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Villa holiday rentals in Wailea

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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 spacious living area is featured with leather sofas and wooden accents. Natural light enters through large windows, illuminating the contemporary decor. A wooden coffee table is centered on a textured rug, complemented by accent chairs and a dining area visible in the background.
Villa in Wailea
5 out of 5 average rating, 9 reviews

Beautiful Ground Floor Penthouse!H102

Wailea Beach Villas has been ranked #4 in Hawaii by Condé Nast Readers. This recognition places WBV among the very best resorts in Hawaii, and the best on Maui! Beautifully appointed ground floor, garden view penthouse at the famous Wailea Beach Villas! Enjoy a relaxing Maui getaway in Wailea Beach Villa H102. This 2 bedroom / 2 bathroom plus enclosed den is perfect for small families and couples.

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, 70 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, 116 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.

Popular amenities for villa rentals in Wailea

KitchenWifiPoolFree parking on premisesAir conditioning

Private villa rentals

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, 70 reviews

Kihei Villa: Pool, Near Ocean & Garden Views

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

Guest favourite
A spacious living area is featured with leather sofas and wooden accents. Natural light enters through large windows, illuminating the contemporary decor. A wooden coffee table is centered on a textured rug, complemented by accent chairs and a dining area visible in the background.
Villa in Wailea
5 out of 5 average rating, 9 reviews

Beautiful Ground Floor Penthouse!H102

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, 116 reviews

Walk to Cove Beach Park from a Refined Villa

Villa rentals with a pool

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, 70 reviews

Kihei Villa: Pool, Near Ocean & Garden Views

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

Guest favourite
A spacious living area is featured with leather sofas and wooden accents. Natural light enters through large windows, illuminating the contemporary decor. A wooden coffee table is centered on a textured rug, complemented by accent chairs and a dining area visible in the background.
Villa in Wailea
5 out of 5 average rating, 9 reviews

Beautiful Ground Floor Penthouse!H102

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, 116 reviews

Walk to Cove Beach Park from a Refined Villa

When is the best time to visit Wailea?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$3,018 SGD$3,211 SGD$3,121 SGD$3,332 SGD$2,447 SGD$3,342 SGD$2,714 SGD$2,714 SGD$2,374 SGD$2,407 SGD$2,306 SGD$2,389 SGD
Avg. temp16°C16°C16°C17°C18°C18°C19°C20°C19°C19°C18°C17°C

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 $450 SGD per night before taxes and fees

  • Verified guest reviews

    Over 670 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    50 of Wailea holiday rentals include wifi 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!

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