Title: Kaupo Vacation Home Rentals : 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 [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=11826&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=11826&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=11826&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=11826&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=VACATION_HOME&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) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22730000/22722300/22722218/c11638c9.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) ![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) ### Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002 Hana 9.6/10 Exceptional (402) "We enjoyed our Stay, especially the near zu the entrance of the Volcano NP was really great." ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Katja Monika B. CA $244 CA $498 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Hana-Hotels-STHA-20170002-Across-From-Hana-Bay.h22722218.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/33000000/32490000/32488600/32488569/700bd98f.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 had a really nice stay at the Hana Bay View. The property had a really updated bathroom and good kitchen appliances. The covered deck was the best for winding down in the evening after all of our fun hiking and beach excursions! The AC in the bedrooms was a huge bonus. I highly recommend this place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ross C. CA $246 CA $625 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Hana-Hotels-Beautiful-Home-In-The-Heart-Of-Hana.h32488569.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) ![Dining](https://images.trvl-media.com/lodging/33000000/32440000/32432200/32432118/eea0d2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32440000/32432200/32432118/513057ec.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 (143) "Wonderful property and so beautiful! " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Michael CA $491 CA $927 total includes taxes & fees Oct 22 - Oct 23 [](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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/25e08687.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) ![Interior](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/f7f2f5f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fisher's Hana Bay Hale, Across from Hana Bay Kahului 9.4/10 Exceptional (406) "Wonderful property and a great place to stay in Hana" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $273 CA $559 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Hana-Hotels-Fishers-Hana-Bay-Hale.h22720139.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) ![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) ![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/w1242h1656x0y276-798b978b.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) "Phenomenal property for your stay in Hana - especially for a large group " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Logan G. CA $841 CA $1,483 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) ![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) ![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) ### Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you! Hana 9.8/10 Exceptional (231) "Overall we had a great stay in Hana. It was so nice to be able to enjoy that side of the island without rushing to drive back. There were more than a few light bulbs out and a few geckos but would still recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa E. CA $421 CA $880 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Hana-Hotels-Special-Quiet.h33394402.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/34000000/33490000/33489900/33489810/2f2699f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33490000/33489900/33489810/0f4b7dcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33490000/33489900/33489810/4a07e040.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33490000/33489900/33489810/e4c1ee89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Home in paradise! Hana 9.6/10 Exceptional (171) "Ticked all the boxes of what we were looking for. We would recommend to others " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John B. CA $491 CA $927 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Hana-Hotels-Beautiful-Home-In-Paradise.h33489810.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) ![Exterior](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/606a40d5.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) ![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) "Amazing Property!! Host was very friendly and gracious with time for checking in and out. Our whole family wish we could have stayed longer. Perfect spot for all of our activities" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carrie W. CA $2,236 CA $4,266 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) ![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) ![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) ### Hana Homestead by the Beach Hana 9.8/10 Exceptional (134) "This property is amazing! Not right on the water but great view of the ocean, can hear the ocean and 3minute walk to the beach!! Beautiful property and plenty of extras such as a jacuzzi, sauna, boogie boards, beach chairs, beach toys for the kids, and an on-site private outside shower to clean up after walking or playing in the beach. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $655 CA $1,705 total includes taxes & fees Oct 26 - Oct 27 [](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=2025-11-02&endDate=2025-11-03®ionId=11826&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&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 ## Find out more about Kaupo ## Kaupo Vacation Homes information | Number of reviews | | | --- | --- | | Accommodation | Vacation Homes | | Lowest Price | | | Highest Price | | ## 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) - 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[Farmstay in Olowalu](https://www.expedia.ca/Olowalu-Agritourism.d11584-aaAgritourism.Travel-Guide-Accommodation) - [Cabin Rentals in Olowalu](https://www.expedia.ca/Olowalu-Cabins.d11584-aaCabins.Travel-Guide-Accommodation) - [Rv Parks in Olowalu](https://www.expedia.ca/Olowalu-RV-Parks.d11584-aaRVParks.Travel-Guide-Accommodation) - [Residences in Olowalu](https://www.expedia.ca/Olowalu-Residences.d11584-aaResidences.Travel-Guide-Accommodation) - [Lgbt Friendly Hotels in Puuiki](https://www.expedia.ca/Puuiki-Hotels-LGBT-Friendly-Hotel.0-0-d11829-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [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) - [Cottages in Upcountry Maui](https://www.expedia.ca/Upcountry-Maui-Cottages.d553248621593965869-aaCottages.Travel-Guide-Accommodation) - [Guest Houses in Upcountry Maui](https://www.expedia.ca/Upcountry-Maui-Guest-Houses.d553248621593965869-aaGuestHouses.Travel-Guide-Accommodation) - [Houseboats in Upcountry Maui](https://www.expedia.ca/Upcountry-Maui-Houseboats.d553248621593965869-aaHouseboats.Travel-Guide-Accommodation) - [Inns in Upcountry Maui](https://www.expedia.ca/Upcountry-Maui-Inns.d553248621593965869-aaInns.Travel-Guide-Accommodation) - [Vacation Homes in Upcountry Maui](https://www.expedia.ca/Upcountry-Maui-Private-Vacation-Homes.d553248621593965869-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Resorts in Upcountry Maui](https://www.expedia.ca/Upcountry-Maui-Resort-Hotels.d553248621593965869-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Upcountry Maui](https://www.expedia.ca/Upcountry-Maui-Townhomes.d553248621593965869-aaTownhomes.Travel-Guide-Accommodation) - [Villas in Upcountry Maui](https://www.expedia.ca/Upcountry-Maui-Villas.d553248621593965869-aaVillas.Travel-Guide-Accommodation) - [Flights to Kipahulu](https://www.expedia.ca/Cheap-Flights-To-Kipahulu.d11827.Travel-Guide-Flights) - [Flights from Haou](https://www.expedia.ca/lp/flights/11828/flights-from-haou) - [Haleakala Crater](https://www.expedia.ca/Haleakala-Crater-Kula.d501684.Vacation-Attraction) - [Haleakala National Park](https://www.expedia.ca/Haleakala-National-Park-Hawaii.d507525.Vacation-Attraction) - [Kipahulu Visitor Center](https://www.expedia.ca/Kipahulu-Visitor-Center-Hana.d553248635998149541.Vacation-Attraction) - [Visit Kipahulu](https://www.expedia.ca/Kipahulu.dx11827) - [Ohe'o Gulch](https://www.expedia.ca/Oheo-Gulch-Hana.d553248621532639047.Vacation-Attraction) - [Palapala Hoomau Church](https://www.expedia.ca/Palapala-Hoomau-Church-Hana.d553248621532639044.Vacation-Attraction) - [Visit Puuiki](https://www.expedia.ca/Puuiki.dx11829) - [Car rentals near Haleakala National Park](https://www.expedia.ca/Car-Rentals-In-Haleakala-National-Park.d507525.Car-Rental-Guide) - [Car rentals near Hana Forest Reserve](https://www.expedia.ca/Car-Rentals-In-Hana-Forest-Reserve.d6261193.Car-Rental-Guide) - [National Car Rental Rental Cars in Kipahulu](https://www.expedia.ca/National-Car-Rental-Car-Rentals-In-Kipahulu.d11827-c42.Car-Rental-Guide-Suppliers) - [Kipahulu Vacation Rentals](https://www.expedia.ca/Kipahulu-Vacation-Rentals.d11827.Travel-Guide-VacationRentals) - [Things to do in Kipahulu](https://www.expedia.ca/Things-To-Do-In-Kipahulu.d11827.Travel-Guide-Activities) - [Book Vacation Homes in Kaupo on Expedia.com](https://www.expedia.com/Kaupo-Private-Vacation-Homes.d11826-aaPrivateVacationHomes.Travel-Guide-Accommodation)