
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.

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.

Beach Hideaway • 1 Min Walk to Ocean • Sleeps 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.

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.

2BR/2BA • 1 Min Walk to Ocean • Sleeps 4
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!

Luxury Oceanview Wailea Retreat with Sunset Views
Escape to Hōkū Hale, a serene oceanview retreat in the heart of Wailea. This designer oasis offers modern comforts, a private lanai with stunning ocean views, on the fairway of a private golf course. Walk to world-class beaches, dining, golf or relax in a peaceful, breezy, tropical setting. Perfect for large families and groups seeking upscale luxury and the best of Maui.

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.

Chic Villa 6 – Beach Vibes & Walkable Paradise!
Welcome to 1 Bedroom, 1 Bathroom Villa 6 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. Whether you're here for adventure or relaxation, Villa 6 offers the comfort of home in a prime island location.
Popular amenities for Wailea villa rentals
Private villa rentals

Luxury Oceanview Wailea Retreat with Sunset Views

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!

2BR/2BA • 1 Min Walk to Ocean • Sleeps 4

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

Luxury Oceanview Wailea Retreat with Sunset Views

Chic Villa 6 – Beach Vibes & Walkable Paradise!

Chic Villa 2 | Modern Vibes by the Ocean

Ocean Front Cottage, 30 steps to the beach!

Ocean View Villa at Villas by the Cove!

Modern 2 bedroom/2bath Villa near Beach!

2BR/2BA • 1 Min Walk to Ocean • Sleeps 4

Ocean View 2BR Villa Steps To The Beach
Villa rentals with a pool

Luxury Oceanview Wailea Retreat with Sunset Views

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!

Ocean View 2BR Villa Steps To The Beach

2BR/2BA • 1 Min Walk to Ocean • Sleeps 4
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $4,022 NZD | $4,279 NZD | $4,159 NZD | $4,440 NZD | $3,260 NZD | $4,453 NZD | $3,616 NZD | $3,616 NZD | $3,163 NZD | $2,576 NZD | $3,704 NZD | $3,204 NZD |
| 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 40 holiday rentals in Wailea

Nightly prices starting at
Wailea holiday rentals start at $513 NZD per night before taxes and fees

Verified guest reviews
Over 610 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
40 of Wailea holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Wailea rentals

5 Average rating
Wailea stays are highly rated by guests—averaging 5 out of 5!
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