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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

Maui Kamaole #H-211 Ocean View, Full A/c, Newly Renovated! Close To Beach! - Wailea, HI
9.8 76 reviews
Wailea, HI
10/16 – 10/28
$348/nighttotal: $4176 (12 )

Maui Kamaole #H-211 Ocean View, Full A/c, Newly Renovated! Close To Beach!

2 1
apartment , Wailea
This two-bedroom condo is located in the Maui Kamaole complex, just across the street from Kamaole Beach Park III, a popular beach in South Maui. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The 1050 square foot condo can accommodate up to six guests and features a fully equipped kitchen, washer and dryer, two patios, and air conditioning. Guests can enjoy resort-style amenities like swimming pools, hot tubs, tennis courts, and gas grills, as well as free long-distance calls, beach chairs, and towels.
Hale Kamole 210 1bd Ocean View Walk To The Beach And Pool - Wailea, HI
9.0 44 reviews
Wailea, HI
10/16 – 10/28
$242/nighttotal: $2904 (12 )

Hale Kamole 210 1bd Ocean View Walk To The Beach And Pool

1 1
apartment , Wailea
This Kihei condo is located in South Kihei, a short walk from Kamaole Beach Park III and a brief drive from Wailea's resorts and golf courses.
This 780 square foot apartment accommodates up to 4 guests with 1 bedroom and 1 bathroom, featuring a fully equipped kitchen, air conditioning, a swimming pool, and a furnished lanai with ocean views.
Kamoale Sands 9-410! Favorite Locale Near Everything And Ocean Views!! - Wailea, HI
9.6 101 reviews
Wailea, HI
10/16 – 10/28
$258/nighttotal: $3096 (12 )

Kamoale Sands 9-410! Favorite Locale Near Everything And Ocean Views!!

1 1
apartment , Wailea
This oceanfront Wailea condo is located near Kihei, a short distance from Kamaole Beach Park III (0.2 miles) and Wailea Beach (2.8 miles), offering stunning sea views.
This 820-square-foot unit features two bathrooms, a fully equipped kitchen, in-unit laundry, free WiFi, a private balcony, and access to a swimming pool, jacuzzi, fitness center, spa, and tennis court.
Hale Kamaole Condo W/ A/c, Shared Outdoor Pool - Beach Lovers Dream - Wailea, HI
9.1 77 reviews
Wailea, HI
10/16 – 10/28
$231/nighttotal: $2772 (12 )

Hale Kamaole Condo W/ A/c, Shared Outdoor Pool - Beach Lovers Dream

1 1
apartment , Wailea
This oceanfront Wailea condo is located less than half a mile from Kamaole Beach Park III and about three miles from Wailea Beach, offering stunning sea views and proximity to Kihei.
The one-bedroom, one-bathroom unit sleeps four with a comfortable sofa bed, a fully equipped kitchen including a dishwasher, in-unit laundry, and access to a swimming pool, tennis court, and barbecue grills.

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.

Remodeled-ocean Views-well Equipped-ac-close To The Beach-meticulous Cleaning - Wailea, HI
9.8 179 reviews
Wailea, HI
10/16 – 10/28
$353/nighttotal: $4236 (12 )

Remodeled-ocean Views-well Equipped-ac-close To The Beach-meticulous Cleaning

1 1
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.
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.
Maui Paradise: Steps To Sand-blg#1. Partial Ocean View, Ac's, Wifi, 1st Floor - Wailea, HI
10 108 reviews
Wailea, HI
10/16 – 10/28
$370/nighttotal: $4440 (12 )

Maui Paradise: Steps To Sand-blg#1. Partial Ocean View, Ac's, Wifi, 1st Floor

1 1
apartment , Wailea
This Kihei condo is steps from Kamaole Beach Park III and a short drive (2.8 miles) from Wailea Beach, offering convenient access to both areas.
The 820-square-foot unit features one bedroom, two bathrooms, sleeps four guests, and includes a fully equipped kitchen, private lanai, in-unit washer/dryer, and access to a pool, fitness center, spa, and tennis court.
Hale Kamaole 208 - Relax And Enjoy Your Beautiful Ocean View Suite - Wailea, HI
9.4 140 reviews
Wailea, HI
10/16 – 10/28
$251/nighttotal: $3012 (12 )

Hale Kamaole 208 - Relax And Enjoy Your Beautiful Ocean View Suite

1 1
apartment , Wailea
This one-bedroom apartment is located in Kihei, just a mile from Kamaole Beach Park 3 and Kamaole Beach Park, and a short drive from Wailea Beach. The apartment has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment offers 800 square feet of living space and can accommodate up to 5 guests. You'll enjoy amenities like a fully equipped kitchen, a private balcony, a swimming pool, a spa, and a garden, perfect for relaxing and enjoying the beautiful Hawaiian weather.

Frequently Asked Questions about vacation rentals in Wailea, HI

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Best Wailea, HI vacation rentals with parking

Maui Family Owned/managed - Keawakapu Beauty - Wailea, HI
9.9 218 reviews
Wailea, HI
10/16 – 10/28
$297/nighttotal: $3564 (12 )

Maui Family Owned/managed - Keawakapu Beauty

2 1
apartment , Wailea
This Wailea apartment is located across the street from Keawakapu Beach, offering a peaceful retreat just a short walk from the lively Wailea resort area. The apartment boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This 2-bedroom, 1-bathroom apartment spans 830 square feet and comfortably accommodates up to 4 guests. Enjoy amenities like a fully equipped kitchen, air conditioning, a jacuzzi, a terrace, a garden, a spa, and parking, as well as access to a shared outdoor BBQ area.
Luxurious One Bedroom, Two Bath Condo In South Kihei; Sleeps 4 - Wailea, HI
9.9 128 reviews
Wailea, HI
10/16 – 10/28
$309/nighttotal: $3708 (12 )

Luxurious One Bedroom, Two Bath Condo In South Kihei; Sleeps 4

1 1
apartment , Wailea
This ground floor apartment in the Kihei district is a short walk from the beach, shops, restaurants, and bars, making it a perfect base for exploring Wailea. It consistently receives excellent ratings for location, cleanliness, and user experience.
The 850 square foot apartment has one bedroom, two bathrooms, and comfortably accommodates four guests. You'll find everything you need for a relaxing stay, including a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a garden, and a spa.
Beautiful Beaches For Swimming And Sunsets!  Kamaole Sands 3-207 - Wailea, HI
9.8 89 reviews
Wailea, HI
10/16 – 10/28
$269/nighttotal: $3228 (12 )

Beautiful Beaches For Swimming And Sunsets! Kamaole Sands 3-207

2 1
apartment , Wailea
This Kamaole Sands Resort condo, located in Kihei across from Kamaole Beach III, offers easy access to other beaches in Kihei, Wailea, and Makena, and proximity to Wailea and Makena's golf courses.
The 820-square-foot, one-bedroom, two-bathroom unit sleeps four and features a fully equipped kitchen, air conditioning, a private terrace, access to resort amenities including a pool, jacuzzi, and tennis courts, and pet-friendly accommodations.
Your Paradise - Entire > 800 Square Feet Apartment With Affordable Rate - Wailea, HI
9.8 91 reviews
Wailea, HI
10/16 – 10/28
$191/nighttotal: $2292 (12 )

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

1 1
apartment , Wailea
This Kihei condo is a short walk from Kamaole Beach Park III and about 3 miles from Wailea Beach, offering easy access to popular South Maui beaches and the Kihei Boat Ramp.
This 820-square-foot one-bedroom, two-bathroom rental sleeps two, features a fully equipped kitchen, in-unit laundry, a private balcony, and access to a swimming pool, jacuzzi, tennis court, and garden.

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 50 reviews
Wailea, HI
10/16 – 10/28
$300/nighttotal: $3600 (12 )

Charming Kihei Oasis Vistas

1 1
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.
Nicely Remodeled-ocean Views-large Lanai-well Equipped-ac-meticulous Cleaning - Wailea, HI
9.6 68 reviews
Wailea, HI
10/16 – 10/28
$287/nighttotal: $3444 (12 )

Nicely Remodeled-ocean Views-large Lanai-well Equipped-ac-meticulous Cleaning

1 1
apartment , Wailea
This Kihei condo, a short drive from Kamaole Beach Park III (0.1 miles) and Wailea Beach (2.8 miles), offers convenient access to both beaches and the Kihei Boat Ramp.
The 820-square-foot, one-bedroom, two-bathroom unit sleeps four and includes a fully equipped kitchen, in-unit laundry, a private terrace, and access to a swimming pool, jacuzzi, fitness center, and tennis court.
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.
Beautiful*partial Ocean View By Top Swimming Beach - Wailea, HI
9.7 243 reviews
Wailea, HI
10/16 – 10/28
$229/nighttotal: $2748 (12 )

Beautiful*partial Ocean View By Top Swimming Beach

1 1
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.

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.

Ocean And Golf Course Views 2 Bed 2 Bath - Grand Champions  112 - Wailea, HI
9.5 64 reviews
Wailea, HI
10/16 – 10/28
$319/nighttotal: $3828 (12 )

Ocean And Golf Course Views 2 Bed 2 Bath - Grand Champions 112

2 1
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.

Nicely Remodeled-ocean Views-large Lanai-well Equipped-ac-meticulous Cleaning - Wailea, HI
9.6 68 reviews
Wailea, HI
10/16 – 10/28
$287/nighttotal: $3444 (12 )

Nicely Remodeled-ocean Views-large Lanai-well Equipped-ac-meticulous Cleaning

1 1
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.

Kamaole Sands 8-402 - Wailea, HI
9.1 241 reviews
Wailea, HI
10/16 – 10/28
$309/nighttotal: $3708 (12 )

Kamaole Sands 8-402

1 1
apartment , Wailea
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