Villa vacation rentals in Wailea

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Top-rated villa rentals in Wailea

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The living area features a comfortable seating arrangement with a sectional sofa and two armchairs. A large flat-screen TV is mounted on the wall, and a wooden coffee table sits in the center. Floor-to-ceiling sliding glass doors provide views of the beach and garden.

Villa in Lahaina

5 out of 5 average rating, 3 reviews

Come Play on Maui & Save $ ~Ocean Front Kapalua

Hawaii State Tax ID # TA‐183-831-8080-01 OUR PICTURES REALISTICALLY REPRESENT; The entire villa has been remodeled. NO DISAPPOINTMENTS HERE!!! This villa is located in building 25 on the lower Ocean Front row of the Kapalua Bay Villas INCLUDED: ~Wifi / internet ~Phone Service to US mainland and CANADA ~Central AC, (new 2023) ~Quality King bed w/ linens & bath towels ~Beach Gear: chairs, towels, ice cooler, & boogie boards ~24/7 on call on island contact ~Parking, Resort Shuttle & No Hidden Fees!

Guest favorite

A private rear deck features a shaded area with tropical foliage and bamboo fencing. Two surfboards and beach gear are neatly stored, along with a round table and colorful chairs for seating. A large black container sits in the corner, adding to the functional outdoor space.

Villa in Kihei

4.93 out of 5 average rating, 309 reviews

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.

Top guest favorite

A resort landscape is depicted, featuring a lagoon-style pool surrounded by palm trees and lounge areas. Ocean waves gently lap at the shore in the background, with a clear blue sky above. The building architecture showcases multiple levels, blending naturally with the tropical environment.

Villa in Lahaina

5 out of 5 average rating, 16 reviews

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

Guest favorite

A coastal view features tall palm trees swaying gently against a clear blue sky. The sandy beach stretches along the shoreline, leading to calm turquoise waters. In the distance, a glimpse of a distant landmass is visible, adding to the serene atmosphere.

Villa in Wailea-Makena

4.96 out of 5 average rating, 96 reviews

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!

Superhost

The image captures a vibrant sunset over an oceanfront resort. Lush palm trees surround a large pool area, with lounge chairs set on the grass. The horizon showcases warm hues, blending into the tranquil sea, while two resort buildings frame the scene on either side.

Villa in Lahaina

Westin Ka’anapali North OCEAN FRONT 2 Bed Villa

This reservation is OCEAN FRONT for the week with arrival on Friday Oct 3, 2025 thru Oct 10, 2025. Please inquire for other date preferences. Westin Ka’anapali Ocean Resort Villas North is a full service resort with everything needed for the perfect stress-free vacation, with or without the kids! Each villa is equipped with luxurious Westin Heavenly King size beds, a full kitchen, in room laundry, 2 bedrooms, 2 bathrooms, 2 sofa beds, a living room, dining room and spacious balcony/patio.

Guest favorite

The living area features a mix of seating options, including a light-colored sofa and a dark leather recliner. A large television is mounted on the wall, with natural light streaming through expansive windows. Lush greenery can be seen outside, enhancing the room's connection to nature.

Villa in Lahaina

4.97 out of 5 average rating, 38 reviews

Our Kapalua Golf Villa piece of paradise, Specials

Enjoy our condo in the spectacular Kapalua area. Nestled on the 4th fairway of the beautiful Kapalua Bay Course, has unobstructed views of the golf course with ocean views in the background. The peaceful setting is perfect for any getaway without the madness of the hotel scene. The condo has all kitchen amenities, full size washer / dryer, king size bed in master, 2 bathrooms, pull out couch in living room, WiFi, cable tv and no stairs! Come enjoy our piece of paradise!

Guest favorite

The image captures a spacious pool area surrounded by lush tropical landscaping. Lounge chairs are arranged neatly around the large swimming pool, which glimmers under the clear blue sky. A multi-story resort building stands in the background, providing a glimpse of the beach and ocean.

Villa in Lahaina

4.9 out of 5 average rating, 81 reviews

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

Superhost

A living area is shown with a large flat-screen TV mounted on a wooden media console. A comfortable sofa is paired with a wooden coffee table, complemented by colorful accents on the chair cushions. Large glass doors offer views of the outdoor dining area and surrounding landscape.

Villa in Lahaina

4.88 out of 5 average rating, 8 reviews

The Westin Nanea 2 Bedroom Ocean Villa

Between exploring the island and relaxing at the resort, you'll revel in your Maui retreat. Your stylish sanctuary at The Westin Nanea Ocean Villas is a spaciou two-bedroom villa that offers many of the key amenities of home, with signature Westin touches. Complementing picturesque Maui views with contemporary furnishings hīna‘i-themed fixtures, and culturally inspired patterns and artwork, the soothing spirit of pu‘uhounua will help you unwind.

A bright and airy dining area features a wooden table set for four, complemented by a cozy green armchair. Floor-to-ceiling sliding glass doors provide stunning ocean views and natural light, with tropical greenery visible beyond the balcony. Ceiling fans circulate gentle breezes throughout the space.

Villa in Lahaina

4.86 out of 5 average rating, 44 reviews

Spacious Ocean & Golf Course Views Kapalua 2B/3B

We welcome and thank you for your support of Maui. Beautiful spacious ocean view, 2 bdrm/3 ba Villa. Lanai, new sofabed, platform bed, flooring, 2 Pools, BBQ area, wifi, free parking, new washer/dryer. Photos do not do it justice. Views across the Kapalua Golf course is the Ritz Carlton gives you an idea of this exclusive neighborhood. Popular for returning guests which speaks volumes. Feel free to ask questions. Professional Cleaners

Superhost

A spacious outdoor area features a private pool with clear blue water, framed by stone landscaping. An arched structure offers shade near the pool, and a red bowl sculpture adds a pop of color. Lush greenery surrounds the space, enhancing the serene environment.

Villa in Lahaina

4.8 out of 5 average rating, 88 reviews

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.

Guest favorite

A vibrant landscape showcases lush greenery and colorful flowering plants, leading to a spectacular view of the ocean and sandy beach. The deep blue water contrasts with the bright green and colorful foliage under a clear sky, offering an inviting tropical atmosphere.

Villa in Lahaina

4.93 out of 5 average rating, 102 reviews

Kapalua Ridge 2012- Whale Watching Ocean Views

Enjoy the 5th Night Free for stays between now and December 15, 2025. *Applies to new reservations only. Upon entering this one bedroom/two bath Ridge Villa at The Kapalua® Resort, it is impossible not to be taken aback by the spectacular sweeping ocean views!