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

Ocean Front Modern 2br 2ba, King Bed, Beach, Pool! - Wailea, HI
10 1 review

Ocean Front Modern 2br 2ba, King Bed, Beach, Pool!

apartment, Wailea
This beachfront apartment in Wailea is located 5.4 kilometres from Wailea Emerald Course and 27.3 kilometres from Iao Valley State Park, with direct access to the sea and proximity to Kamaole Beach.
This 74 square metre flat offers a family-friendly stay for up to 10 guests with two bedrooms, two bathrooms, a fully equipped kitchen, air conditioning, WiFi, a swimming pool, and a balcony, all within a 22.5 kilometre drive of Kahului Airport.
Luxurious Top Floor Kamaole Sands 6-404 - Wailea, HI
8.2 18 reviews

Luxurious Top Floor Kamaole Sands 6-404

apartment, Wailea
This luxurious Kamaole Sands apartment boasts stunning sea views and is a short walk from Kamaole and Keawakapu Beaches, and 2.7km from Mokapu Beach, with the Wailea Emerald Course 6.1km away.
The 102 square metre property features two bedrooms, two bathrooms with a hot tub, a fully equipped kitchen, and accommodates up to 11 guests, offering a private pool, terrace, garden, free Wi-Fi, and parking.
Oceanview 1 Level Split Ac @ Kam 3 Beach Bldg 5 - Wailea, HI
9.9 107 reviews

Oceanview 1 Level Split Ac @ Kam 3 Beach Bldg 5

apartment, Wailea
This Kihei condo, situated 0.5km from Kamaole Beach Park 3 and 4.7km from Wailea Beach, offers convenient access to multiple beaches and the Kihei Boat Ramp.
The 96 square metre apartment features two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, swimming pool, fitness centre, and spa, making it ideal for families or small groups.
Spacious Home Steps From Kamaole 3 Beach - Wailea, HI
10 1 review

Spacious Home Steps From Kamaole 3 Beach

apartment, Wailea
This Kihei condominium is located directly opposite Kamaole Beach Park 3, offering immediate access to its sandy shores and a short drive to Wailea Beach and Makena State Park.
This 97 square meter apartment sleeps up to five guests, featuring two bedrooms, two bathrooms, a fully equipped kitchen, air conditioning, a private lanai, and complimentary beach gear, with access to a communal swimming pool and barbecue grills.

Best Wailea, HI vacation rentals with a pool

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

A.r.a Retreats: The Soaking Tub - Wailea, HI
9.8 65 reviews

A.r.a Retreats: The Soaking Tub

apartment, Wailea
This spacious, newly renovated apartment is located within the Grand Champions Villas in Wailea, offering a serene escape and a 1.4-kilometre distance to the Shops at Wailea.
This family-friendly holiday home accommodates up to six guests, featuring two bedrooms, two bathrooms, air conditioning, Wi-Fi, a fully equipped kitchen, a swimming pool, and a jacuzzi, with a unique wet room primary bedroom set for completion in Autumn 2024.
Cool & Quiet Wailea Oasis, Big Lanai + Two Pools - Wailea, HI
9.9 69 reviews

Cool & Quiet Wailea Oasis, Big Lanai + Two Pools

apartment, Wailea
This Wailea apartment is ideally located a short walk from Ulua Beach and approximately 1.6km from Wailea Beach, also close to Mokapu Beach and the Wailea Emerald Golf Course.
This two-bedroom, two-bathroom property boasts 111 square metres of living space, featuring a fully equipped kitchen, private terrace, access to swimming pools, a jacuzzi, tennis court, and free parking; enjoying excellent user ratings for cleanliness, location and overall experience.
Walk To Beach | Pools, Pickleball, Kihei - Wailea, HI
9.9 31 reviews

Walk To Beach | Pools, Pickleball, Kihei

apartment, Wailea
This two-bedroom, two-bathroom apartment is situated in Kihei, directly opposite Kamaole Beach Park III, and within a short walk of local shops and restaurants.
This resort-style accommodation for six guests offers a fully equipped kitchen, air conditioning, a swimming pool, Jacuzzi, fitness centre, and complimentary beach gear, with keyless entry for a smooth arrival.
Summer Sale! Remodeled 1br Across Beach- Kas 10203 - Wailea, HI
9.4 208 reviews

Summer Sale! Remodeled 1br Across Beach- Kas 10203

apartment, Wailea
This apartment is conveniently located near Kamaole Beach Parks 3 and 2, a short walk away, and is just 2.5 miles from Wailea Beach. The property has received excellent user and location ratings, and a very good cleanliness rating.
The apartment has a floor area of 76 square metres, and provides a full kitchen, two bathrooms, a washer/dryer, a flat-screen TV and DVD player, as well as access to a swimming pool, Jacuzzi, spa, fitness centre, tennis court and garden.

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

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.
Conveniently Located Two Bedroom Two Bath Hk319 - Wailea, HI
10 14 reviews

Conveniently Located Two Bedroom Two Bath Hk319

apartment, Wailea
This South Kihei flat is situated a short walk from Kamaole Beach Park III and conveniently close to local shops and restaurants, offering direct access to swimming, snorkelling, and sunset viewing across the street.
This 102 square metre apartment accommodates up to six guests with two bedrooms and two bathrooms, featuring a fully equipped kitchen, air conditioning, a private lanai, and access to an on-site pool and BBQ area, with opportunities for water sports and whale watching nearby.
Kamaole Sands Unit 8-406 - 2 Br - 2 Ba Condo In Th - Wailea, HI
8.8 49 reviews

Kamaole Sands Unit 8-406 - 2 Br - 2 Ba Condo In Th

apartment, Wailea
This Wailea condo is situated directly opposite Kamaole Beach III, offering immediate beach access and proximity to Kihei's shops and restaurants.
The 111 square metre (1194 square feet) property features two bedrooms, two bathrooms, and sleeps up to six guests, boasting a full kitchen, washer/dryer, three TVs, and access to resort amenities including a swimming pool, hot tubs, and a fitness centre.
Feel At Home-stunning Remodel-great Location-ac - Wailea, HI
9.8 149 reviews

Feel At Home-stunning Remodel-great Location-ac

apartment, Wailea
This Kihei condo, near Kamaole Beaches 2 & 3 and a 4.5km drive from Wailea Beach, offers easy access to the ocean and local amenities.
The 110 square metre property features two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, swimming pool, jacuzzi, fitness centre, and tennis court.

Best Wailea, HI vacation rentals with parking

Kamaole Sands 3-405-remodeled-well Equipped - Wailea, HI
9.8 103 reviews

Kamaole Sands 3-405-remodeled-well Equipped

apartment, Wailea
This Wailea oceanfront condo, near Kihei, is situated 0.16 km from Kamaole Beach Park 3 and 4.8 km from Wailea Beach, offering stunning sea views.
The 110 square metre apartment sleeps six, boasting two bedrooms, two bathrooms, a fully equipped kitchen, free Wi-Fi, a terrace, swimming pool, jacuzzi, fitness centre, and tennis court.
Haleakala Shores #B-309 Across From Kamaole Lll, Great Rates, Full Kitchen - Wailea, HI
8.8 172 reviews

Haleakala Shores #B-309 Across From Kamaole Lll, Great Rates, Full Kitchen

apartment, Wailea
This two-bedroom apartment is situated directly across the street from Kamaole Beach #3 in Kihei, offering easy access to a beautiful beach and a central location for exploring the island. The apartment enjoys excellent ratings for location, cleanliness, and overall user experience.
The apartment spans 97 square metres and provides comfortable sleeping arrangements for up to six guests. It features a fully equipped kitchen, a washer and dryer, a private terrace, a swimming pool, and free parking, ensuring a relaxing and convenient stay.
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.
8-403 Kamaole Sands - Wailea, HI
9.4 554 reviews

8-403 Kamaole Sands

house, Wailea
This Wailea home is just a two-minute walk from Kamaole Beach 3, placing you right in the heart of the vibrant Wailea resort area. It's also close to other popular beaches, such as Keawakapu and Mokapu, and has consistently received excellent ratings for location, cleanliness, and user experience.
The property is newly renovated, ensuring a comfortable and modern stay. You'll enjoy a fully equipped kitchen, air conditioning, free Wi-Fi, and access to a swimming pool, Jacuzzi, fitness centre, tennis court, and parking.
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