Villa holiday rentals in Wailea

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!

4.93 out of 5 average rating, 42 reviews

Ground floor, ocean view, private, Kapalua Ridge

Welcome to Kapalua Ridge Villa 612. This large 1 bedroom, 2 bathroom 1125 sq ft condo features an open floor plan with a large private shaded lanai. Admire Honolulu Bay, sunsets, whale watching, sailboats, & more. This condo has ocean views from the lanai, living area, dining area, & kitchen. The unit can comfortably accommodate 4 people. The pool is a few steps away & there is a walk path that leads you all the way down to the resorts/beach. Kapalua Ridge Villas is coastal Luxury at it's best.

4.93 out of 5 average rating, 309 reviews

Villa in Kihei

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 favourite

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

4.96 out of 5 average rating, 96 reviews

Villa in Wailea-Makena

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 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.

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!

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

5 out of 5 average rating, 7 reviews

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.

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.