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2026-11-03
2026-11-04
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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 heated pool, the 1-bedroom Enjoy Your Oceanside Dream At Kihei Surfside Wailea villa is located nearly a 5-minute walk from Redline Rafting and is ideal for up to 4 guests. This… More

From US$ 379 Book Now

Wailea Grand Champions 87

Wailea (Maui), United States Show map

To enjoy your vacation in Wailea, stay at the 1-bedroom Wailea Grand Champions 87 Apartment, which is only 1.8 km from the Sandy Wailea Public Beach and a mere 11 minutes on foot from Enchantress… More

From US$ 344 Book Now

Luxury Condo At Kameole Beach T106

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

Welcoming guests with a Jacuzzi, the 1-bedroom Luxury Condo At Kameole Beach T106 Wailea villa is located merely 6 minutes' walk from the sandy Kamaole Beach Park II and can host up to 4 guests. This… 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 provides easy access to various city attractions, such as Surf Shack, situated merely 6 minutes' walk away. More

From US$ 356 Book Now

Kihei Condo W/ Resort Amenities: Walk To The Beach

Wailea (Maui), United States Show map

Located just 400 metres from Kamaole Beach Park III, the 1-bedroom Kihei Condo W/ Resort Amenities: Walk To The Beach Wailea villa offers guests to relax in a Jacuzzi, or enjoy snorkelling. The… More

From US$ 375 Book Now

Gorgeous Oceanfront Kihei Condo W/ Balcony!

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

Providing guests with spa therapy and a terrace to ensure a memorable stay, the 2-bedroom Gorgeous Oceanfront Kihei Condo W/ Balcony! Wailea villa is within easy reach of Keawakapu Beach. Located… More

From US$ 521 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 easily reach Kamaole Beach Park 2, located just 300 metres away. Providing opportunities for snorkelling, hiking, and… More

From US$ 198 Book Now

8-403 Kamaole Sands

2695 S Kihei Rd #8-403, Wailea (Maui), United States Show map

Suitable for 6 guests, 8-403 Kamaole Sands Wailea villa is located merely 7 minutes' walk from Kamaole Beach Park III and provides a Jacuzzi for a relaxing stay. Located 3.1 km from the Sandy Wailea… More

From US$ 598 Book Now

Oceanfront Hale Hui Kai 313 Large Lanai, Ac, Incredible Views On Keawakapu Beach

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

The 2-bedroom Oceanfront Hale Hui Kai 313 Large Lanai, Ac, Incredible Views On Keawakapu Beach Wailea villa accommodates up to 4 guests and offers proximity to Keawakapu Beach, located only a 5… More

From US$ 963 Book Now

Kihei Akahi D113

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

Along with proximity to the sandy Kamaole Beach Park II, merely 200 metres away, the 1-bedroom Kihei Akahi D113 Villa Wailea offers opportunities for windsurfing, snorkelling, and hiking in the area.… More

From US$ 223 Book Now

Wailea Haven - Updated With Stunning Ocean View

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

Featuring an outdoor swimming pool, the 2-bedroom Wailea Haven - Updated With Stunning Ocean View Wailea villa is located around 5 minutes' walk from Wailea Old Blue Clubhouse and is suitable for up… More

From US$ 458 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 located nearly a 5-minute walk from Kamaole Beach Park III and is ideal for up to 6… More

From US$ 501 Book Now

Discover Wailea Ekahi 39E - Breathtaking Ocean Views, Renovated, Wi-Fi, Split Ac

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

Hosting up to 4 guests, the 1-bedroom Discover Wailea Ekahi 39E - Breathtaking Ocean Views, Renovated, Wi-Fi, Split Ac villa offers a beachfront location approximately 25 minutes' walk from sports… More

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Kamaole Sands 1-304

Wailea (Maui), United States Show map

To enjoy your vacation in Wailea, stay at the 1-bedroom Kamaole Sands 1-304 Wailea apartment, which is 2.3 km from A Promise Made in Paradise and just an 8-minute stroll from Kihei Boat Landing. More

From US$ 172 Book Now

Wailea Ekolu Village 203

10 Wailea Ekolu Pl Unit 203, Wailea (Maui), United States Show map

Offering a location within a 10-minute drive of Kihei Boat Ramp, the 100 m² Wailea Ekolu Village 203 apartment also gives access to a variety of tourist spots in the vicinity. More

From US$ 333 Book Now

Kamaole Sands 1-403 - Ultimate Getaway! Spacious 2/2 With Split Ac, Large Lanai

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

Kamaole Sands 1-403 - Ultimate Getaway! Spacious 2/2 With Split Ac, Large Lanai Wailea villa enjoys a prime location, a 10-minute walk from Kihei Boat Ramp, and offers guests to unwind in a Jacuzzi. More

From US$ 297 Book Now

Mbh109 Charming & Updated Maui Banyan 2 Bath

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

Located only a 7-minute walk from Kamaole Beach Park III, the 1-bedroom Mbh109 Charming & Updated Maui Banyan 2 Bath Wailea villa boasts a swimming pool and can accommodate up to 4. The holiday home… 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 Keawakapu Beach, located a 14-minute walk away. Offering horse riding… More

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Wailea Sunset Condo - Ekolu #607

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

Boasting a prime location about a 20-minute walk from Lily Pond, Wailea Sunset Condo - Ekolu #607 villa invites guests to enjoy hiking, lawn tennis, and table tennis. Located within reach of Wailea… 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

Offering a Jacuzzi, Tropical Paradise 1-Bed 2-Bath Oasis At The Pool Wailea villa is located a 19-minute walk from Kihei Coastal Trail. Offering windsurfing, snorkelling, and cycling, the 1-bedroom… 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

Offering a location about 25 minutes' walk from Mokapu Beach, the 2-bedroom Summer Sale! Penthouse Ocean Views, Spacious Layout, Beautiful Renovation, Ac! Wailea villa gives access to various tourist… More

From US$ 491 Book Now

Mbp103Ii Beautiful Modern Remodeled Maui Banyan Suite

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

Overlooking the mountain, Mbp103Ii Beautiful Modern Remodeled Maui Banyan Suite Wailea villa enjoys a convenient setting a 6-minute walk from Kamaole Beach Park 2. Located 2.5 km from Mokapu Beach… More

From US$ 330 Book Now

Mbp103S Beautiful Modern Remodeled Maui Banyan Studio

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

Mbp103S Beautiful Modern Remodeled Maui Banyan Studio Wailea villa is situated 500 metres from the sandy Kamaole Beach Park II and provides a Jacuzzi for a relaxing stay. The 1-bedroom holiday home… More

From US$ 306 Book Now

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$ 197 Book Now

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 Keawakapu Beach, which is only 0.8 km away. More

From US$ 847 Book Now

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 just 5 minutes' walk from Rainbow Mall Kihei, can host up to 6 guests. More

From US$ 281 Book Now

Grand Champions 179 - Gc 179 Last Minute Deal At 3Bd Wailea Cond

155 Wailea Ike Place, Unit 179, Wailea (Maui), United States Show map

The 3-bedroom Grand Champions 179 - Gc 179 Last Minute Deal At 3Bd Wailea Cond villa offers proximity to such city sites as Wailea Town Center, located nearly a 5-minute walk away. More

From US$ 509 Book Now

Maui Kamaole C 202

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

Nestled within 5 minutes' walk of Kihei Coastal Trail, the 2-bedroom Maui Kamaole C 202 Villa Wailea comes with barbecue and a golf course for added enjoyment. Located 2.7 km from Lava Fields, this… More

From US$ 546 Book Now

Kamaole Sands 3-303

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

Situated nearly 5 minutes' walk from Kamaole Beach Park III, the 1-bedroom Kamaole Sands 3-303 Wailea villa entices guests with snorkelling, hiking, and table tennis in the area. Providing guests… 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 is situated around 5 minutes' walk from Redline Rafting and offers guests to relax with a Jacuzzi. Featuring a swimming pool… More

From US$ 1297 Book Now

Elua 2001

3600 Wailea Alanui, #2001, Wailea (Maui), United States Show map

The 2-bedroom Elua 2001 Villa Wailea is located nearly 25 minutes' walk from Redline Rafting and allows guests to enjoy diving, canyoning, and cycling. Offering a heated pool, this Wailea villa… More

From US$ 1320 Book Now

Kihei Akahi C210

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

Offering an outdoor swimming pool, the 1-bedroom Kihei Akahi C210 Villa Wailea is located approximately a 5-minute walk from the sandy Kamaole Beach Park II and is ideal for up to 4 guests. This… More

From US$ 368 Book Now

Maui Kamaole J 108

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

The 1-bedroom Maui Kamaole J 108 Villa Wailea is located about a 10-minute walk from Keawakapu Beach and provides an outdoor swimming pool, ensuring a relaxing stay. Offering horse riding tours, this… More

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Kamaole Sands 4-306 - Steps To Kamaole III Beach - Split Ac + Pool + King Bed

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

Welcoming guests with a hot tub, the 1-bedroom Kamaole Sands 4-306 - Steps To Kamaole III Beach - Split Ac + Pool + King Bed Wailea villa is located about 5 minutes' walk from Kamaole Beach Park III… More

Book Now

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

Located approximately 25 minutes' walk from Foodland Kihei, the 2-bedroom Kamaole Sands 10-406 Wailea villa has an outdoor swimming pool and is ideal for up to 6 guests. Guests can enjoy windsurfing,… More

From US$ 590 Book Now

Grand Champions Villas #184

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

During the stay at Grand Champions Villas #184 Wailea, guests can indulge in windsurfing, snorkelling, and hiking or visit the Sandy Wailea Public Beach, located a 20-minute walk away. Offering horse… More

From US$ 669 Book Now

Kamaole Sands 7-100

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

Kamaole Sands 7-100 Wailea villa is located 25 minutes' walk from A Promise Made in Paradise and invites guests to join windsurfing, snorkelling, and horseback riding. Offering horse riding tours… More

From US$ 274 Book Now

Kamaole Sands 5-316

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

Situated around 5 minutes on foot from Kamaole Beach Park III, the 2-bedroom Kamaole Sands 5-316 Wailea villa is suitable for 6 guests and provides an outdoor swimming pool to relax in. The Wailea… More

From US$ 516 Book Now

Maui Kamaole - Nohea -Front Row - Huge Ocean Views

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

Overlooking the ocean, Maui Kamaole - Nohea -Front Row - Huge Ocean Views Villa Wailea enjoys a convenient setting a 5-minute walk from Kihei Coastal Trail. Located a short way from Redline Rafting… More

From US$ 712 Book Now

Steps To Beach | King Bed + Resort Amenities

2575 South Kihei Road Unit P207A, Wailea (Maui), United States Show map

Steps To Beach | King Bed + Resort Amenities Wailea villa is situated only a 6-minute walk from Kamaole Beach Park 2, featuring such comforts as Wi-Fi and a car park. Staying at this accommodation… More

From US$ 208 Book Now

Kamaole Sands 10-414

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

Situated about 5 minutes on foot from Kamaole Beach Park III, the 3-bedroom Kamaole Sands 10-414 Wailea villa is suitable for 6 guests and provides an outdoor swimming pool to relax in. The property… More

From US$ 868 Book Now

New Bathrooms! Spectacular Penthouse At Oceanview

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

Featuring a swimming pool, the 3-bedroom New Bathrooms! Spectacular Penthouse At Oceanview Wailea villa is located nearly a 5-minute walk from Blue Water Rafting and is suitable for up to 8 guests. More

From US$ 1196 Book Now

Kihei Akahi Resort - Unit C618

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

Offering an outdoor swimming pool, the 1-bedroom Kihei Akahi Resort - Unit C618 Wailea villa is located nearly a 5-minute walk from the sandy Kamaole Beach Park II and is ideal for up to 3 guests. More

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Kamaole Sands 6-401

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

Located around a 5-minute stroll from Kamaole Beach Park III, the 2-bedroom Kamaole Sands 6-401 Wailea villa provides an outdoor swimming pool as well as windsurfing, snorkelling, and hiking to… More

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Maui Parkshore 110

Wailea (Maui), United States Show map

Located in the Kamaole Beach district, the 83 m² Maui Parkshore 110 Wailea apartment is approximately a 5-minute walk from Kamaole Beach Park III and 2.8 km from Wailea Tennis Club, which is… More

From US$ 209 Book Now

Kihei Akahi D308

2531 South Kihei Rd., Unit #D308, Wailea (Maui), United States Show map

Situated nearly a 5-minute walk from the sandy Kamaole Beach Park II, the 1-bedroom Kihei Akahi D308 Villa Wailea is ideal for up to 4 guests. The holiday home features opportunities for snorkelling,… More

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Kamaole Sands 3-405

2695 South Kihei Rd., Unit #3-405, Wailea (Maui), United States Show map

The 2-bedroom Kamaole Sands 3-405 Wailea villa is nestled about a 5-minute walk from Kamaole Beach Park III and can accommodate up to 6 guests. Located within reach of Keawakapu Beach, the holiday… More

From US$ 525 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

Kihei Surfside 306 - Kss 306 Updated Beachfront 1Bd W Ocean View Wailea villa is nestled just a 5-minute walk from Keawakapu Beach and can accommodate up to 4 guests. More

From US$ 786 Book Now

Wailea Ekahi 40E - Wek 40E Dream Getaway W Ac Pools Beaches Golf

3300 Wailea Alanui Drive, Unit 40E, Wailea (Maui), United States Show map

Situated nearly a 20-minute walk from Redline Rafting, the 1-bedroom Wailea Ekahi 40E - Wek 40E Dream Getaway W Ac Pools Beaches Golf villa provides access to numerous tourist attractions in the area. More

Book Now