We found 35 vacation rentals — enter your dates for availability
Immerse yourself in the tropical paradise of Wailea, where stunning beaches meet luxurious living. With the breathtaking Wailea Beach just moments away, families can indulge in sun-soaked adventures, while upscale shopping and delightful local cuisine beckon just around the corner. Choose from an array of spacious vacation rentals, from elegant villas to cozy condos, ensuring that your group enjoys both comfort and convenience for an unforgettable Hawaiian getaway. Experience the warmth of home with amenities that make your stay truly special.
"This is a beautiful home with a wonderful view, conveniently located nearby shops, beach, and poolThis home does not feel like a rental. It’s very clean and well maintained and superior quality built home.Rooms and bathrooms are a good size and the family room and balcony. Make a great hangout for gathering for food or fun. We will definitely return one day thank you.!"
"This is a beautiful home with a wonderful view, conveniently located nearby shops, beach, and poolThis home does not feel like a rental. It’s very clean and well maintained and superior quality built home.Rooms and bathrooms are a good size and the family room and balcony. Make a great hangout for gathering for food or fun. We will definitely return one day thank you.!"
"Accommodations were perfect and views were incredible. Home is equipped with everything you need and then some. Property manager ensures your arrival is as expected and is available if needed during your stay. We could not have asked for more except additional days in this setting. Perfect vacation!"
"Accommodations were perfect and views were incredible. Home is equipped with everything you need and then some. Property manager ensures your arrival is as expected and is available if needed during your stay. We could not have asked for more except additional days in this setting. Perfect vacation!"
"We just spent 5 days enjoying a family vacation at this amazing property. Beautiful location with a large patio view of the ocean and amazing sunsets. The management was very responsive to questions. Well stocked kitchen for cooking meals for a large group and plenty of household sundries to last our whole visit. The pool area with two hot tubs and proximity to walk to the beach were a big plus for our family."
"We just spent 5 days enjoying a family vacation at this amazing property. Beautiful location with a large patio view of the ocean and amazing sunsets. The management was very responsive to questions. Well stocked kitchen for cooking meals for a large group and plenty of household sundries to last our whole visit. The pool area with two hot tubs and proximity to walk to the beach were a big plus for our family."
"Even though there is a handicap elevator, there is no handle or even a soap dish in the glass wall for seniors who have balance problems. We called hosts near the end of our stay to ask for a portable shower handle support (master bath is a large open one - no wall or door at the entrance or end, but were told all of the units are built that way - no help offered. Removable one could be purchased at Home Depot, etc. Had to make do with sponge baths and husband's support - kind of put a big...
"Even though there is a handicap elevator, there is no handle or even a soap dish in the glass wall for seniors who have balance problems. We called hosts near the end of our stay to ask for a portable shower handle support (master bath is a large open one - no wall or door at the entrance or end, but were told all of the units are built that way - no help offered. Removable one could be purchased at Home Depot, etc. Had to make do with sponge baths and husband's support - kind of put a big...
"We previously stayed at the Fairmont a block away two years ago. Our sleeping arrangements and the need for more space, laundry and kitchen, etc. dictated that we would look for short term rentals rather than a hotel resort. We couldn’t be happier with the choice. This is how we intend to do Maui going forward. First of all, the villas are part of a gated community that has its own pool with hot tubs, a poolside cabana massage option, waterfall and grotto, etc. during Covid times, it is much...
"We previously stayed at the Fairmont a block away two years ago. Our sleeping arrangements and the need for more space, laundry and kitchen, etc. dictated that we would look for short term rentals rather than a hotel resort. We couldn’t be happier with the choice. This is how we intend to do Maui going forward. First of all, the villas are part of a gated community that has its own pool with hot tubs, a poolside cabana massage option, waterfall and grotto, etc. during Covid times, it is much...
Stunning Beaches: Enjoy the beautiful Hoolei Wailea Beach and the family-friendly Wailea Beach, perfect for relaxation and fun.
Luxurious Accommodations: Choose from upscale Ho'olei villas, spacious condos, or charming vacation homes for a memorable stay.
Local Shopping: Visit the Shops at Wailea for unique local finds and souvenirs.
Outdoor Adventures: Explore vibrant parks and scenic spots throughout South Maui, ideal for outdoor enthusiasts.
Cultural Experiences: Immerse yourself in Hawaiian culture with local art and upscale dining options.
Popular types of accommodation around Hoolei
Planning your getaway to Hoolei? You’re in for a treat. Discover a variety of popular accommodations, including luxurious Ho'olei villas, spacious condos, and charming houses. Whether you're looking for a cozy bedroom in a Ho'olei condo or a grand experience at Ho'olei at Grand Wailea, there's something for everyone. Start exploring your ideal home away from home today.
Condos: A favored choice among travelers in Hoolei, condos offer a blend of comfort and convenience, often featuring stunning ocean views.
Houses: Ideal for families or groups, these homes provide spacious accommodations and a home-like atmosphere.
Apartments: A practical option for couples or solo travelers, apartments in Hoolei offer essential amenities in a cozy setting.
Villas: Luxurious and spacious, villas provide an upscale experience with private amenities and beautiful surroundings.
Cottages: Quaint and charming, cottages offer a more intimate and cozy getaway, perfect for relaxation.**
Top attractions near Hoolei
During your vacation in Hoolei, Kihei, Hawaii, you'll find a variety of attractions that cater to beach lovers and outdoor enthusiasts. Explore Hoolei Wailea Beach for stunning views and relaxation, visit the Shops at Wailea for local shopping, and enjoy the beautiful Wailea Beach for family-friendly experiences. Whether you seek sun-soaked beaches or vibrant parks, Hoolei has something for everyone to enjoy.
Wailea Beach: A stunning stretch of golden sand located just 0.3 miles from Hoolei. Enjoy the beach vibes, perfect for sunbathing, swimming, and picturesque sunsets.
Kamaole Beach Park 3: This family-friendly park is 2 miles away, featuring picnic areas and gentle waves, ideal for outdoor activities and enjoying time with loved ones.
Makena State Park Beach: Located 3 miles from Hoolei, this romantic nudist beach offers a secluded atmosphere, breathtaking views, and a tranquil setting for couples.
Things to do recommended for couples
For a romantic getaway in Hoolei, indulge in a soothing treatment at Makena Kai Day Spa, just 2 miles away. Enjoy wine tasting at MauiWine and Tedeschi Vineyards, both offering charming atmospheres perfect for couples, located 3 and 4 miles away respectively.
Things to do recommended for families
Families will have a blast at Science City, an arcade adventure zone located 12 miles from Hoolei. With its fun-filled atmosphere and thrilling activities, it's the perfect spot for kids and parents alike to enjoy quality time together.
Things to do recommended for groups
Explore the Shops at Wailea for shopping and entertainment just half a mile from Hoolei, hit the Wailea Blue Golf Course for outdoor sports activities only 0.4 miles away, or enjoy a romantic evening at Maui Brewing Co., located 5 miles from your stay.
*Distances are measured in a straight line; actual driving distances may vary depending on the route.
What do I need to keep in mind when booking a vacation around Hoolei
If you're traveling with a group, your family, pets, or planning an extended stay, it's important to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips to assist you.
Traveling to Hoolei with a group: Think about how many bedrooms you'll require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
Traveling to Hoolei with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are enjoyable for families.
Taking your pets with you to Hoolei: For many families, a trip isn’t truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
Planning for a long term stay visiting Hoolei: If you're seeking vacation rentals with discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. You might also want to consider including features like a parking space, a well-equipped kitchen, or a private pool in your search.
Where to stay near Hoolei
Hoolei offers a stunning gateway to the luxurious enclave of Wailea, where pristine beaches meet Hawaiian culture. Explore the family-friendly atmosphere of South Maui with its romantic settings and secluded excursions. Enjoy breathtaking ocean views, upscale dining, and vibrant local art. Whether you seek relaxation or adventure, Hoolei's surrounding neighborhoods promise unforgettable experiences in this beautiful Hawaiian paradise.
Maui: Maui, an enchanting island located 11 miles from Hoolei, is a paradise for outdoor enthusiasts and beach lovers alike. Known for its stunning scenery and diverse landscapes, Maui offers an array of activities ranging from world-class golf courses to vibrant shopping centers. Visitors can explore beautiful beaches and picturesque bays, or relax in urban parks that showcase the island's natural beauty. Whether you're catching waves, snorkeling in crystal-clear waters, or enjoying a scenic drive on the Road to Hana, Maui promises an unforgettable experience.
Kihei: Kihei, the charming city where Hoolei is situated, is renowned for its family-friendly atmosphere and beautiful beaches. With a variety of outdoor activities available, it's an ideal destination for travelers looking to soak up the sun and enjoy quality time with loved ones. Kihei boasts numerous golf courses and shopping centers, catering to both leisure and retail therapy. Local highlights include pristine family beaches and urban parks, where you can unwind, picnic, or take a leisurely stroll along the coastline.
Wailea: Wailea, a luxurious neighborhood adjacent to Hoolei, is celebrated for its breathtaking beaches and scenic vistas. Visitors flock to Wailea for its outdoor experiences and upscale ambiance, making it a perfect spot for relaxation and adventure. The area features top-notch golf courses and high-end shopping venues, ensuring a delightful experience. With stunning beaches, tranquil bays, and well-maintained urban parks nearby, Wailea invites you to explore its natural wonders while enjoying the serene Hawaiian lifestyle.
Best time to go to Hoolei
If you're planning a trip to Hoolei, it's a good idea to check both the weather and property rates. The warmest months are August, August, September and September. Peak season runs in January, January, March, March, July and July, while off-peak times, like August, August to September, September to October and October tend to have fewer bookings and better deals.
Calendar Month
Temperature
Precipitation
Cloudiness
Occupancy
Pricing
January
72.7°F (22.6°C)
No Rain (Dry)
Mostly Sunny
Slightly High
Slightly High
January
72.7°F (22.6°C)
No Rain (Dry)
Mostly Sunny
Slightly High
Slightly High
February
72.3°F (22.4°C)
No Rain (Dry)
Mostly Sunny
Average
Average
February
72.3°F (22.4°C)
No Rain (Dry)
Mostly Sunny
Average
Average
March
72.7°F (22.6°C)
No Rain (Dry)
Mostly Sunny
Slightly High
Slightly High
March
72.7°F (22.6°C)
No Rain (Dry)
Mostly Sunny
Slightly High
Slightly High
April
74.1°F (23.4°C)
No Rain (Dry)
Mostly Sunny
Average
Average
April
74.1°F (23.4°C)
No Rain (Dry)
Mostly Sunny
Average
Average
May
75.6°F (24.200000000000003°C)
No Rain (Dry)
Mostly Sunny
Average
Slightly Low
May
75.6°F (24.200000000000003°C)
No Rain (Dry)
Mostly Sunny
Average
Slightly Low
June
76.8°F (24.9°C)
No Rain (Dry)
Mostly Sunny
Average
Average
June
76.8°F (24.9°C)
No Rain (Dry)
Mostly Sunny
Average
Average
July
77.9°F (25.5°C)
No Rain (Dry)
Mostly Sunny
Slightly High
Average
July
77.9°F (25.5°C)
No Rain (Dry)
Mostly Sunny
Slightly High
Average
August
78.4°F (25.8°C)
No Rain (Dry)
Mostly Sunny
Slightly Low
Average
August
78.4°F (25.8°C)
No Rain (Dry)
Mostly Sunny
Slightly Low
Average
September
78.4°F (25.8°C)
No Rain (Dry)
Mostly Sunny
Slightly Low
Slightly Low
September
78.4°F (25.8°C)
No Rain (Dry)
Mostly Sunny
Slightly Low
Slightly Low
October
77.7°F (25.4°C)
No Rain (Dry)
Mostly Sunny
Slightly Low
Slightly Low
October
77.7°F (25.4°C)
No Rain (Dry)
Mostly Sunny
Slightly Low
Slightly Low
November
75.7°F (24.3°C)
No Rain (Dry)
Mostly Sunny
Average
Average
November
75.7°F (24.3°C)
No Rain (Dry)
Mostly Sunny
Average
Average
December
73.8°F (23.200000000000003°C)
Light Rain
Mostly Sunny
Average
Slightly High
December
73.8°F (23.200000000000003°C)
Light Rain
Mostly Sunny
Average
Slightly High
Booking with Vrbo is simple
Are you hoping to save on your upcoming travel plans? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.
Vrbo Trips: Planning as easy as it gets
Vrbo’s Trip Board provides a convenient platform for you to plan new getaways, manage your existing arrangements, or review your reservations. Your saved or booked properties are thoughtfully categorized into Potential, Upcoming, or Current Trips for easy access. To check out Trip Boards, simply visit: https://www.vrbo.com/trips.