Wailea-Makena holiday lettings

We found 4,757 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Wailea-Makena

Showing deals for:27 Nov - 4 Dec

Indoor Dining Area
Living Room Area
Kitchen Area - Island Bar
Unwind after beach days with peaceful outdoor living and island breezes
Exceptional
(104 reviews)

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

Kihei

7% off
£3,951
for 7 nights, 1 home
£564 per night
includes taxes & fees
Luxury 3BR Wailea Kihei Retreat. Walk to Beaches, Private Lanai, Newly Remodeled
Private bedroom with queen bed and closet space for your clothing
Golfing in Paradise
Ocean view from the lanai, kitchen and living area
Kihei Akahi is a beautiful complex and is in the middle of South Kihei.
Excellent
(42 reviews)

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

Kihei

8% off
£1,219
for 7 nights, 1 apartment
£174 per night
includes taxes & fees
~Amazing Ocean View on 3rd flr~ MAUI AWAITS YOU!!
Living area looks out to lanai and lush landscaping
Granite countertop, living area
Dining area, kitchen
Community swimming pool on property
Exceptional
(140 reviews)

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

Kihei

7% off
£1,297
for 7 nights, 1 apartment
£185 per night
includes taxes & fees
Kihei, Maui Ground Floor Tropical Getaway - Across street from beach
You'll  love the lanai which is right near the sunken pool area, creating quiet
Lush landscaping provides shade or sun and a waterfall.
Enjoy 2 couches and two chairs, one a recliner
Bring your rackets!
Exceptional
(49 reviews)

S. Kihei spacious garden condo, 2 lanais

Kihei

7% off
£1,763
for 7 nights, 1 apartment
£252 per night
includes taxes & fees
S. Kihei spacious garden condo, 2 lanais
Living Room Sofa/bed
Lower Swimming Pool
Living Room from Master Bedroom Railing
Entry Sign by Kihei Rd
Exceptional
(95 reviews)

D211 Quiet & Private 2br2ba near Wailea 2026 Discount 10% 7 nts or more.

Kihei

5% off
£2,662
for 7 nights, 1 apartment
£380 per night
includes taxes & fees
D211 Quiet & Private 2br2ba near Wailea 2026 Discount 10% 7 nts or more.
View of the living area from the kitchen.
Relax in your private lanai and enjoy the ocean view. This is paradise!
Kamaole Sands resort amenities include pools, hot tubs, gym and tennis.
Pool
Exceptional
(92 reviews)

Maui Escape - Oceanview 70 Yds to Beach, GND Flr, Bldg10 - Everything You Need!

Kihei

7% off
£1,639
for 7 nights, 1 apartment
£234 per night
includes taxes & fees
Maui Escape - Oceanview 70 Yds to Beach, GND Flr, Bldg10 - Everything You Need!
Living area
Seating for 2 with a view of the property, the pool,  and the ocean.
Property grounds
"Remote office" with a view. 2 USB plugs built into the desk for charging.
Exceptional
(91 reviews)

Ocean View South Maui Condo with Lanai plus FREE parking, Wifi and Smart TVs

Kihei

7% off
£1,566
for 7 nights, 1 apartment
£224 per night
includes taxes & fees
Ocean View South Maui Condo with Lanai plus FREE parking, Wifi and Smart TVs
Kamaole Sands III beach
Kamaole Sands refreshing swimming pool
Kamaole Sands fountain
Kamaole Sands
Exceptional
(115 reviews)

Your Hawaiian Beach Get Away, Steps From Great Beach!

Kihei

10% off
£1,383
for 7 nights, 1 apartment
£198 per night
includes taxes & fees
Your Hawaiian Beach Get Away, Steps From Great Beach!
Living area
Exterior
Lanai view
Living area
Exceptional
(110 reviews)

Oceanview Top Floor Condo, with Internet Access.

Kihei

6% off
£1,294
for 7 nights, 1 apartment
£185 per night
includes taxes & fees
Oceanview Top Floor Condo, with Internet Access.
Beautiful view to the pool
Maui Tropical Plantation.
Freds Mexican Cafe & Moose's is located just across the street from Kamaole II.
Parking at the Maui Banyan is convenient and covered
Exceptional
(29 reviews)

TROPICAL MAUI!!! Visit and stay in Comfort and Style...1b/2b

Kihei

8% off
£1,300
for 7 nights, 1 apartment
£186 per night
includes taxes & fees
TROPICAL MAUI!!! Visit and stay in Comfort and Style...1b/2b
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
£3,315
for 7 nights, 1 apartment
£474 per night
includes taxes & fees
Immaculate and Chic - Come relax in our luxury villa…
Living area
Property grounds
Dining
view from lanai over the complex grounds
Exceptional
(165 reviews)

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

Kihei

7% off
£2,173
for 7 nights, 1 apartment
£310 per night
includes taxes & fees
Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed
Pool
Room
Room
Interior
Exceptional
(51 reviews)

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

Kihei

7% off
£1,743
for 7 nights, 1 apartment
£249 per night
includes taxes & fees
Blue Sky Escapes One bedroom Beach Steps Away! Pool Hot tub
Lower Swimming Pool
View from Lanai
Grounds outside our Lanai
Lower Swimming {Pool from our Lanai
Exceptional
(59 reviews)

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

Kihei

6% off
£1,460
for 7 nights, 1 apartment
£209 per night
includes taxes & fees
# 107 Lovely Grnd Flr King bed Unit, accross the street is a white sand beach
Pool
Outdoor dining
Dining
Living area
Exceptional
(31 reviews)

Kihei Getaway in Paradise

Kihei

7% off
£2,384
for 7 nights, 1 apartment
£341 per night
includes taxes & fees
Kihei Getaway in Paradise

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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