Skip to main content

Holiday Rentals in Wailea

Find the holiday rentals that appeal to you the most

The best holiday rentals in Wailea

Check out our pick of great holiday rentals in Wailea

Most booked holiday rentals in Wailea and surroundings in the past month

See all

Popular with guests booking holiday rentals in Wailea

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 22 reviews

Popular with guests booking holiday rentals in Wailea

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 66 reviews

Popular with guests booking holiday rentals in Wailea

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 2 reviews

Popular with guests booking holiday rentals in Wailea

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 40 reviews

Popular with guests booking holiday rentals in Wailea

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 43 reviews

Popular with guests booking holiday rentals in Wailea

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 32 reviews

Popular with guests booking holiday rentals in Wailea

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 24 reviews

Popular with guests booking holiday rentals in Wailea

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 346 reviews

Popular with guests booking holiday rentals in Wailea

Scored out of 10, guest rating 7.9
Good - What previous guests thought, 155 reviews

Popular with guests booking holiday rentals in Wailea

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 450 reviews

Enjoy breakfast in Wailea and nearby

Koa Resort 4I

Wailea
Breakfast options
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 3 reviews

Located in Wailea, less than 1 km from Ulua Beach and 3 km from Wailea Emerald Course, Koa Resort 4I offers air conditioning.

Elua 2001

Wailea
Breakfast options
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 2 reviews

Boasting air-conditioned accommodation with a patio, Elua 2001 is situated in Wailea. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

Elua 406

Wailea
Breakfast options
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 2 reviews

Set in Wailea, less than 1 km from Ulua Beach and 2.8 km from Wailea Emerald Course, Elua 406 offers an outdoor swimming pool and air conditioning.

Elua 2011

Wailea
Breakfast options

Set in Wailea, less than 1 km from Ulua Beach and 2.7 km from Wailea Emerald Course, Elua 2011 offers pool with a view and air conditioning.

Grand Champions 108

Wailea
Breakfast options

Featuring an outdoor pool and sea views, Grand Champions 108 is set in Wailea. The air-conditioned accommodation is 1.6 km from Ulua Beach.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 2 reviews

With garden views, Grand Champions by KBM Resorts is located in Wailea and has a restaurant, a lift, bar, garden, outdoor pool and children's playground.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Set in Wailea, 1.6 km from Ulua Beach and 2.3 km from Wailea Emerald Course, Grand Champions 124 · GC 124 3BD Wailea Condo wAC Pool Hot Tub offers air conditioning.

Grand Champions 8

Wailea
Breakfast options
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 3 reviews

Located in Wailea, 1.5 km from Ulua Beach and 2.3 km from Wailea Emerald Course, Grand Champions 8 offers air conditioning.

Holiday Rentals with swimming pools in Wailea and nearby

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 8 reviews

Boasting air-conditioned accommodation with a patio, BeachFront Kihei Kai Nani - Maui Vista Deluxe Condos is situated in Kihei.

From US$584 per night
Scored out of 10, guest rating 7.9
Good - What previous guests thought, 14 reviews

Set about 200 metres from Kamaole Beach, Kihei Kai Nani 161 offers accommodation with an outdoor pool and free WiFi.

Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 10 reviews

Situated about 200 metres from Kamaole Beach, Kihei Kai Nani 169 offers accommodation with an outdoor pool and free WiFi.

From US$554.07 per night
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 6 reviews

Set 500 metres from Kamaole Beach, Maui Vista 1121 offers accommodation in Kihei with access to an outdoor pool, free WiFi and a lift.

From US$591.75 per night
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 16 reviews

Located about 500 metres from Kamaole Beach, Maui Vista 3101 offers accommodation with an outdoor pool and free WiFi.

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 7 reviews

Situated in Kihei, 500 metres from Kamaole Beach and 7.1 km from Wailea Emerald Course, Maui Vista 1422 offers air conditioning.

Scored out of 10, guest rating 3.8
Poor - What previous guests thought, 4 reviews

Situated 500 metres from Kamaole Beach, Maui Vista 1114 features accommodation in Kihei with access to an outdoor pool, free WiFi and a lift.

From US$565.87 per night
Scored out of 10, guest rating 7.3
Good - What previous guests thought, 9 reviews

Located 500 metres from Kamaole Beach, Maui Vista 2207 provides accommodation in Kihei with access to an outdoor pool, free WiFi and a lift.

From US$580.25 per night

These holiday rentals in Wailea and nearby have options with free cancellation

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 31 reviews

Boasting air-conditioned accommodation with a heated pool, 1BD Condo with Ocean Views: 40% OFF, Self Check-In is situated in Kihei.

Maui Diver's Dream at Kihei Bay Surf

Kihei
Free cancellation options available
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 42 reviews

Boasting air-conditioned accommodation with a private pool, mountain view and a balcony, Maui Diver's Dream at Kihei Bay Surf is set in Kihei.

Nona Lani Cottages

Kihei
Free cancellation options available
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 104 reviews

Located in Kihei and only 80 metres from Mai Poina Beach, Nona Lani Cottages provides accommodation with sea views, free WiFi and free private parking.

Wailea Grand Champions 87

Wailea
Free cancellation options available
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 40 reviews

Featuring air-conditioned accommodation with a balcony, Wailea Grand Champions 87 is set in Wailea. With mountain views, this accommodation offers a patio.

Grand Champions 101

Wailea
Free cancellation options available
Scored out of 10, guest rating 7.3
Good - What previous guests thought, 3 reviews

Set in Wailea, 1.6 km from Ulua Beach and 2.3 km from Wailea Emerald Course, Grand Champions 101 offers air conditioning.

WAILEA GRAND CHAMPION, #142 condo

Wailea
Free cancellation options available

WAILEA GRAND CHAMPION, #142 condo is a property with a heated pool, situated in Wailea, within just 1.7 km of Wailea Beach and 1.9 km of Mokapu Beach.

WAILEA GRAND CHAMPION, #148 condo

Wailea
Free cancellation options available

Featuring an outdoor pool and a hot tub, WAILEA GRAND CHAMPION, #148 condo is located in Wailea, 2.3 km from Wailea Emerald Course and 31 km from Iao Valley State Park.

Grand Champions 32 condo

Wailea
Free cancellation options available

Set in Wailea in the Hawaii region, with Wailea Blue Course nearby, Grand Champions 32 condo provides accommodation with access to a fitness room.

Highly rated holiday rentals in Wailea and nearby

Maui Vista 1411

Kihei
8.0+ review score
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 14 reviews

Situated in Kihei, 500 metres from Kamaole Beach, Maui Vista 1411 features accommodation with a spa and wellness centre, free WiFi, a 24-hour front desk, and a lift.

Maui Sunset B215

Kihei
8.0+ review score
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 10 reviews

Set in Kihei, 500 metres from Waipuilani Beach, Maui Sunset B215 offers accommodation with an outdoor swimming pool, free WiFi, a 24-hour front desk, and a lift.

From US$757.14 per night

Menehune Shores 309

Kihei
8.0+ review score
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 7 reviews

Located in Kihei, a few steps from Waipuilani Beach and 12 km from Wailea Emerald Course, Menehune Shores 309 offers free WiFi, ski-to-door access and air conditioning.

Maui Tranquility

Kihei
8.0+ review score
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 40 reviews

Boasting air-conditioned accommodation with a patio, Maui Tranquility is situated in Kihei. This apartment features a private pool, a garden, barbecue facilities, free WiFi and free private parking.

From US$382.55 per night

Kihei Bay Surf 233

Kihei
8.0+ review score
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 17 reviews

Set about 200 metres from Kalepolepo Beach, Kihei Bay Surf 233 offers accommodation with an outdoor pool and free WiFi.

From US$565.87 per night

Kihei Bay Surf 117

Kihei
8.0+ review score
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 19 reviews

Featuring a hot tub, Kihei Bay Surf 117 is set in Kihei. The property is around 12 km from Wailea Emerald Course, 21 km from Iao Valley State Park and 34 km from Lahaina Boat Harbor.

From US$565.87 per night
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 33 reviews

Tiki Tiki - Gorgeous Boho Beach Hideaway!, a property with a terrace, is located in Wailea, 2.2 km from Wailea Emerald Course, 31 km from Iao Valley State Park, as well as 46 km from Lahaina Boat...

Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 23 reviews

Aloha Moon - A Chic and Dreamy Modern Tropical Hideaway!, a property with a terrace and barbecue facilities, is set in Wailea, 31 km from Iao Valley State Park, 44 km from Lahaina Boat Harbor, as well...

FAQ about holiday rentals in Wailea