Wailea-Makena holiday rentals

We found 4,761 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Wailea-Makena

Showing deals for:11 Dec - 18 Dec

Private kitchen
Outdoor dining
Living area
Pool
Exceptional
(40 reviews)

Beachfront Condo E 303/ Incredible views/ Pickleball/Great Snorkeling

Kihei

5% off
S$13,041
for 7 nights, 1 apartment
S$1,863 per night
includes taxes & fees
Beachfront Condo E 303/ Incredible views/ Pickleball/Great Snorkeling
Guest room with XL twins or king—great for couples, kids, or friends.
Relax in oceanfront luxury with beach views, sunsets, and breezy lanai mornings.
Your expansive indoor outdoor lanai has a beautiful Maui view
Wake up to island beauty with local art and tropical Maui-inspired style.
Exceptional
(93 reviews)

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

Kihei

5% off
S$10,358
for 7 nights, 1 apartment
S$1,480 per night
includes taxes & fees
Makena Surf • Bright and Airy Retreat • Steps to the Beach: Swim w/Turtles
Spacious lanai with enough seating for the whole family.
View on the pool
Lobby
Lobby
Exceptional
(256 reviews)

Mana Kai Maui Condo - Right on the Beach!

Kihei

8% off
S$5,661
for 7 nights, 1 apartment
S$809 per night
includes taxes & fees
Mana Kai Maui Condo - Right on the Beach!
View of the 2nd hole
Close to the swimming pool with Jacuzzi and BBQs
Living room
Master Bedroom on golf course with ocean view
Wonderful
(101 reviews)

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

Kihei

7% off
S$2,798
for 7 nights, 1 apartment
S$400 per night
includes taxes & fees
Wailea Sensation Vacation! Spectacular Oceanview Villa! On the 2nd hole.
Dining
Oasis Pool with waterfall, Cabana, Kitchen, additional BBQs and Restrooms
Beautiful Kitchen
Barbeque Area in Gazebo and near pool area
Exceptional
(177 reviews)

Maui Kamaole CONDO M102 TOTALLY RENOVATED

Kihei

7% off
S$2,779
for 7 nights, 1 apartment
S$397 per night
includes taxes & fees
Maui Kamaole CONDO M102 TOTALLY RENOVATED
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
S$2,272
for 7 nights, 1 apartment
S$325 per night
includes taxes & fees
Kihei, Maui Ground Floor Tropical Getaway - Across street from beach
Private kitchen
Outdoor dining
Interior
View from the heated pool.
Exceptional
(79 reviews)

Newly Renovated 6th floor Panoramic Beachfront Condo Fully Air Conditioned

Kihei

8% off
S$6,887
for 7 nights, 1 apartment
S$984 per night
includes taxes & fees
Newly Renovated 6th floor Panoramic Beachfront Condo Fully Air Conditioned
Dining
Pool
Dining
Living area
Exceptional
(28 reviews)

Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo

Kihei

8% off
S$15,337
for 7 nights, 1 apartment
S$2,191 per night
includes taxes & fees
Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo
Entry Sign by Kihei Rd
Lower Swimming Pool
New Kitchen
Living Room
Exceptional
(95 reviews)

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

Kihei

5% off
S$4,489
for 7 nights, 1 apartment
S$641 per night
includes taxes & fees
D211 Quiet & Private 2br2ba near Wailea 2026 Discount 10% 7 nts or more.
Circular stairs leads up to Master bedroom
View from our Lanai.
Water fountain greets you when you first arrive
Living Room
Exceptional
(73 reviews)

Highly desirable top floor unit with garden and ocean view has hot summer deals!

Kihei

7% off
S$4,331
for 7 nights, 1 apartment
S$619 per night
includes taxes & fees
Highly desirable top floor unit with garden and ocean view has hot summer deals!
Entrance to the condo
Grand Champions Entrance with Waterfall feature
Pool
Renovated kitchen with built in bar
Exceptional
(110 reviews)

Escape to Paradise – Your Dream Wailea Getaway Awaits!

Kihei

7% off
S$3,241
for 7 nights, 1 apartment
S$463 per night
includes taxes & fees
Escape to Paradise – Your Dream Wailea Getaway Awaits!
Living Room
Living Room
Kitchen
Dining Area
Exceptional
(169 reviews)

Wailea 1 BR Condo, close to everything, good pricing

Kihei

7% off
S$3,037
for 7 nights, 1 apartment
S$434 per night
includes taxes & fees
Wailea 1 BR Condo, close to everything, good pricing
Walk to the beach or sit on the lanai and enjoy the view.
Outdoor dining
Room
Tile floor throughout living and bedroom areas. Two rocking chairs for relaxing.
Exceptional
(108 reviews)

Kihei Akahi D514- Panoramic view! Owner managed- Hotel zoned- A/C throughout

Kihei

6% off
S$3,149
for 7 nights, 1 apartment
S$450 per night
includes taxes & fees
Kihei Akahi D514- Panoramic view! Owner managed- Hotel zoned- A/C throughout
Upper Pool a Few Steps from the Lanai.
Kihei Akahi's Grounds.  Flowers Everywhere
Flat Screen TV, DVD/VCR Player.  DVDs and VHS Tapes. Books
Bright and Tropical Living Room with PC and Printer.
Exceptional
(132 reviews)

Beautiful Maui Home Away from Home

Kihei

6% off
S$1,782
for 7 nights, 1 apartment
S$255 per night
includes taxes & fees
Beautiful Maui Home Away from Home
Living area
Exterior
Great bedroom with king bed
Living area
Exceptional
(110 reviews)

Oceanview Top Floor Condo, with Internet Access.

Kihei

7% off
S$2,173
for 7 nights, 1 apartment
S$310 per night
includes taxes & fees
Oceanview Top Floor Condo, with Internet Access.
Golf
Property grounds
Living area
Interior
Exceptional
(56 reviews)

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

Kihei

7% off
S$3,449
for 7 nights, 1 apartment
S$493 per night
includes taxes & fees
Updated Designer Condo w/ Ocean Views within five minutes to the beach
Dining
Outdoor dining
Room
Private kitchen
Exceptional
(71 reviews)

Immaculate and Chic - Come relax in our luxury villa…

Kihei

7% off
S$4,777
for 7 nights, 1 apartment
S$682 per night
includes taxes & fees
Immaculate and Chic - Come relax in our luxury villa…
view from lanai over the complex grounds
Property grounds
Private kitchen
Living area
Exceptional
(167 reviews)

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

Kihei

7% off
S$3,513
for 7 nights, 1 apartment
S$502 per night
includes taxes & fees
Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed
Our 3 turtles welcome you
Living area
New kitchen with sliding table. Small table position shown. Seats 3 to 5.
Dresser Drawers in bedroom. AC cabinet to the right of TV.
Exceptional
(50 reviews)

Beachfront 1-bedroom corner condo on Kameole Beach II, with two ocean views.

Kihei

8% off
S$5,153
for 7 nights, 1 apartment
S$736 per night
includes taxes & fees
Beachfront 1-bedroom corner condo on Kameole Beach II, with two ocean views.
Living room
Property grounds
Property grounds
Dining
Exceptional
(88 reviews)

Ekahi 29C, Ocean View, Steps away from the pool

Kihei

7% off
S$6,801
for 7 nights, 1 apartment
S$972 per night
includes taxes & fees
Ekahi 29C, Ocean View, Steps away from the pool
Living area
Our beloved 5 Palms is gone but new restaurant slated to open here December 2023
Pool and 2 hot tubs
Kamaole Sands grounds
Exceptional
(89 reviews)

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

Kihei

7% off
S$2,987
for 7 nights, 1 apartment
S$427 per night
includes taxes & fees
Beautifully renovated luxury condo steps from the sand on premier Kihei beach!
Kitchen
Clubhouse pool and hot tub
Kitchen bar view
View from entryway
Exceptional
(10 reviews)

Fully Remodeled Modern Island Style!

Kihei

7% off
S$6,477
for 7 nights, 1 apartment
S$925 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:

  • Wailea Emerald Golf Course (0.3 mi / 0.4 km)
  • Wailea Gold Golf Course (0.3 mi / 0.5 km)
  • Maui Nui Golf Club (5.6 mi / 9 km)
  • Maui Spa Retreat (14.3 mi / 23 km)
  • Wailea Blue Golf Course (0.4 mi / 0.7 km)
  • Makena South Course (1.6 mi / 2.6 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)
  • Polo Beach (0.6 mi / 1 km)
  • Maluaka Beach (1.6 mi / 2.6 km)
  • Ulua Beach (1.6 mi / 2.6 km)
  • Keawakapu Beach North (2.5 mi / 4 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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