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Upcountry Maui holiday homes

We found 5,225 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Upcountry Maui

Showing deals for:4 Dec - 11 Dec

Property grounds
Living area
Pet-friendly
Room
Exceptional
(159 reviews)

JJs Hāna Hale - Farm House

Hana

8% off
NZ$4,127
for 7 nights, 1 room
NZ$590 per night
includes taxes & fees
JJs Hāna Hale - Farm House
Exterior
Living area
Property grounds
Lanai
Exceptional
(206 reviews)

Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01

Hana

11% off
NZ$4,935
for 7 nights, 1 cottage
NZ$705 per night
includes taxes & fees
Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01
Jasmine Suite living room with panoramic ocean view
View from the Jasmine Suite Deck
Jasmine Suite
Entrance  to Ekena
Exceptional
(159 reviews)

360 Degree Ocean And Mountain Views From This Stunning Home.

Hana

8% off
NZ$4,655
for 7 nights, 1 home
NZ$665 per night
includes taxes & fees
360 Degree Ocean And Mountain Views From This Stunning Home.
Master bedroom king bed
Living area
Kitchen
outdoor deck
Exceptional
(110 reviews)

Paia Family Cottage - Walk to everything in Paia Town

Paia

7% off
NZ$4,050
for 7 nights, 1 home
NZ$579 per night
includes taxes & fees
Paia Family Cottage - Walk to everything in Paia Town
Mana's Fishouse just 10 minutes away island favorite
Outdoor dining
Home Sweet Home!
Private kitchen
Exceptional
(30 reviews)

Pineapple Cottage B&B Vacation Rental Haiku Maui, Lic#BBPH2015/0011

Haiku

7% off
NZ$4,847
for 7 nights, 1 cottage
NZ$692 per night
includes taxes & fees
Pineapple Cottage B&B Vacation Rental Haiku Maui, Lic#BBPH2015/0011
2nd floor dining table
2nd floor lanai with views of Hana Bay
3 bed/2 bath double suite rental. View of lanai from the backyard.
2nd floor open living/kitchen space
Exceptional
(34 reviews)

Hana Bay View 3 BR/2 BA house sleeps 6 comfortably with 2 patios.

Hana

7% off
NZ$6,986
for 7 nights, 1 home
NZ$998 per night
includes taxes & fees
Hana Bay View 3 BR/2 BA house sleeps 6 comfortably with 2 patios.
Next to the new fridge is a washer/dryer
The Lanai and the hint of the view from outside
View of the manicured grounds from the Lanai
The comfortable King-size master bed with the pillow-top mattress
Exceptional
(151 reviews)

195-295/night, Oceanfront with 2 Master Suites, Fully Stocked, Amazing View!!!

Wailuku

7% off
NZ$5,233
for 7 nights, 1 apartment
NZ$748 per night
includes taxes & fees
195-295/night, Oceanfront with 2 Master Suites, Fully Stocked, Amazing View!!!
Relax in oceanfront luxury with beach views, sunsets, and breezy lanai mornings.
Lush poolside area for sunny days and breezy island nights in Maui.
You will soak in ocean views from the kitchen—paradise with every meal.
Your cozy ocean view nook with local art and memory foam sleeper sofa.
Exceptional
(92 reviews)

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

Kihei

5% off
NZ$14,076
for 7 nights, 1 apartment
NZ$2,011 per night
includes taxes & fees
Makena Surf • Bright and Airy Retreat • Steps to the Beach: Swim w/Turtles
Private Wailea/Kihei retreat just minutes from Maui’s most beautiful beaches
Living Room Area
Unwind after beach days with peaceful outdoor living and island breezes
Indoor Dining Area
Exceptional
(104 reviews)

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

Kihei

7% off
NZ$8,431
for 7 nights, 1 home
NZ$1,204 per night
includes taxes & fees
Luxury 3BR Wailea Kihei Retreat. Walk to Beaches, Private Lanai, Newly Remodeled
Salt water pool
View on the pool
Spacious lanai with enough seating for the whole family.
Lobby
Exceptional
(256 reviews)

Mana Kai Maui Condo - Right on the Beach!

Kihei

7% off
NZ$7,646
for 7 nights, 1 apartment
NZ$1,092 per night
includes taxes & fees
Mana Kai Maui Condo - Right on the Beach!
Maui Sunset resort from beach
Property grounds
A nice view at sunset from the lanai
Sunset viewed from the pool
Exceptional
(107 reviews)

Maui Sunset B201: Beautiful 2 Bedroom, 2 Bath, Kihei Condo. Sleeps up to Six

Kihei

7% off
NZ$4,773
for 7 nights, 1 apartment
NZ$682 per night
includes taxes & fees
Maui Sunset B201: Beautiful 2 Bedroom, 2 Bath, Kihei Condo. Sleeps up to Six
Dining
Beachfront property
Room
Living area
Exceptional
(46 reviews)

Classic Beachfront Studio Apartment Right On Charley Young Beach

Kihei

7% off
NZ$2,833
for 7 nights, 1 apartment
NZ$405 per night
includes taxes & fees
Classic Beachfront Studio Apartment Right On Charley Young Beach
Lobby of Wailea Beach Villas Check In Desk on left. Concierge Desk on right!
Natural Waterfall feature next to the adult ocean-front Pool & Spa area.
Excellent Ocean & Outer Island Views & Pastoral, Tropical Grounds on the
Ocean.
Kitchen opens to fabulous rear lanai. Two Sub-Zero fridges, new quartz counters!
Exceptional
(136 reviews)

DIRECT BEACHFRONT 4Bd 3BA 3892 s.f. WAILEA PANORAMIC OCEAN & OUTER ISLAND VIEWS

Kihei

8% off
NZ$26,305
for 7 nights, 1 apartment
NZ$3,758 per night
includes taxes & fees
DIRECT BEACHFRONT 4Bd 3BA 3892 s.f. WAILEA PANORAMIC OCEAN & OUTER ISLAND VIEWS
Interior
Pool
Dining
Living area
Exceptional
(28 reviews)

Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo

Kihei

8% off
NZ$20,091
for 7 nights, 1 apartment
NZ$2,870 per night
includes taxes & fees
Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo
Dining
Property grounds
Private kitchen
Pool
Exceptional
(89 reviews)

Breathtaking penthouse ocean view in South Kihei

Kihei

7% off
NZ$4,512
for 7 nights, 1 apartment
NZ$645 per night
includes taxes & fees
Breathtaking penthouse ocean view in South Kihei
Beautiful views from rooftop terrace
private pool
Room
entrance for Royal Mauian
Wonderful
(130 reviews)

Top Floor Unit ~ Endless Ocean Views

Kihei

6% off
NZ$5,634
for 7 nights, 1 apartment
NZ$805 per night
includes taxes & fees
Top Floor Unit ~ Endless Ocean Views
Dresser Drawers in bedroom. AC cabinet to the right of TV.
Living area
Interior
New kitchen with sliding table. Small table position shown. Seats 3 to 5.
Exceptional
(49 reviews)

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

Kihei

8% off
NZ$6,884
for 7 nights, 1 apartment
NZ$983 per night
includes taxes & fees
Beachfront 1-bedroom corner condo on Kameole Beach II, with two ocean views.
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
NZ$3,801
for 7 nights, 1 apartment
NZ$543 per night
includes taxes & fees
Maui Escape - Oceanview 70 Yds to Beach, GND Flr, Bldg10 - Everything You Need!
Living area
Pool
Living area
Exterior
Exceptional
(181 reviews)

Read our Reviews! Newly Updated Condo! Perfect Getaway Steps to Beach & Dining!

Kihei

7% off
NZ$3,998
for 7 nights, 1 apartment
NZ$571 per night
includes taxes & fees
Read our Reviews! Newly Updated Condo! Perfect Getaway Steps to Beach & Dining!
Walk to the beach or sit on the lanai and enjoy the view.
Outdoor dining
Room
Pool, shaded area  and BBQ within steps.
Exceptional
(107 reviews)

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

Kihei

7% off
NZ$3,890
for 7 nights, 1 apartment
NZ$556 per night
includes taxes & fees
Kihei Akahi D514- Panoramic view! Owner managed- Hotel zoned- A/C throughout
Kamaole Sands fountain
Kamaole Sands refreshing swimming pool
Living area
Kamaole Sands
Exceptional
(115 reviews)

Your Hawaiian Beach Get Away, Steps From Great Beach!

Kihei

11% off
NZ$3,112
for 7 nights, 1 apartment
NZ$445 per night
includes taxes & fees
Your Hawaiian Beach Get Away, Steps From Great Beach!
Front view of Ilima Building, where the I-117 condo is located
Pool
Maui early morning view from the condo. Enjoy coffee & singing birds on lanai
55" HD LED TV in living room is on a swivel and can be seen from anywhere
Exceptional
(130 reviews)

Ocean View Maui Condo Right Across from the Beach! 1 of 6 larger MK condos, A/C

Kihei

7% off
NZ$3,508
for 7 nights, 1 apartment
NZ$501 per night
includes taxes & fees
Ocean View Maui Condo Right Across from the Beach! 1 of 6 larger MK condos, A/C
Dining
Property grounds
Living area
view from lanai over the complex grounds
Exceptional
(165 reviews)

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

Kihei

7% off
NZ$4,506
for 7 nights, 1 apartment
NZ$644 per night
includes taxes & fees
Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed
Exterior detail
Living area
Private kitchen
Kitchen with new cabinets, counters and appliances
Exceptional
(41 reviews)

Kihei 1 Bedroom Beach Condo

Kihei

5% off
NZ$2,538
for 7 nights, 1 apartment
NZ$363 per night
includes taxes & fees
Kihei 1 Bedroom Beach Condo
  • 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

Travel to relaxing Upcountry Maui

The parks, island views and gardens are the perfect backdrop to your holiday home in Upcountry Maui. This city is relaxing and romantic, recognised for its yoga, spas and whale watching. Haleakala National Park and Wailea Beach 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.

Sightseeing in and around Upcountry Maui

Do you want to discover things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Upcountry Maui a fun spot to go on holiday. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Maui Nui Golf Club (13.2 mi / 21.2 km)
  • Wailea Gold Golf Course (14 mi / 22.5 km)
  • The Dunes at Maui Lani (17.1 mi / 27.6 km)
  • Hoʻomana Spa Maui (5.9 mi / 9.5 km)
  • Maui Spa Retreat (8.2 mi / 13.1 km)
  • Pukalani Country Club (8.6 mi / 13.9 km)

Exploring the natural features in Upcountry Maui

Whether you're looking for adventure or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Upcountry Maui. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Haleakala National Park (6.2 mi / 10 km)
  • Wailea Beach (14 mi / 22.5 km)
  • Hosmer Grove (1 mi / 1.5 km)
  • Haleakalā Visitor Center (2.8 mi / 4.6 km)
  • Haleakala Crater (3.1 mi / 5 km)
  • Maui Garden Of Eden - Botanical Gardens & Arboretum (8.9 mi / 14.3 km)

Frequently asked questions

What is the best area to stay in Upcountry Maui when booking a holiday home?
Spreckelsville is one of the more popular areas where you can book a Bookabach holiday home in Upcountry Maui. Browse our selection of relaxing properties and then get out and experience the best of this destination.
What is the most popular type of holiday home accommodation in Upcountry Maui?
Houses are the most popular type of holiday home in Upcountry Maui, according to our data. Even if you have a different idea about what you want, Bookabach has holiday homes in all sizes and shapes. Look through our options to find your perfect fit.
How much does it cost to rent a holiday home in Upcountry Maui?
A range of factors affect what you'll pay for a holiday home in Upcountry Maui, like the length of stay, type of property and season. However, all our holiday homes have one thing in common — amazing value. Simply add your travel dates to find your ideal match.
How much does it cost to rent a beach house in Upcountry Maui?
When you travel and the size and style of the property will help determine the cost of your beachside stay. Enter your Upcountry Maui travel dates to view your options on Bookabach. Can't live without a private pool? Use our filters to select the features and amenities you want in your holiday home.
What are popular home amenities in Upcountry Maui?
When it comes to home amenities that guests are on the lookout for in Upcountry Maui, off-street parking options, a microwave oven and a fridge are the most popular. With Bookabach holiday homes, you'll enjoy options to suit your style and taste, whether you're on a trip with friends, family or even pets.
Are there large group holiday homes in Upcountry Maui?
With four properties that can host 10 people or more in Upcountry Maui, you won't have to limit the invite list. From extended family holidays to special events like anniversary parties and weddings, Bookabach will help you find a large group home to suit the occasion.
Can I find two-bedroom holiday homes in Upcountry Maui?
Take your pick of eight two-bedroom properties in Upcountry Maui. Give the kids the second room or maybe fill it with a couple of your besties. There's space for whoever's lucky enough to be joining your adventure.
Are there holiday homes with WiFi in Upcountry Maui?
You'll have a choice of 22 holiday homes with WiFi in Upcountry Maui. If you'd like to disconnect from daily life on your trip, but still want to be connected to the web, these properties are for you. Narrow your search by applying the WiFi filter on Bookabach.
How old do you have to be to rent a holiday home in Upcountry Maui?
The minimum required age is generally 16, 18 or 21. It can differ from property to property on Bookabach, so look at the rules of your preferred Upcountry Maui holiday home before booking.
How long can I rent a holiday home in Upcountry Maui for?
The amount of time you can rent an Upcountry Maui holiday home for is down to the property. Simply put in your preferred travel dates to browse options offering longer term stays. They come with all the things you need to make your extended break more convenient and comfortable, like kitchens and air conditioning. Some holiday homes might also offer weekly or monthly discounted prices, so you can stay longer for less money.

More holiday ideas