Villa holiday rentals in Wailea

Find and book unique villas on Airbnb

Quick stats about villa rentals in Wailea

Total holiday rentals
Explore 50 holiday rentals in Wailea
Nightly prices starting at
Wailea holiday rentals start at $456 AUD per night before taxes and fees
Verified guest reviews
Over 710 verified reviews to help you choose
Family-friendly holiday rentals
50 properties offer extra space and kid-friendly amenities
Holiday rentals with a pool
50 properties feature pools
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wi-Fi availability
50 of Wailea holiday 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 favourite

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

Luxury at it's Finest, Truly a Home away from Home

Remodeled in 2020, this 2 /2 Villa is located at Grand Champion Golf & Tennis Villas in the exclusive resort destination of Wailea, Maui. We have been named a Super Hosts on Airbnb due to the great amenities, comfort, safety, cleanliness and luxurious accommodations this Villa provides. Wailea is the Gold Coast of Maui, close to pristine beaches, shopping and dining and this is a legal, exclusive vacation rental. Spacious and luxurious, feel Refreshed and Anew in your Home away from Home!

Guest favourite

A bright living area features a comfortable sofa with coordinating armchairs, complemented by a round wooden coffee table. Large glass doors provide an unobstructed view of the ocean and tropical landscape, allowing natural light to fill the space.

Villa in Wailea

5 out of 5 average rating, 12 reviews

Ocean Views! Remodeled Redecorated Pretty & Modern

Our collection of Maui vacation residences are HOTEL-Zoned or have LEGAL short-term rental permits. Reserve with Private Paradise Villas with confidence knowing you will be luxuriating in a location legally designated for visitor accommodations and managed by our local on-island professional staff. NEW! NEW! NEW! VIEWS! VIEWS! VIEWS! Surf Song Villa 203, a newly remodeled and redecorated direct ocean view resort residence set in the beachfront and upscale Wailea Elua Village Resort, is ...

Top Guest favourite

Villa in Wailea

5 out of 5 average rating, 37 reviews

Luxury Oceanview Wailea Retreat with Sunset Views

Escape to Hōkū Hale, a serene oceanview retreat in the heart of Wailea. This designer oasis offers modern comforts, a private lanai with stunning ocean views, on the fairway of a private golf course. Walk to world-class beaches, dining, golf or relax in a peaceful, breezy, tropical setting. Perfect for large families and groups seeking upscale luxury and the best of Maui.

Guest favourite

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, 74 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.

Guest favourite

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, 119 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.