Compare Upcountry Maui Vacation Rentals

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Upcountry Maui Rentals

Wailea Ekahi - CoralTree Residence Collection

Wailea Ekahi - CoralTree Residence Collection

3 out of 5
3300 Wailea Alanui Kihei HI
13.63 mi from city center
Guests staying at Wailea Ekahi - CoralTree Residence Collection enjoy 4 outdoor pools, free WiFi in public areas, and laundry facilities. If you decide to drive, there's free parking. Front-desk staff can help with concierge services, and provide local restaurant recommendations. Other amenities at this beach condo building include a picnic area and barbecue grills.
Pool
Kitchen
Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
515 S. Kihei Road Kihei HI
14.1 mi from city center
Guests staying at Maui Beach Vacation Club enjoy an outdoor pool, free WiFi in public areas, and a hot tub. If you drive, put free parking to good use. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. Other amenities at this beach aparthotel include barbecue grills and a garden.
Pool
Hot Tub
Kahana Falls Maui by VRI Americas

Kahana Falls Maui by VRI Americas

3.5 out of 5
4260 Lower Honoapiilani Rd Lahaina HI
31.9 mi from city center
Kahana Falls Maui by VRI Americas features an outdoor pool, a children's pool, and a gym. A stay here includes free parking. The 24-hour front desk has staff standing by to help with concierge services, and answer any questions about the accommodations. Other amenities at this family-friendly aparthotel include free WiFi in public areas, a hot tub, and an arcade/game room.
Pool
Hot Tub
Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

3 out of 5
45 Kai Ala Dr Lahaina HI
Free Cancellation
Reserve now, pay when you stay
31.59 mi from city center
$390 nightly
The price is $463 total per night
$463 total
Apr 1 - Apr 2
Total with taxes and fees
Guests of Aston Maui Kaanapali Villas have access to a full-service spa, 2 outdoor pools, and a children's pool. You'll find limited parking. The 24-hour front desk has staff standing by to help with concierge services, luggage storage, and dry cleaning/laundry. Other amenities at this beach aparthotel include a 24-hour gym, 2 hot tubs, and meeting rooms.
Pool
Hot Tub
The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas

4 out of 5
6 Kai Ala Dr Lahaina HI
31.63 mi from city center
$475 nightly
The price is $564 total per night
$564 total
Apr 7 - Apr 8
Total with taxes and fees
Guests of The Westin Ka'anapali Ocean Resort Villas have access to a full-service spa, 2 outdoor pools, and a lazy river. Parking is available for USD 35 per day (USD 40 per day for valet parking), and there's also an airport shuttle for a fee. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, concierge services, and securing valuables. Other amenities at this beach condominium resort include a children's pool, a gym, and a sauna.
Pool
Hot Tub
Royal Kahana Maui by OUTRIGGER

Royal Kahana Maui by OUTRIGGER

3 out of 5
4365 Lower Honoapiilani Rd Lahaina HI
31.99 mi from city center
Guests staying at Royal Kahana Maui by OUTRIGGER enjoy an outdoor pool, a gym, and free WiFi in public areas. Self parking is available for USD 18.85 per day. Front-desk staff can help with concierge services, and provide local restaurant recommendations. Additional amenities include a meeting room, express check-out, and laundry facilities.
Pool
Kitchen
Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
4221 Lower Honoapiilani Road Lahaina HI
31.98 mi from city center
Kahana Beach Vacation Club offers an outdoor pool, free WiFi in public areas, and a hot tub. If you drive, put free parking to good use. Staff members can help with accommodation requests, and provide concierge services. Other amenities at this beach condo building include laundry facilities and barbecue grills.
Pool
Hot Tub
The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
2481 Kaanapali Pkwy Lahaina HI
Free Cancellation
Reserve now, pay when you stay
31.48 mi from city center
$685 nightly
The price is $814 total per night
$814 total
Mar 23 - Mar 24
Total with taxes and fees
At this condo, guests have access to an outdoor pool, outdoor tennis courts, and free WiFi in public areas. If you drive, take advantage of free parking. The front desk has multilingual staff standing by 24 hours a day to assist with tours/tickets and luggage storage. Other amenities at this beach condo building include a 24-hour business center, a computer station, and laundry facilities.
Pool
Kitchen
The Westin Nanea Ocean Villas, Ka'anapali

The Westin Nanea Ocean Villas, Ka'anapali

4 out of 5
45 Kai Malina Pkwy Lahaina HI
31.77 mi from city center
$703 nightly
The price is $835 total per night
$835 total
Mar 21 - Mar 22
Total with taxes and fees
Guests of The Westin Nanea Ocean Villas, Ka'anapali enjoy 2 outdoor pools, a children's pool, and a gym. Parking is available for USD 30.00 per day (USD 35.00 per day for valet parking), and there's also a free area shuttle. Front-desk staff can answer questions 24/7, and assist with tours or tickets, securing valuables, and dry cleaning/laundry. Other amenities at this beach condominium resort include 3 hot tubs, a sauna, and free WiFi in public areas.
Pool
Hot Tub
OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa

4.5 out of 5
130 Kai Malina Parkway Lahaina HI
31.87 mi from city center
$789 nightly
The price is $859 total per night
$859 total
Mar 12 - Mar 13
Total with taxes and fees
OUTRIGGER Honua Kai Resort & Spa features 4 outdoor pools, a lazy river, and a children's pool. There's free valet parking if you drive. The 24-hour front desk has staff standing by to help with tours or tickets, and answer any questions about the accommodations. Other amenities at this beach condominium resort include a gym, a terrace, and barbecue grills.
Pool
Kitchen
Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
3445 Lower Honoapiilani Hwy Lahaina HI
Free Cancellation
Reserve now, pay when you stay
31.9 mi from city center
$344 nightly
The price is $408 total per night
$408 total
Mar 8 - Mar 9
Total with taxes and fees
Guests of Aston Kaanapali Shores have access to a full-service spa, 2 outdoor pools, and a gym. Self parking is offered for USD 11.95 per day. Front-desk staff can answer questions 24/7, and assist with dry cleaning/laundry, concierge services, and luggage storage. Other amenities at this beach aparthotel include 2 hot tubs, a sauna, and outdoor tennis courts.
Pool
Hot Tub
Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014

Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014

Lahaina HI
31.96 mi from city center
$812 nightly
The price is $951 total per night
$951 total
Mar 28 - Mar 29
Total with taxes and fees
Guests of this condo enjoy features like an outdoor pool, a hot tub, and laundry facilities. Staff members can answer questions about accommodations, and also provide concierge services. Other amenities at this beach condo building include barbecue grills and a garden.
Pool
Hot Tub
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Upcountry Maui Large Group Rentals

How to Book Vacation Rentals in Upcountry Maui



🏠 What is the best price for Upcountry Maui vacation rentals?

Upcountry Maui vacation rentals range in price, starting at $308 per night.


🏠 What types of vacation rentals in Upcountry Maui can I rent?

Orbitz offers a wide range of Upcountry Maui rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Upcountry Maui condo rentals.


🏠 Is it free to cancel my Upcountry Maui vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Upcountry Maui vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Upcountry Maui. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Upcountry Maui?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Upcountry Maui apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Upcountry Maui?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Upcountry Maui package deals will get you even more savings.

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