Wailea Beachfront Vacation Rentals

Experience Wailea beachfront vacation rentals where comfort meets unmatched oceanfront access. Wake to sweeping Pacific views and spend your days steps from soft sand, crystal clear waters, and unforgettable sunsets.

Sort by
  • Random
  • Name
  • Bedrooms
  • Sleeps
  • Price
  • Quality
Map View
Favorites
Compare Favorites
Viewed
viewed
You have not recently viewed any properties.
Properties Available 151 properties available
Sort by:
Random
Sort Random Down
  • Random
  • Bedrooms
  • Sleeps
  • Price
  • Quality
Welcome to the Makena Surf F208 Beachfront Resort, your perfect Hawaiian retreat. This stunning 2-bedroom, 2-bathroom ocean front condo offers a luxurious escape for up to six guests. Step inside to find a spacious, open-concept living area with a fully-equipped kitchen, perfect for preparing meals after a day of beach fun. The living room is cozy
Makena Surf F208 Beachfront Resort
2 Bedroom Oceanfront Condo - Platinum
Rating 4.9 (54)
2 bedrooms
2 baths
6 guests
Location Wailea, HI Icon of Oceanfront View Oceanfront View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
Warm breezes and lush tropical gardens greet guests of Wailea Beach Villas E202 as the spacious and comfortably appointed interior blends seamlessly onto the private outdoor lanai. Contemporary neutral and earth-toned furnishings are complimented by splashes of color throughout, accentuating the natural light, swaying palms and fresh air of Maui.Tw
Wailea Beach Villas E202
3 Bedroom Garden View Villa - Platinum
Rating 4.9 (19)
3 bedrooms
3.5 baths
8 guests
Location Wailea, HI Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space Icon of Resort Golf Resort Golf
View Details
Welcome to your serene oasis at Wailea Elua Village 2012, a stunning 1-bedroom, 2-bathroom ocean view condo nestled in the heart of Wailea. This meticulously designed retreat offers a perfect blend of comfort and luxury, ideal for your next Hawaiian getaway. Step inside to discover a spacious, open-concept living area that seamlessly flows into a p
Wailea Elua Village 2012
1 Bedroom Ocean View Condo
Rating 5 (14)
1 bedrooms
2 baths
4 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1103Elua Village sits steps from Ulua Beach and connects directly to the 3.2-mile Wailea Beach Walk — the most beach-accessible address in the area. This ground floor 1,336 sq.ft., 2-bedroom condo features an extra large patio with ocean views, 2 resort pools, a shared hot tub, and 24
Wailea Elua Village 1103
2 Bedroom Ocean View Condo
Rating 5 (13)
2 bedrooms
2 baths
6 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
Welcome to the Makena Surf G202 Beachfront Resort, your perfect oasis in Wailea, Hawaii. This stunning 2-bedroom, 2-bathroom oceanfront condo offers a luxurious escape for up to six guests. Step inside to find a spacious, open-concept living area that seamlessly blends modern elegance with coastal charm. The living room features a comfortable sofa
Makena Surf G202 Beachfront Resort
2 Bedroom Oceanfront Condo
Rating 5 (19)
2 bedrooms
2 baths
6 guests
Location Wailea, HI Icon of Oceanfront View Oceanfront View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
Welcome to the serene and luxurious Wailea Elua Village 1303, your perfect short-term rental in the heart of Wailea. This stunning 2-bedroom, 2-bathroom ocean front condo offers a blend of modern elegance and comfort, ideal for your Hawaiian getaway. Step inside to discover a spacious, open-concept living area with sleek, contemporary design. The l
Wailea Elua Village 1303
2 Bedroom Oceanfront Condo - Platinum
Rating 4.9 (40)
2 bedrooms
2 baths
4 guests
Location Wailea, HI Icon of Oceanfront View Oceanfront View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 17BA spacious 1,000-sq.ft. 1-bedroom condo with 2 full bathrooms, offering step-free ground-floor walkout access and an extra large covered lanai. Enjoy distant ocean views over 34 acres of tropical gardens, 4 resort pools, and an 8-minute walk down shaded paths to Keawakapu Beach alon
Wailea Ekahi Village 17B
1 Bedroom Garden View Condo
Rating 5 (66)
1 bedrooms
2 baths
4 guests
Location Wailea, HI Icon of Garden View Garden View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
Wailea Beach Villas Penthouse 502 boasts a panoramic ocean vista, ideal for whale watching in the winter, and with spectacular sunset views all year long. This top floor penthouse has been exquisitely redecorated with an elegant, casual decor.Your private elevator landing on the top floor offers a glimpse of the dramatic and towering Haleakala - so
Wailea Beach Villas PH502
2 Bedroom Ocean View Condo - Platinum
Rating 5 (8)
2 bedrooms
2 baths
6 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 44BA recently remodeled 600 sq.ft. ground-floor studio, offering step-free access and a lovely garden lanai with private gas BBQ. Located just steps from 1 of 4 resort pools, pickleball courts and a pleasant walk down a grassy hill to the beachfront pavilion and Keawakapu Beach. Perfec
Wailea Ekahi Village 44B
Studio Garden View Condo
Rating 5 (11)
1 baths
2 guests
Location Wailea, HI Icon of Garden View Garden View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
Wailea Beach Villas Penthouse 504 enjoys 180 degree views of the Pacific Ocean, Kaho‘olawe, Molokini crater, and Lanai. This generous two-bedroom, two-bathroom condo provides over 1900 sq. ft. of living space, outdoor lanai, entertaining space, plus a den. Located on the fifth floor, guests can take advantage of the elevated views! Lounge on the s
Wailea Beach Villas PH504
2 Bedroom Ocean View Condo - Platinum
Rating 5 (15)
2 bedrooms
2 baths
6 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 9AThis spacious 945 sq.ft. ground-floor condo offers lush tropical garden views and step-free walkout access. It is located right across from the oceanfront pool pavilion on a gentle slope. Enjoy 4 resort pools, pickleball, and a short stroll down to Keawakapu Beach known for the best
Wailea Ekahi Village 9A
1 Bedroom Garden View Condo
Rating 5 (14)
1 bedrooms
1 baths
4 guests
Location Wailea, HI Icon of Garden View Garden View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
Welcome to the Makena Surf C105 Beachfront Resort, a stunning 2-bedroom oceanfront condo nestled in the heart of Wailea, Hawaii. This luxurious retreat offers a perfect blend of comfort and elegance, ideal for families or groups of friends seeking a memorable beach getaway.Step inside to discover a thoughtfully designed layout that maximizes space
Makena Surf C105 Beachfront Resort
2 Bedroom Oceanfront Condo
Rating 5 (40)
2 bedrooms
2 baths
6 guests
Location Wailea, HI Icon of Oceanfront View Oceanfront View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details

Tell us what you're looking for and someone will contact you with available options.

I agree