
Holiday rentals in Wailea
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Top-rated holiday rentals in Wailea
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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.

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.

Upscale and Elegant Vistas
Spacious and elegant condo in the much sought after Wailea area. Fantastic unobstructed ocean and sunset views. Completely remodeled and freshly outfitted. No expense was spared to create our ocean view oasis. This one-bedroom, two-bathroom condo features thoughtful luxurious finishes throughout. Located in sunny and luxurious Wailea, with all of Maui is within reach. Beach chairs, umbrellas, luxury beach towels and a cooler are all provided to enjoy a day at the beach nearby.

A.R.A Retreats: The Townhouse
Nicknamed “The Townhouse” this is a rare Townhouse in Wailea Ekolu Village. It has almost 1500 square feet and was completely renovated from top to bottom. While there are many things that make this unique from the view to the renovation the amazing townhouse layout is a rare treat for any guest in the area of Wailea. Steps from food, shopping, and some world class beaches. Sit and enjoy your drink whilst taking in our amazing views and when the sun goes down.

*Last Minute Deal*Luxurious*2b/2b OceanView Wailea
This ground floor 1071 square foot unit is situated just above the 11th fairway of the Wailea Blue Course. The living room and master bedroom have private lanais that step out to a relaxing open lawn with sweeping ocean views. Features include AC throughout the property, bamboo floors throughout, brand new tile in the master bathroom, granite counter tops, and cherry cabinets. Tastefully decorated this spacious condo truly has everything you will need!

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

130K Hawaiian Reno on Wailea Blue Golf *Ocean View
BRAND NEW 130K Renovation+BRAND NEW Hawaiian Styled Contemporary Decor. Located right on Wailea Blue Golf course in the Grand Champions at Wailea with incredible ocean views from the patio.We are perfectly located just down from Money Pod+up from The Shops of WaileaCheck out our other property #201 VRBO (2050379)+#1905 VRBO(1222713) in The Palms we are Super Host with 5 STAR reviews)!! BOOK UP TO 365 DAYS.

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

Wailea Escape/Golf Views, Beaches & Family Comfort

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

Luxury Wailea Beach Condo

Fabulous Ocean Views at Ho'okipa at Wailea Ekolu!

Wailea Ekahi Gem |Walk to Beach |May/June Special!

Palms 902 - Private Luxury Partial Ocean View

Newly Renovated High-end 1 bed 2 bath Wailea Condo

Maui Resort Rentals: Wailea Elua 2204
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £261 | £263 | £265 | £232 | £209 | £216 | £206 | £199 | £190 | £203 | £232 | £274 |
| 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 £52 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 & child-friendly amenities

Pet-friendly holiday rentals
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

Wifi availability
1,900 of Wailea holiday rentals include wifi 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
- Polo Beach
- Kapalua Bay Beach
- Wailea Beach
- Maui Ocean Center
- Ka'anapali Golf Courses
- Hāmoa Beach
- Old Lahaina Luau
- Ulua Beach
- Black Rock Beach
- Big Beach
- Maui Vista Condominium
- Whalers Village
- Peahi
- Haleakala National Park
- Maui Arts & Cultural Center
- Black Sand Beach
- Maui Sunset
- Kihei Kai Nani
- Kahana Beach
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