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

Aloha Aku Bamboo Suite – Discover Beachfront Seren
Our luxury Beachfront estate has 4 beachfront one-bedroom suites and a garden view two-bedroom Ohana. Each suite has a private entrance, separate living room, full kitchen and is like having your own condo at the beach in Maui. This special place is hidden behind a private, double gated entrance, lined with 700 ft of lighted coconut palms that lure you into the feeling of leaving the world behind. But is still centrally placed in Kihei nearly all of the amenities you might desire. BBKM 2013/0002

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.

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.

Endless Ocean Views - 1bd/2 bath
Experience island living at its finest in this beautiful 1-bedroom, 2-bathroom condo located in the heart of Wailea/Kihei, Hawaii. This serene retreat offers breathtaking ocean views and a peaceful atmosphere, perfect for unwinding after a day of exploring. Just a short stroll from world-renowned beaches and minutes from top-rated shopping, dining, and entertainment, the location couldn’t be more ideal. This well-appointed space is designed for comfort and relaxation.

Luxury Condo w/wide Ocean View (Palms at Wailea)!
There is no better location than Wailea to experience your Maui vacation! This quiet and spacious condo has every amenity you could want to make your Maui vacation truly unforgettable. This condo is only a short walk to one of the best beaches (Keawakapu) on Maui and is also in close proximity to the Shops at Wailea. We spared no expenses in stocking this condo with everything you need to make your Maui experience memorable and luxurious.

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 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.

A.R.A Retreats: The Hideaway
This beautiful addition to A.R.A Retreats nicknamed the “The Hideaway”. Right on the Wailea Golf course this quiet and serene condo is a wonderful escape from the noise and fast pace of life. Located in Grand Champions Villas in Wailea. Guests can enjoy the spacious NEW condo that has everything you should need for your trip--including including smart TV's in each room :)

Luxurious Tropical Retreat with Oceanview
Welcome to your luxurious 1-bedroom, 1-bathroom tropical oasis in the prestigious Wailea area of Maui, where modern design meets tropical paradise. This stunning retreat offers an upscale, contemporary living experience with stunning views of the Pacific Ocean and lush, manicured gardens.

Tiki Tiki - A Gorgeous Boho Beach Hideaway!
Fall in ALOHA with Tiki Tiki!! This special studio is truly a piece of Paradise! A magical retreat that will have you feeling zen & refreshed. Tiki Tiki is the perfect home for honeymooners, girlfriend getaways, or any adults looking for a tropical stay in the the heart of Wailea.

Wailea Ekolu 510 - Sweeping Ocean Views, Split AC!
This extra-spacious two-story town-home-styled condo has no common walls and no one above, with a premiere location at Wailea Ekolu unit 510. Enjoy panoramic ocean views from Makena and Molokini to the West Maui Mountains, from the lanai and from the inside of the unit as well.
Popular amenities for Wailea holiday rentals
Stay near Wailea's top sights
Other great holiday rentals in Wailea

Maui Perfection! 1 bdrm/2 bath Ekahi Village condo

Maui View Condo – 1324

*Maalaea Kai 212* Maui Stunning Prime Ocean Front

Oceanfront Dream 2Bed/2Bath-Mana Kai Maui Resort

Enjoy Your Oceanside Dream at Kihei

Remodeled Penthouse24 Ocean Front at Sugar Beach

Wailea Grand Champions Unit 33: Large 2 Br for 6

Fantastic 1BR Oceanfront | Pool
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $492 AUD | $496 AUD | $500 AUD | $438 AUD | $394 AUD | $407 AUD | $388 AUD | $374 AUD | $359 AUD | $383 AUD | $436 AUD | $516 AUD |
| 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
What types of vacation rentals are available in Wailea-Makena?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Wailea-Makena. From over 50 house rentals to over 1,460 condo rentals, we've got you covered.
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 house rentals in Wailea-Makena?
Experience the best of Wailea-Makena with our house rentals, starting at about $70 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 House Rentals in Wailea-Makena?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with wifi, over 10 homes with a gym, over 20 homes with self check-in, over 120 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there Wailea-Makena house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 house rentals with pools in Wailea-Makena, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Wailea-Makena have self check-in?
Absolutely! We offer over 20 house rentals with self check-in in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Wailea-Makena have wifi?
Absolutely! We offer over 40 house rentals with wifi in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Wailea-Makena have a bbq area?
Absolutely! We offer over 120 house rentals with a bbq area in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Wailea-Makena have a gym?
Absolutely! We offer over 10 house rentals with a gym in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Wailea

Total holiday rentals
Explore 1,910 holiday rentals in Wailea

Nightly prices starting at
Wailea holiday rentals start at $99 AUD per night before taxes and fees

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

Family-friendly holiday rentals
1,090 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday 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 holiday 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
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- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Honolua Bay
- Polo Beach
- Kapalua Bay Beach
- Maui Ocean Center
- Ka'anapali Golf Courses
- Wailea Beach
- Hāmoa Beach
- Old Lahaina Luau
- Ulua Beach
- Big Beach
- Black Rock Beach
- Whalers Village
- Haleakala National Park
- Peahi
- Maui Sunset
- Maui Vista Condominium
- Kihei Kai Nani
- Kahana Beach
- Black Sand Beach
- Maui Arts & Cultural Center
- Things to do Wailea
- Nature and outdoors Wailea
- Food and drink Wailea
- Sports activities Wailea
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