Wailea Discount Rental
400 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $194/Night
For 7 Nights US $1,357
450 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Hot Tub
- Pool
- Ocean View
US $214/Night
For 7 Nights US $1,496
646 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $226/Night
For 7 Nights US $1,581
4 Guests
1 Bedroom
2 Bathrooms
House
- Oceanfront
- Ocean View
- View
US $239/Night
For 7 Nights US $1,673
450 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $251/Night
For 7 Nights US $1,759
500 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
US $251/Night
For 7 Nights US $1,760
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Hot Tub
- Pool
- Ocean View
US $252/Night
For 7 Nights US $1,761
904.17 ft²
4 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Apartment
- Hot Tub
- Pool
- Balcony/Terrace
US $255/Night
For 7 Nights US $1,785
646 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $256/Night
For 7 Nights US $1,789
740 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Pool
- Balcony/Terrace
US $256/Night
For 7 Nights US $1,792
740 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Hot Tub
- Pool
- Ocean View
US $257/Night
For 7 Nights US $1,796
602.78 ft²
2 Guests
1 Bedroom
1 Bathroom
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $263/Night
For 7 Nights US $1,841
Why Choose Rent By Owner for your Wailea Discount Rental?
What makes our Discount Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Wailea
How to Book Your Wailea Discount Rental
What's our booking process?
Our platform allows you to browse a curated selection of discount rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Wailea
Common Discount Rental Amenities
What amenities can you expect?
Our Discount Rental are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Wailea, HI
South Maui
Keawakapu Beach
Mokapu Beach
Ulua Beach
Ulua Beach Park
Wailea Shopping Village Shopping Center
Shops at Wailea
Wailea Beach
Polo Beach
Wailea Blue Golf Course
Palauea Beach
Makena
Wailea Discount Rental Frequently Asked Questions
1. What are the top Discount 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 Discount Rentals 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
- Featured on A&E's Vacation Rental Potential! Luxury Family Condo! AC and Pool!
- 🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈
2. How many Discount Rentals are available in Wailea?
Currently, the total number of properties listed by RBO in 2026 is over 1878 in the Wailea area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Discount Rentals in Wailea.
More Rentals You May Like Near Wailea
1216.32 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- View
- Breakfast
- Parking
US $272/Night
For 7 Nights US $1,904
908 ft²
4 Guests
1 Bedroom
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $277/Night
For 7 Nights US $1,939
4 Guests
2 Bedrooms
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Ocean View
Condo
- Hot Tub
- Pool
- Ocean View
US $286/Night
For 7 Nights US $2,004
1069 ft²
4 Guests
1 Bedroom
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $288/Night
For 7 Nights US $2,019
1119.45 ft²
4 Guests
1 Bedroom
2 Bathrooms
Family Friendly
House
- Pool
- View
- Breakfast
US $289/Night
For 7 Nights US $2,023
1 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
US $291/Night
For 7 Nights US $2,035
900 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $297/Night
For 7 Nights US $2,077
908 ft²
4 Guests
1 Bedroom
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $298/Night
For 7 Nights US $2,084
1070 ft²
2 Guests
1 Bedroom
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $299/Night
For 7 Nights US $2,091
4 Guests
1 Bedroom
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
US $299/Night
For 7 Nights US $2,091
1022.57 ft²
3 Guests
1 Bedroom
2 Bathrooms
Family Friendly
House
- View
- Parking
- Internet
US $299/Night
For 7 Nights US $2,093
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $313/Night
For 7 Nights US $2,189
