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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

2br Kihei Condo Near Top Beaches And Pool - Wailea, HI
9.3 81 reviews

2br Kihei Condo Near Top Beaches And Pool

apartment, Wailea
This 2-bedroom condo is located in Kihei, just 0.6 miles from Keawakapu Beach North and 2.6 miles from Wailea Beach. The apartment offers a fully equipped kitchen, free Wi-Fi, a spa tub, and access to a swimming pool, Jacuzzi, fitness center, tennis court, and parking.
Romantic One Br Condo (Remodeled) - Wailea, HI
9.7 258 reviews

Romantic One Br Condo (Remodeled)

apartment, Wailea
This Wailea apartment is located in the Grand Champions complex, just a short walk from the Wailea Blue Course and Tennis Center, and minutes from Ulua and Mokapu beaches, offering a peaceful escape from the hustle and bustle of the resorts. The apartment has earned excellent ratings for location, cleanliness, and overall user experience.
The one-bedroom, one-bathroom apartment spans 700 square feet and features a fully equipped kitchen with stainless steel appliances and a spacious lanai. Enjoy amenities like two swimming pools, hot tubs, and a garden, as well as beach gear including snorkel equipment, boogie boards, and beach chairs.
Maui Kamaole D103 By Coldwell Banker Island Vacations - Wailea, HI
9.7 4 reviews

Maui Kamaole D103 By Coldwell Banker Island Vacations

apartment, Wailea
Maui Kamaole D103, a one-bedroom condo in Wailea, is a 6-minute walk from Kamaole Beach and 3.2 miles from Wailea's golf courses.
This 1040-square-foot unit sleeps seven, features two bathrooms, a full kitchen with dishwasher, and offers access to a pool, hot tub, tennis court, and complimentary Wi-Fi.
Kamaole Sands 3-305-ocean Views-well Equipped-ac - Wailea, HI
9.8 113 reviews

Kamaole Sands 3-305-ocean Views-well Equipped-ac

apartment, Wailea
This Kihei condo, a short distance from Kamaole Beach Park III and a 10-minute drive from Wailea Beach, offers convenient access to nearby attractions.
The 820-square-foot unit features one bedroom, two bathrooms, accommodates four guests, and includes a fully equipped kitchen, in-unit laundry, free Wi-Fi, a luxurious spa tub, and access to a swimming pool, Jacuzzi, fitness center, and tennis court.

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.

Tropical Wailea Retreat With Pool - Wailea, HI
9.3 38 reviews

Tropical Wailea Retreat With Pool

apartment, Wailea
This Wailea Grand Champions condo boasts magnificent ocean and fairway views, situated on the Wailea Blue Golf Course, minutes from the Shops at Wailea and Wailea Beach.
The 1,050-square-foot, two-bedroom, two-bathroom unit sleeps six and features a fully equipped kitchen, resort amenities including pools and a Jacuzzi, and on-site security.
Condo ∙ 2 Bedrooms ∙ 6 Guests - Wailea, HI
9.9 73 reviews

Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Wailea
This 2-bedroom condo in South Kihei, adjacent to Wailea, offers direct ocean views and is a short walk to Kamaole III Beach and Keawakapu Beach.
This family-friendly vacation rental accommodates up to 6 guests and features a recently updated interior, a master bedroom loft, a private lanai, and resort amenities including two swimming pools, two hot tubs, and two tennis courts.
Sale! Gorgeous 3br/2ba With Ocean & Sunset Views - Wailea, HI
9.8 223 reviews

Sale! Gorgeous 3br/2ba With Ocean & Sunset Views

apartment, Wailea
This Wailea apartment is located just a short walk from Maui's beautiful beaches, a world-class shopping mall, and 5-star resorts. It has earned excellent ratings for location, cleanliness, and overall user experience.
The spacious 3-bedroom, 2-bathroom apartment comfortably accommodates up to 6 guests. Amenities include a private lanai, access to two shared pools with hot tubs, air conditioning, a fully equipped kitchen, and beach supplies.
76 M² Condo ∙ 1 Bedroom ∙ 4 Guests - Wailea, HI
9.7 36 reviews

76 M² Condo ∙ 1 Bedroom ∙ 4 Guests

apartment, Wailea
This 820 sq ft condo in South Kihei is located across the street from Kamaole III Beach and a short drive from Wailea and Makena beaches, offering a ground-floor unit with a private lanai and partial ocean view.
This family-friendly apartment features 1 bedroom, 2 bathrooms, a full kitchen, in-unit laundry, and access to Kamaole Sands Resort amenities including multiple swimming pools, spas, a fitness center, and tennis courts, accommodating up to 4 guests.

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Best Wailea, HI vacation rentals with parking

Airy And Updated Condo Across From Kam-iii Beach - Wailea, HI
9.6 92 reviews

Airy And Updated Condo Across From Kam-iii Beach

apartment, Wailea
This newly remodeled Hale Kamaole Resort condo in Kihei offers a short walk to Kamaole III Beach, known for snorkeling and watersports.
The one-bedroom, one-bathroom unit sleeps five, features a fully stocked kitchen, private lanai with sunset views, access to two pools, tennis courts, and BBQ grills, plus ocean views and on-site parking.
Kamaole Sands 4-213  Designer Oasis Steps To Beach - Wailea, HI
9.8 989 reviews

Kamaole Sands 4-213 Designer Oasis Steps To Beach

apartment, Wailea
This Wailea apartment is situated just steps from Kamaole Beach Parks 3 and 2, offering easy access to the stunning beaches of Wailea. The apartment consistently receives excellent ratings for its location, cleanliness, and overall user experience.
The apartment features a fully equipped kitchen, two bathrooms, and a washing machine, providing all the comforts of home. Enjoy ocean views from your private balcony, relax in the on-site fitness center and spa tub, or take advantage of the tennis court, swimming pool, and barbecue grills.
21b Grand Champions Studio -Ulua & Mokapu Beaches - Wailea, HI
9.7 66 reviews

21b Grand Champions Studio -Ulua & Mokapu Beaches

apartment, Wailea
This Wailea studio rental is located in the Grand Champions resort, a short walk from Ulua Beach and The Shops at Wailea, offering easy access to snorkeling, upscale shopping, and dining.
The unit features a California king bed, a lanai, a small kitchen with a refrigerator and microwave, one bathroom, accommodates two guests, and includes free resort parking and access to pools and Jacuzzis.
Charming Beachside Garden Vistas - Wailea, HI
9.8 6 reviews

Charming Beachside Garden Vistas

house, Wailea
This Wailea vacation home is located a 4-minute walk from Kamaole Beach, 3.8 miles from Wailea Emerald Course, and 14 miles from Kahului Airport.
This 800 square foot residence accommodates up to six guests with two bathrooms, a full kitchen, air conditioning, a swimming pool, a jacuzzi, a garden, and a fitness center, offering complimentary Wi-Fi and elevator access.

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.

Beautiful Kihei Front Row Ocean View  L  Top Beach - Wailea, HI
10 48 reviews

Beautiful Kihei Front Row Ocean View L Top Beach

apartment, Wailea
This Maui Kamaole condo in South Kihei is a 3-minute walk to Kamaole Beach Park III and offers direct ocean views from its prime 'G' building location.
This 1053 sqft apartment features 1 bedroom, 2 bathrooms, and sleeps 4, with amenities including a full kitchen, air conditioning, two pools, and beach gear, all within walking distance of Keawakapu Beach and Wailea's dining.
Ground Floor-newly Remodeled-ac-well Equipped - Wailea, HI
9.8 79 reviews

Ground Floor-newly Remodeled-ac-well Equipped

apartment, Wailea
This oceanfront Wailea condo is located near Kamaole Beach Parks 2 and 3, a 2.8-mile drive from Wailea Beach and within 10 minutes of the Kihei Boat Ramp.
This 820-square-foot unit features one bedroom, two bathrooms, accommodates four guests, and includes a fully equipped kitchen, in-unit laundry, a private balcony, and access to a fitness center, swimming pool, and jacuzzi.
Sweeping Ocean Views; Private High End Condo! - Wailea, HI
9.6 105 reviews

Sweeping Ocean Views; Private High End Condo!

apartment, Wailea
This 1-bedroom, 2-bathroom condo in Wailea offers sweeping ocean views of Molokini Crater, Kahoolawe, Lanai, and the West Maui Mountains, located minutes from Wailea's shopping and dining and a short drive to premier beaches.
This ground-floor corner unit in Wailea Ekolu Village features a designer-styled interior, a gourmet kitchen, and access to a solar-heated pool, entertainment pavilion, and BBQ area, with the Wailea Blue golf course an easy walk away.
Maui Kamaole J 108 - Wailea, HI
9.8 7 reviews

Maui Kamaole J 108

house, Wailea
Maui Kamaole J 108, a one-bedroom Wailea rental home, is conveniently located 3.2 miles from the Wailea Emerald Golf Course and 15 miles from Kahului Airport, near popular beaches like Kamaole and Keawakapu.
This vacation property sleeps seven guests and boasts two bathrooms, a fully equipped kitchen with a dishwasher, air conditioning, a private swimming pool, a tennis court, free Wi-Fi, and free parking.

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.

Secluded, Private, Across Kamaole Iii, Mkf210 - Wailea, HI
9.8 263 reviews

Secluded, Private, Across Kamaole Iii, Mkf210

apartment, Wailea
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
Large, Sunny 2br/2ba Penthouse, Great Beach - Wailea, HI
9.7 161 reviews

Large, Sunny 2br/2ba Penthouse, Great Beach

apartment, Wailea
Maui Parkshore 307 - Stunning Remodel, Ocean Views - Wailea, HI
9.9 168 reviews

Maui Parkshore 307 - Stunning Remodel, Ocean Views

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.

Grand Champions 35 Condo - Wailea, HI
9.6 1664 reviews

Grand Champions 35 Condo

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.

Fairmont Kea Lani, Maui - Wailea, HI
9.6 1220 reviews

Fairmont Kea Lani, Maui

resort, 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
Spectacular 3rd Row Villa At Ho'olei With Ocean Views - Wailea, HI
10 63 reviews

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

house, Wailea
Luxury 3bd Villa With Ocean Views Near Wailea Beach & Grand Wailea - Hoolei Residences 15-4 - Wailea, HI
9.0 4 reviews

Luxury 3bd Villa With Ocean Views Near Wailea Beach & Grand Wailea - Hoolei Residences 15-4

apartment, Wailea
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