Book Hotels in Kaupo, HI

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Top Kaupo hotels

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

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

Makawao
$2,730 nightly
The price is $3,175 total per night from Nov 17 to Nov 18
$3,175 total
Nov 17 - Nov 18
Total with taxes and fees
This vacation home features an outdoor pool and a hot tub. A terrace, a garden, and a picnic area are also on offer.
Rooms were clean. Timely response by host.Couple of times locked ourself out of our rooms. Host showed up in minutes and had them unlocked for us. Kitchen was clean and spacious for a group of 13 adults.Plenty of fans provided. Air conditioning in the bedrooms would have made this a luxurious place ...

Reviewed on Oct 1, 2025

Opens in a new windowHistoric Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Exceptional Upcountry Villa with breathtaking views

Exceptional Upcountry Villa with breathtaking views

Makawao
This vacation home features an outdoor pool and a hot tub. Enjoy the sauna and conveniences like a garden and laundry facilities.
Incredible stay! Off the grid and an amazing view of the whole island. Everything was clean and organized and the pool and Hot tub and sauna combo made it feel like I was down at the resorts except with my own peace and serenity. Would come again

Reviewed on Oct 20, 2025

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Opens in a new windowExceptional Upcountry Villa with breathtaking views
Private lush 2 Acre Mountain Home Maui w/ many amenities

Private lush 2 Acre Mountain Home Maui w/ many amenities

Makawao
This vacation home features a garden, a living plant wall, and laundry facilities. Barbecue grills are provided for your convenience.
I've never stayed at such an amazing property. The description simply doesn't tell you all of the wonderful perks, from a gourmet's dream kitchen with everything you could possibly needs, the view out the back porch while you have coffee or wine, to the supply of beach items available. The house ...

Reviewed on Oct 8, 2025

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Opens in a new windowPrivate lush 2 Acre Mountain Home Maui w/ many amenities
Spacious Beautifully Updated Condo, Large Lanai, Near Wailea Beaches

Spacious Beautifully Updated Condo, Large Lanai, Near Wailea Beaches

Kihei
A hot tub is featured at this condo, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Loved the location and quality of the space! Everything worked well and for the price it's perfect! Will stay here again for sure!

Reviewed on Sep 19, 2025

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Opens in a new windowSpacious Beautifully Updated Condo, Large Lanai, Near Wailea Beaches
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
555 Kaukahi Street, Kihei, HI
Fully refundableReserve now, pay when you stay
$1,042 nightly
The price is $1,229 total per night from Nov 4 to Nov 5
$1,229 total
Nov 4 - Nov 5
Total with taxes and fees
This luxury resort includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the business center, laundry service, and valet ...
This place. So special. The crème de la creme. 5+stars. Cannot WAIT to go back!

Reviewed on Sep 23, 2025

Opens in a new windowHotel Wailea, Relais & Chateaux - Adults Only
Oceanview Condo in Hana-Let the ocean lull you to sleep

Oceanview Condo in Hana-Let the ocean lull you to sleep

Hana
$341 nightly
The price is $397 total per night from Oct 31 to Nov 1
$397 total
Oct 31 - Nov 1
Total with taxes and fees
This apartment features a garden, laundry facilities, and barbecue grills.
This condo has a great view of the black sand beach and easy access down to it. It’s very clean and nice looking. It’s a perfect place for two. Loren was available to answer any questions we had and it’s an easy place to get to. I highly recommend it!

Reviewed on Oct 18, 2025

Opens in a new windowOceanview Condo in Hana-Let the ocean lull you to sleep
Hana-Maui Resort, a Destination by Hyatt Residence

Hana-Maui Resort, a Destination by Hyatt Residence

4 out of 5
5031 Hana Hwy, Hana, HI
Fully refundableReserve now, pay when you stay
$469 nightly
The price is $553 total per night from Nov 25 to Nov 26
$553 total
Nov 25 - Nov 26
Total with taxes and fees
This resort features a full-service spa, 2 outdoor pools, and a restaurant. Families will appreciate the mini golf and onsite laundry facilities. Enjoy the gym ...
Exceeded all expectations. And the staff was wonderful.

Reviewed on Oct 20, 2025

Opens in a new windowHana-Maui Resort, a Destination by Hyatt Residence
Charming bed & breakfast on the slopes of Haleakala with AC, WiFi.

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

Makawao
$357 nightly
The price is $415 total per night from Oct 28 to Oct 29
$415 total
Oct 28 - Oct 29
Total with taxes and fees
Book a stay at this golf B&B in Makawao. Enjoy air conditioning. Popular attractions Pukalani Country Club and Maui Spa Retreat are located nearby.
Excellent location for visiting Haleakala NP. The drive for a sunrise reservation was not difficult at all and was fairly close. It was also easy to get down into town to the Target and other stores but was nicely located in a residential neighborhood on the slopes in Up Country. The host was communicative ...

Reviewed on Oct 6, 2025

Opens in a new windowCharming bed & breakfast on the slopes of Haleakala with AC, WiFi.
Wailea Ekolu - CoralTree Residence Collection

Wailea Ekolu - CoralTree Residence Collection

3.5 out of 5
10 Wailea Ekolu Place, Kihei, HI
This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a picnic area, and dry cleaning are also on offer.
It’s a great place to Stay for the family vacation.

Reviewed on Aug 22, 2025

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Opens in a new windowWailea Ekolu - CoralTree Residence Collection
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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.

Frequently asked questions

What are the top kid-friendly hotels in Kaupo?
Family vacations are where amazing memories are made, but it's no secret that traveling with children can be stressful. These kid-friendly Kaupo hotels offer perks designed to keep adventurers of all ages relaxed and happy: Hana Ocean Palms Bungalow will help make your next trip the most memorable one yet. It features a host of conveniences aimed at families, such as a nearby beach and animal viewing activities. Breathtaking Oceanfront Location, Gorgeous Views, Stroll to Hamoa Beach, Hot Tub is another top pick. After a long day of exploring, come back home to your cozy room and perks like a nearby beach and a swimming pool.
Where can I find cheap hotels in Kaupo?
At Travelocity you'll find really nice hotels in Kaupo at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Kaupo rather than in Kaupo. We may find you even better rates, too.
How do I find the best Kaupo hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Kaupo then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Kaupo?
The cheapest hotel in Kaupo is $397. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Kaupo?
There are 150 hotels in Kaupo on Travelocity.
What are the best hotels in Kaupo?
Kaupo has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Kaupo for you!
When is the best time to visit Kaupo?
If you want the joy of a fun-filled trip in peak season, visit Kaupo during February, March and April. If you'd prefer the peace of off-season, book a stay during quieter months, such as October, November and December.
When is the cheapest time to stay in Kaupo?
Based on historic data is usually the cheapest month to visit Kaupo. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Kaupo?
There are multiple hotels in Kaupo that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Kaupo. We have plenty of kid-friendly hotels in Kaupo to choose from on Travelocity!
Why book a hotel in Kaupo through Travelocity?
Because we have the top hotels in Kaupo! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Kaupo on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Kaupo hotel reviews by fellow wanderers

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

5 out of 5
Posted 6 days ago
Travelocity Verified Review
"Lovely home, clean and stocked with all necessities. Quick replies from host. Spend most of our time on the adorable lanai."
A verified traveler stayed at Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

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