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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

Kamaole Sands Resort: Poolside Paradise - Wailea, HI
9.0 15 reviews

Kamaole Sands Resort: Poolside Paradise

apartment, Wailea
This apartment is located in Kihei, a short drive from Wailea Beach and Kamaole Beach Parks. It has excellent user, location, and cleanliness ratings.
The 820 square foot apartment has one bedroom, two bathrooms, and can comfortably accommodate four guests. Enjoy access to a swimming pool, jacuzzi, fitness center, and on-site parking, as well as a fully equipped kitchen and a private terrace.
Steps To The Beach With Ocean View - Wailea, HI
9.5 4 reviews

Steps To The Beach With Ocean View

apartment, Wailea
This Wailea condo is steps from Kamaole Beach Park, 3.8 miles from the Wailea Emerald Golf Course, and 15 miles from Kahului Airport (OGG).
The 860-square-foot unit features one bedroom, two bathrooms, sleeps seven, and includes a fully equipped kitchen, private lanai, access to a pool, jacuzzi, tennis court, and free Wi-Fi and parking.
Ocean View, Large Lanai, Steps From The Beach, Bldg 10 - Wailea, HI
9.6 85 reviews

Ocean View, Large Lanai, Steps From The Beach, Bldg 10

apartment, Wailea
This oceanfront Wailea condo, near Kamaole Beach Parks 2 and 3 (a 15-minute walk), offers stunning ocean views and easy beach access, situated 2.6 miles from Wailea Beach.
This 820-square-foot unit features one bedroom, two bathrooms, accommodates four guests, and includes a fully equipped kitchen, in-unit laundry, a private terrace, and access to a swimming pool, fitness center, and spa.
Maui Kamaole Oceanfront Oasis - South Kihei - Wailea, HI
9.8 269 reviews

Maui Kamaole Oceanfront Oasis - South Kihei

apartment, Wailea
This two-bedroom apartment is located in South Kihei, just across the street from Kamaole Beach III and within walking distance of shops and restaurants. The apartment has excellent user, location, and cleanliness ratings.
The apartment features a spacious open kitchen, living room, and dining area, as well as three lanais. Enjoy access to two swimming pools, hot tubs, gas grills, tennis courts, and a private entrance with a dedicated parking spot.

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.

97 M² Condo ∙ 1 Bedroom ∙ 4 Guests - Wailea, HI
9.1 15 reviews

97 M² Condo ∙ 1 Bedroom ∙ 4 Guests

apartment, Wailea
Maui Kamaole D103, a ground-floor condo in Wailea's resort area, offers direct access to Kamaole Beach III and is minutes from shopping, dining, and golf courses.
This 1030-square-foot Wailea apartment features one bedroom, two bathrooms, sleeps four, and includes a full kitchen, washer/dryer, lanai, and access to resort amenities like pools, tennis courts, and a spa.
Luxurious Kihei Remodeled 2br Condo Sweeping Ocean Views Near Keawakapu - Wailea, HI
10 4 reviews

Luxurious Kihei Remodeled 2br Condo Sweeping Ocean Views Near Keawakapu

apartment, Wailea
This two-bedroom condo in South Kihei offers a prime location, just a 5-minute walk to Keawakapu Beach and close to Mana Kai Resort amenities.
This 890 square foot apartment accommodates up to four guests with a renovated kitchen, private lanai with ocean views, split air conditioning, and on-site parking.
Kamaole Sands 9-210-new Remodel-ac-ocean Views - Wailea, HI
9.8 179 reviews

Kamaole Sands 9-210-new Remodel-ac-ocean Views

apartment, Wailea
This family-friendly apartment is located in Kihei, just a short distance from Kamaole Beach Park and a few miles from Wailea Beach, offering easy access to both the relaxed atmosphere of Kihei and the upscale amenities of Wailea. The apartment boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This one-bedroom rental comfortably accommodates four guests and features a fully equipped kitchen, a washer and dryer, and a flat-screen TV with a DVD player. Enjoy the convenience of a swimming pool, jacuzzi, fitness center, tennis court, and barbecue grills, all within the apartment complex, making it ideal for a relaxing and fun-filled vacation.
New Fall Deal Sunny Kihei Condo Near Kamaole Beach Iii - Wailea, HI
9.4 21 reviews

New Fall Deal Sunny Kihei Condo Near Kamaole Beach Iii

apartment, Wailea
This Kihei condo is located in South Kihei, directly across from Kamaole Beach Park III, a prime spot for swimming and snorkeling, and minutes from three other Kamaole beaches.
This 850 square foot apartment sleeps four guests and offers amenities such as a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, jacuzzi, and a terrace/balcony, all within the Maui Kamaole® condo resort.

Frequently Asked Questions about vacation rentals in Wailea, HI

Popular destinations

Best Wailea, HI vacation rentals with parking

*Walk To Beach* Kamaole Sands Courtyard Gnd Floor - Wailea, HI
9.7 256 reviews

*Walk To Beach* Kamaole Sands Courtyard Gnd Floor

apartment, Wailea
This one-bedroom condo is located in the Kamaole Sands Resort in South Kihei, just a short walk from Kamaole Beach III and a few minutes drive from the upscale shops and restaurants of Wailea. The property has received excellent ratings for user experience, location, and cleanliness.
The 820-square-foot apartment comfortably accommodates up to 5 guests with a king bed, queen sleeper sofa, and twin cot. Enjoy a peaceful retreat with access to a large swimming pool, Jacuzzi, fitness center, tennis courts, game room, gas BBQ grills, and a cafe within the resort.
Kamaole Sands 4-208 | Walk To Kam Iii Beach - Wailea, HI
9.3 261 reviews

Kamaole Sands 4-208 | Walk To Kam Iii Beach

apartment, Wailea
This Wailea apartment is just a 2-minute walk from Kamaole Beach and a 15-minute walk from Keawakapu Beach, offering easy access to the area's beautiful shores. The apartment has earned excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The accommodation features a fully equipped kitchen for convenient meal preparation, along with a private balcony for relaxing and enjoying the tropical views. You'll also have access to a fitness room, a swimming pool, a spa, and a tennis court, providing plenty of opportunities for recreation and relaxation during your vacation.
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 South Kihei apartment is conveniently located within a 15-minute walk of Kamaole Beach Parks 3 and 2, known for their calm waters and snorkeling, and just a short drive from the luxurious Wailea Beach. The apartment consistently receives excellent user and location ratings and a very good cleanliness rating.
The apartment offers 820 square feet of comfortable living space, perfect for a relaxing getaway. Enjoy a fully equipped kitchen, a private terrace, and access to a swimming pool, jacuzzi, fitness center, tennis court, and spa.
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 a short distance from Keawakapu Beach North and Kamaole Beach Park, and within a 4.1-mile drive of Wailea Beach. The 1,050-square-foot apartment features a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, and a 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.

Kamaole Sands Ground Floor | Walk To Beach & Pool - Wailea, HI
10 1 review

Kamaole Sands Ground Floor | Walk To Beach & Pool

apartment, Wailea
This 1-bedroom condo in Kihei is located just across the street from Kamaole Beach Park III, a prime ground-floor unit offering easy access to this popular South Maui beach renowned for swimming, snorkeling, and sunset views, and is also within walking distance of shops and restaurants.
This accommodation features air conditioning, a full kitchen with a dishwasher, a private lanai, and a guest capacity of 4, with resort pool facilities nearby and opportunities to observe sea turtles while snorkeling.
Quiet Grd Flr Unit, Steps To Resort Pool. Mkk103 - Wailea, HI
10 258 reviews

Quiet Grd Flr Unit, Steps To Resort Pool. Mkk103

apartment, Wailea
This garden view condominium, unit K109, is located in the southernmost part of Kihei, bordering Wailea, offering direct access to Wailea's five-star resorts, restaurants, golf courses, and The Shops at Wailea, and is just steps from a tropical pool with a waterfall and sand-bottom Jacuzzi.
This 1070 square foot condo accommodates up to 4 guests with 1 bedroom and 2 bathrooms, featuring a well-appointed kitchen, air conditioning, high-speed wireless internet, and a private lanai, with on-site amenities including two swimming pools, two Jacuzzis, and tennis courts.
Hale Kamaole 141 - Wailea, HI
9.2 695 reviews

Hale Kamaole 141

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.
Kamaole Sands Condo With Updates And King Bed. - Wailea, HI
9.6 158 reviews

Kamaole Sands Condo With Updates And King Bed.

apartment, Wailea
This Kihei condo, steps from Kamaole Beach Park II and a short drive from Wailea Beach, offers convenient access to multiple beaches.
The 830-square-foot unit features one bedroom, two bathrooms, sleeps four, and includes a full kitchen, free WiFi, a private patio, and access to an on-site pool, fitness center, and spa.

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.

Haleakala Shores A-308 - Ocean & Mountain Views, King, Pool, Walk To Kamaole Iii - Wailea, HI
9.8 129 reviews

Haleakala Shores A-308 - Ocean & Mountain Views, King, Pool, Walk To Kamaole Iii

apartment, Wailea
Kamaole Sands Condo | Ground Floor, 2 Bath, Pool, Hot Tub, Ac, Walk To Beach - Wailea, HI
No reviews

Kamaole Sands Condo | Ground Floor, 2 Bath, Pool, Hot Tub, Ac, Walk To Beach

apartment, Wailea
Hale Kamaole 330 - Wailea, HI
9.1 467 reviews

Hale Kamaole 330

apartment, Wailea
8-403 Kamaole Sands - Wailea, HI
9.4 555 reviews

8-403 Kamaole Sands

house, 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.

Ground Floor-newly Remodeled-ac-well Equipped - Wailea, HI
9.8 79 reviews

Ground Floor-newly Remodeled-ac-well Equipped

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.

Spectacular 3rd Row Villa At Ho'olei With Ocean Views - Wailea, HI
10 64 reviews

Spectacular 3rd Row Villa At Ho'olei With Ocean Views

house, Wailea
Fairmont Kea Lani, Maui - Wailea, HI
9.5 1218 reviews

Fairmont Kea Lani, Maui

resort, Wailea
Wailea Grand Champions 87 - Wailea, HI
No reviews

Wailea Grand Champions 87

apartment, Wailea
New Fall Deal Sunset Ocean Views On Wailea's Golf Course - Wailea, HI
9.0 30 reviews

New Fall Deal Sunset Ocean Views On Wailea's Golf Course

apartment, Wailea
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