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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

Kihei Condo W/ Resort Amenities: Walk To The Beach - Wailea, HI
8.8 115 reviews
Wailea, HI
10/16 – 10/28
$262/nighttotal: $3144 (12 )

Kihei Condo W/ Resort Amenities: Walk To The Beach

1 1
house , Wailea
This one-bedroom Wailea condo is located just a short walk from the beach and just over 3 miles from the Wailea Emerald Course.
This 870-square-foot apartment features a private entrance, a terrace with ocean views, and access to resort amenities including a swimming pool, Jacuzzi, and spa.
Maui Kamaole H-101 - Wailea, HI
8.8 1120 reviews
Wailea, HI
07/10 – 07/13
$379/nighttotal: $1137 (3 )

Maui Kamaole H-101

1 2
apartment , Wailea
The Maui Kamaole F-204 is a 3-star hotel located in Wailea, a short walk from Kamaole Beach and a bit further from Keawakapu Beach. It has received very good user ratings, with excellent ratings for location and cleanliness.
The 2-bedroom unit comfortably sleeps six people and includes a fully equipped kitchen, air conditioning, private bathrooms, and a terrace. You can enjoy swimming in the pool, relaxing in the jacuzzi, or working out in the fitness center.
Stunning Remodel-large Lanai-ac Throughout-well Equipped-meticulous Cleaning - Wailea, HI
9.9 179 reviews
Wailea, HI
10/16 – 10/28
$366/nighttotal: $4392 (12 )

Stunning Remodel-large Lanai-ac Throughout-well Equipped-meticulous Cleaning

1 1
apartment , Wailea
This oceanfront condo is ideally located near Kamaole Beach Parks II and III in Wailea, Maui, a short 2.9-mile drive from Wailea Beach.
The one-bedroom, two-bathroom unit sleeps four guests and boasts a fully equipped kitchen, in-unit laundry, a private terrace, access to a swimming pool, jacuzzi, fitness center, and tennis court, plus nearby barbecue grills and a garden.
Oceanview Condo Across From Kamaole Beach Iii | Updated Kihei Getaway - Wailea, HI
8.9 323 reviews
Wailea, HI
09/08 – 09/11
$316/nighttotal: $948 (3 )

Oceanview Condo Across From Kamaole Beach Iii | Updated Kihei Getaway

2 4
apartment , Wailea
This 2-bedroom apartment is located in Kihei, just a short drive from the upscale resort area of Wailea, and within walking distance of two popular beaches. Guests have praised the apartment for its excellent location, cleanliness, and overall quality.
The 890 square foot apartment includes a fully equipped kitchen, a comfortable living space, and a private terrace. Enjoy amenities such as a swimming pool, a jacuzzi, a fitness center, and a tennis court, all within the complex.

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.

Newly Renovated Kihei Condo With Sunset Views  Steps From A Beautiful Beach! - Wailea, HI
9.8 143 reviews
Wailea, HI
10/24 – 11/03
$273/nighttotal: $2730 (10 )

Newly Renovated Kihei Condo With Sunset Views Steps From A Beautiful Beach!

1 2
apartment , Wailea
This Kihei condo, a short 0.2-mile walk from Kamaole Beach Park III and 2.8 miles from Wailea Beach, offers convenient access to swimming, sunbathing, and upscale resort amenities.
The 900-square-foot, two-bedroom, two-bathroom unit sleeps four and features a fully equipped kitchen, in-unit laundry, a private terrace, and access to a swimming pool, jacuzzi, fitness center, tennis court, and spa.
Cool & Quiet Wailea Oasis, Big Lanai + Two Pools - Wailea, HI
9.9 67 reviews
Wailea, HI
10/16 – 10/28
$414/nighttotal: $4968 (12 )

Cool & Quiet Wailea Oasis, Big Lanai + Two Pools

2 1
apartment , Wailea
This Wailea condo is conveniently located a short walk from Ulua Beach and a mile from Wailea Beach, also near Mokapu Beach and the Wailea Emerald Golf Course.
The 1190-square-foot unit features two bedrooms, two bathrooms, a fully equipped kitchen, in-unit laundry, a lanai with garden views, access to two swimming pools, a jacuzzi, a tennis court, and free parking.
2 Bed, 2 Bath Ocean View, A/c Kamaole Sands A Graded Condo - Wailea, HI
9.4 114 reviews
Wailea, HI
10/16 – 10/28
$313/nighttotal: $3756 (12 )

2 Bed, 2 Bath Ocean View, A/c Kamaole Sands A Graded Condo

2 1
apartment , Wailea
This Kihei condo, a 10-minute walk from Kamaole Beach Parks II and III and a 2.7-mile drive from Wailea Beach, offers mountainside tranquility with easy beach access.
This 1180-square-foot, two-bedroom, two-bathroom vacation rental sleeps eight, boasting a full kitchen, private terrace, access to a pool, jacuzzi, fitness center, tennis court, and free Wi-Fi.
Beautiful, Ground Floor Condo, Steps To The Pool And Beach - Wailea, HI
9.7 234 reviews
Wailea, HI
09/08 – 09/11
$417/nighttotal: $1251 (3 )

Beautiful, Ground Floor Condo, Steps To The Pool And Beach

2 4
apartment , Wailea
This Wailea ground-floor condo offers easy access to Kamaole III Beach, renowned for its snorkeling and sunsets.
The 1,070-square-foot unit features two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, private lanai, and access to a shared pool and BBQ area.

Frequently Asked Questions about vacation rentals in Wailea, HI

Destinations nearby

Best Wailea, HI vacation rentals with parking

Maui Kamaole #A-102 Front Row, Ocean View, Across Kamaole Bch Iii, Full A/c - Wailea, HI
9.2 55 reviews
Wailea, HI
10/16 – 10/28
$306/nighttotal: $3672 (12 )

Maui Kamaole #A-102 Front Row, Ocean View, Across Kamaole Bch Iii, Full A/c

1 1
apartment , Wailea
This Kihei condo, a short drive from Wailea Beach (2.5 miles) and near the Kihei Boat Ramp (0.2 miles), offers easy access to multiple beaches within a 10-minute radius.
This 850-square-foot one-bedroom, two-bathroom unit sleeps two and features a fully equipped kitchen, in-unit laundry, a private terrace, and access to a swimming pool, Jacuzzi, and tennis court.
Gorgeous Remodel-close To The Beach-well Equipped-meticulous Cleaning - Wailea, HI
9.8 79 reviews
Wailea, HI
07/10 – 07/13
$407/nighttotal: $1221 (3 )

Gorgeous Remodel-close To The Beach-well Equipped-meticulous Cleaning

1 2
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.
Maui Kamaole #F-210 Private, Across Kamaole Iii, Full A/c, Great Location - Wailea, HI
9.8 256 reviews
Wailea, HI
10/16 – 10/28
$300/nighttotal: $3600 (12 )

Maui Kamaole #F-210 Private, Across Kamaole Iii, Full A/c, Great Location

2 1
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.
Romantic 1 Br Condo With King Tempurpedic - Wailea, HI
9.7 258 reviews
Wailea, HI
07/10 – 07/13
$332/nighttotal: $996 (3 )

Romantic 1 Br Condo With King Tempurpedic

1 2
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.

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 #7-403 Great Rates, Garden And Partial Ocean Views, A/c! - Wailea, HI
9.6 181 reviews
Wailea, HI
10/24 – 11/03
$334/nighttotal: $3340 (10 )

Kamaole Sands #7-403 Great Rates, Garden And Partial Ocean Views, A/c!

2 2
apartment , Wailea
This 2-bedroom, 2-bathroom apartment is located in Wailea, just a short distance from Kamaole Beach Park 3 and Kamaole Beach Park, and a 2.5-mile drive from Wailea Beach.
The 1,180 square foot apartment features a fully equipped kitchen, a private terrace, a swimming pool, a fitness center, and can accommodate up to 6 guests.
Cozy, Well-furnished Studio - Wailea, HI
9.4 391 reviews
Wailea, HI
07/10 – 07/13
$236/nighttotal: $708 (3 )

Cozy, Well-furnished Studio

1 2
studio , Wailea
This Wailea condo rental, located in the Grand Champions development adjacent to the Wailea Blue Golf Course, is a two-minute drive from Wailea beaches, restaurants, and the oceanfront boardwalk.
This 450-square-foot, one-bedroom, one-bathroom unit sleeps two guests and boasts a fully equipped kitchenette, king-size Tempur-Pedic bed, private terrace, access to two pools, hot tubs, and barbecue facilities, plus complimentary beach gear.
Maui Kamaole #L-105 Beautiful Ocean View, Great Location, Great Rates, A/c - Wailea, HI
9.6 106 reviews
Wailea, HI
09/08 – 09/11
$389/nighttotal: $1167 (3 )

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

2 4
apartment , Wailea
This ground-floor condo in the Maui Kamaole complex is located directly across the street from Kamaole Beach III in Wailea, putting you steps away from the sand and close to shops, restaurants, and activities. The apartment consistently receives excellent ratings for location, cleanliness, and overall user experience.
The 1040 square foot condo comfortably sleeps six guests in two bedrooms and two bathrooms. Enjoy ocean views, a private balcony, a fully equipped kitchen, a swimming pool, a Jacuzzi, a garden, parking, and other amenities.
Redesigned 1bd/2ba Condo With Haleakala Views Near Wailea's Beaches And Dining - Wailea, HI
9.2 107 reviews
Wailea, HI
10/16 – 10/28
$281/nighttotal: $3372 (12 )

Redesigned 1bd/2ba Condo With Haleakala Views Near Wailea's Beaches And Dining

1 1
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.

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.

Brand New Remodel-ocean Views-ac-close To The Beach-meticulous Cleaning - Wailea, HI
9.9 224 reviews
Wailea, HI
07/10 – 07/13
$446/nighttotal: $1338 (3 )

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

1 2
apartment , Wailea
Comfy Sunny Kihei Condo @ Haleakala Shores, Across - Wailea, HI
9.8 52 reviews
Wailea, HI
09/08 – 09/11
$510/nighttotal: $1530 (3 )

Comfy Sunny Kihei Condo @ Haleakala Shores, Across

2 4
apartment , Wailea
Maui Parkshore 110 - Wailea, HI
8.6 110 reviews
Wailea, HI
07/10 – 07/13
$391/nighttotal: $1173 (3 )

Maui Parkshore 110

2 2
apartment , Wailea
Ocean & West Maui Mountain Views, Steps From Beach - Wailea, HI
9.6 44 reviews
Wailea, HI
09/08 – 09/11
$367/nighttotal: $1101 (3 )

Ocean & West Maui Mountain Views, Steps From Beach

2 4
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.

Maui Kamaole #G-107 Gorgeous Ocean View, Full Ac, Wifi, Hot Tub, Near Beach - Wailea, HI
9.4 101 reviews
Wailea, HI
09/08 – 09/11
$372/nighttotal: $1116 (3 )

Maui Kamaole #G-107 Gorgeous Ocean View, Full Ac, Wifi, Hot Tub, Near Beach

2 4
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.

Andaz Maui At Wailea Resort - A Concept By Hyatt - Wailea, HI
9.1 1439 reviews
Wailea, HI
07/10 – 07/13
$1097/nighttotal: $3291 (3 )

Andaz Maui At Wailea Resort - A Concept By Hyatt

1 2
resort , Wailea
I.p.m Presents: Hoolei 99-2 Brand New Remodel - Wow! Flexible Cancelation Policy - Wailea, HI
9.4 20 reviews
Wailea, HI
10/24 – 11/03
$1378/nighttotal: $13780 (10 )

I.p.m Presents: Hoolei 99-2 Brand New Remodel - Wow! Flexible Cancelation Policy

3 2
house , Wailea
Ho Olei Residences - Coraltree Residence Collection - Wailea, HI
8.8 1307 reviews
Wailea, HI
10/24 – 11/03
$793/nighttotal: $7930 (10 )

Ho Olei Residences - Coraltree Residence Collection

1 2
resort , Wailea
Summer Sale Panoramic Ocean Views Fourth Row Ho'olei, 112-4 - Wailea, HI
10 31 reviews
Wailea, HI
07/10 – 07/13
$1887/nighttotal: $5661 (3 )

Summer Sale Panoramic Ocean Views Fourth Row Ho'olei, 112-4

3 2
apartment , Wailea
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