Compare Vacation Rentals & Airbnb in Wailea, HI

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Wailea, HI vacation rentals
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7542 Rentals and Airbnb in Wailea, HI

Best family friendly Wailea, HI vacation rentals

Among the 7542 accommodations in Wailea, HI, here are the 4 best family friendly rentals

Kamaole Sands 6-107, 1 Bedroom, Ground Floor Condo, Pool, Gym - Wailea, HI
9.2 242 reviews

Kamaole Sands 6-107, 1 Bedroom, Ground Floor Condo, Pool, Gym

apartment, Wailea
This apartment is located in Wailea, just a 2-minute walk from Kamaole Beach and less than a mile from Keawakapu Beach, offering easy access to the beautiful beaches and the vibrant atmosphere of the area. It has excellent user ratings and very good ratings for both location and cleanliness.
This ground floor property features a fully equipped kitchen, air conditioning, and breathtaking ocean views. Guests can enjoy the on-site swimming pool, gym, free Wi-Fi, and nearby activities such as cycling and exploring attractions like Mokapu Beach and Wailea Emerald Course.
*Fully Remodeled* Modern Island Style* - Wailea, HI
10 161 reviews

*Fully Remodeled* Modern Island Style*

apartment, Wailea
This Wailea condo, near the intersection of Wailea Alanui Drive and Okolani Drive, offers easy access to beaches and upscale amenities within a short distance of world-class resorts.
This fully renovated 111-square-metre apartment sleeps six, boasting two bedrooms, two bathrooms, a fully equipped kitchen, and a terrace with stunning ocean views; beach equipment, including towels, chairs, and snorkelling gear, is provided.
New Bathrooms! Modern Spacious Penthouse Oceanview - Wailea, HI
9.5 50 reviews

New Bathrooms! Modern Spacious Penthouse Oceanview

apartment, Wailea
This three-bedroom Wailea penthouse, situated in the Kamaole Sands Resort, offers stunning ocean views and is directly opposite Kamaole Beach Park III.
The 3-bathroom apartment sleeps eight, boasts a fully equipped kitchen, and provides access to resort amenities including a swimming pool, fitness centre, and BBQ area.
126 Hale Kamaole - Wailea, HI
9.6 307 reviews

126 Hale Kamaole

apartment, Wailea
This Wailea vacation home is located just a short walk from Kamaole Beach, a popular spot for swimming and snorkeling, and within easy reach of Keawakapu Beach and Mokapu Beach. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
This one-bedroom, one-bathroom property offers 72 square metres of space, comfortably accommodating up to five guests. The house features a fully equipped kitchen, air conditioning, free Wi-Fi, a private swimming pool, a tennis court, and a concierge service for added convenience.

Best Wailea, HI vacation rentals with a pool

Among the 7542 accommodations in Wailea, HI, here are the 4 best rentals with a pool

Haleakala Shores A-301, Panoramic Views, Split Ac - Wailea, HI
9.7 173 reviews

Haleakala Shores A-301, Panoramic Views, Split Ac

apartment, Wailea
This apartment is situated directly across the street from Kamaole III beach in South Kihei, offering easy access to restaurants, shops and nightlife within a short walk. This property has received excellent ratings for its location, cleanliness and user experience.
The apartment features two bedrooms, sleeping six comfortably, and covers 97 square metres. Guests can enjoy a fully equipped kitchen, a terrace or balcony, a swimming pool, a garden and parking, as well as access to beach chairs, towels, an umbrella and a cooler.
Haleakala Shores A-308 - Ocean/mountain Views, Stylish 2br/2ba, Lanai, Ac, Wi-fi - Wailea, HI
9.8 129 reviews

Haleakala Shores A-308 - Ocean/mountain Views, Stylish 2br/2ba, Lanai, Ac, Wi-fi

apartment, Wailea
This Kihei condo, situated directly opposite Kamaole Beach Park III, offers easy access to shops, restaurants, and other South Kihei attractions.
The 97 square metre (1044 square feet) apartment sleeps six guests, boasting three bedrooms, two bathrooms, a gourmet kitchen with stainless steel appliances, and a terrace with breathtaking Pacific Ocean and Haleakala Mountain views; complimentary beach gear is also provided.
Kamaole Sands 5-112-rare 2 Bedroom Ground Floor-ac - Wailea, HI
9.5 122 reviews

Kamaole Sands 5-112-rare 2 Bedroom Ground Floor-ac

apartment, Wailea
This Kihei condo, a short walk from Kamaole Beach Park 3 and 4.5km from Wailea Beach, offers easy access to both beaches and nearby attractions.
The 101-square-metre property features two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, swimming pool, fitness centre, and tennis court.
Wailea Jewel! Near Shops,5 Star Hotels,beaches - Wailea, HI
9.7 145 reviews

Wailea Jewel! Near Shops,5 Star Hotels,beaches

apartment, Wailea
This Wailea Ekolu ground-floor apartment, a short walk from The Shops at Wailea and a 0.8km drive from Mokapu and Ulua Beaches, offers easy access to Wailea's amenities.
The 99-square-metre property features two bedrooms, two bathrooms, a fully equipped kitchen, and access to multiple pools, barbecue areas, and panoramic ocean views within the Wailea Ekolu complex; beach chairs, a cooler, and towels are provided.

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.

Popular destinations

Best Wailea, HI vacation rentals with a balcony

2 Bed, 2 Bath Ocean View, A/c Kamaole Sands A Graded Condo - Wailea, HI
9.4 120 reviews

2 Bed, 2 Bath Ocean View, A/c Kamaole Sands A Graded Condo

apartment, Wailea
This Wailea condo, situated in Kihei, is a 1.6km walk from Kamaole Beach Parks II & III and 4.3km from Wailea Beach.
The 110 square metre property boasts two bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, swimming pool, jacuzzi, and free Wi-Fi.
Haleakala Shores B205~ Spacious 2 Bedroom, 2 Bath, Across From Kamaole Iii - Wailea, HI
8.8 28 reviews

Haleakala Shores B205~ Spacious 2 Bedroom, 2 Bath, Across From Kamaole Iii

apartment, Wailea
This Kihei condominium is located directly across from Kamaole Beach Park III, offering immediate access to the beach and a short walk to local shops and restaurants in the Wailea district.
This 109 square metre apartment accommodates up to six guests across two bedrooms with en-suite bathrooms, featuring a full kitchen, a spacious lanai, and access to communal amenities including a swimming pool and BBQ grills.
Spectacular Ocean View 2 Bedroom Condo. - Wailea, HI
10 188 reviews

Spectacular Ocean View 2 Bedroom Condo.

apartment, Wailea
This oceanfront apartment in Wailea offers breathtaking sunset views and is just a short distance from the beach, making it ideal for travellers looking for a peaceful and relaxing escape. The property has received excellent ratings for location, cleanliness and overall user experience.
The two-bedroom apartment spans 98 square metres and can comfortably accommodate up to six guests. The property boasts a fully equipped kitchen, a private balcony, a swimming pool and a jacuzzi, as well as a range of other amenities including a spa, a garden and free Wi-Fi access.
Large Designer 2 Bed/2 Bath Condo With Ocean Views & Beach Across The Street - Wailea, HI
9.8 77 reviews

Large Designer 2 Bed/2 Bath Condo With Ocean Views & Beach Across The Street

apartment, Wailea
This two-bedroom, two-bathroom apartment is located in South Kihei, a mere 200 metres from Kamaole Beach III and a 5-minute walk from Kihei Boat Ramp, with Wailea's golf courses and shops a 5-kilometre drive away.
This well-appointed condo accommodates up to five guests, featuring a private ocean-view lanai, a fully equipped kitchen with a washer/dryer, and access to resort amenities including a swimming pool, hot tubs, fitness centre and tennis courts.

Best Wailea, HI vacation rentals with parking

Upper Floor,  A/c, Tropical Garden View, Mkb206 - Wailea, HI
9.5 220 reviews

Upper Floor, A/c, Tropical Garden View, Mkb206

apartment, Wailea
This two-bedroom apartment is located in Kihei, just 0.3 kilometres from the Kihei Boat Ramp and 4 kilometres from Wailea Beach. The 98 square metre apartment offers a fully equipped kitchen, a terrace, and access to a swimming pool, jacuzzi, and tennis court.
Garden View Wifi A/c Across Beach Park Ks7408 - Wailea, HI
9.6 185 reviews

Garden View Wifi A/c Across Beach Park Ks7408

apartment, Wailea
This two-bedroom apartment is situated in South Kihei, just under 2 kilometres from Kamaole Beach Park 3 and Kamaole Beach Park.
The 110 square metre property offers a fully equipped kitchen, a terrace, a swimming pool, a fitness centre, and parking, and can accommodate up to six guests.
Ocean View, Great Location, Great Rates! Mkl105 - Wailea, HI
9.6 109 reviews

Ocean View, Great Location, Great Rates! Mkl105

apartment, Wailea
This ground-floor apartment is located in the upscale Maui Kamaole complex, just across the street from the famous Kamaole Beach III in Wailea, a popular destination known for its beautiful beaches and stunning ocean views. The apartment has excellent user, location and cleanliness ratings.
This two-bedroom, two-bathroom apartment is 97 square metres and can accommodate up to six guests. The apartment offers a range of amenities, including a fully equipped kitchen, air conditioning, a washing machine and dryer, free Wi-Fi, cable TV and a Blu-ray player, as well as access to two swimming pools, hot tubs, tennis courts and a garden.
Ocean View*acrossfrombeach*2pool*tennis*3pickleball - Wailea, HI
9.8 31 reviews

Ocean View*acrossfrombeach*2pool*tennis*3pickleball

apartment, Wailea
This Wailea beachfront apartment, situated 0.3km from Kamaole Beach Park 3 and 4.5km from Wailea Beach, offers direct beach access and proximity to excellent swimming and sunbathing spots.
The 95 square metre property features two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, in-unit laundry, a smart TV, plus access to a swimming pool, jacuzzi, fitness centre, and parking.
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