1.800.559.2850 | 1.519.266.6711
Save Time and Money. Utilize our Expertise with our Villa Recommendation Feature
Search Properties

View All Maui Villa Rentals

Maui Villa Rentals

Maui Hawaii Villas

A true island paradise, if you've ever seen an episode of LOST, the amazing waterfalls in Jurassic Park or that famous episode of the Brady Brunch (the one with the spooky tiki totem), then you've been vicariously transported to Maui. Until they have 4-D technology though, what you won't experience are the amazing smells and cool mountain breezes.

First, there's the fresh air. How fresh is the air? Ever had a bottle of Fiji water? How's that compare to tap? Well the air in Maui is like that! Then there is the unbelievable cacophony of fragrant smells. Hawaii has thousands of species of unique flowers. The island flower of Maui is the pink lokelani (Rosa damascene) or the pink cottage rose, which you will probably receive in the form of a lei when you arrive on the island. Oh did we mention the rainbows? You'll see them around every turn. Because of the differing elevations on the beautiful volcanic island, there's always a light mountain mist and therefore multiple rainbows on any given day.

It's no wonder then that it's known as the "Magic Island." Maui offers guests world class resorts and luxurious amenities. The Island of Maui is the second largest of six very special Hawaiian Islands in the South Pacific Ocean. Enjoy Maui's beaches, national parks, magical waterfalls, and the finest of entertainment and luaus, shopping, dining and endless activities for all ages.

We have selected Maui as our only destination within Hawaii due to the services that are offered. Each guest enjoys private concierge services and impeccably appointed villas and beach houses in our four resort locations. Kapalua and Ka' anapali are in the region of West Maui. Wailea and Makena are in the region of South Maui.

Distances from Kahului Airport to:

Maui Distances from Airports
Kapalua38 miles/1 hour drive
Ka' anapali31 miles/50 minute drive
WaileaX miles/ x minute drive
Makena19 miles/40 minute drive

Maui does have two smaller commuter airports that are located in Kapalua (JHM) and Hana (HNM). Some carriers may utilize these airports depending on connection location and if your connection is within another Hawaiian Island. Our concierge is here to accommodate any arrival.

Concierge Services
Hawaii Maui - Concierge Services

Maui Hawaii - Concierge Services


All of our guests to Maui will enjoy our personal concierge service which has been created to maximize your enjoyment while vacationing in Maui. We have a representative for each location that is there to assist you with any request including:

• Lei Greeting at Airport
• Pre-provisioning and Shopping Service
• Catered in Villa Dinners and Private Chef Service
• Luxury and Sports Car Rentals, Sedan and Limousine Services
• Dinner and Entertainment Reservations
• Tee Times
• Tours, excursions and Charters
• Sailing or Power Boats
• Cultural Guides and Family Programs
• Personal Trainers and Instructors
• In Villa Massage and Pedicure/Manicure Services
• Floral Deliveries
• Family Portrait Photography
• Private Housekeeping
• Childcare Services
• Reservations for theater, music and dinner shows.
• Reservation services for adventures and outings such as helicopter tours, sports fishing, snorkeling cruises, horseback riding, mountain biking, luaus, Haleakala night sky star tours, surf lessons, jet ski rentals and more.
• Inter-Island Flights


A private villa vacation in Wailea is a true luxury experience. The Wailea Resort is a stunning and exclusive 1500 acre oceanfront resort community that is known for its beautiful beaches and pristine golf courses.

Safe and secure, our hand-picked private Wailea Beach Villas provide guests with the privacy of their own home with all of the amenities and services of a world class resort.

The Marriott, Grand Wailea, Four Seasons, Wailea Point and Fairmont Resorts are neighbours to your Private Wailea Villa accommodations within the Wailea Resort and offer world class golf, spas, restaurants and shopping.

We know you will love Wailea. Take a moment to view our collection of hand-picked Luxury Villas and start planning your Wailea vacation today.

Wailea Beach Villas Amenities:
• Beachfront infinity adult pool and hot tub, family pool and hot tub, pool attendants, beach chairs, umbrellas, Egyptian cotton towels, sunscreen, cold water, outdoor showers.
• Beachfront Spa Treatments available.
• State-of-the-art Fitness Center
• Billiards Room
• Deluxe Stainless Viking Propane Barbeque Grills with Rotisseries
• Billiard Room
• Business Center with two computers and printer
• Complimentary Wi-Fi
• Free Parking
• Private security gated pedestrian access to The Shops of Wailea and beaches.
• 24 Hour Security Personnel

The Beaches of Wailea

Beach in Wailea

Wailea Beach Villa

Enjoy the Beaches that have made Wailea Famous.

Wailea Beach
Offers guests the opportunity to enjoy a pathway that connects through the resort and enjoy the facilities of hotels, restaurants and shopping. A favorite for swimming, snorkeling and stand-up paddle boarding, Wailea Beach also provides restroom amenities and water sport equipment rentals.

Polo Beach
Enjoy a day at this very popular beach where vacationers and locals meet. Polo beach is also furnished with picnic tables and restrooms.

Keawkapu Beach
Located just above Wailea in Kihei, a beautiful half mile walk and you are surrounded by a classic beach with beautiful views.

Kamaole Beach Parks I, II & III
Located above Wailea in Kihei town, these three beaches offer ample parking, volleyball courts, spacious white sand beaches and excellent swimming conditions.

The Golf Courses of Wailea

Wailea Golf Villas

Enjoy the three Golf Courses that have made Wailea Famous. Golf club rentals, pro shop, golf lounge, snack bar and driving range available.

Wailea Resort Gold Course
Known as the most challenging golf course in Wailea, this Robert Trent Jones II's has woven his expertise into the stunning natural landscape of Wialea. This masterpiece focuses on golfing accuracy and control.
Par: 72
Distance: 7,078 yards
Rates: $190 for guests of the resort ($225 per round regular rate)
Golf package rates are also available

Wailea Resort Emerald Course
A great course that Robert Trent Jones II has designed for golfers of all levels to enjoy. Forgiving fairways and greens open up to topical landscaping and floral scents
Par: 72
Distance: 6,825 yards
Rates: $190 for guests of the resort ($225 per round regular rate)
Golf package rates are also available

Wailea Resort Old Blue Course
Designed by Arthur Jack Snyder, golfers have enjoyed this classic Maui landmark since 1972. As tropical flowers line the holes, enjoy views of the neighboring islands of Lanai, Molokai, Kohoolawe and Molokini.
Par: 72
Distance: 6,765 yards
Rates: $160 for guests of the resort ($90 per round regular rate)

Spas in Wailea

Spas in Wailea

While staying at the Wailea Beach Villas, you will enjoy a seemingly endless selection of world class spa services. Visit Spa Grande at the Grand Wailea Waldorf Astoria, Spa KeaLani at the Fairmont, The Spa at the Four Seasons and Mandara Spa at the Mariott.


Shopping in Wailea

Located adjacent to the Wailea Beach Villas, The Shops at Wailea represent Maui's center for shopping, fashion and dining. Enjoy art galleries, fashion and jewelry with selections such as Banana Republic, Tiffany & Co., Lois Vuitton and Swarovski Crystal.

Snacks, sundries and gifts are also available at shops at Wailea as well as dining options from Cheeseburger Island Style, Ruth's Chris Steak House, Tommy Bahama Restaurant & Bar, KAI Wailea Asian and Longhi's Mediterranean Cuisine.

Ka'anapali Villas

Rich in history, Ka' anapali is renowned for its beautiful beach, accommodations and world class shopping at Whalers Village. Guests also enjoy championship golf at the Royal Kaanapali and Kaanapali Kai.

Ka'anapali offers a unique experience that combines luxury with culture. It was once the place where Hawaiian Royalty vacationed, a re-enacted cliff dive at sunset pays tribute to the culture at each sunset at Black Rock. With its connection with nature, it is not uncommon to see a whale in the waters off of Ka'anapali.

Ka'anapali Beach House

Ka'anapali Villas

We have selected a private beach front vacation home for our collection in Ka'anapali. It is one of the few approved hotel zone vacation rental properties on the island of Maui and offers a luxurious 3 bedroom, 5 bathroom setting with a heated lagoon pool right on the spectacular Ka'anaplai beach.

Click here to view Villa

The Golf Courses of Wailea

Hawaii Golf Villas

Royal Kaanapali Golf Course
This is the very first golf course built in Hawaii and was designed by the late Robert Trent Jones Sr. It offers scenic views of West Maui through a layout of expansive fairways that play into changing trade winds and difficult Bermuda grass greens.
Par: 71
Distance: 6,700 yards
Rates: $249 per round
Golf package rates are also available

Kaanapali Kai Golf Course
Offers guests a shorter golf alternative to the Royal Kaanapali course. Designed through rolling terrain, Norfolk Pines and coconut palms, it is a course that all golfers can enjoy with its more forgiving fairways and greens.
Par: 70
Distance: 6,388 yards
Rates: $205 per round
Golf package rates are also available


Shopping in Kaanapali Hawaii

Whalers Village
Known as Maui's finest oceanfront shopping, Whalers Village offers 90 shops, restaurants and a renowned whale museum at beautiful Ka'anapali Beach.

Beaches in Ka'anapali

Beach Villas Kaanapali Hawaii

Whalers Village
Over 3 miles long with white sand and tropical blue waters, Ka'anapali's Beach is known as one of the finest beaches in Maui and throughout the world. Pu'u Keka'a, also known as Black Rock, on the northernmost section of the beach, is excellent for snorkeling.


Surrounded by pineapple groves, rainforest and marine sanctuaries, Kapalua is a place of wellness and helps to expand the energy of self-awareness.

Located on the western point of Maui, Kapalua offers guests a true luxury experience and is known as one of the islands finest resort areas. The Kapalua Resort is a world class master planned resort destination offering a safe and secure community with world class golf, dining, shopping and beaches.

World renowned for their diversified farming, care for the land and attention to detail, Kapalua is a very special resort destination in West Maui and the world.

Ritz-Carlton Club Villa at Kapalua

Ritz-Carlton Club in Kapalua

The newest addition to Kapalua, enjoy a professionally managed and privately owned condominium villa within the new Ritz-Carlton Club and Residences within the Kapalua Resort. It offers 3700 square feet of living space and spectacular ocean views of Kapalua Bay through expansive lanais. Guests have access to two swimming pools as well as restaurants and bars within the facilities of the Ritz Carlt

The Golf Courses of Kapalua

Kapalua Golf

Plantation Course
Among the world's greatest golf courses, the Plantation course at Kapalua has been scribed into the natural setting of the resort. This course is host to the annual Hyundai PGA tournament of Champions and has hosted the world's greatest golfers.
Par: 73
Distance: 7,411 yards
Rates: $218 per round for guests of the resort ($268 per round regular rate)
Golf package rates are also available

Bay Course
Designed by Arnold Palmer and Francis Dune, the Bay Course is one of the earliest features of Kapalua. Offering endless views of the Pacific Ocean as the fairways are placed through majestic palm trees. It is carefully designed to challenge both amateurs and advanced golfers.
Par: 72
Distance: 6,600 yards
Rates: $184 per round for guests of the resort ($208 per round regular rate)
Golf package rates are also available

Kapalua Golf Academy
A world class golf facility that offers you all of the tools and instruction to refine and better your golf game. Rated as one of the best golf schools in the world and designed by Hale Irwin, the Kapalua Golf Academy offers half day to full week programs
Ask our concierge for assistance

Junior Tees
From 2:30 pm daily, the front 9 holes of the Bay Course are set up for juniors to play. Rental clubs for juniors are complimentary and a 9 hole round is complimentary for juniors who are accompanied by a playing adult


Spas in Kapalua

This carefully designed 30,000 square foot spa facility offers guests the serenity that comes with its carefully placed location between the West Maui Mountains and Kapalua Bay with a stunning view of the nearby island of Moloa'i.

Guests enjoy a selection of indoor and outdoor spa treatments and services which highlight locally sourced and produced treatment products. Additional services include steam, sauna, hot tubs, rainfall showers, fitness facility, salon, Spa Café and Boutique


Activities in Kapalua

Kapalua offers you the ability and choice to relax at your villa, beach or poolside as well as the opportunity to get involved in some great leisure and physical activities. Enjoy, the spa, golf, the Kapalua Trail System, award winning beaches, zip lining, tennis club as well as weddings and special events.

Kapalua Trail System
Enjoy four trail systems all offering a unique experience.
The Coastal Trail, The Honolua Ridge & Maunalei Arboretum Trails, The Mahana RidgeTrail and the Village Walking Trails.

Zip Line
Enjoy one of the country's largest zip lining courses with almost two miles of parallel zip lining as you fly through the Maui West Mountains. All equipment is checked daily to meet safety standards and you will be accompanied by a professionally trained guide at all times.

Kapalua Tennis Garden
At the Bay Course
One of the top rated tennis destinations in the world, the Kapalua Tennis Garden offers everything that you want within a tennis club. Featuring Peter Burwash International professionals you have all of the support and instruction you want while on vacation.
Open daily 8:00 am through 6:00pm.
Bay Course. Dine indoors or outside on the lanai.


Kapalua Beach Villas

An outing to the beach in Maui is a very special activity. From Kapalua you have the opportunity to enjoy the beach at Kapalua Bay which is recognized as one of America's best beaches, D.T Fleming Beach located right in front of the Ritz-Carlton Club, Oneleo Bay and the Holnolua and Mokule'ia Bays located just north of Kapalua.

Private Events and Weddings

Kapalua Villas

Kapalua is the perfect place and has all of the facilities and services to host your wedding, special event and corporate retreats. Contact your concierge for details.


Makena is a true beach lover's paradise. Located in the south region of Maui, it is a destination that offers the true natural beauty of Maui in a more secluded and less populated setting with personalized service.

Known as "The Big Beach", Makena Beach is one of the island's treasures. Enjoy luxury villas with stunning views of the nearby islands of Molokini and Kahoolawe as well as the natural watersports in the gentle surf. The largest beach on Maui, Makena is known for being plentiful with dolphins, turtles and breathtaking sunsets.

Enjoy our secluded beachfront estate property or our villa within the Makena Surf Resort within a secluded beachfront gated community.

Activities at Makena

Makena Activities

Boogie Boarding

Maui Villa Reviews
Total Rating: 5 out of 5 based on 7 customer ratings


This is not the last time you will hear from me. We will be back, for many reasons including we are now hooked on surfing, and renting a house from your company is the only way to go!


"Our family thoroughly enjoyed the house and Maui! One of our best vacations ever. Owners of the house and the management company were fantastic."


This is a wonderful spot, exactly as represented. Excellent service. Loved the whale watching every day.


We had a great stay thank you very much. Everything went smooth.


We had a wonderful time, the house is really great!!


The home adds to a remarkable experience on the island. It was more than we expected. Attention to detail was evident in the way the kitchen was stocked and the home was furnished. Thank you for providing us with a wonderful vacation experience for our 3-month old grandson to our sons who are 30, 34 and 37; and all the rest of the family. Mahalo!!


Our whole Maui experience was excellent, everything recommended was top notch, from the Old Lahaina Luau to the Shangri La. We had no trouble booking anything our family wanted to do. Thank you for recommending Villa 50 for our family - it truly was a vacation to remember. Jana was a god send - we would also highly recommend her - excellent chef, wonderful, kind, caring attitude.

The Best Villa Vacation You Will Ever Have