
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.

Westin Nanea Kaanapali Ocean Villa 2BR Sleeps 6
2 Bedroom Westin Nanea Ocean Villa at Kaanapali Beach on Maui Island in Hawaii; 1,260 SQ FT; SLEEPS UP TO 6 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; Pool. Renter can check-in late or check-out early anytime during reservation period without penalty but no refunds or credits will be provided. Actual villa unit is assigned at check-in and views will vary; Free self-parking

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!

Westin Kaanapali Resort North Ocean-View Studio
OCEANVIEW STUDIO @ Westin Kaanapali Ocean Resort Villas NORTH on Kaanapali Beach; 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. Renter can check-in late or check-out early anytime during reservation period without penalty but no refunds or credits will be provided. Actual unit is assigned at check-in & OCEANVIEWS will vary; Free self-parking

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 Ka’anapali Ocean Resort Villas, beach front
Westin Nanea, north or south Ocean Resort Villas, 2 bedroom (sleeps 6) Bring the whole family to this beautiful beach front property with lots of room for fun or get away for a romantic vacation. This is a timeshare and dates are flexible depending on availability at the time of booking. Includes multiple on site restaurants, 2 pools, water slides, store, poolside service, rentals, beach views, convenient free shuttle to downtown Lahaina. Sports bar, live music & more! Use of all resorts.

Westin Nanea Kaanapali Luxury Ocean Villa Sleeps 6
Westin Nanea Ocean Villa @ Kaanapali Beach, Maui. Spacious living and dining areas, full kitchens, washer/dryers, & remarkable resort views. This 2 Bedroom 2 Bath sleeps 6 w/free parking. **Available Only June 28th, 2026 - July 5th, 2026.- 7 Night Stay.** Eat at one of the on premise restaurants, lounge by a rejuvenating pool, surf several nearby breaks, enjoy a spa, or work out in the Fitness Studio. When the sun sets behind the palms of Kaanapali, sink into your Westin Heavenly® Bed.

Kaanapali Beach Club "Scenic View"
**PLEASE ASK! We have many more weeks, dates and many GUARANTEED views!** Prices based on views, events, etc. **HOTEL TAX of approx 19.00 per night paid to resort upon check in.** Located on Maui's world famous Ka'anapali Beach. Vibrant tropical landscaping, first-rate amenities and exclusive array of leisure activities. Kaanapali Beach Club offers a one-acre swimming pool with separate kids pool, as well as calming outdoor whirlpool hot tubs. *Stock Photos

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.

Maui Westin Kaanapali 1Bdrm Villa in Paradise
Westin Kaanapali sits on the beach. This studio sleeps 4 has a full kitchen, dining, and washer and dryer. This resort has it all. Gym, spa, pools and spas for adults and children, restaurants, bars, and equipment rentals. Close to Lahaina and golf courses you don't need to go far to have it all.

1 Bdrm Condo on Bch, KBC in Ka'anapali beach
Beautiful ocean front resort features 1 bedroom villa suites directly on world famous Ka'anapali Beach! Relax in the king size bed. Living room features queen sofa bed with Tempurpedic mattress. Each unit has a private Lanai! Tax ID TA-056-945-7152-01R
Popular amenities for villa rentals in Wailea
Private villa rentals

Ka'anapali Beach Club "Ocean View"

Westin Kaanapali Beach Resort IslandView 1BR Villa

1 Bdr Condo on Ka'anapali Bch, scenic view

Kaanapali beach KBC, 1 bdrm on ocean, scenic view

Westin Kaanapali Resort North 1BR IslandView Villa

Westin Kaanapali Ocean Resort Villas North Studio

Westin Nanea Kaanapali Ocean Villa 2BR Sleeps 6

Westin Nanea Kaanapali Ocean Villa 2BR Sleeps 6
Villa rentals with a pool

Kaanapali Beach Club "Scenic View"

Westin Nanea Kaanapali Ocean Villa 2BR Sleeps 6

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

Ka'anapali Beach Club "Ocean View"

Westin Kaanapali Resort North Ocean-View Studio

Kaanapali Beach Club "Deluxe Ocean View"

Kaanapali Beach Club "Scenic View"

Kihei Villa: Pool, Near Ocean & Garden Views
Villa rentals with a hot tub

Kaanapali Beach Club "All Views"

Westin Nanea Kaanapali Ocean Villa 2BR Sleeps 6

Ka'anapali Beach Club "Ocean View"

Kaanapali Beach Club "All Views"

Kaanapali Beach Club "Scenic View"

Ka'anapali Beach Club "Ocean View"

Westin Nanea Kaanapali Ocean Villa 2BR Sleeps 6

Kaanapali Beach Club "Deluxe Ocean View"
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £1,743 | £1,854 | £1,803 | £1,924 | £1,413 | £1,930 | £1,567 | £1,567 | £1,371 | £1,390 | £1,331 | £1,380 |
| 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 £260 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!
Destinations to explore
- Rentals with outdoor seating Wailea
- Pet-friendly rentals Wailea
- Hotel rooms Wailea
- Rentals with pools Wailea
- Rentals with an EV charger Wailea
- Flat rentals Wailea
- Waterfront rentals Wailea
- Family-friendly rentals Wailea
- Rentals with a sauna Wailea
- Apartment rentals Wailea
- House rentals Wailea
- Rentals with a washing machine and dryer Wailea
- Fitness-friendly rentals Wailea
- Rentals with a hot tub Wailea
- Townhouse rentals Wailea
- Beach apartment rentals Wailea
- Rentals with a patio Wailea
- Rentals with a kayak Wailea
- Serviced apartment rentals Wailea
- Beachfront rentals Wailea
- Luxury rentals Wailea
- Rentals with beach access Wailea
- Villa rentals Maui County
- Villa rentals Hawaii
- Villa rentals United States
- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Honolua Bay
- Kapalua Bay Beach
- Wailea Beach
- Polo Beach
- Hāmoa Beach
- Maui Ocean Center
- Ka'anapali Golf Courses
- Old Lahaina Luau
- Ulua Beach
- Whalers Village
- Big Beach
- Haleakala National Park
- Black Rock Beach
- Maui Vista Condominium
- Maui Sunset
- Peahi
- Kihei Kai Nani
- Kahana Beach
- Maui Arts & Cultural Center
- Black Sand Beach
- Things to do Wailea
- Food and drink Wailea
- Sports activities Wailea
- Nature and outdoors Wailea
- Things to do Maui County
- Sports activities Maui County
- Food and drink Maui County
- Nature and outdoors Maui County
- Things to do Hawaii
- Entertainment Hawaii
- Nature and outdoors Hawaii
- Art and culture Hawaii
- Wellness Hawaii
- Tours Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Food and drink Hawaii
- Things to do United States
- Sightseeing United States
- Food and drink United States
- Nature and outdoors United States
- Wellness United States
- Art and culture United States
- Entertainment United States
- Tours United States
- Sports activities United States






