptional value, blending comfort and luxury. Enjoy spaciousness and convenience at a HawaiiVillas property in Wailea.
Looking for last-minute deals or the best available offers on cottages, condos, private villas, and large vacation homes? With HawaiiVillas in Wailea, you can effortlessly compare various options with a simple click. Whether you seek properties with swimming pools, hot tubs, pet-friendly policies, or expansive master suites with large screen TVs, you'll find vacation rentals by owner (RBOs) and other popular Airbnb-style accommodations near Wailea. The average room size in accommodations near Wailea is 1245.18 ft². Prices average US $1,052 per night.
HawaiiVillas streamlines and secures your search for vacation rentals in Wailea, often offering savings of 30-40% compared to hotel prices. Start your search today and book with confidence.
Top Rental Accommodation Types in Wailea
| Type | Count |
|---|---|
| Holiday Apartments | 215 |
| Vacation Homes | 197 |
| Villas | 118 |
| Cottages | 6 |
Use these Quick Filters to Find a Vacation Rental in Wailea
★ Pro Tip: HawaiiVillas simplifies comparison of top listings across various online vacation rental platforms like Booking.com and others. Use the Advanced Filter feature to switch effortlessly between HawaiiVillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, property types, cancellation policies, prices, and more. These tools streamline the search for your ideal accommodation for your next vacation in Wailea.
Weather in Wailea, HI
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Other Places to Stay in Wailea, HI
Frequently Asked Questions About Wailea?
What are the top vacation rentals in Wailea?
Currently, HawaiiVillas lists over 1847 properties in the Wailea area for 2026, with more being added continuously. By consolidating listings from various websites, HawaiiVillas provides a wide selection of top properties in Wailea.
- Romantic, Luxury, Sensual Retreat - Couples Only
- Hawaiian Cottage and Personal Paradise/BBKM 2013/0004
- Ekahi 34F - Best Panoramic Ocean View!
- Luxury Cottage w/Private Pool. Under The Warm Maui Sun Pmt #BBKM20160004
- 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
- Owner Direct - Check our 160 Reviews! - Elua Village 701, Luxury 2BR, Ocean View
- Walk to Beach, Ocean Views, Relax by the Pool
- 🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈
- Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
How many vacation rentals have private pools in Wailea?
Discover 85 vacation rentals featuring private pools near Wailea. Highly-rated HawaiiVillas properties with swimming pool access include:
- Oceanfront Private Home
- Grand Champions Upgraded 3-Bedroom with Wraparound Lanai, Complimentary Rental Car Included GCH-134 by KBM
- Fairmont Kea Lani Maui Villa Experience
- KBM Resorts | FREE CAR | Wailea Elua Village | Ocean view | Spacious 2-Bedroom Condo! WEV-2103
Which vacation homes in Wailea are best for families?
If you're searching for a family-friendly vacation residence in Wailea, explore one of these highly-rated properties, all praised for their excellent reviews among families or groups visiting Wailea:
How many Hawaii.Villas vacation rentals are available in Wailea?
At present, HawaiiVillas showcases more than 1847 properties available in the Wailea area for 2026, with new listings added regularly. By aggregating listings from multiple sources, HawaiiVillas offers a diverse range of premier properties in Wailea.
