Summer 2026 Wailea Vacation Rentals

Send a postcard from Maui this summer!  Explore this curated collection of Wailea residences with newly available summer stays for travel this June, July, and August, including preferred pricing for a limited time.  With fully stocked kitchens, in-residence washers and dryers, and spacious layouts designed for effortless stays, it’s the perfect way to settle into island time.

Sort by
  • Random
  • Name
  • Bedrooms
  • Sleeps
  • Price
  • Quality
Map View
Favorites
Compare Favorites
Viewed
viewed
You have not recently viewed any properties.
Properties Available 91 properties available
Sort by:
Random
Sort Random Down
  • Random
  • Bedrooms
  • Sleeps
  • Price
  • Quality
Makena Surf G202 is an inviting oceanfront vacation home located on the peaceful southern side of the Makena Surf community. Set on the second floor and surrounded by lush tropical landscaping, the residence offers beautiful views toward the secluded beach at the southern edge of the property and a relaxed setting for enjoying the natural beauty of
Makena Surf G202 Beachfront Resort
2 Bedroom Oceanfront Condo
Rating 5 (8)
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
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 307At 1,336 square feet, 307 is the largest unit in the Elua — a remodeled 2-bedroom condo with a private wrap-around lanai and sweeping ocean views. Adjacent to Ulua Beach and the 3.2-mile Wailea Beach Walk, yet tucked into 24 acres of secluded tropical grounds. Two resort pools, inclu
Wailea Elua Village 307
2 Bedroom Ocean View Condo
Rating 4.6 (3)
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
Wailea Elua Village 2005 is a stunning two-bedroom, two-bathroom vacation rental located in the desirable Wailea region of Maui. This beautifully appointed condo offers a perfect blend of luxury and comfort. The spacious interior features an open-concept design that maximizes natural light and ocean views. A lack of clutter and unnecessary furnish
Wailea Elua Village 2005
2 Bedroom Ocean View Condo
Rating 5 (7)
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
Wailea Elua 1704 is a stunning oceanfront vacation rental located a short stroll from one of the top snorkeling beaches on Maui. This spacious two-bedroom, two-bathroom corner unit spans approximately 1,600 square feet and comfortably accommodates up to six guests, making it perfect for families or groups of friends seeking a luxurious getaway. Th
Wailea Elua Village 1704
2 Bedroom Oceanfront Condo
Rating 5 (10)
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
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 39ASome settings at Wailea Ekahi face the ocean. 39A faces the garden — and that's the point. Tucked into a quiet corner of 34-acre tropical grounds, with a private lanai and its own Weber grill, this is one of the most secluded 1-bedroom settings in the complex. Keawakapu Beach is a s
Wailea Ekahi Village 39A
1 Bedroom Garden View Condo
Rating 5 (5)
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 your serene oasis at Wailea Ekahi Village 35C, a beautifully designed 1-bedroom, 1-bathroom condo nestled in the heart of Wailea. This stunning garden view condo 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 priv
Wailea Ekahi Village 35C
1 Bedroom Garden View Condo
Rating 5 (1)
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
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 18CA spacious 1,000 sq.ft. 1-bedroom condo with 2 full bathrooms, and step-free ground-floor walkout access to a covered wrap-around lanai. Enjoy serene garden views with distant ocean glimpses, 4 resort pools, and a 5 to 10-minute stroll down scenic botanical paths to resort's oceanfr
Wailea Ekahi Village 18C
1 Bedroom Garden View Condo
Rating 5 (6)
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
Welcome to your serene oasis at Wailea Ekahi Village 42D, a meticulously designed 1-bedroom garden view condo that promises an unforgettable stay. This charming retreat features a king-sized bed in the bedroom, ensuring a restful night's sleep, and a cozy living room with a convenient Murphy bed for additional guests. The condo boasts two full bath
Wailea Ekahi Village 42D
1 Bedroom Garden View Condo
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
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1604Elua Village sits right on Ulua Beach and connects directly to the 3.2-mile Wailea Beach Walk. This recently renovated 1,336 sq.ft., 2-bedroom condo looks out over the lawn to open Pacific water, with accordion doors folding the living room onto the elevated lanai. 2 resort pools, p
Wailea Elua Village 1604
2 Bedroom Oceanfront Condo - Platinum
Rating 5 (5)
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
Wailea Ekahi 12C is a beautiful vacation rental nestled within the landscaped 32 acres that make up Wailea Ekahi Village. This upgraded condo offers a perfect blend of comfort and tropical elegance, making it an ideal retreat for those looking to escape the hustle and bustle back home. This Maui vacation rental boasts 945 square feet of living spa
Wailea Ekahi Village 12C
1 Bedroom Ocea View Condo
Rating 5 (13)
1 bedrooms
1 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
Wailea Elua Village 2012 is a luxurious vacation rental located in the stunning Wailea area of Maui. This one-bedroom, two-bathroom condo offers an ideal retreat for couples or small families, providing a perfect blend of comfort and elegance. The property is part of a gated beachfront community, ensuring privacy and tranquility amidst lush tropica
Wailea Elua Village 2012
1 Bedroom Ocean View Condo
Rating 5 (5)
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 Grand Champions 111Wailea Grand Champions is an 11-acre country club-style resort set along the Wailea Blue Golf Course and Wailea Tennis Club. Unit 111 is a spacious 2-bedroom, 2-bathroom retreat that comfortably sleeps 6. Enjoy a private lanai with unique, vibrant views of the tennis courts, plus
Wailea Grand Champions 111
2 Bedroom Garden View Condo
Rating 4.8 (6)
2 bedrooms
2 baths
6 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

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

I agree