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The 10 Best Holiday Rentals in Wailea, USA

Check out our pick of great holiday rentals in Wailea

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest price first Star rating and price Top reviewed

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Situated in Wailea, 300 metres from Keawakapu Beach and 800 metres from Mokapu Beach, Oceanfront Mana Kai 2 bedroom condo offers a terrace and air conditioning. This beachfront property offers access to free WiFi and free private parking. The aparthotel features a pool with pool views, fitness centre and a lift.

Great location. Comfortable apartment. Very helpful owners.

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9.4
Superb
5 reviews
Price from
£479
per night

Set in Wailea and only 400 metres from Kamaole Beach, Live da HI life--great beach and great views! offers accommodation with mountain views, free WiFi and free private parking. This apartment features air-conditioned accommodation with a patio. During your stay at this apartment, you can make use of an outdoor swimming pool, as well as a selection of a hot tub and a 24-hour front desk.

Everything about this place was perfect- it exceeded my expectations in every way! The kitchen was so well equipped, the property itself was great, it was more than I could have asked for!

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9.6
Exceptional
8 reviews
Price from
£310
per night

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.

Excellent location, amazing view.

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9.5
Exceptional
8 reviews
Price from
£332
per night

Offering a terrace and garden view, Aloha Moon - A Chic and Dreamy Modern Tropical Hideaway! is set in Wailea, 1.8 km from Mokapu Beach and 2.2 km from Wailea Emerald Course. The air-conditioned accommodation is 1.5 km from Ulua Beach, and guests can benefit from on-site private parking and complimentary WiFi. The property is non-smoking and is located 1.6 km from Wailea Beach.

Extremely clean, great location, amazing decor, hosts communication is great

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9.8
Exceptional
6 reviews
Price from
£510
per night

Boasting air-conditioned accommodation with a private pool, Tiki Tiki - Gorgeous Boho Beach Hideaway! is set in Wailea. This property offers access to a balcony, free private parking and free WiFi. The property is non-smoking and is located 1.5 km from Ulua Beach.

The property has everything one could possibly need on vacation. This includes even beach chairs, ukulele, thermo bag, iPhone and watch wireless chargers and weighted blanket. Another great point is that the apartment is aesthetically pleasant in terms of decoration and furniture. It is enjoyable to spend time there. Also, it has a balcony which is perfect for relaxed quiet breakfasts.

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9.9
Exceptional
13 reviews
Price from
£422
per night

Situated in Wailea and only 500 metres from Kamaole Beach, Tropical Maui Kamaole B-Bldg features accommodation with sea views, free WiFi and free private parking. With pool views, this accommodation offers a balcony. The apartment provides an outdoor swimming pool with a fence, as well as a hot tub and full-day security.

Very well located, large and extremely comfortable apartment. Well thought out and equipped to a high standard, especially the kitchen; very good beds. A plus was the community pool and nearby Kamaole Beach. We left earlier because of the Lahaina fires, we would have loved to have stayed longer and would book here again in a heartbeat.

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9.1
Superb
17 reviews
Price from
£375
per night

Featuring air-conditioned accommodation with a pool with a view, Beautiful 2 Bedroom Oceanview Condo at Maui Kamaole Located at South End of Kihei Adjacent to Wailea Traditional Hawaiian Style is located in Wailea. This beachfront property offers access to a patio, free private parking and free WiFi. The property is non-smoking and is set 500 metres from Kamaole Beach.

Location was fantastic. Walking distance to beach across the road which was popular with tourists and locals. Not too crowded which was a bonus. The condo was next level- very spacious, had everything and more for self catering purposes, beach gear was included and utilised daily. The balcony was perfect for morning coffee and evening drinks. The complex was impeccable and the pool looked great (I did not use it though). I would return to this property in a heartbeat.

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9.6
Exceptional
19 reviews
Price from
£294
per night

Offering garden views, South Maui 1 BR Guest Suite - Kamaole Beach Area is an accommodation situated in Wailea, 2.2 km from Cove Beach and 2.4 km from Keawakapu Beach. This property offers access to a patio, free private parking and free WiFi. The property is non-smoking and is set less than 1 km from Kamaole Beach.

It was only a mile from the beach and so close to everything we wanted to do.

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10
Exceptional
6 reviews
Price from
£305
per night

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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9.2
Superb
11 reviews
Price from
£458
per night

This Maui, Hawaii bed and breakfast is less than a mile from Kamaole Beach Park III and has views of the West Maui Mountains. Free Wi-Fi access is available.

Rooms at Maui What a Wonderful World Bed & Breakfast feature a seating area and a private bathroom. They are equipped with a flat-screen TV and a refrigerator.

Due to the COVID restrictions, the breakfast items were provided in the suite for me and it was a feast! The pineapple was heavenly, the pastries delicious, the options almost unending. The freedom to come and go was fabulous. No car parking fee or hassles getting in and out with a car. My phone Maps app got me to the location easily. Less than a 20 minute walk to the beach and some shops.

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9.3
Superb
84 reviews
Price from
£212
per night

Most booked holiday rentals 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.

  • Oceanfront Mana Kai 2 bedroom condo
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 5 reviews

    Situated in Wailea, 300 metres from Keawakapu Beach and 800 metres from Mokapu Beach, Oceanfront Mana Kai 2 bedroom condo offers a terrace and air conditioning.

  • Live da HI life--great beach and great views!
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 8 reviews

    Set in Wailea and only 400 metres from Kamaole Beach, Live da HI life--great beach and great views! offers accommodation with mountain views, free WiFi and free private parking.

  • Enjoy Your Oceanside Dream at Kihei Surfside
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 8 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.

  • Aloha Moon - A Chic and Dreamy Modern Tropical Hideaway!
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 6 reviews

    Offering a terrace and garden view, Aloha Moon - A Chic and Dreamy Modern Tropical Hideaway! is set in Wailea, 1.8 km from Mokapu Beach and 2.2 km from Wailea Emerald Course.

    Well appointed for a couple to show up and enjoy their stay.

  • Tiki Tiki - Gorgeous Boho Beach Hideaway!
    9.9
    Scored 9.9
    Exceptional
    Rated exceptional
     · 13 reviews

    Boasting air-conditioned accommodation with a private pool, Tiki Tiki - Gorgeous Boho Beach Hideaway! is set in Wailea. This property offers access to a balcony, free private parking and free WiFi.

    We had an outstanding stay at Tiki Tiki! The condo was stunningly beautiful, impeccably clean & the bed was THE MOST comfortable bed we’ve ever slept in!

  • Tropical Maui Kamaole B-Bldg
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 17 reviews

    Situated in Wailea and only 500 metres from Kamaole Beach, Tropical Maui Kamaole B-Bldg features accommodation with sea views, free WiFi and free private parking.

    Loved location with beach across street and resting turtles

  • Beautiful 2 Bedroom Oceanview Condo at Maui Kamaole Located at South End of Kihei Adjacent to Wailea Traditional Hawaiian Style
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 19 reviews

    Featuring air-conditioned accommodation with a pool with a view, Beautiful 2 Bedroom Oceanview Condo at Maui Kamaole Located at South End of Kihei Adjacent to Wailea Traditional Hawaiian Style is...

    The room was close to the beach, roomy for a family of 4, had a nice pool, and was comfortable and clean.

These holiday rentals in Wailea have options with FREE cancellation

  • South Maui 1 BR Guest Suite - Kamaole Beach Area
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 6 reviews

    Offering garden views, South Maui 1 BR Guest Suite - Kamaole Beach Area is an accommodation situated in Wailea, 2.2 km from Cove Beach and 2.4 km from Keawakapu Beach.

    The property was in the perfect location and was very nice.

  • Wailea Ekolu #607
    Free cancellation options available
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 11 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...

    Great comm from host. Lovely condo with lovely views.

  • Maui What a Wonderful World Bed & Breakfast
    Free cancellation options available
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 84 reviews

    This Maui, Hawaii bed and breakfast is less than a mile from Kamaole Beach Park III and has views of the West Maui Mountains. Free Wi-Fi access is available.

    Clean and unique. Very nice service. A lot of courtesy.

  • Maui Banyan Vacation Club
    Free cancellation options available
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 140 reviews

    Surrounded by lush tropical landscape, Maui Banyan Vacation Club faces Kamaole Beach Park II and is just 10 minutes’ walk away from Kamaole Beach Park 1.

    I like how it came with a microwave and also pool!!

  • Aston Maui Hill
    Free cancellation options available
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 469 reviews

    Featuring spacious suites with fully-equipped kitchens, this Kihei resort is 6 minutes' walk from Kamaole Beach Park III. The resort features a heated outdoor pool and hot tub.

    Condo was quite spacious. Grounds were immaculate.

  • Gorgeous Oceanfront Kihei Condo with Balcony!
    Free cancellation options available
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 8 reviews

    Boasting air-conditioned accommodation with a balcony, Gorgeous Oceanfront Kihei Condo with Balcony! is set in Wailea. This beachfront property offers access to a terrace and free WiFi.

  • King Suite: Walk to Beach, Pool
    Free cancellation options available
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 15 reviews

    Set in Wailea, King Suite: Walk to Beach, Pool offers accommodation with private pool, free WiFi and free private parking for guests who drive.

    It was an amazing appartement with a great view on the ocean. We really enjoyed our stay here.

  • Kihei Condo with Resort Amenities Walk to the Beach
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 27 reviews

    Situated in Wailea, 500 metres from Kamaole Beach and 800 metres from Keawakapu Beach, Kihei Condo with Resort Amenities Walk to the Beach features air-conditioned accommodation with a patio and free...

    It had two patios that were very nice and the view was pretty.

Highly rated holiday rentals in Wailea

  • Mana Kai 611C
    8.0+ review score
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 20 reviews

    Set in Wailea, just 300 metres from Keawakapu Beach, Mana Kai 611C offers beachfront accommodation with an outdoor swimming pool, a terrace, a bar and free WiFi.

    Location and views and condo was well equipped with dishes and things for the pool

  • Wailea Ekahi 21F
    8.0+ review score
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 8 reviews

    Located 4.4 km from Makena Landing Beach Park, Wailea Ekahi 21F offers accommodation in Wailea. The holiday home is 7 km from Little Beach. There is a seating area and a kitchen.

    This property is in a great part of the Wailea Ekahi complex, and is VERY comfortable and upscale. You can see and hear the ocean from the patio. Clean and quiet.

  • Mana Kai 710A
    8.0+ review score
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 5 reviews

    Located 5 km from Makena Landing Beach Park, Mana Kai 710A offers accommodation in Wailea. The holiday home is 8 km from Little Beach. There is a dining area and a kitchen equipped with dishwasher.

  • Kihei Akahi C308
    8.0+ review score
    8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 32 reviews

    Located in Wailea in the Maui Region, this apartment is 7 km from Makena Landing Beach Park. The property features views of the sea and is 9 km from Little Beach.

    Very good location and condo. I had a perfect stay for a week

  • KBM Resorts Kamaole Sands KSD-10-312 1 Bdm Views
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 1 review

    Set in Wailea, 400 metres from Kamaole Beach and 1.1 km from Keawakapu Beach, KBM Resorts Kamaole Sands KSD-10-312 1 Bdm Views offers a bar and air conditioning.

  • K B M Resorts Maui Banyan MBY-H413 NEW Remodeled 1B MB retreat with AC
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Set in Wailea, 200 metres from Kamaole Beach and 1.7 km from Cove Beach, K B M Resorts Maui Banyan MBY-H413 NEW Remodeled 1B MB retreat with AC offers a bar and air conditioning.

  • K B M Resorts- POL-109 Expansive 2Bd, ocean front resort, easy access, steps to beach
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 2 reviews

    Situated in Wailea, a few steps from Polo Beach and 500 metres from Palauea Beach, K B M Resorts- POL-109 Expansive 2Bd, ocean front resort, easy access, steps to beach offers a bar and air...

  • Mana Kai 710C
    8.0+ review score
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 4 reviews

    Mana Kai 710C offers accommodation in Wailea. Makena Landing Beach Park is 5 km away. The accommodation comes with a dining area and a seating area with a cable TV.

FAQ about holiday rentals in Wailea






Holiday rentals that guests love in Wailea

  • Avg. price/night: £1,040.31
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 182 reviews
    Villa location and view was fantastic. Staff were great!
    Angela
    Group
  • Avg. price/night: £2,203.64
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 6 reviews
    Gorgeous villa with fantastic ocean view
    Deborah
    Group
  • 8.2
    Scored 8.2
    Very good
    Rated very good
     · 4 reviews
    The villa looked nice and clean. Nice ocean view.
    Medardo
    Solo traveller
  • 7.9
    Scored 7.9
    Good
    Rated good
     · 533 reviews
    The pool and the boigonvillas
    Wendy
    Family with young children
  • Avg. price/night: £4,287.13
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 3 reviews
    The villa is amazing! It came with a lot of extra perks like a welcome basket, golf cart service to take you around the property and a car to drive you to the store or drop you for dinner. I would recommend this property to all.
    gina
    Family with young children
  • 7.9
    Scored 7.9
    Good
    Rated good
     · 533 reviews
    The location is excellent very close to beautiful beaches and Kihei village. The facilities are nice especially the spacious room including kitchen a nd washing machine/dryer and the garden.
    Alessandro
    Family with young children
  • Avg. price/night: £1,040.31
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 182 reviews
    We upgraded to a villa with a plunge pool and it was perfect for our family. Gorgeous sunset views and a great beach walk with coffee shops on route. Good breakfast options.
    Micha
    Family with young children
  • 9.4
    Scored 9.4
    Superb
    Rated superb
     · 17 reviews
    We stayed in a villa which was spacious and had a full, beautiful kitchen, plus a high quality grill available on the lanai. The hosts provided all the home conveniences our family of four would need. Linens/towels/toiletries. Washer/dryer in unit was wonderful.
    John
    Family with young children
  • 8.4
    Scored 8.4
    Very good
    Rated very good
     · 39 reviews
    First of all this is vacation rental and as a rental I'm surprised that everything was functional and management included everything and when I say everything believe me everything. We pretty much felt like we are at home so it was awesome. Location is perfect and you can walk to restaurants, beaches etc. Overall it was beautiful and quite place and perfect for family.
    mehmethinc
    Family with young children
  • Avg. price/night: £1,040.31
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 182 reviews
    We got upgraded to a villa. It was amazing.
    Vivek
    Young couple