Title: Kaupo Vacation Home Rentals from CA $496: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Kaupo](https://expedia.ca/Kaupo-Hotels.d11826.Travel-Guide-Hotels)[Vacation Rentals in Kaupo](https://expedia.ca/Kaupo-Vacation-Rentals.d11826.Travel-Guide-VacationRentals)[Things to do in Kaupo](https://expedia.ca/Things-To-Do-In-Kaupo.d11826.Travel-Guide-Activities)[Kaupo Car Rentals](https://expedia.ca/Car-Rentals-In-Kaupo.d11826.Car-Rental-Guide)[Kaupo Vacation Packages](https://expedia.ca/Kaupo.d11826.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/412ef9807c8494de27c2c701b373deea.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Tim & Nat ✈ # Kaupo Vacation Rentals - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=11826&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=11826&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=11826&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=11826&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Kaupo Vacation Homes ![Beach towels](https://images.trvl-media.com/lodging/23000000/22730000/22722300/22722218/530ff241.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/23000000/22730000/22722300/22722218/2f01dccf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22730000/22722300/22722218/55a71571.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/23000000/22730000/22722300/22722218/70f3f0eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002 Hana 9.6/10 Exceptional (403) "Very clean, excellent directions and instructions, loved the lanai, fans helped keep one comfortable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jean J. CA $244 CA $496 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Hana-Hotels-STHA-20170002-Across-From-Hana-Bay.h22722218.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/33000000/32440000/32432200/32432118/ae00579e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32440000/32432200/32432118/5a659f93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/33000000/32440000/32432200/32432118/cdc3c9df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/33000000/32440000/32432200/32432118/eea0d2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm Hana 9.8/10 Exceptional (145) "Really wonderful place! We enjoyed the space so much and its views and lush backyard " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Noah CA $490 CA $926 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Hana-Hotels-Romantic-Hana-Hideaway.h32432118.Hotel-Information) ![Beach towels](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/51ee3252.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/a42f39cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/f7f2f5f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/58ae806d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fisher's Hana Bay Hale, Across from Hana Bay Kahului 9.6/10 Exceptional (407) "Quiet location. Nice bedroom. Good instruction from host. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy M. CA $273 CA $559 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Hana-Hotels-Fishers-Hana-Bay-Hale.h22720139.Hotel-Information) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/33000000/32490000/32488600/32488569/167b0628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32490000/32488600/32488569/da2f3e3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/33000000/32490000/32488600/32488569/446450bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/33000000/32490000/32488600/32488569/bbb1f045.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b Hana 9.4/10 Exceptional (144) "We liked the flat very much. Clean, cosy, like described." ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Petra W. CA $334 CA $742 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Hana-Hotels-Beautiful-Home-In-The-Heart-Of-Hana.h32488569.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/50000000/49220000/49216300/49216296/95afb621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach towels](https://images.trvl-media.com/lodging/50000000/49220000/49216300/49216296/w1242h1242x0y483-55e80f1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, stereo](https://images.trvl-media.com/lodging/50000000/49220000/49216300/49216296/b05506bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/50000000/49220000/49216300/49216296/fff4e05a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006 Hana 9.8/10 Exceptional (76) "We had a very relaxing time at this property! Such a beautiful place. We will definitely stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth C. CA $757 CA $1,371 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Hana-Hotels-3-Bedroom-Ocean-View-Private-Home-In-Hana-PermitSUP2-20190006.h49216296.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33400000/33394500/33394402/963f0910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33400000/33394500/33394402/71d86e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/34000000/33400000/33394500/33394402/007570d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, Netflix, DVD player, books](https://images.trvl-media.com/lodging/34000000/33400000/33394500/33394402/bd738079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you! Hana 9.8/10 Exceptional (234) "Great place to stay if you are looking to get away from it all. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacques C. CA $410 CA $867 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Hana-Hotels-Special-Quiet.h33394402.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/c4332c51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/3fdca3f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/972eccb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/93574a25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16 Makawao 10/10 Exceptional (70) "There is absolutely nothing we could think of that was missing from our week at Banyon Tree! The property is beautiful, lovingly maintained, and made this our best trip to Hawaii ever!! Actually, our best-ever family vacation! Plenty of room for swimming, playing Capture the Flag, enjoying family dinners, playing card and table games, and just hanging out. We enjoyed seeing the turtles at Ho’okepa Beach, playing in the river at Íao State Park, and shopping local markets. Comfortable island... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sheridan B. CA $2,235 CA $4,449 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Makawao-Hotels-Historic-Upcountry-Maui-Property-With-Pool.h29873066.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32650000/32643100/32643004/735ba3b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/33000000/32650000/32643100/32643004/1515fb96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/33000000/32650000/32643100/32643004/fc2f57f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32650000/32643100/32643004/846341ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hana Homestead by the Beach Hana 9.8/10 Exceptional (136) "Very comfortable for a mid-sized group" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David L. CA $856 CA $1,970 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hana-Hotels-Hana-Homestead-By-The-Beach.h32643004.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17®ionId=11826&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FKaupo-Private-Vacation-Homes.d11826-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FKaupo-Private-Vacation-Homes.d11826-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Kaupo Hotel Reviews ![Fisher's Hana Bay Hale, Across from Hana Bay](//images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/51ee3252_y.jpg) ### Fisher's Hana Bay Hale, Across from Hana Bay 10/10 Excellent "Cute place. Well equipped kitchen, plenty of space. " [](https://expedia.ca/Hana-Hotels-Fishers-Hana-Bay-Hale.h22720139.Hotel-Information) ![Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002 ](//images.trvl-media.com/lodging/23000000/22730000/22722300/22722218/530ff241_y.jpg) ### Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002 10/10 Excellent "Lovely home, clean and stocked with all necessities. Quick replies from host. Spend most of our time on the adorable lanai." [](https://expedia.ca/Hana-Hotels-STHA-20170002-Across-From-Hana-Bay.h22722218.Hotel-Information) ![Exceptional Upcountry Villa with breathtaking views](//images.trvl-media.com/lodging/67000000/66180000/66179400/66179304/1435ac08_y.jpg) ### Exceptional Upcountry Villa with breathtaking views 10/10 Excellent "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 " [](https://expedia.ca/Makawao-Hotels-Luxury-Upcountry-Villa-With-Breathtaking-Views.h66179304.Hotel-Information) ![Hana-Maui Resort, a Destination by Hyatt Residence](//images.trvl-media.com/lodging/1000000/10000/1000/933/f8d26b60_y.jpg) ### Hana-Maui Resort, a Destination by Hyatt Residence 10/10 Excellent "Exceeded all expectations. And the staff was wonderful." [](https://expedia.ca/Hana-Hotels-Hana-Maui-Resort.h933.Hotel-Information) ![Oceanview Condo in Hana-Let the ocean lull you to sleep](//images.trvl-media.com/lodging/72000000/71600000/71595200/71595183/b6438d27_y.jpg) ### Oceanview Condo in Hana-Let the ocean lull you to sleep 10/10 Excellent "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!" [](https://expedia.ca/Hana-Hotels-Oceanview-Condo-In-Hana-Let-The-Ocean-Lull-You-To-Sleep.h71595183.Hotel-Information) ![Hale Akua Garden Farm & Eco-Retreat](//images.trvl-media.com/lodging/107000000/106630000/106624200/106624196/e67a8e88_y.jpg) ### Hale Akua Garden Farm & Eco-Retreat 10/10 Excellent "Perfect stay for my husband and I on our anniversary. Private, sensual, absolutely perfect" [](https://expedia.ca/Haiku-Hotels-Hale-Akua-Garden-Farm-Eco-Retreat.h106624196.Hotel-Information) ![Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views](//images.trvl-media.com/lodging/24000000/23270000/23269000/23268927/02fc15e9_y.jpg) ### Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views 10/10 Excellent "This property is such a cozy place to dial in the views and tranquility! The location is ideal for summit and upcountry places, while being easily accessed from airport. Everything is well-stocked and clean. I appreciate the thoughtful details--from lap blankets, to beach chairs, to modern conveniences, to the warm welcome of the host. I will forever cherish the memories we made here." [](https://expedia.ca/Kula-Hotels-Eco-Friendly-Modern-Home.h23268927.Hotel-Information) ![Private lush 2 Acre Mountain Home Maui w/ many amenities](//images.trvl-media.com/lodging/28000000/27130000/27128800/27128737/4158f61e_y.jpg) ### Private lush 2 Acre Mountain Home Maui w/ many amenities 10/10 Excellent "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 has space for even a large group to find quiet nooks to relax or to gather together. The location was perfect for us and our host was very attentive and communicated immediately. Love. Love love!" [](https://expedia.ca/Makawao-Hotels-Private-Lush-2-Acre-Mountain-Home-Maui-Permittedstmp-2013-0001-Many-Amenities.h27128737.Hotel-Information) ![Charming bed & breakfast on the slopes of Haleakala with AC, WiFi. ](//images.trvl-media.com/lodging/110000000/109560000/109553800/109553718/w1290h786x0y679-d85238ce_y.jpg) ### Charming bed & breakfast on the slopes of Haleakala with AC, WiFi. 10/10 Excellent "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 and helpful. The B&B was nicely decorated with unique and beautiful furniture and very clean and very organized. Everything is helpfully labeled. We would definitely consider staying here again on a return trip! " [](https://expedia.ca/Makawao-Hotels-Charming-Bed-Breakfast-On-The-Slopes-Of-Haleakala-With-AC.h109553718.Hotel-Information) ## Find out more about Kaupo ## Kaupo Vacation Homes information | Number of reviews | 1,519 | | --- | --- | | Accommodation | 41 Vacation Homes | | Lowest Price | CA $496 | | Highest Price | CA $4,449 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [3 Star Hotels in Puuiki](https://www.expedia.ca/3Star-Puuiki-Hotels.s30-0-d11829.Travel-Guide-Filter-Hotels) - [Hotels near Bamboo Forest](https://www.expedia.ca/Bamboo-Forest-Hotels.0-l553248621526965200-0.Travel-Guide-Filter-Hotels) - [Hotels near Haleakala Crater](https://www.expedia.ca/Haleakala-Crater-Hotels.0-l501684-0.Travel-Guide-Filter-Hotels) - [Hotels near Haleakala National Park](https://www.expedia.ca/Haleakala-National-Park-Hotels.0-l507525-0.Travel-Guide-Filter-Hotels) - [Hotels near Haleakalā Visitor Center](https://www.expedia.ca/Haleakala-Visitor-Center-Hotels.0-l553248621526965459-0.Travel-Guide-Filter-Hotels) - 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[Puuiki Hotels](https://www.expedia.ca/Puuiki-Hotels.d11829.Travel-Guide-Hotels) - [Resorts in Puuiki](https://www.expedia.ca/Puuiki-Resort-Hotels.d11829-aaResortHotels.Travel-Guide-Accommodation) - [Farmstay in Upcountry Maui](https://www.expedia.ca/Upcountry-Maui-Agritourism.d553248621593965869-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Upcountry Maui](https://www.expedia.ca/Upcountry-Maui-Apart-Hotels.d553248621593965869-aaApartHotels.Travel-Guide-Accommodation) - [Apartments in Upcountry Maui](https://www.expedia.ca/Upcountry-Maui-Apartments.d553248621593965869-aaApartments.Travel-Guide-Accommodation) - [B&B in Upcountry Maui](https://www.expedia.ca/Upcountry-Maui-Bed-And-Breakfast.d553248621593965869-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Upcountry Maui](https://www.expedia.ca/Upcountry-Maui-Cabins.d553248621593965869-aaCabins.Travel-Guide-Accommodation) - [Condo Rentals in Upcountry Maui](https://www.expedia.ca/Upcountry-Maui-Condos.d553248621593965869-aaCondos.Travel-Guide-Accommodation) - 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