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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

Oceanview2br Condo W/ Pool And Lanai - Wailea, HI
9.4 45 reviews

Oceanview2br Condo W/ Pool And Lanai

apartment, Wailea
This oceanfront Wailea condo is located near Kamaole Beach Parks 2 and 3, 2.5 miles from Wailea Beach, and within 15 minutes of the Kihei Boat Ramp.
The two-bedroom, two-bathroom unit features a fully equipped kitchen, free WiFi, a terrace, access to a swimming pool, spa, fitness center, and tennis court, plus on-site barbecues and sleeps multiple guests with a sofa bed.
Kamaole Sands 3-405-remodeled-well Equipped - Wailea, HI
9.8 103 reviews

Kamaole Sands 3-405-remodeled-well Equipped

apartment, Wailea
This oceanfront Wailea condo, near Kihei, offers stunning sea views and is 0.1 miles from Kamaole Beach Park 3 and 2.8 miles from Wailea Beach.
The 1180-square-foot unit features two bedrooms, two bathrooms, a sofa bed accommodating up to six guests, and amenities including a swimming pool, jacuzzi, fitness center, and tennis court.
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.
Large Designer 2 Bed/2 Bath Condo With Ocean Views & Beach Across The Street - Wailea, HI
9.8 77 reviews

Large Designer 2 Bed/2 Bath Condo With Ocean Views & Beach Across The Street

apartment, Wailea
This Kihei condo, a two-bedroom, two-bathroom rental near Kamaole Beach III, offers easy access to snorkeling, swimming, and a boat ramp, all within a two-minute walk.
The 5-guest unit features an ocean-view lanai perfect for whale watching (seasonal), a split-bedroom design, a fully stocked kitchen, and proximity to Wailea's golf courses, shops, Haleakala National Park (90-minute drive), and the Road to Hana (45-minute drive).

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.

Ocean Front Modern 2br 2ba, King Bed, Beach, Pool! - Wailea, HI
10 1 review

Ocean Front Modern 2br 2ba, King Bed, Beach, Pool!

apartment, Wailea
This beachfront condo in Wailea offers direct sea views and immediate beach access near Kamaole Beach, 3.4 miles from Wailea Emerald Course and 14 miles from Kahului Airport.
This 800 sq ft, 2-bedroom, 2-bathroom vacation rental accommodates up to 10 guests with a king bed, balcony, equipped kitchen, shared pool, WiFi, and private parking, ideal for snorkeling enthusiasts.
Spacious Condo With Pool And Lanai - Charming Family Retreat - Wailea, HI
No reviews

Spacious Condo With Pool And Lanai - Charming Family Retreat

apartment, Wailea
This condo is centrally located in Kihei, 100 feet from Kamaole Beach parks, and a short drive from Wailea's shopping and dining.
This 2-bedroom, 2-bathroom unit sleeps up to 6 guests and offers a fully equipped kitchen, private lanai with garden and peekaboo ocean views, and access to on-site amenities including a swimming pool, hot tubs, and fitness center, plus complimentary daily activities through Xplorie.
Maui Kamaole F203 - Wailea, HI
No reviews

Maui Kamaole F203

apartment, Wailea
This 2-bedroom, 2-bathroom condo in Sunny South Kihei offers a prime location in Wailea, just a short walk from Keawakapu Beach and Kamaole III Beach, with the Shops of Wailea a 5-minute drive away.
This recently remodeled apartment accommodates up to 6 guests with air conditioning in every room, a private lanai, and access to on-site amenities including swimming pools, hot tubs, and tennis courts.
2 Bed, 2 Bath Ocean View, A/c Kamaole Sands A Graded Condo - Wailea, HI
9.4 120 reviews

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

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.

Frequently Asked Questions about vacation rentals in Wailea, HI

Popular destinations

Best Wailea, HI vacation rentals with parking

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.
Hale Kamaole 330 - Wailea, HI
9.1 467 reviews

Hale Kamaole 330

apartment, Wailea
This apartment is situated in South Kihei, a mile from Kamaole Beach Parks 3 and 2, and just over two miles from Wailea Beach, offering a quieter and more relaxed atmosphere than the bustling Wailea area. The apartment has consistently received excellent ratings for user experience, location, and cleanliness.
The apartment has two bedrooms and comes with a fully equipped kitchen, two bathrooms, and a washing machine. Enjoy amenities like a swimming pool, tennis court, barbecue grills, and a terrace or balcony, perfect for relaxing and enjoying the Hawaiian sunshine.
Summer Deals! Huge 2 Bed+sofabed - Best Location! - Wailea, HI
9.8 111 reviews

Summer Deals! Huge 2 Bed+sofabed - Best Location!

apartment, Wailea
This ground-floor Maui Hill condo is a short walk from Keawakapu Beach, conveniently located between Kihei and Wailea.
The spacious two-bedroom, two-bathroom unit sleeps six, features a double lanai with south-facing views, in-unit laundry, and access to resort amenities including a pool, hot tub, and tennis court.
Ocean View, Great Location, Great Rates! Mkl105 - Wailea, HI
9.6 109 reviews

Ocean View, Great Location, Great Rates! Mkl105

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.

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.

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

Maui Beach Condomountain And Ocean Views

apartment, Wailea
This beachfront apartment is located in Kihei, just a short walk from Kamaole Beach Parks 3 and 2, and a quick drive to Wailea Beach. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The apartment has 2 bedrooms and 2 bathrooms, covering 1100 square feet and accommodating up to 6 guests. Enjoy the convenience of a fully equipped kitchen, air conditioning, a swimming pool, and a terrace with a garden view.
Haleakala Shores #B-102 Ground Floor, Best Location, Pool View, Full Kitchen - Wailea, HI
9.6 83 reviews

Haleakala Shores #B-102 Ground Floor, Best Location, Pool View, Full Kitchen

apartment, Wailea
This 2-bedroom, 2-bathroom apartment is located in a beachfront building within walking distance of Kamaole Beach Parks 3 and 2, and just a short drive from Wailea Beach.
The 1,040 square foot apartment features a fully equipped kitchen, air conditioning, a swimming pool, a garden, and parking, and can accommodate up to 6 guests.
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.

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.

Kamaole Sands #1-406 Front Row, Ocean View, Fitness Center, Great Rates! - Wailea, HI
9.0 61 reviews

Kamaole Sands #1-406 Front Row, Ocean View, Fitness Center, Great Rates!

apartment, Wailea
Private Cottage @ Keawakapu Beach Sleeps  6 - Mmc2 - Wailea, HI
9.4 91 reviews

Private Cottage @ Keawakapu Beach Sleeps 6 - Mmc2

apartment, Wailea
Upgraded Unit With Panoramic Ocean And Mountain Views - Wailea, HI
9.8 112 reviews

Upgraded Unit With Panoramic Ocean And Mountain Views

apartment, Wailea
Ocean View Condo With Pool & Beach Access - Wailea, HI
8.9 253 reviews

Ocean View Condo With Pool & Beach Access

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.

Haleakala Shores A-301, Panoramic Views, Split Ac - Wailea, HI
9.7 173 reviews

Haleakala Shores A-301, Panoramic Views, Split Ac

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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