Wailea Vacation Rentals
<p>Wailea is located on Maui's sunny southern coast and known for pristine beaches and artfully designed hotels, condominiums, and exclusive residential communities. Golf, tennis, ocean fun and upscale shopping and dining are all hallmarks of the Wailea experience.</p><p><br></p><p><b>Things To Do</b><br>Numerous beaches in the Wailea area offer fine white sands and inviting blue water. Offshore views include Molokini Islet as well as the islands of Lanai and Kahoolawe. During the winter months humpback whales are common in these waters and can be seen from the shore or on a humpback whale watching tour. Golfers will love their choices in the Wailea area with four top-quality courses to choose from including the Blue Course, Emerald Course, Gold Course and nearby seaside Makena Golf Course. Wailea's Blue Course is known for its wide fairways as well as panoramic mountain and ocean views. Lush tropical landscaping makes the Emerald Course and enjoyable experience, while natural hazards, doglegs and narrower fairways provide challenges on the Gold Course which also takes in ocean views. From Wailea you can take a day trip to see the waterfalls of Hana, the scenic Upcountry Maui region or the stunning vistas atop Haleakala Volcano. Boating excursions are also popular including sunset sails, whale watching (during the winter months) and snorkeling and scuba diving trips to Molokini three miles offshore. Wailea also has a state-of-the-art tennis facility. After all the fun pamper yourself at the the Grand Wailea's Spa Grande which is Hawaii's largest spa and offers everything from island-style massage to aromatic mineral baths.</p><p><br></p><p><b>Nearby Beaches</b><br>Wailea Beach and nearby Makena Beach are considered two of Hawaii's finest beaches with white sand and clear blue water ideal for swimming and pleasant days at the beach. Wailea Beach is fronted by the Grand Wailea and Wailea Four Seasons resorts and is the largest and arguably the nicest of Wailea's beac…
78 vacation rentals found. Page 1 of 8 shows 10 properties (10 per page, same as the live site).
Wailea Vacation Rentals
Page 1 of 8 — 78 properties total — 10 per page (matches site listing view).
Aston At The Maui Banyan
Kihei, HI, USRating: 3
- 1 Bed
From $296.41 / night — Total price: $889.24
Aston Kaanapali Shores
Lahaina, HI, USRating: 4
- 1 Bed
From $387.45 / night — Total price: $1162.34
Aston Mahana At Kaanapali
Lahaina, HI, USRating: 3.5
- 1 Bed
From $362.68 / night — Total price: $1088.03
Makena Surf - 2BR Condo #F-108
Wailea, Maui- 2 Bed
- 2 Full Baths
From $589.00 / night — Total price: $1767.00
Welcome to Makena Surf F-108, a ground-floor oceanfront retreat offering comfort, privacy, and stunning views of the Pacific. Located in one of South Mauis most exclusive gated resorts, this spacious two-bedroom condo provides immediate access to the beach, lush tropical landscaping, and premium resort amenities that make every stay unforgettable. Key Features: 2-bedroom, 2-bathroom layout Master bedroom with king bed Guest bedroom with two twin beds Large fully equipped kitchen Washer & d
Makena Surf - 2BR Condo #F-109
Wailea, Maui- 2 Bed
- 2 Full Baths
From $549.00 / night — Total price: $1647.00
Welcome to Makena Surf F-109, a luxurious ground-floor condo in the exclusive Makena Surf. With its prime beachfront location in South Maui, this gated community offers natural beauty and sweeping views of Molokini, Kaho'olawe, and the Pacific Ocean. F-109 offers effortless ground-floor entry and is just steps from Po'olenalena Beach and the sunbathing turtles off your lanai. Enjoy quick access to the largest pool and jacuzzi, located nearby. The master bedroom features a king bed, while the g
Makena Surf - 2BR Condo #F-111
Wailea, Maui- 2 Bed
- 2 Full Baths
From $549.00 / night — Total price: $1647.00
Enjoy luxurious oceanfront living at Makena Surf #F-111, a spacious ground-floor, 2-bedroom, 2-bathroom condo featuring beautiful ocean views and a peaceful island ambiance. With a prime location just steps from the sand, this elegant retreat is ideal for couples or families seeking comfort, privacy, and direct beach access in one of Mauis most exclusive communities. Condo Features: 2-bedroom, 2-bathroom oceanfront condo Sleeps up to 4 guests Master Bedroom: King bed with luxury linens Guest Be
Makena Surf - 2BR Condo #F-212
Wailea, Maui- 2 Bed
- 2 Full Baths
From $669.00 / night — Total price: $2007.00
Welcome to Makena Surf F-212an oceanfront corner unit offering unmatched views, exceptional privacy, and refined interior comfort. Located in the highly sought-after Makena Surf, this two-bedroom, two-bathroom condo delivers the perfect balance of tropical serenity and resort-style luxury. Enjoy the sound of waves from your private lanai and relax in spacious accommodations designed for an unforgettable Maui getaway. Key Features: 2-bedroom, 2-bathroom layout Master bedroom with king bed Gue
Makena Surf - 2BR Condo Ocean Front #F-209
Wailea, Maui- 2 Bed
- 2 Full Baths
From $719.00 / night — Total price: $2157.00
Welcome to Makena Surf F-209, a beautifully elevated second-floor oceanfront condo that blends comfort, elegance, and sweeping views of the Pacific. This two-bedroom, two-bathroom retreat is perfect for guests seeking a peaceful yet luxurious stay on one of Mauis most pristine beaches. Enjoy premium interiors, thoughtful upgrades, and direct access to Makena Surfs exceptional amenities. Key Features: 2-bedroom, 2-bathroom layout Master bedroom with king bed Guest bedroom with one queen bed a
Makena Surf - 2BR Condo Ocean View #C-102
Wailea, Maui- 2 Bed
- 2 Full Baths
From $519.00 / night — Total price: $1557.00
Experience unparalleled oceanfront living in Makena Surf C102, a luxurious ground-floor condo with spectacular views of Po'olenalena Beach. This 1,835-square-foot, two-bedroom, two-bathroom retreat is thoughtfully designed to provide the ultimate Maui vacation. Situated in an exclusive gated community, this condo combines modern elegance, premium amenities, and a serene beachfront setting. Condo Highlights Spacious Interior: Recently remodeled with tasteful, high-end finishes throughout. Master
Makena Surf - 3BR Condo Ocean Front #G-304
Wailea, Maui- 3 Bed
- 3 Full Baths
From $999.00 / night — Total price: $2997.00
Welcome to Makena Surf #G-304, a rare three-bedroom, three-bathroom oceanfront condo in one of South Mauis most exclusive beachfront resorts. With stunning panoramic views, two spacious lanais, and thoughtful upgrades including a wine fridge, this top-floor retreat offers the perfect blend of privacy, comfort, and island luxury for your next Maui escape. Key Features: 3-bedroom, 3-bathroom layout Master bedroom with king bed Second bedroom with queen bed Third bedroom with two twin beds Fully
