Compare Vacation Rentals & Airbnb in Wailea, HI

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Wailea, HI vacation rentals
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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

Luxury 2-bedroom With Ocean And Fairway Views Upgraded And Beautifully Decorated - Wailea, HI
9.4 35 reviews
Wailea, HI
08/09 – 11/09
$670/nightTotal: $2010 (3 )

Luxury 2-bedroom With Ocean And Fairway Views Upgraded And Beautifully Decorated

2 4
apartment , Wailea
This Wailea Grand Champions condo is situated on the Wailea Blue Golf Course, less than 1.6km from the Shops at Wailea, Wailea Beach, and the Wailea Tennis Club.
The 98 square metre apartment offers two bedrooms, two bathrooms, sleeps six, and boasts a private lanai, a fully equipped kitchen, and access to resort amenities including two heated pools, a Jacuzzi, and a fitness centre.
126 Hale Kamaole - Wailea, HI
9.5 313 reviews
Wailea, HI
24/10 – 03/11
$460/nightTotal: $4600 (10 )

126 Hale Kamaole

1 2
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.
Tropical Escape To Wailea With Stunning Oceanview - Wailea, HI
9.9 37 reviews
Wailea, HI
24/10 – 03/11
$397/nightTotal: $3970 (10 )

Tropical Escape To Wailea With Stunning Oceanview

1 2
apartment , Wailea
This studio apartment in Wailea offers ocean views from a shared lanai and is located within the Grand Champions Villas community, a short distance from Wailea's golf courses, dining, and shopping.
This accommodation provides a kitchenette with a microwave and air fryer, air conditioning, Wi-Fi, and access to two swimming pools and hot tubs, with complimentary beach chairs, umbrellas, and towels available for up to three guests.
Clean, Maui Family Owned, Private, Top Floor, Lots Of Amenities, Oceanview! - Wailea, HI
9.4 67 reviews
Wailea, HI
10/07 – 13/07
$514/nightTotal: $1542 (3 )

Clean, Maui Family Owned, Private, Top Floor, Lots Of Amenities, Oceanview!

2 2
house , Wailea
This Wailea condo is situated less than 2km from the Shops at Wailea, Wailea Beach, Ulua Beach Park, and Wailea Shopping Village, offering easy access to major attractions.
The 74 square metre apartment features one bedroom, one bathroom, a fully equipped kitchen, and a private terrace; it also includes a washing machine, a sofa bed, and access to a swimming pool, jacuzzi, tennis court, and barbecue facilities.

Best Wailea, HI vacation rentals with a pool

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

Maui Kamaole #L-105 Beautiful Ocean View, Great Location, Great Rates, A/c - Wailea, HI
9.6 106 reviews
Wailea, HI
08/09 – 11/09
$544/nightTotal: $1632 (3 )

Maui Kamaole #L-105 Beautiful Ocean View, Great Location, Great Rates, A/c

2 4
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.
Brand New Remodel-ocean Views-ac-close To The Beach-meticulous Cleaning - Wailea, HI
9.9 224 reviews
Wailea, HI
24/10 – 03/11
$478/nightTotal: $4780 (10 )

Brand New Remodel-ocean Views-ac-close To The Beach-meticulous Cleaning

1 2
apartment , Wailea
This Wailea apartment, near Kamaole Beach Parks 2 & 3 (a short walk away) and approximately 4.5km from Wailea Beach, offers superb ocean proximity.
The 76-square-metre condo boasts one bedroom, two bathrooms, sleeps four, and includes a fully equipped kitchen, private balcony, free Wi-Fi, access to an on-site fitness centre, swimming pool, jacuzzi, and tennis court.
Spacious S. Kihei Suite New A/c Across From Kam 3 - Wailea, HI
9.9 135 reviews
Wailea, HI
10/07 – 13/07
$330/nightTotal: $990 (3 )

Spacious S. Kihei Suite New A/c Across From Kam 3

1 2
apartment , Wailea
This Wailea apartment is directly opposite Kamaole Beach III, a short distance from the Kihei Boat Ramp and a few minutes’ drive from Keawakapu Beach and Wailea's upscale resorts and shops.
The self-catering suite offers a queen bed, living room, fully equipped kitchen, private lanai with partial ocean views, and access to two swimming pools, a tennis court, and a pickleball court; it sleeps two guests and includes beach chairs and an umbrella.
Completely Remodeled-ac Throughout-well Equipped-meticulous Cleaning - Wailea, HI
9.8 89 reviews
Wailea, HI
10/07 – 13/07
$580/nightTotal: $1740 (3 )

Completely Remodeled-ac Throughout-well Equipped-meticulous Cleaning

1 2
apartment , Wailea
This Kihei apartment, situated steps from Kamaole Beach Parks 2 & 3 and 4.5km from Wailea Beach, offers immediate beach access and proximity to the Kihei Boat Ramp.
The 76 square metre self-catering flat boasts one bedroom, two bathrooms, sleeps four, and includes a fully equipped kitchen, swimming pool, Jacuzzi, fitness centre, tennis court, and on-site BBQ grills.

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

Haleakala Shores By Coldwell Banker Island Vacations - Wailea, HI
9.4 232 reviews
Wailea, HI
10/07 – 13/07
$576/nightTotal: $1728 (3 )

Haleakala Shores By Coldwell Banker Island Vacations

2 2
apartment , Wailea
This apartment is situated in Wailea, just a short walk from Kamaole Beach and 1.6 km from Keawakapu Beach, with Mokapu Beach a further 1.6 km away. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment offers two bedrooms and is equipped with a fully fitted kitchen, including a dishwasher, oven, microwave, toaster, fridge, kitchenware, and coffee machine. Enjoy the on-site fitness room, swimming pool, spa, and tennis court, or explore the area by bike, with access to a garden and a terrace.
Your Paradise - Entire > 800 Square Feet Apartment With Affordable Rate - Wailea, HI
9.8 91 reviews
Wailea, HI
24/10 – 03/11
$278/nightTotal: $2780 (10 )

Your Paradise - Entire > 800 Square Feet Apartment With Affordable Rate

1 2
apartment , Wailea
This Kihei apartment, a short walk from Kamaole Beach Park 3 and 4.6km from Wailea Beach, offers convenient access to Kihei Boat Ramp within a 10-minute drive.
The 76 square metre property features one bedroom, two bathrooms, sleeps two guests, and includes a fully equipped kitchen, private balcony, swimming pool, jacuzzi, tennis court, and free Wi-Fi.
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.
Tropical Escape With Endless Coastal Views - Wailea, HI
9.8 54 reviews
Wailea, HI
10/07 – 13/07
$537/nightTotal: $1611 (3 )

Tropical Escape With Endless Coastal Views

1 2
apartment , Wailea
This one-bedroom condominium in Wailea, Kihei, offers expansive ocean views and is a short 5-minute walk to the Wailea Blue Golf Course, with Ulua and Mokapu beaches also within walking distance.
This 80-square-meter apartment, managed by My Perfect Stays, accommodates up to four guests with a king bed and a queen sleeper sofa, featuring a fully equipped kitchen with a convenient island, two private lanais, and complimentary daily activity admissions.

Best Wailea, HI vacation rentals with parking

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.
Charming Kihei Oasis Vistas - Wailea, HI
9.7 50 reviews
Wailea, HI
24/10 – 03/11
$420/nightTotal: $4200 (10 )

Charming Kihei Oasis Vistas

1 2
house , Wailea
This Kihei condo, part of the Kamaole Sands resort, is directly opposite Kamaole Three Beach and offers stunning ocean views from its lanai.
The one-bedroom, two-bathroom apartment sleeps four, boasts a fully equipped kitchen, washer/dryer, and access to resort amenities including a swimming pool, Jacuzzi, tennis courts, and fitness centre; beach essentials are provided.
Colorful Kamaole Sands Condo, Kihei, With Family Friendly Pool, Steps From Beach - Wailea, HI
9.6 108 reviews
Wailea, HI
10/07 – 13/07
$487/nightTotal: $1461 (3 )

Colorful Kamaole Sands Condo, Kihei, With Family Friendly Pool, Steps From Beach

1 2
apartment , Wailea
This beachfront Kihei condo, less than 1.6km from Kamaole Beach Park 3 and 4.5km from Wailea Beach, offers direct beach access.
The one-bedroom apartment sleeps four, boasts two bathrooms, a fully equipped kitchen including a dishwasher, in-unit laundry, and access to a swimming pool, Jacuzzi, spa, fitness centre, and tennis court.
Remodeled-kamaole Sands-beautiful Ocean Views-ac-meticulous Cleaning - Wailea, HI
9.8 101 reviews
Wailea, HI
24/10 – 03/11
$519/nightTotal: $5190 (10 )

Remodeled-kamaole Sands-beautiful Ocean Views-ac-meticulous Cleaning

2 2
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.
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