Haleakala Vacation Rentals
Haleakala vacation rentals offer peaceful stays in Maui's Upcountry, minutes from sunrise hikes and scenic trails at Haleakala National Park. Choose from rustic cabins, private cottages, and cozy condos with panoramic mountain views, ideal for nature lovers and quiet getaways.
Escape to the cool, quiet elevations of Upcountry Maui with vacation rentals near Haleakala National Park. These accommodations place you closer to one of Hawaii's most unforgettable experiences: watching the sunrise from Haleakala's 10,000-foot summit. Whether you're planning a sunrise hike, stargazing adventure, or exploring the lush landscapes of Kula and Makawao, these rentals offer the perfect base.
Haleakala rentals range from rustic mountain-view cabins and charming plantation-style cottages to modern condos with lanai views. Many feature full kitchens, private lanais, and easy access to hiking trails like Sliding Sands and Hosmer Grove. You'll also find working farms and peaceful retreats ideal for couples, solo travelers, and adventure seekers.
Looking to explore more of Maui? These rentals are within easy reach of Maui beaches, Paia Town, and Road to Hana adventures.
Key Features of Haleakala Rentals
- Cabins, cottages & condos near Haleakala summit
- Ideal for sunrise viewing & hiking access
- Cooler Upcountry climate & scenic vistas
- Nearby towns: Kula, Makawao, Pukalani
- Private lanais, fireplaces & full kitchens
- Stargazing, forest trails & nature-focused retreats
For a quiet mountain escape close to Maui's most majestic volcano, Haleakala vacation rentals are the perfect base.
Live Like a North Shore Local~Walk To Coffee/Store, near Road to Hana, Haleakala
This is it, your peaceful home on the North Shore of Maui, within walking distance to the local coffee shop, small grocery and near the Road to Hana and Haleakala. IMPORTANT: NO LAUNDRY ACCESS - VRBO has a glitch on my property and is showing this amenity but it is not...
OCEANFRONT CONDO with STYLE, COMFORT, & AMAZING VIEWS of OCEAN & HALEAKALA
Ocean Views from the Lanai, are so awesome, you may never want to leave the condo! Everyday brings a one-of -a kind Sunrise over Haleakala. Everyday, turtles feed among the gentle waves of our private beach, which is steps away. During whale season watch the Humpback...
Fantastic 4th Floor Views of Ocean, Pool & Haleakala
Rates for the days of Sept. 8th- 19th 2025 have been reduced because the pool, hot tub, sauna and pool deck will be closed for yearly maintenance. IF you have been hearing on the news that Short Term Rentals on Maui might be phased out beginning in 2025, NO WORRIES...
View whales from modern Top floor Oceanfront condo. Maalaea, Haleakala sunrise!!
Recently remodeled. New everything! New flooring throughout. New Beautiful Hawaiian Bedroom King set with a firm Beauty-rest mattress bed with custom closets. New A/C. This place is great for honeymooners with the ocean making waves every night.To get your attention...
★Jump Start the road to Hana at Haleakala Cottage-PRIVATE HOT TUB +ACESS TO POOL
Welcome to Haleakala Cottage at Huelo Point Lookout, your ideal starting point for a Hawaiian adventure, especially if you're planning to explore the iconic Road to Hana. Our cozy cottage on Maui's unspoiled north shore is surrounded by lush gardens and organic...
Ocean, Greenbelt and Haleakala view Ekahi 33E
Ekahi 33E offers a rare setting with views of the ocean, Ekahi's greenbelt and Haleakala. In Ekahi's lower village it's a short walk to the main pool and Keawakapu Beach. Renovation completed Jan 2020 & new to the rental market, 33E is exceptionally well furnished,...
Maui Stunning Prime Ocean Front View of the Bay and Haleakala! *Maalaea Kai 212*
Enjoy this 2nd floor unit featuring gorgeous views throughout the unit of Maalaea Bay, the grand volcano Haleakala and the sparkling Kihei lights at night. The unit is tastefully decorated with the spirit of Aloha and has a portable a/c unit in the bedroom to keep you...
Maui, island of the Haleakala Volcano is the heart chakra of the earth
Kapalua's history began in 1836 with Dr. Dwight Baldwin's royal land grant, evolving from an agricultural area (Honolua Ranch/Plantation) to a luxury resort, now known for its golf courses, beaches, and upscale amenitiesKapalua simply is 'A Place Of Life', perfectly...
Bed and Breakfast on the Slopes of Haleakala
Enjoy bed and breakfast on the mountain in a tranquil contemporary designed guest-suite with private entrance and patio garden in a friendly and local neighborhood where a unique experience awaits you on the slopes of Maui’s Haleakala Mountain.Within walking distance...
Quaint COTTAGE ~ Walk To Coffee shop, nearby Road to Hana & Haleakala
This is it, your quaint and nicely decorated Haiku Surf Cottage on the North shore of Maui.SUMMARY: Walk out the back gate to the coffee cafe or small local grocery store. Enjoy the outdoor shower, semi-private yard with a surfboard fence and murals and outdoor covered...
Haleakala Shores A-302 - Stunning Ocean Views, Beautiful Renovation, Wi-Fi, & AC
Indulge in the ultimate Maui escape at Haleakala Shores A-302, a meticulously appointed two-bedroom, two-bath ocean-view condo nestled within the coveted A Building of the Haleakala Shores complex. Immerse yourself in luxury and comfort with a newly remodeled, fully...
Maui Kamaole #J-204 Large 2 bedroom 2 bath, Partial Ocean & Haleakala Views
Maui Kamaole #J-204 is an upstairs 2 Bedroom 2 Bath ocean view condo. Equipped with a full kitchen, Cable TV/DVD, complimentary high speed Wi-Fi, a washer/dryer, and lovely partial ocean view and views of Haleakala. Maui Kamaole #J-204 is air-conditioned (wall units)...
Haleakala Shores A-301 - Golden Sand Beaches, Ocean Views, Sleeps 6, Split AC!
You cannot get closer to the beach in South Kihei for this rate. This corner, front row unit features expansive ocean views from the living room and lanai, and just across the street awaits one of the most beautiful beaches in all of the islands -- Kamaole III....
LUANA MOANA SIGNATURE OCEANFRONT MAUI-Ocean&Haleakala Views-FreeWiFi-A/C-Romance
Luana Moana's Lanai is 50 ft from Maui Ocean in Maalaea Bay with 180 degree views of the Ocean. Relish in the Trade Winds blowing through your Hair and the warmth of the Sun against your skin. You will See Life All Around You. When You have entered Luana Moana: You have...
Haleakala Sunrise Home, Kula, Maui, Hawaii
This is a large, two story house with the owners living in part. You have a private entrance, one bedroom and full, private bathroom plus decks front and back. Located at 2600 ft elevation on the west slope of Haleakala, this is a quiet neighborhood with great views of...
Remodeled Maui Sunset Condo A409, Super Ocean View & Mt Haleakala
********************************************************************************************************* THE CONDO OWNERS WILL REQUIRE FROM ALL OUR GUESTS, a signed copy of their rental agreement. It will be provided upon reservation acceptance and a signed copy must...
Haleakala Shores B509: Spacious Top Floor Unit with Stunning Maui Views!
Haleakala Shores B509 offers views of the beautiful Maui waters, West Maui mountains, and Haleakala! Your perfect Maui getaway starts here in this spacious top floor unit at Haleakala Shores! Enjoy the open feel with vaulted ceilings and large windows in every room.As...
Haleakala Shores B205~ Spacious 2 bedroom, 2 bath, across from Kamaole III
Haleakala Shores- Relaxing two bedroom, two bath condo - just across the street from Kamaole Beach Park III and easy walking to shops and restaurants. Features a queen size bed in the master and two twin beds in second bedroom. Each bedroom has an en suite bathroom....
Redesigned 1BD/2BA condo with Haleakala views, near Wailea's beaches + dining
Grand Champions 136 is situated in a lush tropical setting. This 1 bedroom / 2 bathroom is located on the top floor with wonderful views of Haleakala. This condo is newly redesigned and furnished. It is the perfect setting for couples and small families. Its convenient...
Cozy room with beach access, Haleakala sunrise view, pool & amazing location
Island Surf 601AOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy spectacular sunrises over Haleakala volcano from the window of this private, sixth-floor room. Grab the provided...
Royal Mauian 601: Stroll to Shops, Dining, & Witness Haleakalā's Majesty!
Highly cleaned and sanitized for your vacation. Ask about our AlohaSafeStay program. If you have a stay that qualifies for housekeeping services, traditional housekeeping service will be performed every 7th day. This includes refreshing the condo and exchanging bed...
Haleakala Shores A403: Spacious 2-Bed/2-Bath Condo with Mountain and Water Views
Haleakala Shores A403 offers a great location with peeks of the water and West Maui mountains. This 2-bedroom/2-bath condo is perfect for families or couples traveling together. It's spacious, open, and inviting with vaulted ceilings. Enjoy dining or your favorite...
Kihei Akahi C-507: Ocean & Haleakala Views from 1BR/1BA Condo in South Maui
This property is hotel zoned, and not being affected by the recent proposed legislation.Welcome to our condo in popular south Maui at the Kihei Akahi Resort! This beautifully landscaped property, with ocean, island, and volcano views along with a perfect location is a...
Haleakala Shores A309 | 2 Bed, 2 Bath
Two couples can enjoy a perfect Maui getaway at Haleakala Shores A-309, with two bedrooms and bathrooms, there’s plenty of space. Want to play on the beach -- You’re only a block from the turquoise waters of the Pacific Ocean! Want to experience tasty local cuisine?...
Relaxing upcountry retreat on the slopes of Haleakalā. Ideal for families.
After a hot day at the beach, relax at Ke Kīhāpai Bed & Breakfast at the 2400 foot elevation with unobstructed views of our dormant volcano, Haleakalā. Breathe the fresh air with an upcountry view of town, the north shore of Maui and Kahālāwai (West Maui...
Walk to Charley Young Beach - 2BR/2BA Kihei Condo w/ Pool, AC & Haleakalā View
Our 2BR/2BA condo is perfect for families and groups. With split AC in every room, memory foam toppers on both queen beds, and plenty of space to relax, it’s a true Maui home base. • Primary Suite: Queen bed, walk-in closet, private bathroom • Second Bedroom:...