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.
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91 properties available
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Welcome to your serene oasis at Wailea Ekahi Village 20H, a stunning 2-bedroom, 2-bathroom garden view condo nestled in the heart of Wailea. This meticulously designed retreat comfortably accommodates up to six guests, offering a perfect blend of luxury and comfort for your Hawaiian getaway.Step inside to find a spacious, open-concept living area t
Welcome to your serene oasis at Wailea Ekahi Village 3B, a stunning studio condo nestled in the heart of Wailea. This meticulously designed retreat offers a perfect blend of comfort and luxury, ideal for a romantic getaway or a solo retreat. Step inside to discover a thoughtfully laid-out space that maximizes every square foot. The open-concept liv
Welcome to your serene oasis at Wailea Ekahi Village 7B, a beautifully designed 1-bedroom, 2-bathroom condo nestled in the heart of Wailea. This stunning 1,160 sq. ft. garden view condo offers a perfect blend of comfort and luxury, accommodating up to four guests with ease.Step inside to find a spacious, open-concept living area that seamlessly flo
Welcome to your serene oasis at Wailea Grand Champions 97, a luxurious 1-bedroom condo nestled in the heart of Wailea. This meticulously designed retreat offers a perfect blend of comfort and elegance, ideal for your next Hawaiian getaway. Step inside to discover a spacious, open-concept living area that seamlessly flows into a private balcony, whe
Welcome to your serene oasis at Wailea Ekolu Village 1203, a perfect blend of luxury and comfort nestled in the heart of Wailea. This beautifully designed 1-bedroom, 2-bathroom condo offers an idyllic retreat for guests seeking a tranquil getaway. The open-concept living space is bathed in natural light, with sleek, modern furnishings that create a
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
Oceanfront View
Complex Pool
Private Outdoor space
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2 Bedroom Oceanfront Condo - Platinum
Oceanfront View
Complex Pool
Private Outdoor space
Welcome to your serene oasis at Wailea Ekahi Village 18C, a beautifully designed 1-bedroom, 2-bathroom garden view condo nestled in the heart of Wailea. This charming retreat comfortably sleeps up to four guests and offers a perfect blend of modern amenities and tranquil surroundings.Step inside to find a spacious, open-concept living area that sea
Welcome to the serene and luxurious Wailea Elua Village 208, your perfect oasis in the heart of Wailea. This stunning 1-bedroom, 2-bathroom ocean view condo is designed for comfort and elegance, accommodating up to four guests. The master bedroom features a plush king-sized bed, while the living room offers a cozy sofa bed for additional guests. St
Welcome to your serene oasis at Wailea Elua Village 1102, a stunning 1-bedroom, 1-bathroom ocean view condo nestled in the heart of Wailea. This meticulously designed 1,025 sq. ft. condo offers a perfect blend of comfort and luxury, accommodating up to four guests with ease. Step inside to discover a spacious, open-concept living area featuring a p
Welcome to your serene oasis at Wailea Ekahi Village 17B, a beautifully designed 1-bedroom, 2-bathroom condo nestled in the heart of Wailea. This stunning garden view condo offers a perfect blend of comfort and luxury, ideal for a memorable getaway.Step inside to find a spacious and elegantly appointed living area, complete with a cozy sofa bed for
Welcome to the Makena Surf A204 Beachfront Resort, your perfect oasis for a serene and luxurious Hawaiian getaway. Nestled in the heart of Wailea, this stunning 2-bedroom, 2-bathroom oceanfront condo offers a blend of modern comfort and natural beauty. Step inside to discover a spacious, open-concept living area with plush furnishings and a cozy so
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
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