
Villa vacation 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!

Chic Villa 2 | Modern Vibes by the Ocean
Experience an older Hawaiian style charm with a modern twist in this newly remodeled Villa in Kihei. Welcome to 1 Bedroom, 1 Bathroom Villa 2 at Villas by the Cove — a laid-back, beach-chic retreat just across the street from Cove Park and a short 3-minute stroll to Charley Young Beach. This modern villa features a living room with air conditioning, high-speed Wi-Fi, a fully equipped kitchen, a comfortable king bed, a full bathroom with a walk-in shower, a private lanai, and gated 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.

Newly renovated 2BR/2BA with Bonus Family Room
Complete renovation October 2024! This unit is a two bedroom, three bath with downstairs family room condominium villa with direct access to shared pool. Each bedroom, living room, and downstairs family room has its own AC unit for temperature control. Guests may choose from a King bed or two twin beds in the bedrooms, with two queen beds located in the family room. The beach is less than a 2 minute walk! Note: Hawaii GET, TA & MCTAT taxes of 17.962% are included in total price shown.

Newly Remodeled Beach Hideaway, Sleeps up to 8!
Lele Hideaway is a two bedroom, three bath with an additional downstairs family room condominium suite with direct access to the shared pool area. Each bedroom, living room, and family room has its own air conditioning unit for complete temperature control. The bedrooms have a full ensuite bathrooms and are located on the ground floor. The beach is less than a two minute walk! Note: Hawaii GET, TA & MCTAT taxes of 17.962% are included in total price, no additional taxes charged.

Marriott Maui Ocean Club 1BR 2BA
Marriott’s Maui Ocean Club is one of the most popular timeshare resorts - and for good reason! Kids and kids-at-heart will get a kick out of the resort's 3.5- acre super pool complete with a water slide, waterfalls, and children's area. The poolside bar is a great place to rest and relax while the little ones splash until their heart's content. Maui Ocean Club also offers amenities such as a beauty shop, barbecue area, game room, and restaurants.

Modern 2 bedroom/2bath Villa near Beach!
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 is comprised of 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. Dual king bed suites feature full baths with enclosed walk in showers and silent A/C units.

Ocean View Villa at Villas by the Cove!
Enjoy a refreshing dip in the pool before kicking back on a premium white sandy beach. This stylish villa features a modern slate décor, state-of-the-art kitchen, private covered lanai, and tropical garden of mango and palm trees. The condo is part of an upscale property tucked away on a residential oceanfront side street. Surf schools, bicycle rentals, spa treatments, and farmer’s market are just around the corner.

Newly Remodeled 2 Bed/2 Bath - Close to Beach
Ohana Hale is newly remodeled two bedroom, two bathroom ground floor condominium suite on a shared property. Each bedroom has air conditioning, in addition to one full bathroom and its own private entrance to the shared pool. Guests can choose between a King bed or 2 Twin beds. Note: Hawaii GET, TA & MCTAT taxes of 17.962% are included in total price, no additional taxes charged.

Ocean Front Cottage, 30 steps to the beach!
BEACH FRONT!! Stunning views from this charming beach front cottage located in the heart of Kihei town! This 850 square foot one bedroom, two bath home fronts a sandy beach and offers gorgeous sunset views. Conveniently all one level, this home is ideal for families of four or couples. Beach Front Honu Cottage offers the perfect paradise getaway, with a million dollar view!

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.

Ocean View 2BR Villa Steps To The Beach
Villa 4 is a 2 Bedroom, 2 Bathroom remodeled Villa with a spacious living room and ocean view patio. This Villa offers privacy and comfort set back in a tropical lush garden filled with mango and palm trees. This single story, stand-alone villa that is charming, convenient, and clean. Note: Hawaii GET, TA & MCTAT taxes of 17.962% are included in our prices.
Popular amenities for Wailea villa rentals
Private villa rentals

Marriott Maui Ocean Club 1BR 2BA

Chic Villa 6 – Beach Vibes & Walkable Paradise!

Chic Villa 2 | Modern Vibes by the Ocean

Ocean Front Cottage, 30 steps to the beach!

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

Modern 2 bedroom/2bath Villa near Beach!

Newly Remodeled 2 Bed/2 Bath - Close to Beach

Ocean View 2BR Villa Steps To The Beach
Luxury villa rentals

Westin Nanea Kaanapali Ocean Villa 2BR Sleeps 6

Spectacular 3/3 Ocean view Villa with AC, pool

Luxury Living Surrounded by Sweeping Ocean Views

Kapalua Ridge 2422. Luxurious remodeled townhouse!

Panoramic Ocean-View Villa steps from the beach!

Nicely Renovated ~ Reduced Price ~ Ocean Front

Kapalua Ridge 2821-22- Luxury FULL Ocean Views

Peaceful Lanai Hideaway with Sparkling Ocean Views
Villa rentals with a pool

Marriott Maui Ocean Club 1BR 2BA

Chic Villa 6 – Beach Vibes & Walkable Paradise!

Chic Villa 2 | Modern Vibes by the Ocean

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

Ocean View Villa at Villas by the Cove!

Modern 2 bedroom/2bath Villa near Beach!

Newly Remodeled 2 Bed/2 Bath - Close to Beach

Ocean View 2BR Villa Steps To The Beach
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 2,040 | € 2,170 | € 2,109 | € 2,252 | € 1,654 | € 2,259 | € 1,834 | € 1,834 | € 1,604 | € 1,306 | € 1,879 | € 1,625 |
| 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 vacation rentals
Explore 40 vacation rentals in Wailea

Nightly prices starting at
Wailea vacation rentals start at € 260 per night before taxes and fees

Verified guest reviews
Over 620 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
40 of Wailea vacation 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!
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