The resort town of Wailea is known as a romantic destination marked by white sand beaches and spectacular scenic views. Resorts dot the town, along with abundant condo communities and several expansive mansions. Ideal for a romantic getaway, Wailea vacation rentals are perfect for experiencing Maui's finest food, nightlife and idyllic surroundings.

Choose the perfect vacation rental
Best Vacation Home Deals in Wailea-Makena
Save up to 36%
Top-Rated Rentals and Accommodations in Wailea-Makena
Book Vacation Rental Offers with the Highest User Rating
Recommended Vacation Rentals in Wailea-Makena
Find your perfect vacation rental in Wailea-Makena: from $106 per night
Budget-friendly Vacation Rentals in Wailea-Makena
Find Fantastic yet Inexpensive Offers
Vacation rentals and apartments with air conditioning
Keep cool during your trip to Wailea-Makena and book a vacation rental with air conditioning.
Apartments and vacation rentals with a kitchen
Cook up a feast on your next vacation and book a Wailea-Makena rental with full kitchen.
Vacation rentals with Wi-Fi
Stay connected while traveling and book a Wailea-Makena accommodation with high-speed internet.

Popular Rental Amenities in Wailea-Makena
Check above for the most commonly chosen filters in Wailea-Makena and the number of properties that include them. You can easily compare and find a property matching your criteria in Wailea-Makena if you're dreaming of days spent poolside or you would prefer a rental with A/C, as most accommodations include "Pool" or "Air conditioning." Plan your vacation in advance if you want to sweat it out in a sauna or you need a crib for your baby. There are just 217 listed accommodations providing "Sauna" and 312 accommodations with "Crib."
Price and Availability Index in Wailea-Makena
Vacation Rental Price Information in Wailea-Makena
The graph shows average prices of rentals in Wailea-Makena for the next twelve months. Wailea-Makena is more expensive in February (2/10 – 2/17), where prices are on average $873 a night. The week with the lowest average prices is in October (10/5 – 10/12).
Rental availability information in Wailea-Makena
Find out the percentage of available rentals in Wailea-Makena with the graph above. The week with the least available rentals is in December (12/23 – 12/30), with only 21% of the rentals available. People tend to travel less to Wailea-Makena during a week in August (8/24 – 8/31) when only 16% of the rentals are booked.
The Weather in Wailea-Makena
Above are the weather conditions for Wailea-Makena. During August, maximum temperatures go up to more than 90° However, temperatures can go lower than 63° in Wailea-Makena in January. The rainiest month is March while the driest month is January.
7-Day Weather Forecast in Wailea-Makena
Accommodations for your vacation in Wailea-Makena
Hawaiian regional cuisine in Wailea
With miles of beautiful beaches, Wailea has abundant dining options with incredible views. Seafood is a staple at most restaurants, but there's much more to Wailea's culinary scene.
Since 1991, chefs have been serving up Hawaiian regional cuisine, a term used to describe dishes designed to highlight ingredients like the locally raised cattle and fresh vegetables, while infusing the varying ethnic cuisines present on the island. Ka'Ana Kitchen is the perfect example of this.
Evenings in Wailea: Sunset cruises and live music
The variety of attractions make Wailea a popular destination, especially at night. A vacation home is ideal for a quiet place to relax but is still convenient to the upscale resort restaurants and live music venues in the area.
Visitors can start the evening with a sunset cruise, many of which feature cocktails and appetizers. Afterwards, abundant dining options exist before heading out for live music on the beach at Haui's Life's A Beach or Lobby Lounge.
Wailea's festival scene: Film, food & wine
Wailea's natural beauty is the perfect backdrop for a number of annual events. June brings about the Maui Film Festival held in Wailea, and visitors can check out film discussion panels in addition to plentiful film screenings.
Film-loving foodies can add the Taste of Wailea to their itinerary; the event, in conjunction with the film festival, allows pass-holders to sample food and beverage from some of Wailea's best chefs. Fall brings another fun food event: the Wailea Wine and Food Festival, boasting the best food and wines from Wailea Resort's top chefs.
Information about vacation rentals in Wailea-Makena
🏡 Vacation rentals available | 4,130 homes |
---|---|
💳 Possible discounts | up to 31% |
🌙 Nightly prices starting at | $106 |
⭐ Popular amenities | Pool, Air conditioning and Balcony/Patio |
🏊 Vacation rentals with pools | 3,807 homes |
Frequently Asked Questions
What is the typical nightly price for a vacation rental in Wailea-Makena?
The price of a night's stay in Wailea-Makena starts at $106. If you are looking for a house rental, the nightly price is $1,480 on average. A apartment rental Wailea-Makena will cost on average $655 per night.
How many vacation rentals are available to book in Wailea-Makena?
Currently there are 4,130 vacation homes available for booking for your upcoming vacation.
What amenities are most popular for vacation homes in Wailea-Makena?
Travelers search for Pool, Air conditioning, and Balcony/Patio when booking a vacation rental in Wailea-Makena.
How many vacation homes with pools are in Wailea-Makena?
There are 3,807 vacation homes across 20 providers in Wailea-Makena.
Are pets allowed in vacation rentals in Wailea-Makena?
Absolutely, there are 45 vacation rentals in Wailea-Makena that allow dogs , with an average nightly cost of $2,184.
What are the best months to travel to Wailea-Makena?
If looking for a vacation home in Wailea-Makena, keep in mind that rainy season is typically in March or November, with January often being the driest.
Find the perfect Wailea-Makena home to match your style
Top cities to visit
- Vacation Rentals in Branson, MO
- Dallas Condos & Vacation Rentals
- Vacation Rentals in Austin
- Vacation Rentals in Palm Springs
- Condos & House Rentals in Tampa
- Houses & Vacation Rentals in Fort Lauderdale
- House Rentals & Condos in Phoenix
- Vacation Rentals in Siesta Key
- Vacation Rentals in Hershey
- Vacation Rentals in Saint Augustine
- House Rentals & Condos in Philadelphia
- Condo & House Rentals in Albuquerque
- Vacation Rentals in Breckenridge
- Mason Vacation Rentals
Vacation Destinations Near Wailea-Makena
-
Condos in Kīhei
-
Kahului Vacation Rentals
-
Wailuku Vacation Rentals
-
Paia Vacation Rentals
-
Condos in Lahaina
-
Kaanapali Vacation Rentals
-
Accommodation in Hana
-
Kahana Vacation Rentals
-
Kapalua Vacation Rentals
-
Vacation Home in Hawi
-
Kaunakakai Vacation Rentals
-
Hapuna Beach Vacation Rentals
-
Mauna Lani Vacation Rentals
-
Puako Vacation Rentals
-
Condos in Waikoloa Village
-
Kohala Vacation Rentals
-
Waimea Vacation Rentals
-
Honokaa Vacation Rentals
-
Vacation Rentals in Kailua-Kona
-
Waimanalo Vacation Rentals
-
Lanikai Vacation Rentals
-
Vacation Rentals in Kailua
-
Vacation Rentals in Honolulu
-
Kaneohe Vacation Rentals
-
Vacation Rentals in Hilo
-
Ewa Beach Vacation Rentals
-
Waipahu Vacation Rentals
-
Punaluu Vacation Rentals
-
Hauula Vacation Rentals
-
Mililani Vacation Rentals
-
Kapolei Vacation Rentals
-
Laie Vacation Rentals
-
Ko Olina Vacation Rentals
-
Pahoa Vacation Rentals
-
Waianae Vacation Rentals
-
Haleiwa Vacation Rentals
-
Waialua Vacation Rentals
-
Lihue Vacation Rentals
-
Kapaa Vacation Rentals
-
Koloa Vacation Rentals
-
Anini Beach Vacation Rentals
-
Princeville Vacation Rentals
-
Hanalei Vacation Rentals
-
Kekaha Vacation Rentals
-
Condos & House Rentals in Orange Beach
-
Vacation Rentals on St. Simons
-
House Rentals in Fenwick Island
-
Durham Vacation Rentals
-
Conway Vacation Rentals
-
Grass Valley Vacation Rentals
What are the top neighborhoods in Wailea-Makena?
Top Vacation Ideas
- Romantic Getaways in Ohio
- Christmas Markets in Vancouver
- Romantic Getaways in Pennsylvania
- Romantic Getaways in Florida
- Bali Honeymoon
- Romantic Getaways in Colorado
- South Padre Island Spring Break Hotels & Vacation Rentals
- Christmas Markets in New York
- Costa Rica Honeymoon
- Romantic Getaways in Virginia
- Lake Havasu Spring Break Hotels & Vacation Rentals
Explore More Vacation Ideas
-
Airbnbs in Moab
-
March Vacations in the USA
-
Airbnbs in West Jefferson
-
Airbnbs in Palo Alto
-
Airbnbs in Cape Coral
-
Hotels with Pools in Baton Rouge
-
Washington State Parks
-
US Events
-
Bed and Breakfast Accommodation in Idaho
-
Airbnbs in Lewes
-
Airbnbs in Michigan City
-
Must-See Events in California
-
Virginia Beach Hotels & Vacation Rentals for Christmas
-
Pet Friendly Rentals in Avon
-
Atlanta Hotels & Vacation Rentals for Christmas
-
Florida 4th of July Vacation
-
Honeymoon in Orlando
-
Bed and Breakfast Accommodation in Vermont
-
Bed and Breakfast Accommodation in Healdsburg
-
Hotels with Pools in Rapid City
-
Airbnbs near Lake Winnipesaukee