Whether you choose a condo or villa as your Wailea vacation rental, you'll have the perfect base to explore the beauty of Maui.
Great place, everything you need and want for you stay. Living area and Master bedroom views great.
Discover your ideal Wailea vacation rental with real-time comparisons of 6,102 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.
Enjoy affordable vacation rentals in Wailea offering exceptional value for money
Book the highest-rated Wailea vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money
Choose local, trusted payment methods, plus trip insurance and add-on services.
Experience seamless, hands-on support for any booking questions or concerns.
Trust in the quality and comfort of your stay with verified guest reviews.
Spend your budget exactly as planned by comparing thousands of providers.
Transform vacation planning into a joy with advanced, AI-powered search tools.
Explore 15 million+ rentals, the world’s biggest selection of vacation homes.
Finding a rental with a pool is easy in Wailea. Nearly all of the rentals include pools. In addition, more Condo have pools than any other property type. They are an excellent choice if you go in a group of 5, as that is the number of people they can accommodate on average. If you would also like to be close to the water, nearly half of the properties with a pool are within 2 miles of the waterfront.
We analyzed price data and input them into this graph, which shows vacation rental prices for the next year in Wailea. The most expensive prices are in February (2/14 – 2/21). Prices reach an average of $605 per night. Prices decrease in a week of December (12/6 – 12/13), where average prices are $545.
The availability graph shows the busiest months to book a vacation rental in Wailea. The week with the highest booking rate is in October (10/24 – 10/31). Only 19% of the rentals are still available. On the contrary, only 27% of vacation rentals are unavailable in December (12/13 – 12/20).
Learn more about Hawaiian sea life with your family at the Maui Ocean Center, the top-rated aquarium of Hawaii. You don't need to get in the water to see live coral, sharks, turtles, and countless colorful fish. Aside from their many exhibits, they also offer educational tours and interactive presentations for a guided encounter with Hawaii's marine life.
For an even deeper ocean experience, travel a hundred feet below the surface with Atlantis Submarines. Their comfortable passenger vessels will carry your family under the sea in style, letting you observe sea life that's rarely seen by humans.
Wailea Beach is consistently rated as one of the best beaches in the world. A wide, crescent-shaped beach with golden sand, Wailea beach also has calm waters—making it perfect for snorkeling, paddle boarding, and swimming.
Set on Maui's southwestern shores, Makena Beach State Park offers a secluded alternative to some of the more crowded beaches. Also known as Big Beach, Makena Beach is dramatically set between two black lava outcroppings.
| 🏡 Vacation rentals available | 6,102 rentals |
|---|---|
| 🌙 Nightly prices starting at | $214 |
| ⭐ Popular amenities | Pool, Air conditioning and Kitchen |
| 🏊 Vacation rentals with pools | 5,491 homes |
Prices for vacation rentals in Wailea start from $214 per night. Nightly prices for condos are $636 on average. Apartment rentals in Wailea cost on average $546 per night.
There are 6,102 vacation rentals in Wailea to browse and rent for your next trip.
Travelers search for Pool, Air conditioning, and Kitchen when booking a vacation rental in Wailea.
There are 5,491 vacation homes across 29 providers in Wailea.
Absolutely, there are 184 vacation rentals in Wailea that allow dogs , with an average price of $2,098 per night.