On the back side of Haleakala crater is Kaupo, the drive is spectacular and quite different from the rest of the island. the ocean to one side and the volcano on the other. Take it slow and enjoy the drive. #GoldenHour

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B&B in Kaupo

"Very nice property. It was easy to communicate with the host. The room was very cozy and had everything we needed for our stay. Perfect end to the road to Hāna. Thank you!"

$265 nightly

Aug 13 - Aug 14

Total includes taxes and fees

"Charming decorations and immaculately clean. Tasty fresh fruit, bread, milk, and yogurt provided by the host. Couldn't recommend this place more. "

$355 nightly

Aug 11 - Aug 12

Total includes taxes and fees

"All the comforts of home in a tropical paradise."

$397 nightly

Aug 10 - Aug 11

Total includes taxes and fees

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Top Kaupo Hotel Reviews

Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

10/10 Excellent

"This villa is beautiful and we highly recommend. Charlene and Celestine were exceptional hosts. Gave us tons of information on places to dine and things to do. The neighborhood is quiet, the property is actually a working farm. It was lovely for a quiet place to rest, but reasonably close to the airport. We all enjoyed staying there and would do it again."

Hana-Maui Resort, a Destination by Hyatt Residence

10/10 Excellent

"My husband and I stayed at the Hana Maui resort for our honeymoon. We stayed for 10 nights, which we were quickly told by locals is much longer than most people tend to stay in Hāna. We are so glad that we did! This resort is beautiful, clean, and perfect for anyone who enjoys a quiet stay. Upon checking in we were given a free upgrade without even asking! Staff are very kind and helpful, and they have golf carts available to drive you between locations at the resort. We would highly recommend trying the water journey at the spa! "

Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

10/10 Excellent

"The property is a dream. Large house with separate entries for the walk out basement and upstairs units, perfect for two families to share. We loved the views, the fruit trees (particularly the lychees and mangoes) and my daughter was obsessed with the neighbour's goats who kept sneaking into our yard. The Eddie Tam park next door is huge and beautiful, great for sunset walks. We always stay in upcountry when we visit Maui, as we like the quiet and cooler temperatures, and central location on the island. The house had everything we needed - beach towels, sand toys, beach chairs and umbrella, small kitchen appliances, and a ton of washers and dryers so everyone could do laundry at the same time. The only negative was that the bathroom in the basement smelled awful. It was something we were able to tolerate but would reconsider staying in the basement if the problem isnt rectified. The owner was super responsive during our stay and also said she'd fix the bathroom issue. Overall we loved the place and we have wonderful memories from our visit. We look forward to returning. "

Breath taking ocean and volcano views! Pool,Close to beaches and everything else

10/10 Excellent

"We came to Maui to celebrate my 60th birthday with our three adult children who live in different parts of the country and world. We just wanted a place to relax and spent time together as a family as we don't have that very often. This home was perfect! It was very clean and we felt very comfortable there. The beds and furniture are all comfortable. The kitchen is very well stocked - we really enjoyed all the outdoor drink and serveware! The pool is exquisite. There is a hot tub as well, but we spent much of our time in the pool. There is plenty of outdoor furniture to relax in and eat at. The fire pit was also very nice and we used the built in bbq to make dinner. We did spend some time sightseeing but I feel like most of our time was spent at the house, as we loved it so much! We met the owner's son who was very pleasant and eager to answer all of our questions. The owners are very communicative and welcoming. Everything is better than you see in the pictures! "

Hawaiian Cottage and Personal Paradise /BBKM 2013/0004

10/10 Excellent

"Auntie Kali's cottage is magical. Plain and simple. I knew it would be special just looking at the pictures, but even those can't capture just how wonderful it is. It is a private oasis; we found it hard to leave and explore Maui on any given day! Of course the pool is incredible, and we enjoyed using the grill and fire pit to make s'mores. The home is so incredibly comfortable, with quite literally anything you could possibly need to make your stay perfect. We arrived to an abundance of fruit (some grown right on the property!), homemade banana bread, and such wonderful hospitality from Carrie, the owner. It is located close to beaches, shopping, and restaurants, but when you're behind those doors, it is as if you are far, far away in your own special resort that is 100% yours! There is no doubt...this place is very special. "

Fisher's Hana Bay Hale, Across from Hana Bay

10/10 Excellent

"Check-in was easy, home was fun to stay and prepare our meals. At first we were concerned upon arrival as the home doesn’t have air conditioning. The home cooled down after opening windows & doors. Two fans, plus a ceiling fan kept us comfortable at night. There is a general store nearby which was helpful. Sunrise was beautiful and we enjoyed the walk to the beach from this home. Recommend staying here and thank you to our host and owner."

Exceptional Upcountry Villa with breathtaking views

10/10 Excellent

"We had the most amazing experience in Hawaii and was mostly due to where we stayed! David and Dawn were the most amazing hosts! Very responsive and helpful with restaurants, things to do and made our stay very comfortable! This place was perfect for our family of 5 and the views - stunning!! We plan to come back and know exactly where we would stay!! "

Hotel Wailea, Relais & Chateaux - Adults Only

10/10 Excellent

"It was an amazing boutique resort the property is beautiful and very relaxing a different vibe from the other Wailea resorts the staff is great and the amenities are nice including the shuttles to anywhere in the Wailea area. Definitely would come back and say if you get a chance to check it out loved our suite"

Find out more about Kaupo

Kaupo B&B information

Number of reviews	129
Accommodation	4 B&B
Lowest Price	$309
Highest Price	$462

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Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Kaupo?

Prices for B&Bs in Kaupo often vary, but you can find a great deal from $309 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Kaupo B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.

When is the best time to book a Bed & Breakfast in Kaupo?

The best time to book a B&B in Kaupo is during the peak season, which runs from January to March. This period is particularly attractive for travelers looking to experience the natural beauty of Maui, as the weather is typically warm and inviting, with temperatures ranging from the mid-60s to mid-80s Fahrenheit. Visitors can indulge in a variety of outdoor activities, such as hiking the lush trails of Haleakalā National Park or exploring the nearby stunning beaches, superb for swimming and sunbathing.

With January and February being the most popular months, you'll find that the vibrant atmosphere is complemented by an abundance of festivals and events celebrating Hawaiian culture. The scenery is undeniably picturesque, making it an ideal time for photography enthusiasts to capture Kaupo's breathtaking landscapes.

For those considering a more budget-friendly option, June is an excellent time to visit. While it's outside of the peak season, June still offers lovely weather and an opportunity to enjoy quieter attractions without the crowds. This month is superb for those who appreciate a relaxed pace and still want to explore the beauty of the island.

What is the difference between a Kaupo Bed & Breakfast and a hotel?

Every Kaupo B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Kaupo B&Bs.

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Book Kaupo Bed & Breakfast

Upfront pricing

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B&B in Kaupo

Hana Garden Room 1 & 2 night stays, its Perfect! Longer stays available.

Charming bed & breakfast on the slopes of Haleakala with AC, WiFi.

Haleakala Sunrise Home, Kula, Maui, Hawaii

Relaxing upcountry retreat on the slopes of Haleakalā. Ideal for families.

Top Kaupo Hotel Reviews

Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

Hana-Maui Resort, a Destination by Hyatt Residence

Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

Breath taking ocean and volcano views! Pool,Close to beaches and everything else

Hawaiian Cottage and Personal Paradise /BBKM 2013/0004

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Fisher's Hana Bay Hale, Across from Hana Bay

Exceptional Upcountry Villa with breathtaking views

Hotel Wailea, Relais & Chateaux - Adults Only

Find out more about Kaupo

Kaupo B&B information

Explore a world of travel with Expedia

Frequently asked questions