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2026-08-05
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Vacation Rentals in Wailea (Maui)

Wailea Ekahi 32B - Wek 32B Remodeled Wailea Getaway W Ac Pool

3300 Wailea Alanui Drive, Unit 32B, Wailea (Maui), United States Show map

The 1-bedroom Wailea Ekahi 32B - Wek 32B Remodeled Wailea Getaway W Ac Pool Villa hosts up to 2 guests and is nestled merely 13 minutes' stroll from natural sites such as the Keawakapu Beach. More

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The Palm Coast F202 At Wailea Beach Villas

3800 Wailea Alanui Drive, Wailea Resort, Maui, Wailea (Maui), United States Show map

Offering guests to unwind in a Jacuzzi, The Palm Coast F202 At Wailea Beach Villas is located a 12-minute walk from the Olavine Spa & Salon. Offering horse riding tours, the 3-bedroom villa can… More

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Kamaole Sands #7-403 Great Rates, Garden And Partial Ocean Views, A/C

2695 S. Kihei Rd, Kamaole Sands #7-403, Wailea (Maui), United States Show map

The spacious 110 m² Kamaole Sands #7-403 Great Rates, Garden And Partial Ocean Views, A/C Wailea apartment is a good choice for accommodating up to 6 guests, offering a prime setting within 25… More

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Maui Kamaole I 214

2777 South Kihei Rd., Unit I214, Wailea (Maui), United States Show map

Featuring an outdoor swimming pool, the 2-bedroom Maui Kamaole I 214 Villa Wailea is located approximately 5 minutes' walk from Kihei Coastal Trail and is suitable for up to 6 guests. Guests can… More

From US$ 469 Book Now

Ho'Olei 24-3

24-3 Ho'Olei Circle, Unit #24-3, Wailea (Maui), United States Show map

The 3-bedroom Ho'Olei 24-3 Villa Wailea, located approximately a 5-minute walk from Spa at the Four Seasons Maui at Wailea, can host up to 10 guests. The holiday home features opportunities for… More

From US$ 1613 Book Now

Hale Kamaole, #215

2737 South Kihei Road One Bedroom / One Bath Garden View Condominium, Wailea (Maui), United States Show map

Featuring a prime location a 6-minute walk from Blue Water Rafting, the spacious Hale Kamaole, #215 Apartment Wailea accommodates up to 4 guests. Guests can relax in a private garden at this… More

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Kihei Akahi By Maui Rental Group

2531 S Kihei Rd, Wailea (Maui), United States Show map

The 65 m² Kihei Akahi By Maui Rental Group Wailea apartment features convenient proximity to such city attractions as Kamaole Beach Park 2, situated nearly a 5-minute walk away. Wi-Fi is provided for… More

From US$ 253 Book Now

Maui Kamaole #A-109 Spacious, Ocean View, Full A/C, Across Kamaole Beach III

2777 S. Kihei Rd., Maui Kamaole #A-109, Wailea (Maui), United States Show map

Maui Kamaole #A-109 Spacious, Ocean View, Full A/C, Across Kamaole Beach III Wailea apartment features a prime location 800 metres from the Keawakapu Beach and hosts up to 4 guests. Wi-Fi is provided… More

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The Villas At Fairmont Kea Lani

4100 Wailea Alanui Drive, Wailea (Maui), United States Show map

The Villas At Fairmont Kea Lani Wailea is situated in the immediate vicinity of Fairmont Kea Lani, featuring such comforts as Wi-Fi and private parking. Offering a Jacuzzi and a sauna, this Wailea… More

From US$ 3799 Book Now

Mana Kai #805 By Coldwell Banker Island Vacations

2960 S Kihei Rd, Wailea (Maui), United States Show map

Featuring a beachfront location, the 2-room Mana Kai #805 By Coldwell Banker Island Vacations Apartment Wailea offers views of the sea, and is only a 9-minute walk from Kihei Coastal Trail. Situated… More

From US$ 778 Book Now

Wailea Elua 2109 By Coldwell Banker Island Vacations

3600 Wailea Alanui Dr, Wailea (Maui), United States Show map

The spacious 143 m² Wailea Elua 2109 By Coldwell Banker Island Vacations Apartment is just an 8-minute stroll from Makena State Park and welcomes guests with a hot tub. The Kamaole Beach Park III is… More

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Kamaole Sands 6-107 By Coldwell Banker Island Vacations

2695 S Kihei Rd, Wailea (Maui), United States Show map

To enjoy your vacation in Wailea, stay at the spacious 76 m² Kamaole Sands 6-107 By Coldwell Banker Island Vacations Wailea apartment, which is just 1.1 km from the Redline Rafting and nearly 25… More

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The Beach Suite 803 At Andaz Maui Wailea Resort

3550 Wailea Alanui Drive, Wailea Resort, Maui, Wailea (Maui), United States Show map

3-bedroom The Beach Suite 803 At Andaz Maui Wailea Resort villa is located a mere 1.4 km from the Half-mile-long Ulua Sandy Beach Park and provides a Jacuzzi. Offering windsurfing, snorkelling, and… More

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Ultimate Beach Retreat 2Bd Suite With Pool, Hot Tub

2575 South Kihei Road Apartment A103 A103, Wailea (Maui), United States Show map

The 2-room Ultimate Beach Retreat 2Bd Suite With Pool, Hot Tub Wailea lies in a prime location in Wailea, only a 6-minute walk from Kamaole Beach Park 2. Staying in this spacious apartment, nestled… More

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Polo Beach Club 402 By Coldwell Banker Island Vacations

4400 Makena Rd, Wailea (Maui), United States Show map

Situated about 25 minutes' walk from the Mokapu Beach, the spacious 2-bedroom Polo Beach Club 402 By Coldwell Banker Island Vacations Wailea apartment can host up to 5 guests in Wailea. Boasting a… More

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Maui Parkshore 315 By Coldwell Banker Island Vacations

2653 S Kihei Road, Wailea (Maui), United States Show map

The spacious 83 m² Maui Parkshore 315 By Coldwell Banker Island Vacations Wailea apartment is a good choice for accommodating up to 4 guests, offering a prime setting about 20 minutes on foot from… More

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Hale Kamaole 276

2737 S. Kihei Road, Wailea (Maui), United States Show map

The 1-bedroom Hale Kamaole 276 Villa Wailea accommodates up to 6 guests and offers proximity to the Kamaole Beach Park III, located merely a 5-minute walk away. More

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Wailea Seashore Suite K507 At Wailea Beach Villas

3800 Wailea Alanui Drive, Wailea Resort, Maui, Wailea Beach Villas K507, Wailea (Maui), United States Show map

Boasting a Jacuzzi, the 3-bedroom Wailea Seashore Suite K507 At Wailea Beach Villas is located just 550 m from The Shops at Wailea Outdoor Mall and can accommodate 6 guests. The villa features… More

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Palms At Wailea 1704 By Coldwell Banker Island Vacations

3200 Wailea Alanui Dr., Wailea (Maui), United States Show map

The spacious 111 m² Palms At Wailea 1704 By Coldwell Banker Island Vacations Apartment is located around a 10-minute ride from the Kamaole Beach Park III and offers Wi-Fi for either business or… More

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Kihei Surfside, #113

200 E. La Bonte St, # 216, Wailea (Maui), United States Show map

To enjoy your vacation in Wailea, stay at the spacious 1-bedroom Kihei Surfside, #113 Apartment Wailea, which is merely 0.7 km from Surf Shack and approximately 25 minutes' walk from the neighborhood… More

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Ground Floor Garden View Unit With Great Amenities Kadg15

2531 South Kihei Road, Wailea (Maui), United States Show map

Located just a 7-minute walk from Hawaiian Moons Natural Foods, the 87 m² Ground Floor Garden View Unit With Great Amenities Kadg15 Apartment Wailea accommodates up to 5 guests. This 2-bedroom… More

From US$ 413 Book Now

Wailea Ekahi 5E By Coldwell Banker Island Vacations

3300 Wailea Alanui Drive, Wailea (Maui), United States Show map

The spacious 1-bedroom Wailea Ekahi 5E By Coldwell Banker Island Vacations Apartment features a beachfront location nearly 25 minutes' walk from Wailea Golf Club and hosts up to 3 guests. To have an… More

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Hoolei 55-2 By Coldwell Banker Island Vacations

55-2 Kiloa Street, Wailea (Maui), United States Show map

Featuring a convenient location around a 5-minute walk from the Na Pua Gallery, the 243 m² Hoolei 55-2 By Coldwell Banker Island Vacations Apartment Wailea accommodates up to 8 guests. This spacious… More

From US$ 1137 Book Now

Kamaole Sands 7-109 - Romantic, Renovated, Ac

2695 S Kihei Rd, Wailea (Maui), United States Show map

Situated only 0.7 km from the Kamaole Beach Park III, the 1-bedroom Kamaole Sands 7-109 - Romantic, Renovated, Ac Wailea villa can host up to 2 guests and offers a Jacuzzi, ensuring a relaxing stay. More

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Azure Azul M212 At Wailea Beach Villas

3800 Wailea Alanui Drive, Wailea Resort, Maui, Wailea (Maui), United States Show map

Suitable for 8 guests, the 3-bedroom Azure Azul M212 At Wailea Beach Villas is located just 550 metres from The Shops at Wailea Outdoor Mall and provides a Jacuzzi for a relaxing stay. This property… More

From US$ 2945 Book Now

Palms At Wailea 801, Luxurious 1Bedroom, 2 Bath

3200 Wailea Alanui Dr, Wailea (Maui), United States Show map

Palms At Wailea 801, Luxurious 1Bedroom, 2 Bath villa offers proximity to nearby tourist spots, such as Polo Beach Park, situated 2.7 km away. More

From US$ 423 Book Now

Kamaole Sands 5-409

2695 South Kihei Rd., Unit #5-409, Wailea (Maui), United States Show map

During the stay at Kamaole Sands 5-409 Wailea villa, guests can indulge in snorkelling or visit the Lava Fields, located a 25-minute walk away. Located within an 800-metre distance of the Kihei Boat… More

From US$ 570 Book Now

Kamaole Sands 8-402

2695 South Kihei Rd, Wailea (Maui), United States Show map

Located in the Kamaole Beach district a 19-minute walk from Hawaiian Moons Natural Foods, the welcoming Kamaole Sands 8-402 Wailea apartment accommodates up to 6 guests. This apartment offers a car… More

From US$ 451 Book Now

Maui Kamaole #A-112 Spacious, Ocean View, Across Kamaole Bch III

2777 S. Kihei Rd., Maui Kamaole #A-112, Wailea (Maui), United States Show map

Facing the sea, Maui Kamaole #A-112 Spacious, Ocean View, Across Kamaole Bch III Wailea apartment welcomes guests in a residential area, only a 10-minute walk from the Keawakapu Beach. Boasting a… More

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Grand Champions Villas Ocean View 3 Bedroom Sleeps 10 Complimentary Car With 6 Nights Gch Ml-1499 By Kbm

155 Wailea Ike Pl, Wailea (Maui), United States Show map

Featuring a convenient location, the 3-room Grand Champions Villas Ocean View 3 Bedroom Sleeps 10 Complimentary Car With 6 Nights Gch Ml-1499 By Kbm Wailea apartment offers views of the garden… More

From US$ 953 Book Now

Kihei Surfside, #512

2936 South Kihei Road 1 Bedroom 1.5 Bath Oceanfront Condominium, Wailea (Maui), United States Show map

Overlooking the sea, the spacious 1-bedroom Kihei Surfside, #512 Apartment Wailea is a few moments from 5 Palms in Wailea. This 68 m² apartment, suitable for a maximum of 4 guests, boasts a heated… More

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Grand Champions 160

155 Wailea Ike Place, Wailea (Maui), United States Show map

The 3-bedroom Grand Champions 160 Villa Wailea is located nearly a 20-minute walk from the Sandy Wailea Public Beach and provides a swimming pool, ensuring a relaxing stay. Suitable for 8 guests, the… More

From US$ 1117 Book Now

Hoolei 17-3 By Coldwell Banker Island Vacations

17 Makakehau St, Wailea (Maui), United States Show map

Offering a Jacuzzi, the 3-bedroom Hoolei 17-3 By Coldwell Banker Island Vacations Villa Wailea is located just 1.1 km from the Sandy Wailea Public Beach. With a maximum capacity of 8 guests, this… More

From US$ 1533 Book Now

Grand Champions 144

155 Wailea Ike Place, Wailea (Maui), United States Show map

Situated approximately 400 metres from the Wailea Town Center, the spacious 128 m² Grand Champions 144 Apartment Wailea entices guests with a Jacuzzi. The Makena Golf Course is 3.3 km away, while the… More

From US$ 605 Book Now

Grand Champions Villas Ocean View 6 Bedroom Sleeps 16 Complimentary Car With 6 Nights Gch Ml-3785 By Kbm

155 Wailea Ike Pl, Wailea (Maui), United States Show map

Situated nearly 20 minutes' walk from the Sandy Wailea Public Beach, the spacious Grand Champions Villas Ocean View 6 Bedroom Sleeps 16 Complimentary Car With 6 Nights Gch Ml-3785 By Kbm Wailea… More

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Grand Champions 130 By Coldwell Banker Island Vacations

155 Wailea Ike Pl, Wailea (Maui), United States Show map

Featuring a convenient location a 5-minute walk from the Wailea Town Center, the spacious Grand Champions 130 By Coldwell Banker Island Vacations Apartment Wailea accommodates up to 6 guests. This… More

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Kamaole Sands 4-208 By Coldwell Banker Island Vacations

2695 S Kihei Rd, Wailea (Maui), United States Show map

The spacious 1-bedroom Kamaole Sands 4-208 By Coldwell Banker Island Vacations Wailea apartment features a convenient location just 13 minutes' walk from the Kihei Boat Landing and hosts up to 4… More

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Wailea Oceanfront Rental

Wailea Ekahi Village 14F, 3300 Wailea Alanui Drive, Wailea (Maui), United States Show map

Located a 20-minute walk from The Shops at Wailea Outdoor Mall, the spacious Wailea Oceanfront Rental apartment overlooks the sea. This apartment can host up to 4 guests. More

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Grand Champions 40 By Coldwell Banker Island Vacations

155 Wailea Ike Pl, Wailea (Maui), United States Show map

Situated 20 minutes' walk from the Sandy Wailea Public Beach, the spacious Grand Champions 40 By Coldwell Banker Island Vacations Apartment Wailea offers a Jacuzzi for 4 visitors. Guests can use a… More

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Grand Champions Ocean View 1 Bedroom Sleeps 4 Great For Families Complimentary Car With 6 Nights Gch-181 By Kbm

155 Wailea Ike Pl, Wailea (Maui), United States Show map

The 98 m² Grand Champions Ocean View 1 Bedroom Sleeps 4 Great For Families Complimentary Car With 6 Nights Gch-181 By Kbm Wailea apartment features a convenient location just a 12-minute walk from… More

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Kihei Tropical Retreat - Your Home Away From Home In Maui

3204 Mapu Place, Wailea (Maui), United States Show map

Kihei Tropical Retreat - Your Home Away From Home In Maui Wailea offers proximity to nearby tourist spots, such as the Mokapu Beach, situated 3.8 km away. The 3-bedroom holiday home hosts up to 6… More

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Kamaole Sands #7-408 Beautiful Unit, Great Location, Close To Beach, Spacious

2695 S. Kihei Rd, Kamaole Sands #7-408, Wailea (Maui), United States Show map

Kamaole Sands #7-408 Beautiful Unit, Great Location, Close To Beach, Spacious Wailea apartment lies in a prime location in Wailea, 5 minutes' walk from Kamaole Beach Park 2. This apartment features… More

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Wailea Ekolu 1204 - Modern Ocean View Condo W/ Large Lanai, King Bed, & Split Ac

10 Wailea Ekolu Pl, Wailea (Maui), United States Show map

Wailea Ekolu 1204 - Modern Ocean View Condo W/ Large Lanai, King Bed, & Split Ac villa accommodates up to 4 guests and offers a prime location approximately 15 minutes on foot from shopping venues… More

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Wailea Beach Villa H102 By Coldwell Banker Island Vacations

3800 Wailea Alanui Drive, Wailea (Maui), United States Show map

Honolua Surf Co is 6 minutes' walk from Wailea Beach Villa H102 By Coldwell Banker Island Vacations, offering a Jacuzzi for guests' relaxation. The 2-bedroom villa features opportunities for… More

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Makena Surf, #G-301-302

4850 Makena Alanui 4 Bedroom / 5 Bath Ocean Front Condominium, Wailea (Maui), United States Show map

Located just an 8-minute walk from Five Graves and the Makena Snorkeling Beach, the 297 m² Makena Surf, #G-301-302 Apartment Wailea features views of the sea. Boasting a Jacuzzi, the apartment… More

From US$ 2396 Book Now

Hale Hui Kai 202

2994 South Kihei Road, Wailea (Maui), United States Show map

Hale Hui Kai 202 Villa Wailea is nestled fairly close to the Keawakapu Beach and can accommodate up to 4 guests. More

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Grand Champions Villas Ocean View 5 Bedroom Sleeps 14 Complimentary Car With 6 Nights Gch Ml-3786 By Kbm

155 Wailea Ike Pl, Wailea (Maui), United States Show map

The spacious Grand Champions Villas Ocean View 5 Bedroom Sleeps 14 Complimentary Car With 6 Nights Gch Ml-3786 By Kbm Wailea apartment boasts a convenient setting and in in the immediate vicinity of… More

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Hale Kamaole 4-334

2737 South Kihei Road, Unit #4-334, Wailea (Maui), United States Show map

Along with proximity to the Kamaole Beach Park III, just a 5-minute walk away, the 2-bedroom Hale Kamaole 4-334 Villa Wailea offers opportunities for windsurfing, snorkelling, and hiking in the area. More

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Maui Parkshore 410

2653 South Kihei Road, Wailea (Maui), United States Show map

Maui Parkshore 410 Wailea villa accommodates up to 4 guests and offers proximity to the Kamaole Beach Park III, located only 5 minutes' walk away. More

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Ho'Olei Unit 12-2

12 Hoolei Circle, Wailea (Maui), United States Show map

Up to 6 guests can stay at Ho'Olei Unit 12-2 Villa Wailea and enjoy Spa at the Four Seasons Maui at Wailea, located a 5-minute walk away. More

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