Wailea-Makena holiday rentals

We found 4,742 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Wailea-Makena

Showing deals for:13 Nov - 20 Nov

Spacious lanai with enough seating for the whole family.
View on the pool
Lobby
Lobby
Exceptional
(254 reviews)

Mana Kai Maui Condo - Right on the Beach!

Kihei

7% off
S$5,989
for 7 nights, 1 apartment
S$856 per night
includes taxes & fees
Mana Kai Maui Condo - Right on the Beach!
Living Room from Master Bedroom Railing
Lower Swimming Pool
Living Room Sofa/bed
Living Room
Exceptional
(95 reviews)

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

Kihei

5% off
S$4,684
for 7 nights, 1 apartment
S$669 per night
includes taxes & fees
D211 Quiet & Private 2br2ba near Wailea 2026 Discount 10% 7 nts or more.
Kamaole Sands panorama
View from lanai before sunrise coming up over Haleakala
View from lanai towards ocean
Pool area looking towards ocean
Exceptional
(92 reviews)

Unbeatable Location at Kamaole III Beach - Kam Sands Bldg. 1

Kihei

7% off
S$5,354
for 7 nights, 1 apartment
S$765 per night
includes taxes & fees
Unbeatable Location at Kamaole III Beach - Kam Sands Bldg. 1
Lanai view
Exterior
Living area
Living area
Exceptional
(110 reviews)

Oceanview Top Floor Condo, with Internet Access.

Kihei

7% off
S$2,235
for 7 nights, 1 apartment
S$319 per night
includes taxes & fees
Oceanview Top Floor Condo, with Internet Access.
Just one of Maui's great golf courses to test you skills.
Maui Tropical Plantation.
Parking at the Maui Banyan is convenient and covered
Freds Mexican Cafe & Moose's is located just across the street from Kamaole II.
Exceptional
(29 reviews)

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

Kihei

8% off
S$2,230
for 7 nights, 1 apartment
S$319 per night
includes taxes & fees
TROPICAL MAUI!!! Visit and stay in Comfort and Style...1b/2b
Bring your rackets!
Lush landscaping provides shade or sun and a waterfall.
Enjoy 2 couches and two chairs, one a recliner
You'll  love the lanai which is right near the sunken pool area, creating quiet
Exceptional
(49 reviews)

S. Kihei spacious garden condo, 2 lanais

Kihei

7% off
S$2,988
for 7 nights, 1 apartment
S$427 per night
includes taxes & fees
S. Kihei spacious garden condo, 2 lanais
Community swimming pool on property
Granite countertop, living area
Living area, dining, and kitchen
Living area looks out to lanai and lush landscaping
Exceptional
(140 reviews)

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

Kihei

7% off
S$2,238
for 7 nights, 1 apartment
S$320 per night
includes taxes & fees
Kihei, Maui Ground Floor Tropical Getaway - Across street from beach
Makena Surf offers oceanfront serenity, lush grounds & true Hawaiian calm.
Relax on your lanai with lush views and ocean sounds—pure island peace.
Cozy oceanview nook with local art and memory foam sleeper sofa.
Lush poolside area for sunny days and breezy island nights in Maui.
Exceptional
(92 reviews)

Makena Surf • Bright and Airy Retreat • Steps to the Beach: Swim w/Turtles

Kihei

6% off
S$11,121
for 7 nights, 1 apartment
S$1,589 per night
includes taxes & fees
Makena Surf • Bright and Airy Retreat • Steps to the Beach: Swim w/Turtles
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
S$2,596
for 7 nights, 1 apartment
S$371 per night
includes taxes & fees
# 107 Lovely Grnd Flr King bed Unit, accross the street is a white sand beach
Pool and 2 hot tubs
Our beloved 5 Palms is gone but new restaurant slated to open here December 2023
Living area
Outdoor dining
Exceptional
(89 reviews)

Beautifully renovated luxury condo steps from the sand on premier Kihei beach!

Kihei

7% off
S$2,733
for 7 nights, 1 apartment
S$390 per night
includes taxes & fees
Beautifully renovated luxury condo steps from the sand on premier Kihei beach!
Living Room with Circular Staircase
Sunset from lanai
Downstairs bedroom with king bed
Pool from lanai
Exceptional
(20 reviews)

Beautiful Kamaole Sands Oceanview Condominium !!

Kihei

7% off
S$3,312
for 7 nights, 1 apartment
S$473 per night
includes taxes & fees
Beautiful Kamaole Sands Oceanview Condominium !!
Dining
Property grounds
view from lanai over the complex grounds
Private kitchen
Exceptional
(164 reviews)

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

Kihei

7% off
S$3,529
for 7 nights, 1 apartment
S$504 per night
includes taxes & fees
Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed
photo of the ground
Sunset View from Lanai
Living area and Kitchen
Living Room
Exceptional
(108 reviews)

Unobstructed Views – Prime Location - Steps To Beach - Newly Renovated

Kihei

7% off
S$3,399
for 7 nights, 1 apartment
S$486 per night
includes taxes & fees
Unobstructed Views – Prime Location - Steps To Beach - Newly Renovated
Dining
Outdoor dining
Interior
Living area
Exceptional
(31 reviews)

Kihei Getaway in Paradise

Kihei

7% off
S$4,124
for 7 nights, 1 apartment
S$589 per night
includes taxes & fees
Kihei Getaway in Paradise
Golf
Appreciate the easy beach access from the pavilion pool.  (1 of 4 pools)
Ocean View from the front door!
Living area
Exceptional
(93 reviews)

Wailea Ekahi 54A: Panoramic Ocean View. Paint & Refresh August 2026!

Kihei

7% off
S$7,334
for 7 nights, 1 apartment
S$1,048 per night
includes taxes & fees
Wailea Ekahi 54A: Panoramic Ocean View. Paint & Refresh August 2026!
Living area
Property grounds
Property grounds
Interior
Exceptional
(55 reviews)

Updated Designer Condo w/ Ocean Views within five minutes to the beach

Kihei

7% off
S$3,502
for 7 nights, 1 apartment
S$500 per night
includes taxes & fees
Updated Designer Condo w/ Ocean Views within five minutes to the beach
Golf
Property grounds
Kitchen
Dining area
Exceptional
(14 reviews)

NEWLY REMODELED! Partial Ocean View condo along the golf course

Kihei

7% off
S$7,321
for 7 nights, 1 apartment
S$1,046 per night
includes taxes & fees
NEWLY REMODELED! Partial Ocean View condo along the golf course
Common Garden area
Clubhouse pool and hot tub
View from entryway
Kitchen bar view
Exceptional
(10 reviews)

Fully Remodeled Modern Island Style!

Kihei

7% off
S$6,576
for 7 nights, 1 apartment
S$939 per night
includes taxes & fees
Fully Remodeled Modern Island Style!
  • 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:

  • Maui Nui Golf Club (5.6 mi / 9 km)
  • The Dunes at Maui Lani (13.9 mi / 22.3 km)
  • Maui Spa Retreat (14.3 mi / 23 km)
  • Wailea Emerald Golf Course (0.3 mi / 0.4 km)
  • Wailea Gold Golf Course (0.3 mi / 0.5 km)
  • Wailea Blue Golf Course (0.4 mi / 0.7 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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