Wailea-Makena holiday rentals

We found 4,753 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Wailea-Makena

Showing deals for:27 Nov - 4 Dec

Unwind after beach days with peaceful outdoor living and island breezes
Living Room Area
Indoor Dining Area
Private Wailea/Kihei retreat just minutes from Maui’s most beautiful beaches
Exceptional
(104 reviews)

Luxury 3BR Wailea Kihei Retreat. Walk to Beaches, Private Lanai, Newly Remodeled

Kihei

7% off
S$6,899
for 7 nights, 1 home
S$986 per night
includes taxes & fees
Luxury 3BR Wailea Kihei Retreat. Walk to Beaches, Private Lanai, Newly Remodeled
Ocean view from the lanai, kitchen and living area
Golfing in Paradise
Private bedroom with queen bed and closet space for your clothing
Kihei Akahi Grounds are well maintained and tropical
Excellent
(42 reviews)

~Amazing Ocean View on 3rd flr~ MAUI AWAITS YOU!!

Kihei

8% off
S$2,076
for 7 nights, 1 apartment
S$297 per night
includes taxes & fees
~Amazing Ocean View on 3rd flr~ MAUI AWAITS YOU!!
Kamaole 3 beach is right across the street with a beautiful reef for snorkeling
Lush landscaping provides shade or sun and a waterfall.
Bring your rackets!
Enjoy 2 couches and two chairs, one a recliner
Exceptional
(49 reviews)

S. Kihei spacious garden condo, 2 lanais

Kihei

7% off
S$3,102
for 7 nights, 1 apartment
S$443 per night
includes taxes & fees
S. Kihei spacious garden condo, 2 lanais
Dining area, kitchen
Granite countertop, living area
Living area looks out to lanai and lush landscaping
Community swimming pool on property
Exceptional
(140 reviews)

Kihei, Maui Ground Floor Tropical Getaway - Across street from beach

Kihei

7% off
S$2,126
for 7 nights, 1 apartment
S$304 per night
includes taxes & fees
Kihei, Maui Ground Floor Tropical Getaway - Across street from beach
Kamaole Sands III beach
Kamaole Sands refreshing swimming pool
Kamaole Sands
Kamaole Sands fountain
Exceptional
(115 reviews)

Your Hawaiian Beach Get Away, Steps From Great Beach!

Kihei

10% off
S$2,396
for 7 nights, 1 apartment
S$342 per night
includes taxes & fees
Your Hawaiian Beach Get Away, Steps From Great Beach!
Communal bbq area just steps from our unit
just a few steps away from the beach!
view from kitchen window
fully renovated kitchen, with plenty of work space
Exceptional
(109 reviews)

Wailea Ekahi 51F Oceanview - Walk to Beach

Kihei

7% off
S$4,706
for 7 nights, 1 apartment
S$672 per night
includes taxes & fees
Wailea Ekahi 51F Oceanview - Walk to Beach
Living area
Exterior
Living area
Great bedroom with king bed
Exceptional
(110 reviews)

Oceanview Top Floor Condo, with Internet Access.

Kihei

7% off
S$2,219
for 7 nights, 1 apartment
S$317 per night
includes taxes & fees
Oceanview Top Floor Condo, with Internet Access.
Primary bathroom
The best breakfast and dinner spot on the lanai
Room
Primary bathroom with two sinks and walk-in shower
Exceptional
(71 reviews)

Immaculate and Chic - Come relax in our luxury villa…

Kihei

7% off
S$5,703
for 7 nights, 1 apartment
S$815 per night
includes taxes & fees
Immaculate and Chic - Come relax in our luxury villa…
view from lanai over the complex grounds
Property grounds
Dining
Living area
Exceptional
(165 reviews)

Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed

Kihei

7% off
S$3,735
for 7 nights, 1 apartment
S$534 per night
includes taxes & fees
Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed
Lower Swimming {Pool from our Lanai
View from Lanai
Grounds outside our Lanai
New Kitchen
Exceptional
(59 reviews)

# 107 Lovely Grnd Flr King bed Unit, accross the street is a white sand beach

Kihei

6% off
S$2,537
for 7 nights, 1 apartment
S$362 per night
includes taxes & fees
# 107 Lovely Grnd Flr King bed Unit, accross the street is a white sand beach
Room
Room
Interior
Exterior
Exceptional
(51 reviews)

Blue Sky Escapes One bedroom Beach Steps Away! Pool Hot tub

Kihei

7% off
S$2,273
for 7 nights, 1 apartment
S$325 per night
includes taxes & fees
Blue Sky Escapes One bedroom Beach Steps Away! Pool Hot tub
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Wailea-Makena getaway

Learn about the unique charm of Wailea-Makena with a stay in a holiday home rental. This city has something for everyone. Wailea Beach and Haleakala National Park are just a couple of the must-see attractions in the area. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Wailea-Makena

Do you want to discover attractions to visit while you're in town? Venture out of your cosy holiday rental and experience everything that makes Wailea-Makena a one-of-a-kind holiday spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Wailea Emerald Golf Course (0.3 mi / 0.4 km)
  • Maui Nui Golf Club (5.6 mi / 9 km)
  • Wailea Gold Golf Course (0.3 mi / 0.5 km)
  • Wailea Blue Golf Course (0.4 mi / 0.7 km)
  • Makena South Course (1.6 mi / 2.6 km)
  • Kahili Golf Course (12 mi / 19.3 km)

Exploring the natural features in Wailea-Makena

Whether you're looking for adventure or just want to appreciate the scenery, Wailea-Makena is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Wailea Beach (0.9 mi / 1.5 km)
  • Haleakala National Park (18.3 mi / 29.4 km)
  • Po'olenalena Beach (0.4 mi / 0.6 km)
  • Polo Beach (0.6 mi / 1 km)
  • Maluaka Beach (1.6 mi / 2.6 km)
  • Ulua Beach (1.6 mi / 2.6 km)

Frequently asked questions

What is the best area to stay in Wailea-Makena when booking a holiday rental?
Makena is one of the more popular locations to find a holiday home in Wailea-Makena. Searching for some awesome things to see and do in this destination? Be sure to check out Makena State Park Beach and Maluaka Beach.
What is the most popular type of holiday rental accommodation in Wailea-Makena?
The most popular types of holiday rentals in Wailea-Makena are condos. Ready for more choices? Vrbo offers a variety of options to match the diverse needs of our guests, so you'll see properties in lots of sizes and shapes. The ideal home away from home is waiting for you — snap up yours today.
How much does it cost to rent a holiday rental in Wailea-Makena?
The average price for a holiday rental in Wailea-Makena is determined by a number of factors, including length of stay, season and property type. Whether you'd like a sprawling villa with space for the whole family or a cosy cottage for just you and your sweetheart, just add your dates of travel to see stays with unbeatable value.
How much does it cost to rent a beach house in Wailea-Makena?
The average price for a holiday rental close to the beach in Wailea-Makena depends on when you're visiting the area and the style and size of property you're searching for. You can easily and quickly find prices on Vrbo by entering your destination and preferred travel dates. Then use our filter tool to pick the number of bedrooms and amenities that you prefer, like a pool, WiFi and air conditioning.
What are popular rental amenities in Wailea-Makena?
The most popular rental amenities people are searching for in Wailea-Makena include a stovetop, a fridge and a microwave oven. Whether you're on a trip with pals, family or even pets, Vrbo holiday homes have the best amenities for fun and relaxation with the people that matter most.
Are there large group holiday rentals in Wailea-Makena?
Choose from 12 properties in Wailea-Makena that can sleep 10 or more people. Whether you're organising a family holiday or some kind of special event, there's plenty of space to get your favourite people together under the same roof.
What are the top attractions for families in Wailea-Makena?
You'll find loads of fun things to do and see with the family in Wailea-Makena, such as:
  • Keawakapu Beach North
  • Wailea Beach
  • Makena State Park Beach
Can I find two-bedroom holiday rentals in Wailea-Makena?
You can select from 966 two-bedroom holiday rentals in Wailea-Makena. Put your little ones in the second room or maybe fill it with a couple of your best friends. There's plenty of space for whoever's fortunate enough to be coming along.
Are there holiday rentals with WiFi in Wailea-Makena?
Whether you want to keep up with the news, reply to emails or surf social networks, there are 1,102 holiday homes with WiFi in Wailea-Makena. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How old do you have to be to rent a holiday rental in Wailea-Makena?
The minimum age permitted can differ between properties on Vrbo, so be sure to look at the rules of the holiday rental in Wailea-Makena you want to book. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in Wailea-Makena for?
The amount of time you can rent a Wailea-Makena holiday rental for depends on the property. Just enter your travel dates to browse options offering longer term stays. They come with the things you need to make your extended getaway more enjoyable and convenient, such as laundries and air conditioning. Some Vrbo holiday homes may also offer discounted weekly or monthly prices, so you can hang around longer for less.

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