
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 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 March 20th, 2027 - March 27th, 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.

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.

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

Lovely Kahana Condo
Your tropical stay is located at Kahana Villa. This spacious two-story villa can sleep up to six guests. Enjoy the fully equipped kitchen, private lanai, living area downstairs, & two bedrooms upstairs. This is the ideal location, take advantage of the beach just feet away and local dining such as Miso Phat Sushi only a 4-minute walk. You can get a morning swim in at the outdoor pool, and the hot tub makes for a relaxing end to the day

Sands Of Kahana MAUI 1, 2 & 3 BR Some View units
The Sands of Kahana is located on the world famous West Coast of Maui between Kaanapali and Kapalua. The Sands of Kahana is a deluxe beachfront condominium property located on Kahana Beach, midway between the world famous Kaanapali and Kapalua resorts. Spacious two & three bedroom villas. Tennis, pools, spa, restaurant, bar, beach activities center, barbecues and more. Ten minutes to five championship golf courses.

Kaanapali beach KBC, 1 bdrm on ocean, scenic view
beautiful oceanfront resort features one-bedroom Villa Suites directly on world famous Kaanapali Beach! Relax in the king size bed. Living room features Queen sofa bed with Tempur-Pedic mattress. Each unit has a private Lanai. This unit is scenic view. This resort is 5 miles north of where the Lahaina fires took place and was not at all affected. Tax ID TA-056-945-7152-01R

Honua Kai Resort: Luana Upper Villa 18D pool view
Resort amenities include a network of swimming pools, waterfalls and children shallow pool, 24 hour fitness facility and front desk, Duke’s beach house restaurant and Whaler’s general store. *Due to the recent Covid-19 pandemic, resort amenities may be subject to change or closure* Kaanapali Luxury Vacation Rentals (KLVR) Presents Villa 18D in Oceanfront Resort.

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.
Popular amenities for villa rentals in Wailea
Private villa rentals

Westin Kaanapali Resort North 1BR IslandView Villa

1 Bdrm Condo on Bch, KBC in Ka'anapali beach

Westin Kaanapali Ocean Resort Villas North Studio

Ka'anapali Beach Club "Ocean View"

Westin Kaanapali Beach Resort IslandView 1BR Villa

1 Bdr Condo on Ka'anapali Bch, scenic view
Luxury villa rentals

Spectacular 3/3 Ocean view Villa with AC, pool

Kihei Villa: Pool, Near Ocean & Garden Views

Lovely Kahana Condo

Sands Of Kahana MAUI 1, 2 & 3 BR Some View units

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

Westin Nanea Kaanapali Ocean Villa 2BR Sleeps 6

Luana Garden Villa 3D

Kaanapali Beach Club "Scenic View"

Westin Nanea Kaanapali Ocean Villa 2BR Sleeps 6

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

Honua Kai Resort: Luana Upper Villa 18D pool view

Westin Nanea Kaanapali Ocean Villa 2BR Sleeps 6

Kihei Villa: Pool, Near Ocean & Garden Views
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £1,731 | £1,842 | £1,790 | £1,911 | £1,404 | £1,917 | £1,557 | £1,557 | £1,362 | £1,381 | £1,323 | £1,370 |
| 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 £236 per night before taxes and fees

Verified guest reviews
Over 720 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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- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Honolua Bay
- Polo Beach
- Wailea Beach
- Kapalua Bay Beach
- Ka'anapali Golf Courses
- Maui Ocean Center
- Hāmoa Beach
- Ulua Beach
- Black Rock Beach
- Old Lahaina Luau
- Big Beach
- Maui Vista Condominium
- Black Sand Beach
- Whalers Village
- Haleakala National Park
- Maui Sunset
- Peahi
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