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Wailea, HI vacation rentals
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Best Vacation rentals and Airbnb offers in Wailea, HI

Best Wailea, HI vacation rentals with a balcony

Hale Kamaole 205 Second Floor Condo, Easy Access To Best Beach On Maui! - Wailea, HI
9.2 676 reviews

Hale Kamaole 205 Second Floor Condo, Easy Access To Best Beach On Maui!

apartment, Wailea
This apartment is located in South Kihei, just a short distance from Kamaole Beach Parks 3 and 2, and less than 3 miles from Wailea Beach, offering a quiet setting close to the action. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The apartment features a fully equipped kitchen, a Smart TV with a DVD player, and a washer and dryer for added convenience. Enjoy the on-site amenities, including a swimming pool, fitness center, tennis court, and barbecue grills, or relax on the terrace or in the garden.
Summer Sale! Spacious 3br W/ Ac In Wailea - Gc 124 - Wailea, HI
9.5 261 reviews

Summer Sale! Spacious 3br W/ Ac In Wailea - Gc 124

apartment, Wailea
This 3-bedroom condo is located in Wailea, directly on the Wailea Blue Golf Course, a short walk from the Shops at Wailea and the Wailea Tennis Center, and a 15-20 minute walk from Wailea Beach. This apartment has excellent user, location, and cleanliness ratings. The unit is on the ground floor and comfortably accommodates up to 8 guests. You'll have access to two swimming pools, two hot tubs, four gas BBQ grills, and a garden, plus enjoy stunning golf course views from the lanai.
*Last Minute Deal! Beautiful By Top Swimming Beach - Wailea, HI
9.7 258 reviews

*Last Minute Deal! Beautiful By Top Swimming Beach

apartment, Wailea
This apartment is located in Kihei, just steps from the white sand beaches of Kam III and the upscale amenities of Wailea town, offering a peaceful location close to the action. It has received excellent ratings for location, cleanliness, and overall experience.
This one-bedroom, one-bathroom unit spans 780 square feet and comfortably accommodates up to four guests. Enjoy amenities like a fully equipped kitchen, air conditioning, a private lanai with ocean views, a swimming pool, and free parking.
Wailea Condo Near Golf And Shops - Wailea, HI
9.2 108 reviews

Wailea Condo Near Golf And Shops

apartment, Wailea
This Wailea condo is located just a mile from both the Shops at Wailea and Wailea Beach, putting you close to shopping, dining, and the beautiful coastline. The property has earned excellent ratings for its location, cleanliness, and overall experience.
The 900 square foot apartment has one bedroom, two bathrooms, and can accommodate up to four guests. You'll enjoy a full kitchen, a spa tub, barbecue grills, and a balcony, along with access to a swimming pool, fitness center, tennis court, and more.

Browse Family-Friendly Vacation Rentals in Wailea, HI

Perfect for family trips, these spacious Wailea, HI rentals and Airbnbs provide easy access to local beaches.

Ocean View And Beach By Wailea - Wailea, HI
10 178 reviews

Ocean View And Beach By Wailea

apartment, Wailea
This Wailea condo rental, located in the Maui Kamaole complex, offers direct access to Kamaole III and Keawakapu beaches.
The one-bedroom, two-bathroom unit sleeps four guests and features a well-equipped kitchen, lanai, on-site laundry, reserved parking, and access to two pools, a hot tub, and tennis courts within the complex, plus beach gear.
Spectacular Ocean View 2 Bedroom Condo. - Wailea, HI
10 188 reviews

Spectacular Ocean View 2 Bedroom Condo.

apartment, Wailea
This oceanfront condo in Wailea offers stunning views and is just a short distance from beaches and shops, providing a peaceful and relaxing atmosphere. It has received excellent ratings for location, cleanliness, and user experience.
The 1050 square foot apartment has 2 bedrooms, 2 bathrooms, and can accommodate up to 6 guests. Enjoy a comfortable stay with amenities like a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, and a terrace with ocean views.
Maui Vista 3210 Wonderful Unit With New Split Ac, Low Vo And New Paint And Carpet - Wailea, HI
8.6 42 reviews

Maui Vista 3210 Wonderful Unit With New Split Ac, Low Vo And New Paint And Carpet

apartment, Wailea
This Wailea condo rental is steps from Keawakapu Beach South and within a mile of the Kihei Boat Ramp and 1.5 miles from Wailea Beach.
This 590-square-foot, one-bedroom, one-bathroom unit sleeps five and features a fully equipped kitchen, in-unit laundry, free WiFi, a balcony, and access to a swimming pool, spa, tennis court, and concierge services.
Mana Kai Maui - Official Onsite Rental Company - Wailea, HI
9.0 1630 reviews

Mana Kai Maui - Official Onsite Rental Company

resort, Wailea
Mana Kai Maui is located in Wailea, a short walk from Keawakapu Beach, Mokapu Beach, and Kamaole Beach, offering easy access to the beautiful beaches of the area. The hotel has received very good user ratings, excellent location ratings, and very good cleanliness ratings.
The resort has a mix of rooms and suites with private patios featuring ocean views. Amenities include a swimming pool, a spa, a fitness center, and a restaurant and bar, as well as free Wi-Fi and room service.

Frequently Asked Questions about vacation rentals in Wailea, HI

Popular destinations

Best Wailea, HI vacation rentals with parking

Ground Floor Across Kamaole Beach Park Iii - Wailea, HI
9.2 60 reviews

Ground Floor Across Kamaole Beach Park Iii

apartment, Wailea
This South Kihei apartment is located within a mile of Kamaole Beach Park 3 and about 3 miles from Wailea Beach, offering easy access to both the peaceful beaches and the upscale amenities of Wailea. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
This 1-bedroom, 2-bathroom apartment comfortably sleeps 4 guests and offers 820 square feet of living space. Enjoy a fully equipped kitchen, a private terrace, a swimming pool, a spa, a fitness center, and a tennis court, all within the complex.
Nicely Updated-ocean Views-well Equipped-ac - Wailea, HI
9.9 108 reviews

Nicely Updated-ocean Views-well Equipped-ac

apartment, Wailea
This oceanfront Wailea condo is steps from Kamaole Beach Parks II and III, and 2.8 miles from Wailea Beach.
The one-bedroom, two-bathroom unit sleeps four, offering a fully equipped kitchen, in-unit laundry, free WiFi, a pool, jacuzzi, fitness center, tennis court, and BBQ grills; guests enjoy direct ocean views.
Summer Sale- Renovated Condo Ac Near Beach-kkp 208 - Wailea, HI
9.4 83 reviews

Summer Sale- Renovated Condo Ac Near Beach-kkp 208

apartment, Wailea
This 2-bedroom apartment is located in Kihei, just across the street from Keawakapu Beach, a 3-minute walk away, offering easy access to the beautiful beach and nearby shops and restaurants. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The apartment has 810 square feet of living space and comfortably accommodates up to 4 guests. It features a fully equipped kitchen, a private lanai with ocean and mountain views, a garden, a spa, and on-site parking.
Kamaole Sands 1-102-ocean Views-ground Floor-ac - Wailea, HI
9.7 123 reviews

Kamaole Sands 1-102-ocean Views-ground Floor-ac

apartment, Wailea
This one-bedroom, two-bathroom condo is located in Kihei, just under a mile from Kamaole Beach Parks 3 and 2, and about 3 miles from Wailea Beach. The apartment sleeps up to 4 guests and offers amenities such as a swimming pool, jacuzzi, fitness center, and tennis court.

Neighborhoods and points of interest in Wailea, HI

Choose the Right Vacation Rentals with a Pool in Wailea, HI

Complement your beach days with a dip in the pool at these premier vacation rentals in Wailea, HI.

Charming Kihei Oasis Vistas - Wailea, HI
9.7 82 reviews

Charming Kihei Oasis Vistas

house, Wailea
This Kihei condo, part of the Kamaole Sands resort, sits directly across from Kamaole III Beach, offering unparalleled beach access.
The one-bedroom, two-bathroom unit sleeps four, features a fully equipped kitchen, in-unit laundry, and access to resort amenities including a pool, hot tub, fitness center, and BBQ grills; beach chairs, umbrellas, and towels are provided.
Kamaole Sands 6-107, 1 Bedroom, Ground Floor Condo, Pool, Gym - Wailea, HI
9.2 240 reviews

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

apartment, Wailea
This Wailea apartment is just a 2-minute walk from Kamaole Beach, offering easy access to the sand and surf. It has excellent user ratings and very good ratings for location and cleanliness.
The ground-floor unit has a fully equipped kitchen, air conditioning, and a private bathroom. Enjoy on-site amenities like a swimming pool, jacuzzi, spa, restaurant, fitness center, tennis court, and free Wi-Fi, as well as nearby cycling opportunities and access to other popular beaches.
Grand Champions 35 Condo - Wailea, HI
9.6 1660 reviews

Grand Champions 35 Condo

apartment, Wailea
The Wailea Grand Champions 110 condo is located in the desirable Wailea district, just a short walk from stunning beaches like Ulua Beach, Wailea Beach, and Mokapu Beach. This accommodation has earned excellent ratings for its location, cleanliness, and overall experience.
The condo features two bedrooms, perfect for families or groups of friends. Guests can enjoy a fully equipped kitchen, a private balcony, access to a fitness room, free parking, and Wi-Fi, along with a range of other amenities and activities.
Maui Parkshore 410 - Stunning Ocean Views - Wailea, HI
9.7 226 reviews

Maui Parkshore 410 - Stunning Ocean Views

house, Wailea
This Wailea apartment is located in South Kihei, just a short walk from Kamaole Beach Parks 3 and 2 and a short drive from the upscale resort area of Wailea. It boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The rental offers two bedrooms, a sofa bed, and a balcony, perfect for families or groups of friends. Guests can enjoy amenities like a fully equipped kitchen, a swimming pool, a terrace, a garden, and parking, making it ideal for a relaxing vacation.

Find the Best Seaside Vacation Rentals in Wailea, HI

Discover relaxing coastal properties with these seaside vacation rentals in Wailea, HI, located near the shore for an ideal beach-town escape.

Garden View A/c Wi-fi Across Beach Park Ks7304 - Wailea, HI
8.8 59 reviews

Garden View A/c Wi-fi Across Beach Park Ks7304

apartment, Wailea
Kamaole Sands 9-301 - Luxury Renovation, Split Ac - Wailea, HI
9.8 983 reviews

Kamaole Sands 9-301 - Luxury Renovation, Split Ac

apartment, Wailea
Charming Beachside Garden Vistas - Wailea, HI
9.8 6 reviews

Charming Beachside Garden Vistas

house, Wailea
126 Hale Kamaole - Wailea, HI
9.6 304 reviews

126 Hale Kamaole

apartment, Wailea

Traveler-Approved Luxury Vacation Rentals in Wailea, HI

Discover the best of the coast with a luxury vacation rental in Wailea, HI, offering sophisticated rooms and prime locations.

Kamaole Sands 10-306-stunning Remodel-ocean Views - Wailea, HI
9.8 200 reviews

Kamaole Sands 10-306-stunning Remodel-ocean Views

apartment, Wailea

Explore Vacation Rentals with Saunas in Wailea, HI

Maximize your recovery with an on-site sauna, a standard feature at these premier Wailea, HI vacation rentals.

Ho Olei Residences - Coraltree Residence Collection - Wailea, HI
8.8 1293 reviews

Ho Olei Residences - Coraltree Residence Collection

resort, Wailea
Maui Breeze Retreat At Ho'olei! Relax And Enjoy!  Book Now! - Wailea, HI
10 149 reviews

Maui Breeze Retreat At Ho'olei! Relax And Enjoy! Book Now!

apartment, Wailea
Unwind In A Wailea Ocean-view Condo With Pool, Hot Tub & W/d - Wailea, HI
9.0 30 reviews

Unwind In A Wailea Ocean-view Condo With Pool, Hot Tub & W/d

apartment, Wailea
Fairmont Kea Lani Maui Villa Experience - Wailea, HI
No reviews

Fairmont Kea Lani Maui Villa Experience

house, Wailea
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