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Holiday Homes in Wailea

Find the holiday homes that appeal to you the most

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The best holiday homes in Wailea

Check out our pick of great holiday homes in Wailea

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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Enjoy Your Oceanside Dream at Kihei Surfside, holiday home in Wailea

The holiday home comes with 1 bedroom, 1 bathroom, bed linen, towels, a flat-screen TV with streaming services, a dining area, a fully equipped kitchen, and a balcony with sea views. The property has an outdoor dining area.

The location was truly spectacular and the hosts were very responsive and attentive. Beautiful views of multiple islands as promised in the description. Condo was fully supplied with everything we needed for a great stay. Hosts also had a great list of activities and restaurant recommendations available.

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9.3
Superb
11 reviews
Price from
US$378.33
per night
Check availability
Wailea Ekolu #607, holiday home in Wailea

Featuring a garden and panoramic ocean views, Wailea Ekolu #607 is a holiday home situated in Wailea in the Maui Region. this unit is a short walking distance from beaches such as Wailea Beach, Ulua Beach Park and Mokapu Beach Park. Free private parking is available on site.

The property is perfectly situated for the most amazing sunsets. The owners have clearly put a lot of thought into providing absolutely everything you'd need to enjoy a self-catering holiday.

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9.1
Superb
10 reviews
Price from
US$567.79
per night
Check availability
Nahenahe Cottage, holiday home in Wailea

The holiday home is fitted with 2 bedrooms, 1 bathroom, bed linen, towels, a TV, a fully equipped kitchen, and a patio with sea views. For added privacy, the accommodation features a private entrance.

Wailea Blue Course is 4 km from the holiday home, while Wailea Gold Course is 4.1 km from the property. The nearest airport is Kahului Airport, 24 km from Nahenahe Cottage.

Was clean, ocean view from back porch beautiful, beds were very comfortable.

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8.8
Fabulous
6 reviews
Price from
US$407.50
per night
Check availability
4-309 Kamaole Sands**Newly Remodeled** Steps to Kamaole 3 Beach!, holiday home in Wailea

Offering sea views, 4-309 Kamaole Sands**Newly Remodeled** Steps to Kamaole 3 Beach! is an accommodation set in Wailea, 200 metres from Kamaole Beach and 1.4 km from Keawakapu Beach. Both free WiFi and parking on-site are accessible at the holiday home free of charge. The property is non-smoking and is situated 1.7 km from Mokapu Beach.

Nice interior and comfortable.

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8.1
Very good
7 reviews
Price from
US$475.14
per night
Check availability
Wailea Grand Champions, holiday home in Wailea

Set within 1.5 km of Ulua Beach and 1.7 km of Wailea Beach, Wailea Grand Champions offers rooms with air conditioning and a private bathroom in Wailea. The property features mountain views and is 1.9 km from Mokapu Beach and 2.2 km from Wailea Emerald Course. When staying at the holiday home, guests can use private entrance.

10 min walk from grocery store, 20 min walk from the beach. Very quiet area. There was a shared pool and BBQ grills in the inner yard. A lot of kitchen gadgets. Parking included.

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8.4
Very good
54 reviews
Price from
US$837.93
per night
Check availability
New Listing! - Wailea Ekahi 39E - Luxurious Ocean View Condo, Split AC!, holiday home in Wailea

The spacious holiday home is equipped with 1 bedroom, a TV with cable channels and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a toaster. The property offers sea views.

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Maui Kamaole K104, holiday home in Wailea

Set in Wailea, 600 metres from Kamaole Beach and less than 1 km from Keawakapu Beach, Maui Kamaole K104 offers air conditioning. The property is around 1.2 km from Mokapu Beach, 5.2 km from Wailea Emerald Course and 29 km from Iao Valley State Park. Lahaina Boat Harbor is 44 km from the holiday home and Whalers Village Shopping Center is 48 km away.

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Price from
US$343.73
per night
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Hale Hui Kai 106 - Newly Renovated, Split AC, holiday home in Wailea

Situated in Wailea, 500 metres from Mokapu Beach and less than 1 km from Kamaole Beach, Hale Hui Kai 106 - Newly Renovated, Split AC offers air conditioning. Housed in a building dating from 1972, this holiday home is 4.5 km from Wailea Emerald Course and 29 km from Iao Valley State Park. Free WiFi is available throughout the property and Keawakapu Beach is a few steps away.

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Price from
US$418.29
per night
Check availability
Haleakala Shores A305, holiday home in Wailea

Haleakala Shores A305 is located in Wailea, 1.3 km from Keawakapu Beach, 1.7 km from Mokapu Beach, as well as 5.5 km from Wailea Emerald Course. It is set a few steps from Kamaole Beach and provides a lift. Iao Valley State Park is 28 km from the holiday home and Lahaina Boat Harbor is 43 km away.

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Price from
US$422.29
per night
Check availability
Maui Paradise Townhouse, holiday home in Wailea

Featuring air-conditioned accommodation with a private pool, mountain view and a patio, Maui Paradise Townhouse is set in Wailea. The property features garden views and is 1.7 km from Ulua Beach and 2 km from Wailea Beach. There is a sun terrace and guests can make use of free WiFi and free private parking.

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Price from
US$1,129.47
per night
Check availability
All holiday homes in Wailea

Looking for a holiday home?

Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.
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Most booked holiday homes in Wailea this month

Enjoy breakfast in Wailea!

  • The Villas at Fairmont Kea Lani
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 3 reviews

    Facing the seafront, The Villas at Fairmont Kea Lani offers 5-star accommodation in Wailea and features a fitness centre, free bikes and garden.

  • Enjoy Your Oceanside Dream at Kihei Surfside
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 11 reviews

    Located in Wailea, 200 metres from Keawakapu Beach and 700 metres from Mokapu Beach, Enjoy Your Oceanside Dream at Kihei Surfside offers a garden and air conditioning.

    La vue et les infrastructures sont à coupé le souffle ! Rien à redire

  • Wailea Ekolu #607
    Breakfast options
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 10 reviews

    Featuring a garden and panoramic ocean views, Wailea Ekolu #607 is a holiday home situated in Wailea in the Maui Region. this unit is a short walking distance from beaches such as Wailea Beach, Ulua...

  • Nahenahe Cottage
    Breakfast options
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 6 reviews

    Set in Wailea, 3 km from Mokapu Beach and 4 km from Wailea Emerald Course, Nahenahe Cottage offers a garden and air conditioning.

    Sehr schön und modern eingerichtet, super schöner Meerblick

  • Wailea Grand Champions
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 54 reviews

    Set within 1.5 km of Ulua Beach and 1.7 km of Wailea Beach, Wailea Grand Champions offers rooms with air conditioning and a private bathroom in Wailea.

    Gute Lage alles sauber, Küche sehr gut ausgestattet

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

    A recently renovated property, New Listing! - Wailea Ekahi 39E - Luxurious Ocean View Condo, Split AC! is located in Wailea near Keawakapu Beach, Mokapu Beach.

  • Maui Kamaole K104
    Breakfast options

    Set in Wailea, 600 metres from Kamaole Beach and less than 1 km from Keawakapu Beach, Maui Kamaole K104 offers air conditioning.

  • Hale Hui Kai 106 - Newly Renovated, Split AC

    Situated in Wailea, 500 metres from Mokapu Beach and less than 1 km from Kamaole Beach, Hale Hui Kai 106 - Newly Renovated, Split AC offers air conditioning.

Save money on holiday homes in Wailea – budget options available!

  • Haleakala Shores A305
    Budget options available

    Haleakala Shores A305 is located in Wailea, 1.3 km from Keawakapu Beach, 1.7 km from Mokapu Beach, as well as 5.5 km from Wailea Emerald Course.

  • Wailea Ekahi 24B
    Budget options available

    Situated in Wailea, 1.5 km from Keawakapu Beach and 1.6 km from Mokapu Beach, Wailea Ekahi 24B offers air conditioning.

  • Kamaole Sands 7307
    Budget options available

    Situated 1.7 km from Mokapu Beach, 5.5 km from Wailea Emerald Course and 28 km from Iao Valley State Park, Kamaole Sands 7307 offers accommodation located in Wailea.

  • Wailea Elua Village 1002
    Budget options available

    Boasting air-conditioned accommodation with a balcony, Wailea Elua Village 1002 is set in Wailea. Guests may go for a swim in the private pool.

  • Kamaole Sands 4413
    Budget options available

    Located in Wailea and only 200 metres from Kamaole Beach, Kamaole Sands 4413 provides accommodation with sea views, free WiFi and free private parking.

  • Haleakala Shores A410
    Budget options available

    Situated in Wailea, a few steps from Kamaole Beach and 1.3 km from Keawakapu Beach, Haleakala Shores A410 offers air conditioning.

  • Maui Parkshore 213
    Budget options available

    Situated in Wailea, 200 metres from Kamaole Beach and 1.3 km from Keawakapu Beach, Maui Parkshore 213 offers air conditioning. It is located 1.7 km from Mokapu Beach and provides a lift.

  • Mana Kai 501
    Budget options available

    Mana Kai 501 is a beachfront property set in Wailea, 300 metres from Keawakapu Beach and 800 metres from Mokapu Beach.

Great access to the city centre! Check these holiday homes in Wailea

  • Elua 2001
    Central location
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    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
    Central location
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Set in Wailea, less than 1 km from Ulua Beach and a 11-minute walk from Wailea Beach, Elua 406 offers air conditioning. This beachfront property offers access to a patio and free WiFi.

  • Grand Champions 101
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Set in Wailea, 1.6 km from Ulua Beach and 1.7 km from Wailea Beach, Grand Champions 101 offers air conditioning.

  • Wailea Elua Village 803, Ocean Views, Modern Reno
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Wailea Elua Village 803, Ocean Views, Modern Reno is a beachfront property located in Wailea, 1.2 km from Wailea Beach and 1.2 km from Ulua Beach.

  • Beautifully remodeled ocean view condo in Wailea WE27B
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Situated in Wailea, 1.5 km from Keawakapu Beach and 1.6 km from Mokapu Beach, Beautifully remodeled ocean view condo in Wailea WE27B features accommodation with free WiFi, air conditioning, an outdoor...

  • Ho'olei Ocean View by Coldwell Banker Island Vacations
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Situated less than 1 km from Wailea Beach, Ho'olei Ocean View by Coldwell Banker Island Vacations offers air-conditioned accommodation with a patio.

  • Palms at Wailea 705 - Beautiful Reno, Split AC
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    A recently renovated property, Palms at Wailea 705 - Beautiful Reno, Split AC is located in Wailea near Mokapu Beach, Keawakapu Beach.

  • Luxurious Home in Wailea
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Located in Wailea and only 3.4 km from Wailea Emerald Course, Luxurious Home in Wailea provides accommodation with mountain views, free WiFi and free private parking.

  • Hale Kamaole
    Central location
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 3 reviews

    Situated in Wailea, 500 metres from Kamaole Beach and less than 1 km from Keawakapu Beach, Hale Kamaole offers air conditioning.

  • Koa Resort 4I
    Central location
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 3 reviews

    Situated 1.2 km from Mokapu Beach, 3 km from Wailea Emerald Course and 31 km from Iao Valley State Park, Koa Resort 4I provides accommodation set in Wailea.

  • Stunning ocean view! 2-2 in the heart of Wailea
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 3 reviews

    Situated in Wailea, near Wailea Beach and Mokapu Beach, Stunning ocean view! 2-2 in the heart of Wailea is a recently renovated property, featuring, an outdoor swimming pool and garden.

  • Wailea Ekolu Village
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 3 reviews

    Offering sea views, Wailea Ekolu Village is an accommodation situated in Wailea, 1.9 km from Wailea Beach and 2.1 km from Mokapu Beach.

  • Grand Champions 55, Beautiful Renovation, Split AC
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1 review

    Offering sea views, Grand Champions 55, Beautiful Renovation, Split AC is an accommodation situated in Wailea, 1.4 km from Ulua Beach and 1.6 km from Wailea Beach.

  • Ho'olei Garden View by Coldwell Banker Island Vacation
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1 review

    Situated 800 metres from Wailea Beach, Ho'olei Garden View by Coldwell Banker Island Vacation offers air-conditioned accommodation with a patio.

  • 126 Hale Kamaole
    Central location
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 11 reviews

    Set in Wailea, 400 metres from Kamaole Beach and less than 1 km from Keawakapu Beach, 126 Hale Kamaole offers air conditioning.

  • Wailea Ekahi Village
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 4 reviews

    Located in Wailea, just 1.5 km from Keawakapu Beach, Wailea Ekahi Village provides beachfront accommodation with free WiFi. The air-conditioned accommodation is 1.6 km from Mokapu Beach.

  • Palms at Wailea 2108
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 2 reviews

    Set in Wailea and only less than 1 km from Keawakapu Beach, Palms at Wailea 2108 offers accommodation with mountain views, free WiFi and free private parking.

  • 4-309 Kamaole Sands**Newly Remodeled** Steps to Kamaole 3 Beach!
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 7 reviews

    Offering sea views, 4-309 Kamaole Sands**Newly Remodeled** Steps to Kamaole 3 Beach! is an accommodation set in Wailea, 200 metres from Kamaole Beach and 1.4 km from Keawakapu Beach.

  • Hale Hui Kai 313, Direct Ocean Front, Split AC
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 1 review

    Hale Hui Kai 313, Direct Ocean Front, Split AC is set in Wailea, 700 metres from Mokapu Beach, less than 1 km from Kamaole Beach, and 4.6 km from Wailea Emerald Course.

  • Wailea Ekahi 21A
    Central location
    7.0
    Scored 7.0
    Good
    Rated good
     · 1 review

    Located 1.8 km from Ulua Beach, 3.4 km from Wailea Emerald Course and 31 km from Iao Valley State Park, Wailea Ekahi 21A offers accommodation situated in Wailea.

  • Top Floor Oceanfront location with great swimming and snorkeling MKM809
    5.0
    Scored 5.0
    Average
    Rated passable
     · 1 review

    Set in Wailea, 300 metres from Keawakapu Beach and 800 metres from Mokapu Beach, Top Floor Oceanfront location with great swimming and snorkeling MKM809 offers air conditioning.

  • Hale Hui Kai 208, Renovated, Ocean View, Split AC
    5.0
    Scored 5.0
    Average
    Rated passable
     · 1 review

    Situated 400 metres from Mokapu Beach, less than 1 km from Kamaole Beach and 4.4 km from Wailea Emerald Course, Hale Hui Kai 208, Renovated, Ocean View, Split AC provides accommodation set in Wailea.

  • Maui Paradise Townhouse

    Featuring air-conditioned accommodation with a private pool, mountain view and a patio, Maui Paradise Townhouse is set in Wailea.

  • Elua 2011
    Central location

    Set in Wailea, less than 1 km from Ulua Beach and a 11-minute walk from Wailea Beach, Elua 2011 offers pool with a view and air conditioning.

  • Grand Champions 144, 3 Bedrooms, Ocean and Golf Views, 2 Pools, Sleeps 6

    Located in Wailea, 1.7 km from Wailea Beach and 1.9 km from Mokapu Beach, Grand Champions 144, 3 Bedrooms, Ocean and Golf Views, 2 Pools, Sleeps 6 offers air conditioning.

  • Grand Champions 163

    Grand Champions 163 is situated in Wailea, 1.9 km from Mokapu Beach, 2.3 km from Wailea Emerald Course, and 31 km from Iao Valley State Park.

  • Grand Champions 124

    Set in Wailea and only 1.6 km from Ulua Beach, Grand Champions 124 offers accommodation with mountain views, free WiFi and free private parking.

  • Grand Champions 179

    Located in Wailea and only 1.6 km from Ulua Beach, Grand Champions 179 provides accommodation with sea views, free WiFi and free private parking.

FAQ about holiday homes in Wailea

Holiday homes that guests love in Wailea

  • Kihei Akahi D108

    Kihei Akahi D108

    Holiday Home in Wailea
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 3 reviews
    The modern & comfortable interior, the condo was very clean with plenty of towels etc. It was also very well equipped for the beach - chairs, parasol & buggy which was invaluable, thank you. It was also so close to the beach. The ladies at reception were lovely, especially Devon who greeted us when we checked in, she was very friendly & helpful!
    Karen
    Young couple
  • Aston Maui Hill

    Aston Maui Hill

    Holiday Home in Wailea
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 468 reviews
    We were in the unit for only a few days. It was very spacious and although it was dated, the unit was very clean. It was well located for what we wanted to do in Kihei.
    David
    Young couple
  • Kihei Condo with Resort Amenities Walk to the Beach

    Kihei Condo with Resort Amenities Walk to the Beach

    Holiday Home in Wailea
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 26 reviews
    The apartment is very clean, and we like the location so close Wailea. We also like the assigned parking is just outside the apartment and the unit is on the ground level. Checkin instructions are accurate and easy to follow.
    Linette
    Young couple
  • Aston Maui Hill

    Aston Maui Hill

    Holiday Home in Wailea
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 468 reviews
    Beautiful property in walking distance to many shops and restaurants. Beds were very comfortable with high quality sheets. Condo was very clean upon arrival. Very spacious with newer furniture. Beautiful view of the ocean and lovely grounds. There was a flock of green parrots living in the tree outside our unit, amazing!
    Teri017
    Group
  • Hale Kamaole

    Hale Kamaole

    Holiday Home in Wailea
    Avg. price/night: US$789.38
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 3 reviews
    Location was convenient and nice. I wish we could’ve checked in earlier in the day to enjoy the space. Easy combination entry and the A/C was on when we arrived. Very clean and well stocked with towels, pillows and linens.
    S
    SARAH
    Solo traveller
  • Wailea Grand Champions Villas - CoralTree Residence Collection

    Wailea Grand Champions Villas - CoralTree Residence Collection

    Holiday Home in Wailea
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 37 reviews
    I liked the size of the condo and its location. I also liked that it was very clean and well stocked.
    W
    WILLIAM
    Young couple
  • Kihei Akahi

    Kihei Akahi

    Holiday Home in Wailea
    7.9
    Scored 7.9
    Good
    Rated good
     · 182 reviews
    Very clean and well maintained room and grounds
    K
    KEVIN
    Family with young children
  • Maui Kamaole

    Maui Kamaole

    Holiday Home in Wailea
    Avg. price/night: US$733.89
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 106 reviews
    Condo was very clean and pretty nicely stocked with the convenience of being at your own home away from home! Complete kitchen which we totally made good use of. Two bathrooms 👍, hop, skip and a jump from the pool🤙🏼keyless entry No human contact check in/out .
    LEILANI L
    Group
  • Kihei Akahi

    Kihei Akahi

    Holiday Home in Wailea
    7.9
    Scored 7.9
    Good
    Rated good
     · 182 reviews
    Very clean, good size, cool without need for A/C, nice surprise of cool bag with goodies waiting for us.
    Jo
    Young couple
  • Kihei Akahi

    Kihei Akahi

    Holiday Home in Wailea
    7.9
    Scored 7.9
    Good
    Rated good
     · 182 reviews
    Nice suite close to the beach and in the middle of the touristic area with own kitchen and balcony. Very clean and well maintained in a larger vacation setting
    Wouter
    Young couple

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