
Villa holiday rentals in Wailea
Find and book unique villas on Airbnb
Top-rated villa rentals in Wailea
Guests agree: These villas are highly rated for location, cleanliness and more.

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!

Steps from Beach • Park at YOUR Private Back Door
Ground-floor, bottom corner unit across from Cove Beach — close to beach sunset, surf, food trucks and local stores. The only unit with a tandem parking stall right next to your wall and back deck entrance. Step out of your car, walk straight in to your smart lock security door on your own back deck. Fully upgraded with fast Wi-Fi, two AC units, new appliances and a lava rock shower with hot/strong pressure. Sleeps 4 with a master + studio, beach gear, well-stocked kitchen and fresh linens.

Westin Kaanapali Beach Resort IslandView 1BR Villa
Submit your requested dates & I will check availability & respond if I can confirm this owner rental. 1 BR Premium Islandview Villa Westin Kaanapali Ocean Resort; 900 SQ FT; SLEEPS 4 ADULTS Resort is located on beautiful Kaanapali Beach. All the luxuries & amenities of a Westin resort + comfort of a villa w/ furnished kitchen, in-room washer/dryer, private balcony. Resort activities; gym/spa; Pools. Actual unit is assigned at check-in & views will vary; Free self-parking & no resort fees

Westin Kaanapali Ocean Resort Villas North Studio
Submit your requested dates & I will check availability & respond if I can confirm this rental for you. STUDIO Villa @ Westin Kaanapali Ocean Resort Villas NORTH on Maui Island Hawaii; 480SQ FT; SLEEPS UP TO 4 ADULTS All the luxuries & amenities of a Westin resort +comfort of a villa w/ furnished kitchenette, in-room washer/dryer, private balcony. Resort activities; gym/spa; Pool. Actual villa unit is assigned at check-in and views will vary (most likely Island View); Free self-parking

Westin Kaanapali Resort North 1BR IslandView Villa
1BR Premium Island-View Villa @ Westin Kaanapali Ocean Resort Villas NORTH on Maui; 750 SQ FT; SLEEPS 4 ADULTS All the luxuries & amenities of a Westin resort +comfort of a villa w/ furnished kitchen, in-room washer/dryer, private balcony. Resort activities; gym/spa; Pools. Renter can check-in late or check-out early during reservation period without penalty but no refunds or credits will be provided. Actual villa unit is assigned at check-in; Island Views will vary; Free self-parking

Kaanapali Fairway Villa 3BR, 3BA.
Welcome to this Kaanapali Golf course 3 bedroom 3 bath bed and breakfast. Permit number BBWMT 2021/0003-159 Halelo. This beautiful Mediterranean home is conveniently located on hole number 5 of the Kaanapali Golf Course with a private pool, swim up bar, and ocean view. Recently renovated with many added amenities and features, please see in description below.

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.

The Westin Ka'anapali Ocean Resort Villas 1 BR
My place is close to family-friendly activities, great views, restaurants and dining, the beach, and nightlife. You’ll love my place because of the outdoors space, the neighborhood, the comfy bed, the light, and the kitchen. My place is good for couples, solo adventurers, business travelers, families (with kids), and big groups.

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.

Spectacular 3/3 Ocean view Villa with AC, pool
Nestled on the hillside of Ka’anapali, this top-of-the-line quality 3-bedroom/3-bath villa offers panoramic views of the islands of Lanai and Molokai. Every inch of this villa is BRAND NEW!
Popular amenities for Wailea villa rentals
Private villa rentals

Spectacular 3/3 Ocean view Villa with AC, pool

Westin Kaanapali Beach Resort IslandView 1BR Villa

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

Westin Kaanapali Resort North 1BR IslandView Villa

Westin Kaanapali Ocean Resort Villas North Studio

Kihei Villa: Pool, Near Ocean & Garden Views

Steps from Beach • Park at YOUR Private Back Door

Walk to Cove Beach Park from a Refined Villa
Villa rentals with a pool

Spectacular 3/3 Ocean view Villa with AC, pool

Westin Kaanapali Beach Resort IslandView 1BR Villa

The Westin Ka'anapali Ocean Resort Villas 1 BR

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

Westin Kaanapali Resort North 1BR IslandView Villa

Westin Kaanapali Ocean Resort Villas North Studio

Kihei Villa: Pool, Near Ocean & Garden Views

Walk to Cove Beach Park from a Refined Villa
Villa rentals with a hot tub

Westin Kaanapali Resort North 1BR IslandView Villa

Westin Kaanapali Ocean Resort Villas North Studio

Westin Kaanapali Beach Resort IslandView 1BR Villa

The Westin Ka'anapali Ocean Resort Villas 1 BR

Luxury at it's Finest, Truly a Home away from Home
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $3,353 AUD | $3,567 AUD | $3,467 AUD | $3,701 AUD | $2,718 AUD | $3,712 AUD | $3,014 AUD | $3,014 AUD | $2,636 AUD | $2,673 AUD | $2,561 AUD | $2,653 AUD |
| Avg. temp | 16°C | 16°C | 16°C | 17°C | 18°C | 18°C | 19°C | 20°C | 19°C | 19°C | 18°C | 17°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 $499 AUD 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 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!
Destinations to explore
- Rentals with outdoor seating Wailea
- Pet-friendly rentals Wailea
- Family-friendly rentals Wailea
- Rentals with a hot tub Wailea
- Hotel rooms Wailea
- Beach condo rentals Wailea
- Waterfront rentals Wailea
- Rentals with a patio Wailea
- Fitness-friendly rentals Wailea
- Luxury rentals Wailea
- Serviced apartment rentals Wailea
- Rentals with a washing machine and dryer Wailea
- Rentals with pools Wailea
- Rentals with a sauna Wailea
- Condo rentals Wailea
- House rentals Wailea
- Rentals with a kayak Wailea
- Rentals with beach access Wailea
- Beachfront rentals Wailea
- Rentals with an EV charger Wailea
- Apartment rentals Wailea
- Townhouse rentals Wailea
- Villa rentals Maui County
- Villa rentals Hawaii
- Villa rentals United States
- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Honolua Bay
- Polo Beach
- Kapalua Bay Beach
- Ka'anapali Golf Courses
- Maui Ocean Center
- Wailea Beach
- Hāmoa Beach
- Ulua Beach
- Old Lahaina Luau
- Big Beach
- Black Rock Beach
- Whalers Village
- Haleakala National Park
- Peahi
- Maui Sunset
- Maui Vista Condominium
- Kihei Kai Nani
- Kahana Beach
- Black Sand Beach
- Maui Arts & Cultural Center
- Things to do Wailea
- Food and drink Wailea
- Nature and outdoors Wailea
- Sports activities Wailea
- Things to do Maui County
- Food and drink Maui County
- Sports activities Maui County
- Nature and outdoors Maui County
- Things to do Hawaii
- Wellness Hawaii
- Food and drink Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Art and culture Hawaii
- Entertainment Hawaii
- Tours Hawaii
- Nature and outdoors Hawaii
- Things to do United States
- Food and drink United States
- Wellness United States
- Sightseeing United States
- Sports activities United States
- Nature and outdoors United States
- Tours United States
- Entertainment United States
- Art and culture United States






