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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 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.
Discover Kamaole Sands 3-101 - Premium Ground Floor Renovation, Split Ac, Wi-fi - Wailea, HI
9.8 44 reviews

Discover Kamaole Sands 3-101 - Premium Ground Floor Renovation, Split Ac, Wi-fi

apartment, Wailea
This ground-floor condo in South Kihei offers convenient access to Kamaole Beach Park III, located across the street, and is a short drive from Wailea's attractions.
This 820 sq ft apartment accommodates two guests with one bedroom and two bathrooms, featuring a fully stocked kitchen, a private lanai with garden and peek-a-boo ocean views, and access to Kamaole Sands resort amenities including the largest resort pool in South Kihei and two jacuzzies.
Luxurious Top Floor Kamaole Sands 6-404 - Wailea, HI
8.4 19 reviews

Luxurious Top Floor Kamaole Sands 6-404

apartment, Wailea
This luxurious two-bedroom condo in Wailea, Maui, boasts stunning ocean views from its top-floor location, a short walk from Kamaole Beach and a 17-minute walk from Mokapu Beach, and 3.8 miles from the Wailea Emerald Golf Course.
The 1100-square-foot unit features two bathrooms, a private balcony, a fully equipped kitchen, a private pool and outdoor seating area, free Wi-Fi, free parking, and accommodates up to 11 guests.
Haleakala Shores #B-309 Across From Kamaole Lll, Great Rates, Full Kitchen - Wailea, HI
8.8 174 reviews

Haleakala Shores #B-309 Across From Kamaole Lll, Great Rates, Full Kitchen

apartment, Wailea
This 2-bedroom condo is located directly across the street from Kamaole Beach #3 in Kihei, offering easy access to one of the most popular beaches in the area. The apartment has received excellent ratings for location, cleanliness, and overall experience.
The 1,040 square foot condo comfortably sleeps up to 6 guests and features a fully equipped kitchen, a washer and dryer, partial air conditioning, and access to a swimming pool, gas barbeques, and free parking. Guests can enjoy a variety of activities like swimming, snorkeling, windsurfing, and exploring nearby attractions like the Alexander & Baldwin Sugar Museum and Makamakaole Trail.

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.

Oceanfront Mana Kai Penthouse..heaven Meets Earth! - Wailea, HI
9.9 142 reviews

Oceanfront Mana Kai Penthouse..heaven Meets Earth!

apartment, Wailea
This Mana Kai penthouse offers a prime oceanfront location on Keawakapu Beach in Wailea, South Maui, situated on the longest sandy stretch at 2.75 miles.
This family-friendly condo sleeps 4, featuring 2 bedrooms, 2 bathrooms, air conditioning, a full kitchen, and access to a swimming pool, fitness center, and parking, with direct access to water activities like snorkeling and paddleboarding.
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.
Cool & Quiet Wailea Oasis, Big Lanai + Two Pools - Wailea, HI
9.9 70 reviews

Cool & Quiet Wailea Oasis, Big Lanai + Two Pools

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.
A.r.a Retreats: The Curved Slab - Wailea, HI
9.9 360 reviews

A.r.a Retreats: The Curved Slab

apartment, Wailea
This Grand Champions Villas condo in Wailea offers a luxurious two-bedroom, two-bathroom unit, a short walk from Wailea's best beaches and restaurants.
The newly renovated condo boasts a modern design, a 105-inch by 67-inch kitchen peninsula perfect for family meals, access to two pools and Jacuzzis, multiple BBQs, ocean and garden views from the lanai, and includes Tommy Bahama beach chairs and pool/beach towels; it comfortably sleeps six guests.

Frequently Asked Questions about vacation rentals in Wailea, HI

Popular destinations

Best Wailea, HI vacation rentals with parking

Kihei Condo W/ Resort Amenities: Walk To The Beach - Wailea, HI
8.8 116 reviews

Kihei Condo W/ Resort Amenities: Walk To The Beach

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.
Seaside Tropical  Maui Condo - Wailea, HI
9.9 232 reviews

Seaside Tropical Maui Condo

apartment, Wailea
This one-bedroom condo is located in South Kihei, just a short distance from Wailea and across the street from Keawakapu Beach, a popular spot for swimming, snorkeling, and surfing. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience.
The ground floor unit comfortably sleeps two guests and features a fully equipped kitchen, allowing you to prepare meals at your convenience. Guests enjoy access to resort amenities like tennis courts, BBQ areas, swimming pools, hot tubs, and a garden, plus the condo comes with beach towels, chairs, coolers, and a washer/dryer.
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.
Haleakala Shores A-301, Panoramic Views, Split Ac - Wailea, HI
9.7 173 reviews

Haleakala Shores A-301, Panoramic Views, Split Ac

apartment, Wailea
This Kihei apartment is directly across the street from Kamaole III Beach, placing you in the heart of South Kihei's vibrant beach culture with easy access to restaurants, shops, and nightlife. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience.
The two-bedroom unit offers 1040 square feet of comfortable living space. Enjoy ocean views from the living room and lanai, relax in the air-conditioned space, and take advantage of the fully equipped kitchen, swimming pool, and beach gear provided for your enjoyment.

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.

Tropical Paradise/just Steps To Sand & Beach(a.c.) - Wailea, HI
9.9 113 reviews

Tropical Paradise/just Steps To Sand & Beach(a.c.)

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.
Newly Remodeled-rare 2 Bedroom Ground Floor-ac - Wailea, HI
9.7 104 reviews

Newly Remodeled-rare 2 Bedroom Ground Floor-ac

apartment, Wailea
This oceanfront Wailea condo, near Kihei, offers stunning sea views and is just 0.1 miles from Kamaole Beach Park 3 and 2.8 miles from Wailea Beach.
The 1090-square-foot apartment features two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, free WiFi, a swimming pool, Jacuzzi, fitness center, and tennis court.
Kihei Resort Condo, Ac, Across Street From Beach - Wailea, HI
9.7 21 reviews

Kihei Resort Condo, Ac, Across Street From Beach

apartment, Wailea
This 1-bedroom condo in Wailea is located in South Kihei, directly across from Kamaole III Beach Park and within walking distance to shops and restaurants.
This rental sleeps 4 guests and features a full kitchen with stainless steel appliances, split A/C units, a private lanai with Haleakala views, and access to resort amenities including a pool, hot tub, and tennis courts, with beach gear provided.
Wailea Jewel! Near Shops,5 Star Hotels,beaches - Wailea, HI
9.7 147 reviews

Wailea Jewel! Near Shops,5 Star Hotels,beaches

apartment, Wailea
This Wailea Ekolu ground-floor condo offers easy access to The Shops at Wailea and the Wailea Promenade, with Wailea beaches a short five-minute drive away.
This 1,070-square-foot apartment features two bedrooms, two bathrooms, a fully equipped kitchen, and access to resort amenities including multiple pools, barbecue areas, and stunning ocean views; beach chairs, a cooler, and towels are provided.

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.

Steps To The Beach With Ocean View - Wailea, HI
9.5 4 reviews

Steps To The Beach With Ocean View

apartment, Wailea
Hale Kamaole 258 - Wailea, HI
8.8 67 reviews

Hale Kamaole 258

apartment, Wailea
2 Bedroom Partial Ocean View -Kamaole Sands 10408 - Wailea, HI
9.2 12 reviews

2 Bedroom Partial Ocean View -Kamaole Sands 10408

apartment, Wailea
Kamaole Sands: Ocean View Condo W/ Pool & Hot Tub - Wailea, HI
9.0 49 reviews

Kamaole Sands: Ocean View Condo W/ Pool & Hot Tub

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 Beach Condomountain And Ocean Views - Wailea, HI
9.9 139 reviews

Maui Beach Condomountain And 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.

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

Fairmont Kea Lani Maui Villa Experience

house, Wailea
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
Andaz Maui At Wailea Resort - A Concept By Hyatt - Wailea, HI
9.1 1164 reviews

Andaz Maui At Wailea Resort - A Concept By Hyatt

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

Fairmont Kea Lani, Maui

resort, Wailea
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