Wailea-Makena holiday lettings

We found 4,747 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Wailea-Makena

Showing deals for:6 Nov - 13 Nov

Salt water pool
View on the pool
Lobby
Lobby
Exceptional
(253 reviews)

Mana Kai Maui Condo - Right on the Beach!

Kihei

7% off
£3,435
for 7 nights, 1 apartment
£491 per night
includes taxes & fees
Mana Kai Maui Condo - Right on the Beach!
Entry Sign by Kihei Rd
Lower Swimming Pool
Living Room from Master Bedroom Railing
Living Room Sofa/bed
Exceptional
(95 reviews)

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

Kihei

5% off
£2,694
for 7 nights, 1 apartment
£385 per night
includes taxes & fees
D211 Quiet & Private 2br2ba near Wailea 2026 Discount 10% 7 nts or more.
View from lanai towards ocean
View from lanai before sunrise coming up over Haleakala
Pool area looking towards ocean
Kamaole Sands panorama
Exceptional
(92 reviews)

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

Kihei

7% off
£3,109
for 7 nights, 1 apartment
£444 per night
includes taxes & fees
Unbeatable Location at Kamaole III Beach - Kam Sands Bldg. 1
Pool
Outdoor dining
Private kitchen
Property grounds
Exceptional
(51 reviews)

Ekahi 27A: Priceless Ocean View from a Private Lanai

Kihei

11% off
£3,196
for 7 nights, 1 apartment
£457 per night
includes taxes & fees
Ekahi 27A: Priceless Ocean View from a Private Lanai
Living area
Exterior
Great bedroom with king bed
Living area
Exceptional
(110 reviews)

Oceanview Top Floor Condo, with Internet Access.

Kihei

7% off
£1,291
for 7 nights, 1 apartment
£184 per night
includes taxes & fees
Oceanview Top Floor Condo, with Internet Access.
Freds Mexican Cafe & Moose's is located just across the street from Kamaole II.
Maui Tropical Plantation.
Parking at the Maui Banyan is convenient and covered
Just one of Maui's great golf courses to test you skills.
Exceptional
(29 reviews)

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

Kihei

8% off
£1,297
for 7 nights, 1 apartment
£185 per night
includes taxes & fees
TROPICAL MAUI!!! Visit and stay in Comfort and Style...1b/2b
Kamaole Sands resort amenities include pools, hot tubs, gym and tennis.
Relax in your private lanai and enjoy the ocean view. This is paradise!
Pool
View of the living area from the kitchen.
Exceptional
(89 reviews)

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

Kihei

7% off
£1,782
for 7 nights, 1 apartment
£255 per night
includes taxes & fees
Maui Escape - Oceanview 70 Yds to Beach, GND Flr, Bldg10 - Everything You Need!
Grounds outside our Lanai
View from Lanai
Lower Swimming {Pool from our Lanai
Lower Swimming Pool
Exceptional
(59 reviews)

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

Kihei

6% off
£1,546
for 7 nights, 1 apartment
£221 per night
includes taxes & fees
# 107 Lovely Grnd Flr King bed Unit, accross the street is a white sand beach
Outdoor dining
Our beloved 5 Palms is gone but new restaurant slated to open here December 2023
Living area
Kamaole Sands grounds
Exceptional
(89 reviews)

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

Kihei

7% off
£1,430
for 7 nights, 1 apartment
£204 per night
includes taxes & fees
Beautifully renovated luxury condo steps from the sand on premier Kihei beach!
Dining
Property grounds
Living area
Private kitchen
Exceptional
(164 reviews)

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

Kihei

7% off
£2,054
for 7 nights, 1 apartment
£293 per night
includes taxes & fees
Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed
Beach
Property grounds
Living area
Pool
Exceptional
(64 reviews)

Kihei Akahi C310-Owner Managed-Complete Renovation-Modern Luxury-A/C throughout

Kihei

6% off
£1,356
for 7 nights, 1 apartment
£194 per night
includes taxes & fees
Kihei Akahi C310-Owner Managed-Complete Renovation-Modern Luxury-A/C throughout
View of the 2nd hole
Close to the swimming pool with Jacuzzi and BBQs
Miscellaneous
Master Bedroom on golf course with ocean view
Wonderful
(101 reviews)

Wailea Sensation Vacation! Spectacular Oceanview Villa! On the 2nd hole.

Kihei

7% off
£1,645
for 7 nights, 1 apartment
£235 per night
includes taxes & fees
Wailea Sensation Vacation! Spectacular Oceanview Villa! On the 2nd hole.
Golf
Appreciate the easy beach access from the pavilion pool.  (1 of 4 pools)
Living area
Ocean View from the front door!
Exceptional
(93 reviews)

Wailea Ekahi 54A: Remodeled & Panoramic Ocean View.

Kihei

7% off
£4,231
for 7 nights, 1 apartment
£604 per night
includes taxes & fees
Wailea Ekahi 54A: Remodeled & Panoramic Ocean View.
Living area
Property grounds
Property grounds
Golf
Exceptional
(55 reviews)

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

Kihei

7% off
£2,022
for 7 nights, 1 apartment
£289 per night
includes taxes & fees
Updated Designer Condo w/ Ocean Views within five minutes to the beach
Living area
Outdoor dining
Dining
Interior
Exceptional
(31 reviews)

Kihei Getaway in Paradise

Kihei

7% off
£2,359
for 7 nights, 1 apartment
£337 per night
includes taxes & fees
Kihei Getaway in Paradise
Kitchen
Property grounds
Dining area
Golf
Exceptional
(14 reviews)

NEWLY REMODELED! Partial Ocean View condo along the golf course

Kihei

7% off
£4,188
for 7 nights, 1 apartment
£598 per night
includes taxes & fees
NEWLY REMODELED! Partial Ocean View condo along the golf course
Kitchen
Living Room
Dining Area
Living Room
Exceptional
(168 reviews)

Wailea 1 BR Condo, close to everything, good pricing

Kihei

7% off
£1,717
for 7 nights, 1 apartment
£245 per night
includes taxes & fees
Wailea 1 BR Condo, close to everything, good pricing
Common Garden area
Clubhouse pool and hot tub
Kitchen
View from entryway
Exceptional
(10 reviews)

Fully Remodeled Modern Island Style!

Kihei

7% off
£3,920
for 7 nights, 1 apartment
£560 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, 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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