Compare Vacation Rentals & Airbnb in Wailea, HI

4955 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Wailea, HI vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

4955 Rentals and Airbnb in Wailea, HI

Best family friendly Wailea, HI vacation rentals

Among the 4955 accommodations in Wailea, HI, here are the 4 best family friendly rentals

Ocean View Maui Condo Right Across From The Beach! 1 Of 6 Larger Mk Condos, A/c - Wailea, HI
9.7 277 reviews
Wailea, HI
24/10 – 03/11
$407/nighttotal: $4070 (10 )

Ocean View Maui Condo Right Across From The Beach! 1 Of 6 Larger Mk Condos, A/c

1 2
apartment , Wailea
This Wailea apartment, located in Kihei's south end, directly faces Kamaole III Beach and is a short 0.32km walk from the upscale Wailea resort area.
The 116 square metre ground-floor property boasts a one-bedroom, two-bathroom layout sleeping four, offering a private lanai with ocean views, a fully equipped kitchen, free Wi-Fi, and beach gear, plus access to on-site pools, jacuzzies, and parking.
Wailea Ekahi 52b - Wailea, HI
9.2 306 reviews
Wailea, HI
10/07 – 13/07
$548/nighttotal: $1644 (3 )

Wailea Ekahi 52b

1 2
apartment , Wailea
This Wailea apartment is situated in the Wailea Ekahi complex, a short walk from Keawakapu Beach and Mokapu Beach, and about a mile from Ulua Beach. It has consistently received excellent ratings for location, cleanliness and user experience.
The apartment features one bedroom and a fully equipped kitchen with a dishwasher and oven. It offers a range of amenities, including a swimming pool, a tennis court, free Wi-Fi, and a garden, providing guests with plenty of options for relaxation and entertainment.
Beautiful Ocean Views From Maui Kamaole I-118 - Wailea, HI
9.9 207 reviews
Wailea, HI
16/10 – 28/10
$472/nighttotal: $5664 (12 )

Beautiful Ocean Views From Maui Kamaole I-118

1 1
apartment , Wailea
This oceanfront condo in Kihei, Maui offers stunning sea views and is located 0.3km from the Kihei Boat Ramp and 4km from Wailea Beach.
The 99 square metre apartment sleeps four, features one bedroom, two bathrooms, a fully equipped kitchen, in-unit laundry, a private patio, free Wi-Fi, and access to a swimming pool, jacuzzi, tennis court and garden.
Building #1-ocean Views-ground Floor Convenience-ac-meticulous Cleaning - Wailea, HI
9.7 123 reviews
Wailea, HI
24/10 – 03/11
$436/nighttotal: $4360 (10 )

Building #1-ocean Views-ground Floor Convenience-ac-meticulous Cleaning

1 2
apartment , Wailea
This Wailea apartment is situated near Kamaole Beach Park III, approximately 1.6km from the beach and 4.5km from Wailea Beach.
The one-bedroom, two-bathroom condo sleeps four guests and boasts a fully equipped kitchen, in-unit laundry, free Wi-Fi, and access to a swimming pool, jacuzzi, fitness centre, and tennis court.

Best Wailea, HI vacation rentals with a pool

Among the 4955 accommodations in Wailea, HI, here are the 4 best rentals with a pool

Kamaole Sands #3-307 Split A/c, Great Location, Partial Ocean Views, Hot Tub - Wailea, HI
9.4 75 reviews
Wailea, HI
24/10 – 03/11
$392/nighttotal: $3920 (10 )

Kamaole Sands #3-307 Split A/c, Great Location, Partial Ocean Views, Hot Tub

1 2
apartment , Wailea
This apartment is located in South Kihei, just across the street from Kamaole Beach III, a popular spot for swimming, snorkeling, and whale watching. It's also within walking distance of shops, restaurants, and activities, and only a few kilometres from the championship golf courses of Wailea and Makena. The apartment receives excellent ratings for location, cleanliness, and overall user experience.
This one-bedroom apartment is 76 square metres and comfortably sleeps four guests. It features a fully equipped kitchen, a terrace, a swimming pool, a jacuzzi, a fitness centre, and free access to a range of activities, including live music and hula performances.
One-bedroom Apartment - Wailea, HI
9.8 414 reviews
Wailea, HI
10/07 – 13/07
$530/nighttotal: $1590 (3 )

One-bedroom Apartment

1 2
apartment , Wailea
Hale Kamaole 121 condo is situated in Wailea, a short distance from three stunning beaches, perfect for exploring the area. This apartment has consistently received excellent ratings for location, cleanliness and overall user experience.
The apartment is well-equipped for a comfortable stay, with a fully equipped kitchen, air conditioning, a private patio and balcony, and a garden. Guests can enjoy access to a swimming pool, jacuzzi, fitness centre, tennis court, and a children’s playground, making it ideal for families.
Kihei Condo W/ Resort Amenities: Walk To The Beach - Wailea, HI
8.8 115 reviews
Wailea, HI
16/10 – 28/10
$374/nighttotal: $4488 (12 )

Kihei Condo W/ Resort Amenities: Walk To The Beach

1 1
house , Wailea
This one-bedroom apartment is situated in Wailea, a short 5.1 km drive from the Wailea Emerald Course, offering easy access to the beautiful Wailea coastline.
The 81 square metre apartment features a fully equipped kitchen, a private terrace, air conditioning, and free Wi-Fi, making it perfect for a comfortable stay.
Ocean And Golf Course Views 2 Bed 2 Bath - Grand Champions  112 - Wailea, HI
9.5 64 reviews
Wailea, HI
16/10 – 28/10
$446/nighttotal: $5352 (12 )

Ocean And Golf Course Views 2 Bed 2 Bath - Grand Champions 112

2 1
apartment , Wailea
This Wailea Grand Champions Villas condo is situated in the exclusive Wailea resort area, a short drive (under 0.5 km) from Makena Beach and several championship golf courses.
This 98 square metre two-bedroom, two-bathroom property sleeps four guests and boasts a full kitchen, private terrace, access to resort pools and a jacuzzi, plus beach equipment and starter supplies; nearby attractions include the Wailea Tennis Club and upscale shopping.

Frequently Asked Questions about vacation rentals in Wailea, HI

  • What are some interesting places to visit in or near Wailea, HI?

    Wailea is a great base for exploring the island. You can visit the nearby Haleakala National Park, hike to the summit of the dormant volcano for stunning views, or explore the historic town of Lahaina. For a more relaxed day, head to the beach at Makena, just a short drive away.
  • What are the best Airbnb and vacation rentals in Wailea, HI?

  • Which walking or cycling routes are the best in Wailea, HI?

    The paved path along the coast from Wailea to Makena is a popular choice for walking and cycling. There are also some great trails in the nearby state park, offering scenic views and a chance to see local wildlife. For a more challenging ride, try the climb up to the top of the West Maui Mountains.
  • What are the most popular Airbnbs in Wailea, HI?

  • What sports or outdoor activites can visitors enjoy in and around Wailea, HI?

    Wailea is a paradise for water sports enthusiasts. You can go swimming, snorkeling, scuba diving, surfing, or stand-up paddleboarding. There are also plenty of opportunities for hiking, golfing, tennis, and horseback riding in the area.
  • What are the best vacation rentals with a pool in Wailea, HI?

  • What other towns or cities can be easily accessed from Wailea, HI?

    From Wailea, you can easily reach other towns and cities on Maui. You can drive to Kahului, the island's main airport and commercial center, in about 30 minutes. The historic town of Lahaina is about a 45-minute drive, and the charming town of Paia is about an hour away.
  • What are the best rentals for families and kids in Wailea, HI?

  • What amenities are commonly available in vacation rentals in Wailea, HI?

    Vacation rentals in Wailea typically offer a range of amenities, including private pools, hot tubs, fully equipped kitchens, laundry facilities, and stunning ocean views. Many rentals also offer access to resort amenities such as tennis courts, fitness centers, and restaurants.
  • What are the best rentals or Airbnbs with a jacuzzi in Wailea, HI?

  • What time of year is best to rent a vacation rental Wailea, HI?

    The best time to visit Wailea is during the shoulder seasons, from April to May and September to October. The weather is still pleasant, but the crowds are smaller and prices are lower. If you prefer warmer weather, you can visit during the summer months, from June to August.
  • What are the local dishes in Wailea, HI region?

    Maui is famous for its fresh seafood, so you'll find plenty of restaurants serving up delicious dishes like poke, mahi-mahi, and ono. You can also try local specialties like kalua pig, laulau, and poi. For a sweet treat, try a shave ice or a pineapple upside-down cake.

Destinations nearby

Best Wailea, HI vacation rentals with a balcony

Maui Kamaole #H-211 Ocean View, Full A/c, Newly Renovated! Close To Beach! - Wailea, HI
9.8 76 reviews
Wailea, HI
16/10 – 28/10
$487/nighttotal: $5844 (12 )

Maui Kamaole #H-211 Ocean View, Full A/c, Newly Renovated! Close To Beach!

2 1
apartment , Wailea
This two-bedroom apartment is situated in the Maui Kamaole complex, a short walk across the street from Kamaole Beach Park III in South Kihei, just a short drive from the upscale Wailea resort area.
The 98 square metre apartment sleeps up to six guests and boasts a balcony with stunning ocean views, a fully equipped kitchen, a washer and dryer, and access to two swimming pools, hot tubs, tennis courts, and gas grills within the complex.
Luxurious Kamaole Sands 5-211 Upgraded 1bd/2bath With Ocean Views! - Wailea, HI
9.7 63 reviews
Wailea, HI
24/10 – 03/11
$539/nighttotal: $5390 (10 )

Luxurious Kamaole Sands 5-211 Upgraded 1bd/2bath With Ocean Views!

1 2
apartment , Wailea
This Wailea oceanfront condo is situated near Kihei, a short distance (0.3km) from Kamaole Beach Park 3 and 4.5km from Wailea Beach.
The 76 square metre apartment sleeps four, boasting two bathrooms, a fully equipped kitchen, in-unit laundry, free Wi-Fi, a private balcony with ocean views, and access to a swimming pool, jacuzzi, fitness centre, spa, and tennis court.
Spacious, Airy Living With Private Lanai Views - Wailea, HI
9.7 57 reviews
Wailea, HI
10/07 – 13/07
$549/nighttotal: $1647 (3 )

Spacious, Airy Living With Private Lanai Views

2 2
apartment , Wailea
This Wailea golf condo is less than 1.6km from the Shops at Wailea and Wailea Beach, also close to Ulua Beach Park and the Wailea Shopping Village, offering a prime location for exploring this area of Maui.
The two-bedroom, two-bathroom apartment sleeps six, boasting a fully equipped kitchen, private balcony, swimming pool, jacuzzi, tennis court, and concierge services, ensuring a comfortable and convenient stay.
Hale Kamaole 212 - Enjoy Your Beautiful Spacious Suite - Wailea, HI
9.7 32 reviews
Wailea, HI
16/10 – 28/10
$397/nighttotal: $4764 (12 )

Hale Kamaole 212 - Enjoy Your Beautiful Spacious Suite

1 1
apartment , Wailea
This Kihei beachfront apartment offers direct beach access, is 0.5km from Kamaole Beach Park 3 and 4.3km from Wailea Beach.
The 74 square metre property sleeps four, features a fully equipped kitchen, in-unit laundry, private balcony with ocean views, and access to a swimming pool, spa, and tennis court.

Best Wailea, HI vacation rentals with parking

Hale Kamaole Condo W/ Shared Grill, Shared Outdoor Pool, Private Washer/dryer - Wailea, HI
8.9 47 reviews
Wailea, HI
16/10 – 28/10
$335/nighttotal: $4020 (12 )

Hale Kamaole Condo W/ Shared Grill, Shared Outdoor Pool, Private Washer/dryer

1 1
apartment , Wailea
This Wailea apartment, near Kihei, is conveniently located 0.5km from Kamaole Beach Park 3 and 4.3km from Wailea Beach, offering easy access to swimming, sunbathing, and water activities at the Kihei Boat Ramp.
The self-catering flat features one bedroom, one bathroom, sleeps four, and includes a fully equipped kitchen, Wi-Fi, a terrace, a swimming pool, tennis court, and parking.
Remodeled-building #3-ocean Views-well Equipped-ac-meticulous Cleaning - Wailea, HI
9.8 113 reviews
Wailea, HI
16/10 – 28/10
$440/nighttotal: $5280 (12 )

Remodeled-building #3-ocean Views-well Equipped-ac-meticulous Cleaning

1 1
apartment , Wailea
This Kihei apartment, a short distance (0.16 km) from Kamaole Beach Park 3 and a 4.5 km drive from Wailea Beach, offers convenient access to both locations.
The 76 square metre property boasts one bedroom, two bathrooms, sleeps four guests, and includes a fully equipped kitchen, in-unit laundry, a spa tub, and access to a swimming pool, jacuzzi, fitness centre, and tennis court.
Hale Kamaole 208 - Relax And Enjoy Your Beautiful Ocean View Suite - Wailea, HI
9.4 140 reviews
Wailea, HI
16/10 – 28/10
$350/nighttotal: $4200 (12 )

Hale Kamaole 208 - Relax And Enjoy Your Beautiful Ocean View Suite

1 1
apartment , Wailea
This one-bedroom apartment is situated in Kihei, just 0.3 kilometres from Kamaole Beach Park 3 and 4.2 kilometres from Wailea Beach.
The 74 square metre apartment, which can accommodate up to five guests, features a fully equipped kitchen, a private balcony, and access to a swimming pool, spa, tennis court, and garden.
Maui Escape - Oceanview 70 Yds To Beach, Gnd Flr, Bldg10 - Everything You Need! - Wailea, HI
9.8 164 reviews
Wailea, HI
10/07 – 13/07
$572/nighttotal: $1716 (3 )

Maui Escape - Oceanview 70 Yds To Beach, Gnd Flr, Bldg10 - Everything You Need!

1 2
apartment , Wailea
This ground-floor Wailea condo, part of the Kamaole Sands Resort in South Maui, offers direct access to Kamaole Beach III.
The one-bedroom, two-bathroom apartment sleeps four, features a fully equipped kitchen with granite countertops, in-unit laundry, and access to resort amenities including pools, tennis courts, and BBQ grills, plus beach gear is provided.
©2026 cozycozy.com