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 154 properties available
Sort by:
Random
Sort Random Down
  • Random
  • Bedrooms
  • Sleeps
  • Price
  • Quality
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 (5)
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 your serene oasis at Wailea Ekahi Village 44B, a stunning studio 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 into the open-concept living area, where you'll find a plush king-sized bed, perfect for a restful night's sleep
Wailea Ekahi Village 44B
Studio Garden View Condo
Rating 5 (6)
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
Welcome to the enchanting Makena Surf F305 Beachfront Resort, your perfect haven nestled in the heart of Wailea. This stunning 2-bedroom, 2-bathroom oceanfront condo offers a luxurious retreat for up to six guests, combining modern elegance with the natural beauty of Maui.Step inside to discover a thoughtfully designed layout that maximizes comfort
Makena Surf F305 Beachfront Resort
2 Bedroom Oceanfront Condo
Rating 5 (34)
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 your serene oasis at Wailea Elua Village 1607, a luxurious 3-bedroom oceanfront condo that promises an unforgettable stay. This spacious 1,701 sq. ft. retreat comfortably sleeps six guests, featuring a master suite with a king bed, a second bedroom with a queen bed, and a third bedroom with two twin beds. Each bedroom is designed for com
Wailea Elua Village 1607
3 Bedroom Oceanfront Condo
Rating 5 (9)
3 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 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 (9)
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
Welcome to the serene and luxurious Wailea Elua Village 905, your perfect retreat nestled in the heart of Wailea. This stunning 3-bedroom, 2-bathroom garden view condo offers a harmonious blend of comfort and elegance, ideal for families or groups of friends. Step inside to discover a thoughtfully designed layout with three spacious bedrooms. The m
Wailea Elua Village 905
3 Bedroom Garden View Condo
Rating 5 (28)
3 bedrooms
2 baths
8 guests
Location Wailea, HI Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space Icon of Washer/Dryer Washer/Dryer
View Details
Welcome to the Makena Surf E103 Beachfront Resort, your perfect oasis in Wailea. This luxurious 2-bedroom, 2-bathroom oceanfront condo offers a serene escape with breathtaking views of the Pacific Ocean. The master bedroom features a plush king bed, while the second bedroom comfortably accommodates two with a queen bed and a twin bed. Both bathroom
Makena Surf E103 Beachfront Resort
2 Bedroom Oceanfront Condo - Platinum
Rating 4.9 (38)
2 bedrooms
2 baths
5 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 12AStep off the ground-floor walk-out patio and you're on the tropical grounds — Keawakapu Beach a short stroll away, where sea turtles glide offshore year-round. A split-level 1-bedroom, 1.5-bathroom condo sleeping up to 4, with ocean and pool views from the patio — ideal for couples
Wailea Ekahi Village 12A
1 Bedroom Ocean View Condo
Rating 5 (8)
1 bedrooms
1.5 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
Welcome to the Makena Surf F112 Beachfront Resort, where luxury meets the ocean's edge. This stunning 3-bedroom, 2-bathroom oceanfront condo is perfect for your dream Hawaiian getaway. The spacious layout features a primary suite with a king bed, a second bedroom with a king bed, and a third bedroom with two day beds, one of which can slide out on
Makena Surf F112 Beachfront Resort
3 Bedroom Oceanfront Condo - Platinum
Rating 4.9 (20)
3 bedrooms
2 baths
7 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 your serene oasis at Wailea Elua Village 2008, a stunning 1-bedroom, 2-bathroom ocean view condo that promises an unforgettable stay. This meticulously designed 1,025 sq. ft. retreat comfortably sleeps up to four guests, offering a perfect blend of luxury and comfort. Step into the open-concept living area, where the sleek, modern design
Wailea Elua Village 2008
1 Bedroom Ocean View Condo
Rating 5 (9)
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
Welcome to the serene Polo Beach Club 206, your perfect oceanside retreat in Wailea. This stunning 2-bedroom, 2-bathroom condo offers a luxurious escape for up to six guests. Step into the spacious living room, where you can relax on the comfortable sofa bed. The two well-appointed bedrooms each feature a plush king bed, ensuring a restful night's
Polo Beach Club 206
2 Bedroom Oceanfront Condo
Rating 5 (37)
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 Villa G302, your luxurious Hawaiian escape where relaxation meets elegance. This stunning ocean view villa features two walls of retractable sliding doors that seamlessly blend the open living area with a spacious corner lanai, complete with a built-in Viking grill-perfect for sunset barbecues in a tranquil island atmosphere.Designed wit
Wailea Beach Villas G302
3 Bedroom Ocean View Villa - Platinum
Rating 5 (14)
3 bedrooms
3.5 baths
8 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

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

I agree