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Upcountry Maui holiday rentals

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

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

JJs Hāna Hale - Farm House

Hana

8% off
AU$3,397
for 7 nights, 1 room
AU$485 per night
includes taxes & fees
JJs Hāna Hale - Farm House
Lanai
Living area
Room
Exterior
Exceptional
(206 reviews)

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

Hana

12% off
AU$3,990
for 7 nights, 1 cottage
AU$570 per night
includes taxes & fees
Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01
Jasmine Suite
View from the Jasmine Suite Deck
Jasmine Kitchen
Entrance  to Ekena
Exceptional
(159 reviews)

360 Degree Ocean And Mountain Views From This Stunning Home.

Hana

8% off
AU$3,764
for 7 nights, 1 home
AU$538 per night
includes taxes & fees
360 Degree Ocean And Mountain Views From This Stunning Home.
Kitchen
Living area
bathroom 2 - walk in shower
Master bedroom king bed
Exceptional
(110 reviews)

Paia Family Cottage - Walk to everything in Paia Town

Paia

7% off
AU$3,333
for 7 nights, 1 home
AU$476 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
Private kitchen
Living area
Exceptional
(30 reviews)

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

Haiku

7% off
AU$3,920
for 7 nights, 1 cottage
AU$560 per night
includes taxes & fees
Pineapple Cottage B&B Vacation Rental Haiku Maui, Lic#BBPH2015/0011
3 bed/2 bath double suite rental. View of lanai from the backyard.
2nd floor lanai with views of Hana Bay
2nd floor open living/kitchen space
2nd floor dining table
Exceptional
(34 reviews)

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

Hana

7% off
AU$5,690
for 7 nights, 1 home
AU$813 per night
includes taxes & fees
Hana Bay View 3 BR/2 BA house sleeps 6 comfortably with 2 patios.
View of the manicured grounds from the Lanai
The Lanai and the hint of the view from outside
The comfortable King-size master bed with the pillow-top mattress
Living room looking towards the front door
Exceptional
(151 reviews)

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

Wailuku

7% off
AU$4,231
for 7 nights, 1 apartment
AU$604 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.
Your cozy ocean view nook with local art and memory foam sleeper sofa.
Lush poolside area for sunny days and breezy island nights in Maui.
Makena Surf offers you oceanfront serenity, lush grounds & true Hawaiian calm.
Exceptional
(92 reviews)

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

Kihei

6% off
AU$11,186
for 7 nights, 1 apartment
AU$1,598 per night
includes taxes & fees
Makena Surf • Bright and Airy Retreat • Steps to the Beach: Swim w/Turtles
Kitchen Area - Island Bar
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
AU$6,895
for 7 nights, 1 home
AU$985 per night
includes taxes & fees
Luxury 3BR Wailea Kihei Retreat. Walk to Beaches, Private Lanai, Newly Remodeled
Lobby
View on the pool
Lobby
Spacious lanai with enough seating for the whole family.
Exceptional
(256 reviews)

Mana Kai Maui Condo - Right on the Beach!

Kihei

8% off
AU$6,243
for 7 nights, 1 apartment
AU$892 per night
includes taxes & fees
Mana Kai Maui Condo - Right on the Beach!
living dining area
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
AU$3,860
for 7 nights, 1 apartment
AU$551 per night
includes taxes & fees
Maui Sunset B201: Beautiful 2 Bedroom, 2 Bath, Kihei Condo. Sleeps up to Six
Room
Beachfront property
Living area
Exterior
Exceptional
(46 reviews)

Classic Beachfront Studio Apartment Right On Charley Young Beach

Kihei

7% off
AU$2,378
for 7 nights, 1 apartment
AU$340 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.
Water Lily Stream along the Waterfall Beach Pathway to the Adult Pool & Beach
Exceptional
(136 reviews)

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

Kihei

8% off
AU$21,612
for 7 nights, 1 apartment
AU$3,087 per night
includes taxes & fees
DIRECT BEACHFRONT 4Bd 3BA 3892 s.f. WAILEA PANORAMIC OCEAN & OUTER ISLAND VIEWS
Living area
Pool
Dining
Interior
Exceptional
(28 reviews)

Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo

Kihei

8% off
AU$16,582
for 7 nights, 1 apartment
AU$2,369 per night
includes taxes & fees
Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo
Dining
Property grounds
Private kitchen
Living area
Exceptional
(89 reviews)

Breathtaking penthouse ocean view in South Kihei

Kihei

7% off
AU$3,715
for 7 nights, 1 apartment
AU$531 per night
includes taxes & fees
Breathtaking penthouse ocean view in South Kihei
Beautiful views from rooftop terrace
private pool
entrance for Royal Mauian
Room
Wonderful
(130 reviews)

Top Floor Unit ~ Endless Ocean Views

Kihei

6% off
AU$4,557
for 7 nights, 1 apartment
AU$651 per night
includes taxes & fees
Top Floor Unit ~ Endless Ocean Views
Dresser Drawers in bedroom. AC cabinet to the right of TV.
Living area
New kitchen with sliding table. Small table position shown. Seats 3 to 5.
Interior
Exceptional
(49 reviews)

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

Kihei

8% off
AU$5,604
for 7 nights, 1 apartment
AU$801 per night
includes taxes & fees
Beachfront 1-bedroom corner condo on Kameole Beach II, with two ocean views.
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
Feel right at home in this fully-equipped kitchen with granite countertops.
Exceptional
(92 reviews)

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

Kihei

7% off
AU$3,128
for 7 nights, 1 apartment
AU$447 per night
includes taxes & fees
Maui Escape - Oceanview 70 Yds to Beach, GND Flr, Bldg10 - Everything You Need!
Private kitchen
Pool
Living area
Living area
Exceptional
(181 reviews)

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

Kihei

7% off
AU$3,290
for 7 nights, 1 apartment
AU$470 per night
includes taxes & fees
Read our Reviews! Newly Updated Condo! Perfect Getaway Steps to Beach & Dining!
Tile floor throughout living and bedroom areas. Two rocking chairs for relaxing.
Outdoor dining
Walk to the beach or sit on the lanai and enjoy the view.
Room
Exceptional
(107 reviews)

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

Kihei

7% off
AU$3,202
for 7 nights, 1 apartment
AU$457 per night
includes taxes & fees
Kihei Akahi D514- Panoramic view! Owner managed- Hotel zoned- A/C throughout
Living area
Kamaole Sands refreshing swimming pool
Kamaole Sands
Kamaole Sands III beach
Exceptional
(115 reviews)

Your Hawaiian Beach Get Away, Steps From Great Beach!

Kihei

11% off
AU$2,580
for 7 nights, 1 apartment
AU$369 per night
includes taxes & fees
Your Hawaiian Beach Get Away, Steps From Great Beach!
55" HD LED TV in living room is on a swivel and can be seen from anywhere
Pool
Maui early morning view from the condo. Enjoy coffee & singing birds on lanai
Your view from INSIDE the condo. Enjoy morning coffee and toast the sunset.
Exceptional
(130 reviews)

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

Kihei

7% off
AU$2,908
for 7 nights, 1 apartment
AU$415 per night
includes taxes & fees
Ocean View Maui Condo Right Across from the Beach! 1 of 6 larger MK condos, A/C
view from lanai over the complex grounds
Property grounds
Private kitchen
Living area
Exceptional
(165 reviews)

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

Kihei

7% off
AU$3,711
for 7 nights, 1 apartment
AU$530 per night
includes taxes & fees
Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed
Interior
Living area
Kitchen with new cabinets, counters and appliances
Private kitchen
Exceptional
(41 reviews)

Kihei 1 Bedroom Beach Condo

Kihei

5% off
AU$2,132
for 7 nights, 1 apartment
AU$305 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 Stayz 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, Stayz 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 Stayz. 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 Stayz 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, Stayz 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 Stayz.
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 Stayz, 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