Wailea Lodging
Luxury Resorts, WORLD CLASS Golf, AND Upscale Shopping
Wailea is a luxurious resort community in South Maui, renowned for its beautiful crescent shaped beaches. The area is home to several world-class golf courses, luxurious shopping, and exquisite dining options. Known for its upscale accommodations, Wailea boasts numerous resorts and vacation rentals, including family-friendly options, making it ideal for both relaxation and adventure.
travel dates
186 properties available
Sort by:
Random
-
Random
-
Name
-
Bedrooms
-
Sleeps
-
Availability
-
Price
Wailea Ekolu 1107 is a charming ground-floor vacation rental that offers the perfect blend of convenience and stunning views of the ocean, mountains, and the island of Lana'i. Guests can enjoy the soothing sounds of tropical birds without the disturbance of street noise, providing a peaceful atmosphere for relaxation. With three separate lanais, in
This residence has been given the Hawaiian name "Wailea Kapili", which translates to "a Wailea Gathering." It is the perfect accommodation for gathering with friends and family to enjoy the beauty of Maui. This Ho'olei Residence is a spacious 2,426 square foot three bedroom, three and half bath villa sleeps eight guests comfortably. The close prox
Welcome to Makena Surf F208, a luxurious oceanfront vacation residence that offers an unparalleled Hawaiian retreat. Situated on the second floor, this 1,313 square foot residence is designed to provide the ultimate in comfort and relaxation, featuring elegant touches such as textured walls, beautiful tiling, and exquisite tray ceilings with dramat
Wailea Ekolu 912 is a delightful one-bedroom, two-bathroom vacation rental that offers stunning ocean views and a relaxing retreat in the heart of Wailea. This beautifully designed condo features many eye-catching design elements, including wood paneling on the vaulted ceiling, exposed wooden beams, custom tile flooring, jaw-dropping koa cabinets i
Wailea Ekahi Village 12B is a beautiful vacation rental that underwent a complete update in March 2021. Interior designers may want to take notes! This gorgeous ocean view studio is ideal for couples looking for a cozy retreat or solo travelers looking for the perfect home base for remote working. The indoor-outdoor living style allows you to enj
Makena Surf E102 is a prime oceanfront vacation condo that offers a perfect blend of luxury and natural beauty. This 1,510 square foot residence is centrally located within the resort, just a short stroll from the golden sands of Po'olenalena Beach. The condo features a spacious 335 square foot lanai, where guests can relax and enjoy the ocean bree
Makena Surf G203 is a luxurious oceanfront vacation condo located on the second floor of the exclusive Makena Surf resort on Po'olenalena Beach, Maui. This secluded beachfront property offers the ultimate in tropical island relaxation, providing a peaceful retreat for those seeking privacy and tranquility. The resort is nestled within a pristine la
Let the sounds of palm fronds brushing against each other in the gentle trade winds sing you to sleep this vacation. With relaxing views of the ocean and the manicured tropical landscaping, Wailea Beach Villas Penthouse 411 leaves no stone unturned in the pursuit of your delight. Open up your lanai doors and head outside to look for whales or watch
Makena Surf E103 is a stunning 1,510 square foot oceanfront vacation condo that epitomizes luxurious Hawaiian living. This first-floor residence offers an unparalleled indoor/outdoor experience with its innovative design featuring pocket doors that retract to seamlessly blend the interior with the spacious 335 square foot lanai. The open-concept li
Welcome to your dream vacation in Wailea, Maui! This beautiful two-bedroom residence combines comfort, style, and convenience for an unforgettable stay in paradise. Upon entering, you'll be welcomed by a spacious, open living area, tastefully furnished for a relaxed ambiance. The living room offers plush seating and a flat-screen TV, perfect for un
This 1,090 square foot one-bedroom, two bathroom vacation rental sleeps four comfortably. Wailea Ekahi Village 42C is conveniently located close to the pool, but offers a quiet sanctuary surrounded by lush greenery. Featuring contemporary, yet comfortable décor – this vacation residence utilizes an indoor-outdoor lifestyle with a great room and ki
Penthouse 512 at Wailea Beach Villas offers an unparalleled top-floor experience with expansive ocean and island views, ideal for a Hawaiian dream vacation. This 3,000-square-foot home features a wrap-around lanai, providing one of the most breathtaking views in the Wailea Beach resort area. Just a short five-minute walk immerses you in the Pacific
Tell us what you're looking for and someone will contact you with available options.