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2026-08-05
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Holiday Homes in Wailea (Maui)

Enjoy Your Oceanside Dream At Kihei Surfside

2936 South Kihei Road 209, Wailea (Maui), United States Show map

Offering a swimming pool, the 1-bedroom Enjoy Your Oceanside Dream At Kihei Surfside Wailea villa is situated around a 5-minute walk from the Redline Rafting and can accommodate up to 4 guests. This… More

From US$ 379 Book Now

Luxury Condo At Kameole Beach T106

2575 S Kihei Rd, Kihei, Hi 96753, Usa, Wailea (Maui), United States Show map

Located 500 metres from the sandy Kamaole Beach Park II, the 1-bedroom Luxury Condo At Kameole Beach T106 Wailea villa offers a Jacuzzi for additional relaxation. More

From US$ 296 Book Now

Keawakapu 208 - Kkp 208 Renovated Condo W Ac Near Beach Shops

2895 South Kihei Road, Unit 208, Wailea (Maui), United States Show map

The 2-bedroom Keawakapu 208 - Kkp 208 Renovated Condo W Ac Near Beach Shops Wailea villa offers quick access to such city attractions as Surf Shack, located merely 6 minutes' walk away. More

From US$ 356 Book Now

Kihei Surfside 306 - Kss 306 Updated Beachfront 1Bd W Ocean View

2936 South Kihei Road, Unit 306, Wailea (Maui), United States Show map

Situated merely a 5-minute walk from Blue Water Rafting, Kihei Surfside 306 - Kss 306 Updated Beachfront 1Bd W Ocean View Wailea villa entices guests with views of the sea. More

From US$ 786 Book Now

Kihei Condo W/ Resort Amenities: Walk To The Beach

Wailea (Maui), United States Show map

Situated merely 400 metres from the Kamaole Beach Park III, the 1-bedroom Kihei Condo W/ Resort Amenities: Walk To The Beach Wailea villa provides guests with a Jacuzzi for additional relaxation. The… More

From US$ 375 Book Now

Kihei Akahi Resort - Unit C505

2531 South Kihei Road, Unit C505, Wailea (Maui), United States Show map

Staying at the 1-bedroom Kihei Akahi Resort - Unit C505 Wailea villa, guests can visit Kamaole Beach Park 2, which is just 300 metres away. Suitable for up to 2 guests, the Wailea holiday home offers… More

From US$ 198 Book Now

Gorgeous Oceanfront Kihei Condo W/ Balcony!

2994 S Kihei Rd Unit 301, Wailea (Maui), United States Show map

Enjoying a beachfront location around 5 minutes' walk from 5 Palms, the 2-bedroom Gorgeous Oceanfront Kihei Condo W/ Balcony! Wailea villa boasts a wellness area for guests' relaxation. Located in… More

From US$ 521 Book Now

Hale Hui Kai 313, Direct Ocean Front, Split Ac

2994 S Kihei Rd, Wailea (Maui), United States Show map

Located within 5 minutes' walk of Surf Shack, the 2-bedroom Hale Hui Kai 313, Direct Ocean Front, Split Ac Villa Wailea gives easy access to various tourist attractions in the area. Offering… More

From US$ 963 Book Now

Kihei Akahi D113

2531 South Kihei Rd., Unit #D113, Wailea (Maui), United States Show map

The 1-bedroom Kihei Akahi D113 Villa Wailea is located only 1.1 km from Moana Estates Park and allows guests to enjoy windsurfing, snorkelling, and hiking. This Wailea holiday home can accommodate up… More

From US$ 223 Book Now

Upscale Wailea! 2-2 With Ocean View

10 Wailea Ekolu Place #103, Wailea (Maui), United States Show map

Offering a terrace overlooking the sea, the 2-bedroom Upscale Wailea! 2-2 With Ocean View Villa is located about 5 minutes' walk from Wailea Old Blue Clubhouse. The accommodation features… More

From US$ 458 Book Now

Kamaole Sands 3-101

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

Located merely 0.7 km from Kihei Coastal Trail, Kamaole Sands 3-101 Wailea villa provides access to various tourist attractions in the vicinity. More

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Kihei Akahi C616 - Akh C616 Cozy Condo Near Beach W Ocean View P

2531 South Kihei Road, Unit C616, Wailea (Maui), United States Show map

Staying at the 1-bedroom Kihei Akahi C616 - Akh C616 Cozy Condo Near Beach W Ocean View P Wailea villa, guests can visit Kamaole Beach Park 2, which is only 500 metres away. More

From US$ 259 Book Now

New Listing! - Wailea Ekahi 39E - Luxurious Ocean View Condo, Split Ac!

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

Located merely 1.5 km from Makena State Park, the 1-bedroom New Listing! - Wailea Ekahi 39E - Luxurious Ocean View Condo, Split Ac! villa provides access to various tourist attractions in the… More

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Maui Kamaole E202 - Mko E202 Remodeled 2Bd Retreat Wac Pool Near

2777 South Kihei Road, Unit E202, Wailea (Maui), United States Show map

Staying at the 2-bedroom Maui Kamaole E202 - Mko E202 Remodeled 2Bd Retreat Wac Pool Near Villa Wailea, guests can visit the Keawakapu Beach, which is only 0.8 km away. The Wailea holiday home… More

From US$ 847 Book Now

Kihei Akahi D402 - Akh D402 2Bd Condo Across Beach Ocean View Ac

2531 South Kihei Road, Unit D402, Wailea (Maui), United States Show map

Featuring an outdoor swimming pool, Kihei Akahi D402 - Akh D402 2Bd Condo Across Beach Ocean View Ac Wailea villa is suitable for up to 6 people and is located 2 km from the Kihei Kalama Village. More

From US$ 398 Book Now

Mbh109 Charming & Updated Maui Banyan 2 Bath

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

Located merely 5 minutes' walk from Kamaole Beach Park 2, the 1-bedroom Mbh109 Charming & Updated Maui Banyan 2 Bath Wailea villa provides guests with a hot tub. This property features opportunities… More

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Kamaole Sands 5-315

2695 South Kihei Rd., Unit #5-315, Wailea (Maui), United States Show map

During the stay at Kamaole Sands 5-315 Wailea villa, guests can indulge in snorkelling, hiking, and horseback riding or visit the Keawakapu Beach, located a 14-minute walk away. Offering horse riding… More

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Kihei Akahi C302 - Akh C302 Spacious 2Bd Condo W Ocean Breeze Ac

2531 South Kihei Road Unit C302, Wailea (Maui), United States Show map

The 2-bedroom Kihei Akahi C302 - Akh C302 Spacious 2Bd Condo W Ocean Breeze Ac Wailea villa, located merely 5 minutes' walk from Maui Fine Art Gallery, can host up to 6 guests. More

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Kamaole Sands 7-100

2695 South Kihei Rd., Unit #7-100, Wailea (Maui), United States Show map

Featuring horse riding tours to make your visit more entertaining, Kamaole Sands 7-100 Wailea villa is 25 minutes' walk from A Promise Made in Paradise. Guests can enjoy windsurfing, snorkelling, and… More

From US$ 318 Book Now

Wailea Sunset Condo - Ekolu #607

10 Wailea Ekolu Place Building 6, Wailea (Maui), United States Show map

Wailea Sunset Condo - Ekolu #607 villa enjoys its location about a 25-minute walk from Wailea Beach and overlooks the sea. The 1-bedroom holiday home features opportunities for hiking, lawn tennis… More

From US$ 283 Book Now

Tropical Paradise 1-Bed 2-Bath Oasis At The Pool

South Kihei Road 2777, Wailea (Maui), United States Show map

Tropical Paradise 1-Bed 2-Bath Oasis At The Pool Wailea villa is located 19 minutes' walk from Kihei Coastal Trail and invites guests to join windsurfing, snorkelling, and cycling. Featuring a… More

From US$ 353 Book Now

Summer Sale! Penthouse Ocean Views, Spacious Layout, Beautiful Renovation, Ac!

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

Situated a mere 6 minutes' walk from the Kamaole Beach Park III, the 2-bedroom Summer Sale! Penthouse Ocean Views, Spacious Layout, Beautiful Renovation, Ac! Wailea villa is ideal for up to 6 guests. More

From US$ 491 Book Now

Mbp103Ii Beautiful Modern Remodeled Maui Banyan Suite

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

Mbp103Ii Beautiful Modern Remodeled Maui Banyan Suite Wailea villa provides an opportunity to stay a 6-minute walk from Kamaole Beach Park 2 and offers a Jacuzzi, perfect for decompressing. Located 2… More

From US$ 330 Book Now

Kihei Retreat W/ Kamaole Sands Resort Amenities!

2695 S Kihei Rd Unit #5406, Wailea (Maui), United States Show map

Offering an outdoor swimming pool, the 2-bedroom Kihei Retreat W/ Kamaole Sands Resort Amenities! Wailea villa is situated approximately a 5-minute walk from the Kamaole Beach Park III and can… More

From US$ 501 Book Now

Kihei Akahi D316

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

Situated only 150 m from Kamaole Beach Park 2, Kihei Akahi D316 Villa Wailea provides access to numerous tourist attractions in the area. More

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Maui Kamaole C 202

2777 South Kihei Rd., Unit #C 202, Wailea (Maui), United States Show map

The 2-bedroom Maui Kamaole C 202 Villa Wailea is situated within 5 minutes' walk of Kihei Coastal Trail, featuring such comforts as Wi-Fi and private parking. Offering snorkelling, hiking, and… More

From US$ 546 Book Now

Kamaole Sands 3-303

2695 South Kihei Rd., Unit# 3-303, Wailea (Maui), United States Show map

The 1-bedroom Kamaole Sands 3-303 Wailea villa accommodates up to 4 guests and offers proximity to the Kamaole Beach Park III, located only 5 minutes' walk away. This Wailea holiday home features… More

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Upscale & Luxurious Oceanview Resort Vistas

South Kihei Road 777, Wailea (Maui), United States Show map

The 2-bedroom Upscale & Luxurious Oceanview Resort Vistas Wailea villa, located around 5 minutes' walk from the Redline Rafting, can host up to 6 guests. Offering a Jacuzzi, this Wailea holiday home… More

From US$ 1297 Book Now

Palms At Wailea 2108 - Paw 2108 Remodeled Wailea Condo W Ac Infi

3200 Wailea Alanui Drive, Unit 2108, Wailea (Maui), United States Show map

Featuring an outdoor swimming pool, the 1-bedroom Palms At Wailea 2108 - Paw 2108 Remodeled Wailea Condo W Ac Infi villa is suitable for up to 4 people and is located nearly a 20-minute walk from… More

From US$ 730 Book Now

Palms At Wailea #905

3200 Wailea Alanui Dr., Unit #905, Wailea (Maui), United States Show map

The 2-bedroom Palms At Wailea #905 Villa is located around 25 minutes' walk from the Redline Rafting and provides snorkelling, hiking, and horse riding for active guests. Offering horse riding tours,… More

From US$ 465 Book Now

Kihei Akahi C210

2531 South Kihei Rd., Unit #C210, Wailea (Maui), United States Show map

The 1-bedroom Kihei Akahi C210 Villa Wailea accommodates up to 4 guests and offers proximity to the sandy Kamaole Beach Park II, located about a 5-minute walk away. This holiday home features… More

From US$ 368 Book Now

Maui Kamaole J 108

2777 South Kihei Rd., Unit #J 108, Wailea (Maui), United States Show map

Offering an outdoor swimming pool, the 1-bedroom Maui Kamaole J 108 Villa Wailea is situated only an 8-minute walk from the Kamaole Beach Park III and can accommodate up to 4 guests. This villa… More

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Maui Parkshore 414, Top Floor, Amazing Ocean Views

2653 S Kihei Rd Unit 414, Wailea (Maui), United States Show map

Maui Parkshore 414, Top Floor, Amazing Ocean Views Wailea villa is located only 550 m from the Kihei Boat Landing, giving access to various tourist spots nearby. More

From US$ 479 Book Now

Kamaole Sands 4-306 - New Kitchen & Bathrooms, Ac!

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

Suitable for 4 guests, the 1-bedroom Kamaole Sands 4-306 - New Kitchen & Bathrooms, Ac! Wailea villa is located nearly a 5-minute walk from the Kamaole Beach Park III and provides a hot tub for a… More

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Kihei Akahi Resort - Unit D114

2531 South Kihei Road, Unit D114, Wailea (Maui), United States Show map

The 1-bedroom Kihei Akahi Resort - Unit D114 Wailea villa accommodates up to 4 guests and offers a prime location only 9 minutes' stroll from shopping venues such as Maui's World Gallery. Located 2.8… More

From US$ 527 Book Now

Kamaole Sands 10-406

2695 South Kihei Road, Unit #10-406, Wailea (Maui), United States Show map

At the 2-bedroom Kamaole Sands 10-406 Wailea villa, guests can enjoy windsurfing, snorkelling, and horse riding as well as a location approximately 5 minutes' walk from the Kamaole Beach Park III. More

From US$ 590 Book Now

Grand Champions Villas #184

155 Wailea Ike Place, Unit #184, Wailea (Maui), United States Show map

Grand Champions Villas #184 Wailea is located a 5-minute walk from the Wailea Town Center, and offers guided tour service to provide an entertaining experience. The 2-bedroom villa features… More

From US$ 669 Book Now

Kamaole Sands 5-316

2695 S. Kihei Rd., Unit #5-316, Wailea (Maui), United States Show map

Along with proximity to the Kamaole Beach Park III, just 250 metres away, the 2-bedroom Kamaole Sands 5-316 Wailea villa offers opportunities for snorkelling, hiking, and ping-pong in the area. More

From US$ 516 Book Now

Ks507 Spectacular Oceanfront With Split Ac Wailea

2936 South Kihei Road, Wailea (Maui), United States Show map

Located about a 5-minute walk from the Kihei Boat Ramp, the 1-bedroom Ks507 Spectacular Oceanfront With Split Ac Wailea Villa invites guests to enjoy a Jacuzzi. This accommodation features… More

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Elua 406

3600 Wailea Alanui, #406, Wailea (Maui), United States Show map

The 2-bedroom Elua 406 Villa Wailea accommodates up to 6 guests and offers proximity to Makena State Park, located just a 7-minute walk away. This holiday home features opportunities for snorkelling,… More

From US$ 1026 Book Now

Maui Kamaole - Nohea -Front Row - Huge Ocean Views

2777 South Kihei Road, Wailea (Maui), United States Show map

Maui Kamaole - Nohea -Front Row - Huge Ocean Views Villa Wailea, located a 5-minute walk from Kihei Coastal Trail, can host up to 6 guests. More

From US$ 712 Book Now

Ekahi 8E

3300 Wailea Alanui, 8E, Wailea (Maui), United States Show map

During the stay at Ekahi 8E Villa Wailea, guests can indulge in diving, canoeing, and hiking or visit the Half - mile - long Ulua Sandy Beach Park, located 20 minutes' walk away. Offering horse… More

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Kamaole Sands 10-414

2695 South Kihei Rd. Unit 10-414, Wailea (Maui), United States Show map

The 3-bedroom Kamaole Sands 10-414 Wailea villa hosts up to 6 guests and provides proximity to the Kamaole Beach Park III, situated merely 250 metres away. The property features opportunities for… More

From US$ 868 Book Now

Kamaole Sands 10-210

2695 South Kihei Rd., Unit #10-210, Wailea (Maui), United States Show map

Situated merely a 5-minute stroll from the Kamaole Beach Park III, the 1-bedroom Kamaole Sands 10-210 Wailea villa is suitable for 4 guests and provides an outdoor swimming pool to relax in. Located… More

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New Bathrooms! Spectacular Penthouse At Oceanview

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

Boasting a Jacuzzi, the 3-bedroom New Bathrooms! Spectacular Penthouse At Oceanview Wailea villa is located approximately a 5-minute walk from the Kamaole Beach Park III and can accommodate 8 guests.… More

From US$ 1196 Book Now

Kihei Akahi Resort - Unit C313

2531 South Kihei Road, Unit C313, Wailea (Maui), United States Show map

Located nearly 5 minutes on foot from the sandy Kamaole Beach Park II, the 1-bedroom Kihei Akahi Resort - Unit C313 Wailea villa provides an outdoor swimming pool as well as snorkelling to diversify… More

From US$ 308 Book Now

Kihei Akahi Resort - Unit C618

2531 South Kihei Road, Unit C618, Wailea (Maui), United States Show map

Situated approximately a 5-minute walk from the sandy Kamaole Beach Park II, the 1-bedroom Kihei Akahi Resort - Unit C618 Wailea villa is ideal for up to 3 guests. More

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Wailea Ekahi 17D - Wek 17D Wailea Retreat W Ocean View Pool Ac

3300 Wailea Alanui Drive, Unit 17D, Wailea (Maui), United States Show map

Wailea Ekahi 17D - Wek 17D Wailea Retreat W Ocean View Pool Ac Villa is located only 1.9 km from the Sandy Wailea Public Beach and provides an outdoor swimming pool, ensuring a relaxing stay. More

From US$ 272 Book Now

Wailea Elua Village 803, Ocean Views, Modern Reno

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

Along with proximity to Makena State Park, located only 0.7 km away, the 3-bedroom Wailea Elua Village 803, Ocean Views, Modern Reno villa provides access to a fitness room. Hosting up to 6 guests… More

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Kamaole Sands 6-401

2695 South Kihei Rd., Unit #6-401, Wailea (Maui), United States Show map

Situated about a 5-minute stroll from the Kamaole Beach Park III, the 2-bedroom Kamaole Sands 6-401 Wailea villa ensures a great leisure experience by offering windsurfing, snorkelling, and hiking. More

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