Explore Wailea-Makena Vacation Rentals
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- 2426 ft² Villa
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Luxury Places to Stay in Wailea-Makena
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- 3229 ft² Villa
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Top-Rated Vacation Rentals with a Pool in Wailea-Makena
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Pet-Friendly Vacation Rentals in Wailea-Makena
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- 1054 ft² Apartment
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Large Vacation Homes & Villas in Wailea-Makena
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Wheelchair Accessible Vacation Homes in Wailea-Makena
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Wailea-Makena Villas and Airbnb Homes Under $200
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Instantly Bookable Vacation Homes in Wailea-Makena
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Book a Last Minute Place to Stay in Wailea-Makena
About Wailea-Makena Vacation Rentals
Explore more than 2086 vacation rentals available in Wailea-Makena. These accommodations, including vacation homes and HawaiiVillas properties, boast excellent amenities and exceptional value, blending comfort and luxury. Enjoy spaciousness and convenience at a HawaiiVillas property in Wailea-Makena.
Looking for last-minute deals or the best available offers on cottages, condos, private villas, and large vacation homes? With HawaiiVillas in Wailea-Makena, you can effortlessly compare various options with a simple click. Whether you seek properties with swimming pools, hot tubs, pet-friendly policies, or expansive master suites with large screen TVs, you'll find vacation rentals by owner (RBOs) and other popular Airbnb-style accommodations near Wailea-Makena. The average room size in accommodations near Wailea-Makena is 1702.6 ft². Prices average $844 per night.
HawaiiVillas streamlines and secures your search for vacation rentals in Wailea-Makena, often offering savings of 30-40% compared to hotel prices. Start your search today and book with confidence.
Top Rental Accommodation Types in Wailea-Makena
Type | Count |
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Holiday Apartments | 275 |
Vacation Homes | 245 |
Villas | 129 |
Cottages | 6 |
Use these Quick Filters to Find a Vacation Rental in Wailea-Makena
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★ Pro Tip: HawaiiVillas simplifies comparison of top listings across various online vacation rental platforms like Booking.com and others. Use the Advanced Filter feature to switch effortlessly between HawaiiVillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, property types, cancellation policies, prices, and more. These tools streamline the search for your ideal accommodation for your next vacation in Wailea-Makena.
Weather in Wailea-Makena, HI
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Other Places to Stay in Wailea-Makena, HI
Your Guide to Vacation Rentals in Wailea-Makena
Are you dreaming of a tropical vacation that combines luxury, relaxation, and breathtaking natural beauty? Look no further than Wailea, Maui. Tucked away on the southern end of the island, Wailea is a paradise for travelers seeking an escape from the hustle and bustle of everyday life. And, the best way to experience everything this stunning destination has to offer? A vacation rental. Below, we've created a guide to help you find the perfect vacation rental for your Wailea getaway.
Why Choose Wailea for Your Maui Vacation
First things first, let's talk about why Wailea should be at the top of your list for your Maui vacation. First, there are the beaches. Wailea boasts some of the most beautiful stretches of sand in Hawaii. The crystal-clear water and soft sand make it the perfect place to swim, snorkel, or simply soak up the sun. Plus, there's no shortage of upscale shopping and dining experiences here, and the world-class golf courses are enough to make any avid golfer swoon.
The Beauty of Wailea's Beaches
What makes Wailea's beaches so special? It's hard to put into words, but from the moment you set foot on one of Maui's beaches, you'll understand. This is where days blur together in a haze of sunshine, salt water, and relaxation. The water is so clear you can see straight to the bottom, and the sand is so soft it feels like walking on a cloud.
Wailea Beach, in particular, is a must-visit. This stunning beach is consistently ranked as one of the best in Hawaii, and for good reason. With its gentle waves and soft sand, it's the perfect place to spend a lazy afternoon. And, if you're lucky, you might even spot a whale or two in the distance during whale watching season.
If you're looking for a quiet spot to relax, try Polo Beach. This secluded stretch of sand is perfect for those seeking a bit of solitude. Meanwhile, Ulua Beach and Wailea Beach are popular with snorkelers, thanks to the abundance of sea turtles and reef fish. And, if you're a seasoned surfer, Makena Beach is the place to be, with consistently large swells for you to ride.
Upscale Shopping and Dining Experiences
Of course, you can't visit Wailea without indulging in a bit of shopping and dining. The Wailea Beach Resort alone has more than a dozen different restaurants and bars, ranging from casual beachside eateries to award-winning fine dining establishments. And, with shops like Louis Vuitton, Gucci, and Chanel, the Shops at Wailea are perfect for those looking to splurge on some high-end retail therapy.
But, there are also plenty of local shops and eateries to explore. Head to the Maui Ocean Center for a taste of local seafood, or stop by the Maui Brewing Company for a refreshing pint of locally brewed beer. And, for a truly unique experience, check out the Maui Swap Meet, where you can browse local crafts and goods.
World-Class Golf Courses
Finally, we can't talk about Wailea without mentioning the golf. This destination is a must-visit for any golf enthusiast, with a wide range of courses to choose from. The Wailea Golf Club, in particular, is home to three different courses, each with a unique challenge. Whether you're a beginner or a seasoned pro, you'll find a course that suits your skill level and playing style.
And, if you're looking for a truly unforgettable golfing experience, book a tee time at the nearby Kapalua Golf Club. This stunning course is consistently ranked as one of the best in the world, with breathtaking views of the Pacific Ocean and the West Maui Mountains.
In conclusion, Wailea is the perfect destination for anyone looking for a mix of relaxation, adventure, and luxury. With its stunning beaches, upscale shopping and dining experiences, and world-class golf courses, it's no wonder that Wailea is consistently ranked as one of the best vacation spots in Hawaii.
Types of Vacation Rentals in Wailea
Wailea is a paradise for vacationers, with its beautiful beaches, stunning sunsets, and a wide range of vacation rentals to choose from. Whether you're traveling solo, with your partner, or with your family, there's a perfect vacation rental for you in Wailea. Here are some of the most popular types of vacation rentals in Wailea:
Luxury Villas and Estates
If you're looking for the ultimate luxury experience, a villa or estate rental in Wailea might be just what you need. These spacious and elegant properties offer all the amenities you could want, from private pools and hot tubs to fully equipped kitchens and outdoor grills. You'll enjoy plenty of space to relax and unwind, with stunning views of the ocean or the mountains. And, with easy access to Wailea's world-class golf courses, spas, and restaurants, you'll have everything you need for a memorable vacation.
Beachfront Condos
For those who want to be right on the beach, a beachfront condo rental is the perfect choice. These units offer easy access to the sand and surf, with private lanais or balconies that offer breathtaking views of the ocean. You'll have all the comforts of home, with fully equipped kitchens, comfortable living areas, and modern amenities like Wi-Fi and cable TV. And, with on-site amenities like swimming pools, hot tubs, and fitness centers, you'll have everything you need for a relaxing and enjoyable stay in Wailea.
Private Homes and Cottages
If you're looking for a more secluded and private vacation rental, a private home or cottage rental might be just what you need. These properties offer total privacy and seclusion, with plenty of space to relax and unwind. You'll have your own kitchen and living areas, as well as outdoor spaces like patios and gardens. And, with easy access to Wailea's beaches, hiking trails, and other attractions, you'll have plenty to see and do during your stay.
Whatever type of vacation rental you choose in Wailea, you're sure to have an unforgettable experience. With its natural beauty, warm weather, and welcoming culture, Wailea is the perfect destination for your next vacation.
Top Wailea Vacation Rental Communities
Wailea is a beautiful resort community located on the south shore of Maui, Hawaii. With its stunning beaches, world-class golf courses, and luxurious accommodations, it's no wonder that Wailea is a top destination for travelers from around the world. If you're planning a trip to Wailea, one of the best ways to experience all that this amazing community has to offer is by staying in a vacation rental. Here are three of the top Wailea vacation rental communities to consider:
Wailea Beach Villas
Wailea Beach Villas is one of the most popular vacation rental communities in Wailea, and for good reason. These spacious villas feature two to three bedrooms and offer all the luxury amenities you could ask for, including full kitchens, private pools, and stunning ocean views. The villas are beautifully decorated and offer plenty of space for families or groups of friends traveling together. Plus, the community is just steps away from Wailea Beach, making it the perfect spot for those eager to spend time in the sand. Whether you're looking to relax by the pool, take a stroll on the beach, or explore all that Wailea has to offer, Wailea Beach Villas is the perfect home base for your Maui vacation.
Ho'olei at Grand Wailea
If you're looking for something truly next-level, consider a rental at Ho'olei at Grand Wailea. These sprawling townhomes are some of the most luxurious accommodations in all of Wailea, offering unparalleled amenities like private elevators, gourmet kitchens, and outdoor living spaces. The townhomes are beautifully designed and decorated, with plenty of space for families or groups of friends traveling together. Plus, you'll have access to all the services and amenities of the nearby Grand Wailea Resort, including a spa, fitness center, and multiple dining options. Whether you're looking to relax in your own private oasis or take advantage of all the amenities of a world-class resort, Ho'olei at Grand Wailea is the perfect choice for your Maui vacation.
Makena Surf Resort
If you're looking for a beachfront condo rental, Makena Surf Resort is a top choice. These spacious units offer two to three bedrooms and stunning ocean views, as well as access to the resort's pool and hot tub. The condos are beautifully decorated and offer plenty of space for families or groups of friends traveling together. And, with direct beach access, you'll never be far from the sand and surf. Whether you're looking to relax on the beach, explore the nearby shops and restaurants, or take advantage of all the activities that Wailea has to offer, Makena Surf Resort is the perfect home base for your Maui vacation.
No matter which of these top Wailea vacation rental communities you choose, you're sure to have an unforgettable vacation in one of the most beautiful places in the world. So why wait? Book your Wailea vacation rental today and start planning your dream Maui getaway!
How to Find the Perfect Wailea Vacation Rental
Determine Your Budget and Preferences
The first step in finding the perfect Wailea vacation rental is to determine your budget and personal preferences. How much are you willing to spend? How many bedrooms do you need? Do you want to be close to the beach or located in a more secluded area?
When it comes to budget, keep in mind that vacation rentals can range from budget-friendly to luxury. If you're traveling with a group, it may be more cost-effective to split the cost of a larger rental. And if you're looking for a more luxurious experience, consider rentals with amenities like private pools or ocean views.
As for location, Wailea has a variety of options to choose from. If you're looking for a more secluded experience, consider a rental in the hills overlooking the ocean. If you want to be closer to the action, look for rentals within walking distance to the beach or near popular restaurants and shops.
Research and Compare Rental Options
Next, it's time to start researching rental options. Start by browsing online listings on websites like Airbnb or VRBO, but be sure to look into rentals managed by local property management companies as well. These companies often have a wider selection of rentals to choose from and can provide more personal attention during the booking process.
When comparing rentals, it's important to consider not just the price, but also the amenities and location. Some rentals may include extras like beach gear or housekeeping services, which can save you time and money during your stay. And if you're traveling with children, look for rentals with kid-friendly amenities like cribs or high chairs.
Read Reviews and Testimonials
Finally, be sure to read reviews and testimonials from previous renters before making your final choice. These can give you a better sense of what to expect during your stay and can help you avoid any unpleasant surprises.
When reading reviews, pay attention to comments about the rental's cleanliness, location, and amenities. If multiple reviewers mention the same issue, it's worth taking note of.
With these tips in mind, you'll be well on your way to finding the perfect Wailea vacation rental for your next Maui getaway. So, start planning your trip - the sun, sand, and surf are waiting for you in paradise.
Frequently Asked Questions About Wailea-Makena?
What are the top vacation rentals in Wailea-Makena?
Currently, HawaiiVillas lists over 2086 properties in the Wailea-Makena area for 2025, with more being added continuously. By consolidating listings from various websites, HawaiiVillas provides a wide selection of top properties in Wailea-Makena.
- Romantic, Luxury, Sensual Retreat - Couples Only
- Hawaiian Cottage and Personal Paradise/BBKM 2013/0004
- Wailea Custom Home, Pool, Panoramic Ocean View, Waterfalls - Maui Ocean Palms
- Luxury Cottage w/Private Pool. Under The Warm Maui Sun Pmt #BBKM20160004
- Ekahi 34F - Best Panoramic Ocean View!
- Aloha Kai Suite at Wailea Beach Villas. Penthouse 205. Ocean View. 3 BR/3 BA
- 20% off dates in June, July & August! - Elua Village 701, Luxury 2BR, Ocean View
- Beautiful Condo with Great Calif King Bed, Great location & all new appliances
- 🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈
- 125+ 5star REVIEWS SAYS IT ALL! All upgraded/vaulted ceil/Golf & Ocean view!
How many vacation rentals have private pools in Wailea-Makena?
Discover 73 vacation rentals featuring private pools near Wailea-Makena. Highly-rated HawaiiVillas properties with swimming pool access include:
- Beachfront Condo E 303/Incredible views/Pickleball/Great Snorkelingn
- KBM Resorts FREE CAR Wailea Beach Villa WBV-PH412 Spacious wsweeping Ocean Views
- 300 m² Villa ∙ 3 bedrooms ∙ 8 guests
- Fairmont Kea Lani Maui Villa Experience
Which vacation homes in Wailea-Makena are best for families?
If you're searching for a family-friendly vacation residence in Wailea-Makena, explore one of these highly-rated properties, all praised for their excellent reviews among families or groups visiting Wailea-Makena:
- Soooooo Close to the Beach & Completely Remodeled! Relax to the Sound of Waves
- Wailea Elua, #0908 condo
- 138 m² Condo ∙ 2 bedrooms ∙ 6 guests
How many Hawaii.Villas vacation rentals are available in Wailea-Makena?
At present, HawaiiVillas showcases more than 2086 properties available in the Wailea-Makena area for 2025, with new listings added regularly. By aggregating listings from multiple sources, HawaiiVillas offers a diverse range of premier properties in Wailea-Makena.
Nearby Neighborhood (1)
Neighborhood | Property Count |
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Wailea Vacation Rentals in Hawaii | 1292 |