
Vacation rentals in Wailea
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Wailea
Guests agree: these stays are highly rated for location, cleanliness, and more.

Maui's Best - Wailea Ekahi 47A
Ekahi says it all. Don't come all the way to Maui to stay in a bargain space. Unit 47A is a one bedroom (with sleeper sofa), two-bath renovated on the ground floor. This means a larger lanai than upper units. It also means that when you step off that lanai, you step onto A LOT of grass. Our condo is a 5-minute (barefoot) walk to the most wonderful of all Maui beaches; a ten-minute walk to the shops at Wailea. Restaurants nearby. Convenient yet without the road noise.2067153903 Privacy and peace.

Oceanfront Mana Kai Penthouse..Heaven meets Earth!
Aloha and E Komo Mai! (Welcome) Where Heaven meets Earth! Immerse yourself in the best location and bi-coastal oceanfront views to spend your luxury vacation experience in South Maui. This Mana Kai penthouse is on the 8th floor (806) and includes two-bedroom suites on the world-famous Keawakapu Beach. Located on the longest sandy beach in Wailea (2.75 miles), you will enjoy excellent snorkeling, body surfing, whale watching, scuba diving, paddle boarding, and kayaking literally at your doorstep

A.R.A Retreats: The Molokini
FULLY Renovated Summer 2023! Nicknamed “Molokini” this condo has stunning ocean view front and center of Molokini, you can witness multiple humpbacks jumping and playing during whale season from the comfort of your own private lanai. This condo is located in Wailea Ekolu in the well-known luxury resort community of Wailea. It offers a beautiful space for you to unwind after you spend all day taking in the sunshine around the island. Sit and enjoy your coffee whilst taking in our amazing views

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC
Wailea Ekahi is a luxurious resort fronting onto beautiful Keawakapu Beach with acres of tropical grounds and 4 pools. Unit 16B is a mid property, renovated ground floor ocean view studio unit (500 sq feet) with a King sized bed, walk in shower and full kitchen. Enjoy your morning coffee and meals from the peaceful, shaded lanai which opens onto the lush greenspace and gardens while enjoying ocean views. A short walk to the beach, pools, luxury shopping, highend dining and golf courses.

Romantic, Luxury Retreat w/Ocean View-Couples Only
Luxury 1 bedroom 2 bath condo which has been fully renovated. Our condo has lovely ocean views as well as views of the lush tropical gardens and the pool. It has a fully stocked gourmet kitchen with high end appliances, assorted spices, coffee and tea. Sunset views from the lanai are stunning. If our condo is not available during the days of your travel, please check availability at our other Wailea Palms condo at https://www.airbnb.com/rooms/1728525 Not suitable for children or infants.

Coastal Dream Oceanfront Condo!
Take a moment to unwind and appreciate the stunning views from the patio, where you can spot whales from Nov-April and catch a glimpse of surfers riding the "Freight Train" during mid-summer. Venture out for a leisurely walk to Maalaea Harbor Shops and the Maui Ocean Center, or explore with a drive to Lahaina (West), Hana (East), or Wailea (South tip). Enjoy delightful amenities including Heated Pool, Oceanfront BBQ station, and Lounge area on the lawn. Designated parking right out front.

Sweeping Panoramic Ocean Views - Private Ohana
Live like a local at the Ocean Blue Ohana - the private first floor of this amazing Hawaiian pole home on a half acre property in South Maui. As you enter the space, you will be drawn to the sweeping panoramic ocean views. You are sky-high, perched 500 feet above sea level, looking at the most glorious views of the neighboring islands, mountains, coastline, and Maui's amazing skyline. To top it off, you are 5 minutes from the Wailea Resorts and beautiful golden sand, crystal clear beaches.

Stunning Ocean Views
Welcome to our slice of paradise in Maui and enjoy breathtaking 180° ocean views . Located just steps from the sandy Kamaole 1 Beach and a short stroll from vibrant restaurants and bars, our chic coastal-modern condo is the perfect spot for a beach getaway. Condo features all the amenities you need for a comfortable stay, including A/C in all rooms, a luxurious king bed, high-speed internet, fully equipped kitchen and a private lanai to watch sunsets. Your Maui adventure starts here

Wailea Couples Retreat, 300 FT To Keawakapu Beach
Ekahi Ocean Studio is perfectly located in the lower village of Wailea Ekahi (ground floor), a lush-landscaped paradise, just steps from the oceanfront pool and to world-renowned Keawakapu beach. This studio is perfect for couples seeking a peaceful, romantic retreat. You can spend your days lounging at the beach or oceanfront pool, running along the nearby beachfront pathway, exploring nearby Wailea restaurants and resorts or enjoying our cook's kitchen and your private Lanai.

Stunning ocean view, heated pool at home by Wailea
Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

Steps to Beach, Shops & Dining w Views!
Exquisitely remodeled top floor studio condo in one of the most desirable condo complexes in South Maui. Enjoy sunsets and peekaboo ocean views from your private lanai, walk to some of the finest beaches & restaurants and lounge in the multiple pools & hot tubs on property! Everything is recently remodeled and stocked with everything you'll need to feel right at home (including 2 beach chairs and a beach umbrella).

Grand Champions - King Bed - Close to Wailea Beach
We are located in the heart of Wailea at the Grand Champions Villas, close to Maui's best beaches and within walking distance to great restaurants, the Shops of Wailea and surrounded by Championship Golf Courses. Grand Champions is a serene 12-acre park-like resort next to the Wailea Tennis Club and Wailea Blue Golf Course. Have fun with the whole family at this stylish place.
Popular amenities for Wailea-Makena vacation rentals
Stay near Wailea's top sights
Wailea-Makena house rentals

Cajudoy's Hale - STKM 2O13-OO18 / TA-081-709-8752-01

Mana Hale Vacation Rental

South Maui Guesthouse

12 Minute Walk Kamaole Beach II-Quiet Private Easy

Oceanview Townhome • Modern • 2 Min Walk to Beach!

Beautiful Beachfront Townhouse !

PAIA HALE Walk to beach and town

Walk-Out To Beach | Sunset Lanai | Quiet Location
Wailea-Makena condo rentals

Tropical Escape to Wailea with Stunning Oceanview

Enjoy while you can, Charming Wailea Studio

Upscale and Elegant Vistas

Gem near Keawakapu Beach - Privacy and Ocean Views

Stunning Wailea 2/2, AC, Upper Fl , walk to beach

Fabulous Ocean Views at Ho'okipa at Wailea Ekolu!

☀Very Desirable South Kihei | Enlivening Getaway ☀

Modern Renovated Palms at Wailea Condo!
Other great vacation rentals in Wailea

Remodeled 6th floor Oceanview condo, AC, beach

Oceanfront Maui Ohana: Best Beach & Wow Sunsets

Kihei Maui Getaway

Newly Remodeled Maui Banyan 1 bedroom Oasis

Wailea Ekahi Gem |Walk to Beach |May Special!

Gorgeous Condo in Wailea Ekahi Village!

Wailea Ocean View Escape

Ground Floor, Garden View, Full a/c, Wifi, GC135
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$72,807 GYD | G$73,435 GYD | G$74,063 GYD | G$64,857 GYD | G$58,371 GYD | G$60,254 GYD | G$57,534 GYD | G$55,442 GYD | G$53,141 GYD | G$56,698 GYD | G$64,648 GYD | G$76,364 GYD |
| Avg. temp | 16°C | 16°C | 16°C | 17°C | 18°C | 18°C | 19°C | 20°C | 19°C | 19°C | 18°C | 17°C |
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Wailea-Makena?
Yes! Work meets play with ease at over 1,130 vacation rentals in Wailea-Makena featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Wailea-Makena?
Four-legged friends are welcome in Wailea-Makena. Choose from more than 10 vacation rentals for guests traveling with pets.
How much does it cost to stay in condo rentals in Wailea-Makena?
Experience the best of Wailea-Makena with our condo rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for Condo Rentals in Wailea-Makena?
Enhance your stay in our Condo Rentals with the most popular amenities: over 660 homes with a gym, over 1,450 homes with wifi, over 580 homes with a bbq area, over 420 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there Wailea-Makena condo rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 1,410 condo rentals with pools in Wailea-Makena, available on Airbnb. Make a splash and soak up the sun in style!
Do condo rentals in Wailea-Makena have self check-in?
Absolutely! We offer over 420 condo rentals with self check-in in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Wailea-Makena have wifi?
Absolutely! We offer over 1,450 condo rentals with wifi in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Wailea-Makena have a bbq area?
Absolutely! We offer over 580 condo rentals with a bbq area in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Wailea-Makena have a gym?
Absolutely! We offer over 660 condo rentals with a gym in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly condo rentals in Wailea-Makena?
Wailea-Makena has more than 820 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
All about Wailea
Located on the southern shore of the Hawaiian island of Maui, Wailea is a resort area famous for its white-sand beaches, sprawling golf courses, and relaxing spas. Wailea-Mākena provides a great base for visiting southern Maui’s sandy shores, such as the nearby Wailea Beach, which is just a short walk from town, or Mākena Beach, where you can go for a refreshing swim or explore the pristine coastline by paddleboard or kayak.
You can also find many interesting natural attractions nearby, such as La Perouse Bay or Ahihi-Kinau Natural Area Reserve, which is teeming with marine life. Take a break from the sun and water by visiting the Shops at Wailea, a complex that features 70 retail stores — art galleries, boutiques selling Hawaiian shirts and water-sports gear —and restaurants serving creative takes on local mahi mahi and deep-water ahi tuna.
What are the top things to do in Wailea?
Mākena State Park
Mākena Beach State Park, on the south side of town, is home to one of the largest undeveloped beaches on Maui. This stretch of shoreline, commonly referred to as “Big Beach,” features glistening white sand and cerulean waters surrounded by native kiawe forests and mango groves. Wander inland and you can hike up the 360-foot-tall Pu’u Olai, a dormant volcanic cinder cone, where you can survey the coastline from on high.
Ahihi-Kinau Natural Area Reserve
Located less than a 10-minute drive from Mākena State Park, this marine reserve offers one of the area’s best snorkeling spots. The ocean floor is covered by a coastal lava field intermixed with coral, making it a popular home for many different species of tropical fish, including butterfly fish, parrotfish, surgeonfish, and turtles. At the reserve, you can snorkel directly from the shoreline.
La Perouse Bay
Just 20 minutes south of Wailea-Mākena, La Perouse Bay is outlined by lush green vegetation and jagged lava rock formations, created when the now-dormant Haleakalā Volcano last erupted in 1790. Now the blackened lava rocks shelter numerous tide pools. If you’d like to peer in at the marine creatures living there, bring shoes with thick soles, as lava rock has many sharp edges.
Quick stats about vacation rentals in Wailea

Total vacation rentals
Explore 1,910 vacation rentals in Wailea

Nightly prices starting at
Wailea vacation rentals start at G$14,645 GYD per night before taxes and fees

Verified guest reviews
Over 52,500 verified reviews to help you choose

Family-friendly vacation rentals
1,090 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
1,800 properties feature pools

Rentals with dedicated workspaces
1,130 properties have a dedicated workspace

Wi-Fi availability
1,900 of Wailea vacation rentals include wi-fi access

Popular amenities for guests
Guests love Self check-in, Gym, and BBQ grill across Wailea rentals

4.8 Average rating
Wailea stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Honolulu Vacation rentals
- Oahu Vacation rentals
- Kauai Vacation rentals
- Island of Hawai'i Vacation rentals
- Waikīkī Beach Vacation rentals
- Kailua-Kona Vacation rentals
- Kona Vacation rentals
- Kihei Vacation rentals
- Kaanapali Vacation rentals
- North Kona Vacation rentals
- Princeville Vacation rentals
- Hilo Vacation rentals
- Rentals with a patio Wailea
- Rentals with an EV charger Wailea
- Rentals with outdoor seating Wailea
- Pet-friendly rentals Wailea
- Waterfront rentals Wailea
- Serviced apartment rentals Wailea
- Condo rentals Wailea
- Rentals with a kayak Wailea
- Luxury rentals Wailea
- Rentals with beach access Wailea
- Rentals with a sauna Wailea
- Hotel rooms Wailea
- Rentals with a hot tub Wailea
- Townhouse rentals Wailea
- Beach condo rentals Wailea
- Apartment rentals Wailea
- Rentals with pools Wailea
- Family-friendly rentals Wailea
- Rentals with a washer and dryer Wailea
- Beachfront rentals Wailea
- Villa rentals Wailea
- Fitness-friendly rentals Wailea
- House rentals Wailea
- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Honolua Bay
- Kapalua Bay Beach
- Wailea Beach
- Polo Beach
- Maui Ocean Center
- Hāmoa Beach
- Ka'anapali Golf Courses
- Old Lahaina Luau
- Ulua Beach
- Black Rock Beach
- Big Beach
- Whalers Village
- Haleakala National Park
- Maui Vista Condominium
- Kahana Beach
- Maui Arts & Cultural Center
- Maui Sunset
- Kihei Kai Nani
- Peahi
- Black Sand Beach
- Things to do Wailea
- Nature and outdoors Wailea
- Food and drink Wailea
- Sports activities Wailea
- Things to do Maui County
- Nature and outdoors Maui County
- Food and drink Maui County
- Sports activities Maui County
- Things to do Hawaii
- Nature and outdoors Hawaii
- Art and culture Hawaii
- Entertainment Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Tours Hawaii
- Wellness Hawaii
- Food and drink Hawaii
- Things to do United States
- Entertainment United States
- Tours United States
- Food and drink United States
- Sightseeing United States
- Nature and outdoors United States
- Sports activities United States
- Art and culture United States
- Wellness United States






