Villa vacation rentals in Wailea

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Quick stats about villa rentals in Wailea

Total vacation rentals
Explore 50 vacation rentals in Wailea
Nightly prices starting at
Wailea vacation rentals start at ﺩ.ﺇ 845 per night before taxes and fees
Verified guest reviews
Over 770 verified reviews to help you choose
Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities
Vacation rentals with a pool
50 properties feature pools
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wi-Fi availability
50 of Wailea vacation rentals include wi-fi access
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Wailea rentals
5 Average rating
Wailea stays are highly rated by guests—averaging 5 out of 5!

Top-rated villa rentals in Wailea

Guests agree: these villas are highly rated for location, cleanliness, and more.

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Guest favorite

Villa in Wailea

5.0 out of 5 average rating, 7 reviews

A bit of paradise - Ocean Views Villa 1 bedroom

MAUI IS OPEN AND WELCOMING — Despite rumors, short-term rentals are still legal- the island and people need your respectful tourism. After 25 years of visiting, we finally got our own place, to someday retire and enjoy island life. We searched out the perfect place so you don't have to! In Grand Champions Villas, this 1-bed 2-bath condo/villa (#167 is on the Wailea Blue Golf Course with amazing ocean views and an updated master suite. You'll love the beautiful sunsets from the lanai (balcony)!

Superhost

Villa in Wailea

4.8 out of 5 average rating, 10 reviews

Relax in Paradise- 3 bedroom Ocean Views Villa

MAUI IS OPEN AND WELCOMING — Despite rumors, short-term rentals are still legal-the island and people needs your help to rebuild after the horrific Lahaina fire. After 25 years of visiting, we finally got our own place, to someday retire and enjoy island life. We searched out the perfect place so you don't have to! In Grand Champions Villas, this updated 3-bed 2-bath condo/villa (#69) is on the Wailea Blue Golf Course with amazing ocean views! Enjoy sunsets (or anytime) on the lanai.

Guest favorite

A coastal view features tall palm trees swaying gently against a clear blue sky. The sandy beach stretches along the shoreline, leading to calm turquoise waters. In the distance, a glimpse of a distant landmass is visible, adding to the serene atmosphere.

Villa in Wailea

4.96 out of 5 average rating, 102 reviews

Wailea 2BR Villa Near Beach, Shops & Golf

Welcome to our beautifully remodeled, ground-floor villa at Grand Champions, offering over 1,100 square feet of interior space plus a private furnished lanai. Enjoy quiet split-system air conditioning, two shared pools and spas, a queen sofa sleeper, 50-inch TV, full kitchen, and in-unit laundry. The primary bedroom has a king bed; the second has two twins that convert to a king. Sleeps six, near Wailea beaches, golf, dining, and shopping.

Guest favorite

The open kitchen and living area features a large island with seating and modern appliances. A casual sofa is positioned across from the kitchen, and natural light streams through a window framed in dark wood. A patterned area rug adds texture to the space.

Villa in Kihei

4.96 out of 5 average rating, 76 reviews

Kihei Villa: Pool, Near Ocean & Garden Views

Kick back and relax in this calm, stylish space. This Villa features 2 king suites, peek-a-boo ocean views, and private lanais off of each bedroom. The main living area comprises a great room with vaulted ceilings and a large island in the kitchen. Custom cabinetry houses all the essentials needed for cooking and relaxing while at the Villa. This unit is located on a shared property at Villas by the Cove.

Guest favorite

A modern living area features a flat-screen television mounted on the wall. A wooden sideboard offers decorative accents, while a cozy dining nook with a live-edge wooden table provides seating. Large windows allow natural light to illuminate the space, with glimpses of tropical greenery outside.

Villa in Kihei

4.95 out of 5 average rating, 121 reviews

Walk to Cove Beach Park from a Refined Villa

Prep meals in a chic kitchen with granite surfaces and white-washed hardwood floors. Dine at a live-edge table in a cozy corner nook amid nautical décor and modern touches. Unwind in a lounge chair on a sun-drenched patio before taking a swim.