
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.

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.

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.

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.

Enjoy while you can, Charming Wailea Studio
Legal, active studio in Wailea with charming views of palm trees and a sparkling blue pool. Our place is close to the beach, family-friendly activities, Shops of Wailea, many Wailea Hotels: Andaz, Fairmont, Marriott Four Seasons Hotel, etc., restaurants, golf courses, tennis court. You’ll love my place because of the comfy bed, big TV, the views, overlooking pool and palm trees with easy access straight down to pool/jacuzzi/BBQ from your lanai.

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

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.

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 holiday rentals
Stay near Wailea's top sights
Other great holiday rentals in Wailea

Luxury Oceanview Wailea Retreat with Sunset Views

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

Kihei Maui Getaway

Chic Coastal Living in the Heart of Wailea

Luxurious Wailea Ocean Vistas

Wailea Ocean View Escape

Ground Floor, Garden View, Full a/c, Wifi, GC135

Tropical Wailea Retreat
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $575 NZD | $580 NZD | $585 NZD | $513 NZD | $461 NZD | $476 NZD | $455 NZD | $438 NZD | $420 NZD | $448 NZD | $511 NZD | $603 NZD |
| 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.
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 $116 NZD 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!
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- 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
- Big Beach
- Black Rock Beach
- Whalers Village
- Maui Sunset
- Peahi
- Maui Vista Condominium
- Kihei Kai Nani
- Haleakala National Park
- Kahana Beach
- Maui Arts & Cultural Center
- PacWhale Eco-Adventures
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