
Vacation rentals in Wailea
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Top-rated vacation rentals in Wailea
Guests agree: these stays are highly rated for location, cleanliness, and more.

160KReno-Stunning Palms in Wailea Condo-Beach/Golf
Brand New 160K Renovation+Redecoration for a Hawaiian Beach Vibe.Wailea is one of the most sought after resort addresses on Maui.Here you can relax in the luxury of the beautiful grounds+refreshing swimming pool+spa.World Class Golf+Shopping.Ground floor condo with private lanai that overlooks the grass.King Master Bed with a private bath,2 Uber deluxe pull out Queen bed couches.Short stroll to Keawakapu Beach from condo where you can snorkel/take long tropical beach walk.BOOKINGS UP TO 365 DAY

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.

Makani A Kai A9 romantic beachfront Maui, pool,a/c
Halerentals MAK A9 is a romantic and newly renovated beachfront condo, centrally located for day trips around the island, and off the beaten tourist path. Cool A/C in every room and smart home controls-- just steps away from 3 miles of undeveloped beach! Bright spacious ground floor 1bed/1bath condo- with fully stocked kitchen, new 75" SmartTV and views of the beach, bay, & Haleakala volcano. Ideal for swimming, paddle boarding, snorkeling, and surfing-- amazing value for families and couples.

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.

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.

Luxury condo • 180° Ocean Views • Steps to Beach
Enjoy panoramic ocean, mountain, beach & sunset views year round at Hale Meli (short for "Hale Mahina Meli" or “Honeymoon House” in Hawaiian), a top floor condo with exquisite designer interiors and high-end amenities. Ideally located in Kihei, the condo is right across the street from one of the best beaches on Maui and is walking distance to restaurants, shops and grocery stores. It is also your perfect home base for exploring the rest of Maui, being centrally located on the island.

A.R.A Retreats: Big Blue Pacific
Nicknamed “Big Blue Pacific” for its absolutely stunning view of the Pacific Ocean from the living room, kitchen and master bedroom. Our vacation rental condo is located in Wailea Ekolu, the well-known luxury resort community of Wailea. It offers a relaxing 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 and when the sun goes down, watch your favorite shows on on our smart tvs!

Luxury Condo in Wailea Ekahi w/Direct Beach Access
Do you want direct and private access to probably the best beach (i.e. Keawakapu) on Maui? Then look no further than our unit in the Wailea Ekahi complex! This quiet and spacious condo has every amenity you could want to make your Maui vacation truly unforgettable. You are also in walking distance to the stores and restaurants at the Shops at Wailea and also the Wailea Beach Path. This condo has everything you need to make your Maui experience memorable, luxurious, and convenient.

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

Wailea Ekolu Village 2/2 with stunning ocean view!
Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and surrounded by brilliant, lush, flowery grounds. Super-close to dining, golf, shopping, and only a short stroll to award-winning Wailea and Ulua beaches! Please note that this Wailea Resort condo has received government approval to operate as a vacation rental for the next 5 years.

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.

Wailea Gem-Remodeled Ocean View
Beautiful, fully remodeled Wailea Jewel! Peaceful and private location with expansive ocean views. Our newly renovated, one bedroom, 2 bathroom condo has everything you need to enjoy your Maui getaway. Located a short drive from the airport and just minutes away from some of the best beaches and dining in Hawaii. You will truly feel like you're in paradise during your stay.
Popular amenities for Wailea-Makena vacation rentals
Stay near Wailea's top sights
Wailea-Makena beach vacation rentals

Stunning Ocean Views

Newly Remodeled 1bed/1bath, Kihei/Wailea

Stunning Ocean Views - Jan Special $265

Stunning Ocean View Penthouse - Steps to Beach

Sugar Beach Resort Beach / Ocean Front Unit 426

Romantic Beach Retreat, New King Bed & A+ Wi-fi

Top Floor Ocean Views | Beach & Restaurant Access

Oceanfront Spectacular Condo, New Listing
Condo rentals in Wailea-Makena

Tropical Escape to Wailea with Stunning Oceanview

Modern Kihei Studio Steps to Beach *Private Lanai*

Newly Remodeled Maui Banyan 1 bedroom Oasis

Gorgeous Condo in Wailea Ekahi Village!

Amazing Ocean Views at 'Ike Kai at Wailea Ekolu!

Modern Renovated Palms at Wailea Condo!

Beautiful Modern Decor in a Light-Filled Condo

Romantic One BR Condo (Remodeled)
Beach condo rentals in Wailea-Makena

Oceanfront Condo. Pool & Spa, 1 Br.

Maui Kamaole A114 Kihei Ocean View & Whales!

Island Surf #206 Your South Maui Gem is here

Studio with Beach, Pool, Hot Tub, Tennis, & BBQ! 15A

Beachfront Maui Oasis- Fully Remodeled, Beautiful

Luxe Oceanview 2B2B Escape w/AC Near Beach & Shops

Waiohuli Beach Hale – Oceanfront Condo

Amazing views at Oceanfront Studio
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$72,756 GYD | G$73,384 GYD | G$74,011 GYD | G$64,812 GYD | G$58,331 GYD | G$60,212 GYD | G$57,494 GYD | G$55,404 GYD | G$53,104 GYD | G$54,149 GYD | G$58,331 GYD | G$67,739 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 pet-friendly vacation rentals in Wailea-Makena?
Four-legged friends are welcome in Wailea-Makena. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Wailea-Makena?
Yes! Work meets play with ease at over 910 vacation rentals in Wailea-Makena featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do condo rentals in Wailea-Makena have a gym?
Absolutely! We offer over 520 condo rentals with a gym in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
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 $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly condo rentals in Wailea-Makena?
Wailea-Makena has more than 690 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do condo rentals in Wailea-Makena have wifi?
Absolutely! We offer over 1,260 condo rentals with wifi in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
Are there Wailea-Makena condo rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 1,200 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 a bbq area?
Absolutely! We offer over 590 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 air conditioning?
Absolutely! We offer over 1,220 condo rentals with air conditioning in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
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 590 homes with a bbq area, over 1,260 homes with wifi, over 520 homes with a gym, over 1,220 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
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$14,635 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, Beachfront, and Gym across Wailea rentals

4.8 Average rating
Wailea stays are highly rated by guests—averaging 4.8 out of 5!
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- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Honolua Bay
- Kapalua Bay Beach
- Wailea Beach
- Maui Ocean Center
- Polo Beach
- Hāmoa Beach
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- Maui Arts & Cultural Center
- Peahi
- Haleakala National Park
- Maui Vista Condominium
- Kihei Kai Nani
- Black Rock Beach
- Maui Sunset
- Kahana Beach
- PacWhale Eco-Adventures
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