Owner Direct Vacation
Rentals in Wailea
The Best Owner Direct Vacation Rentals in Wailea. Explore thousands of vacation home rentals, large cabins, and villas near Wailea
GUESTS
Explore the Best Wailea Vacation Homes
Looking for the perfect place to stay in Wailea? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Wailea character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Wailea Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Wailea
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Popular Neighborhoods for Wailea Vacation Rentals
What are the best areas to stay in Wailea
Discover the top neighborhoods in Wailea and choose a place that suits your stay.
Tuesday Feb 10
Wailea, Kihei
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Wailea vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Wailea
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How to Reserve Your Wailea Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Wailea Vacation Rental FAQs
1. What are the top vacation 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 Vacation Rentals in Wailea:
- Hawaiian Cottage and Personal Paradise/BBKM 2013/0004
- Romantic, Luxury, Sensual Retreat - Couples Only
- Ekahi 34F - Best Panoramic Ocean View!
- Wailea Custom Home, Pool, Panoramic Ocean View, Waterfalls - Maui Ocean Palms
- Luxury Cottage w/Private Pool. Under The Warm Maui Sun Pmt #BBKM20160004
- 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
- 🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈
- Luxe Townhome, Ocean Views, Relax by the Pool
- Featured on A&E's Vacation Rental Potential! Luxury Family Condo! AC and Pool!
2. How many vacation rentals have private pools in Wailea?
There are 82 vacation rentals with private pools near Wailea. Top-rated homes that have access to a swimming pool include:
3. Which vacation homes in Wailea are best for families?
If you are looking for a family-friendly vacation home in Wailea, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Wailea:
4. How many vacation rentals are available in Wailea?
Currently, the total number of properties listed in 2026 is over 1930 in the Wailea area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Wailea.