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…
85 vacation rentals found. Page 1 of 9 shows 10 properties (10 per page, same as the live site).
Wailea Vacation Rentals
Page 1 of 9 — 85 properties total — 10 per page (matches site listing view).
Aston At Papakea Resort
Lahaina, HI, USRating: 3
- 1 Bed
From $200.98 / night — Total price: $602.95
Aston At The Maui Banyan
Kihei, HI, USRating: 3
- 1 Bed
From $217.14 / night — Total price: $651.42
Aston At The Whaler Kaanapali
Lahaina, HI, USRating: 4
- 1 Bed
From $284.50 / night — Total price: $853.49
Aston Mahana At Kaanapali
Lahaina, HI, USRating: 3.5
- 1 Bed
From $349.33 / night — Total price: $1047.98
Aston Maui Hill
Kihei, HI, USRating: 3
- 1 Bed
From $397.62 / night — Total price: $1192.85
Hotel Wailea
Wailea, HI, USRating: 5
- 1 Bed
From $1275.58 / night — Total price: $3826.73
Hyatt Vacation Club At Kaanapali Beach
Lahaina, HI, USRating: 4
- 1 Bed
From $782.96 / night — Total price: $2348.88
Kihei Garden Estates G-102 by Maui Rental Group
Kihei, HI, USRating: 3
- 1 Bed
From $323.43 / night — Total price: $970.28
Makena Surf - 2BR Condo #F-108
Wailea, Maui- 2 Bed
- 2 Full Baths
From $919.00 / night — Total price: $2757.00
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 $799.00 / night — Total price: $2397.00
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
