Title: Book the Best Kailua WINERY Hotels in 2026 | Expedia.ca [Kailua Travel Guide](https://expedia.ca/Kailua.dx183151)[Hotels in Kailua](https://expedia.ca/Kailua-Hotels.d183151.Travel-Guide-Hotels)[Vacation Rentals in Kailua](https://expedia.ca/Kailua-Vacation-Rentals.d183151.Travel-Guide-VacationRentals)[Flights to Kailua](https://expedia.ca/Cheap-Flights-To-Kailua.d183151.Travel-Guide-Flights)[Things to do in Kailua](https://expedia.ca/Things-To-Do-In-Kailua.d183151.Travel-Guide-Activities)[Kailua Car Rentals](https://expedia.ca/Car-Rentals-In-Kailua.d183151.Car-Rental-Guide)[Kailua Vacation Packages](https://expedia.ca/Kailua.d183151.Destination-Travel-Guides) ![I have photographed the beautiful Lanikai Beach from so many angles, but sunrise is by far my favorite. Before anybody shows up on the beach, when the sea is calm and cotton candy colors dance across a clouded sky. I snapped this photo of my best friend taking a photo. #panorama #lanikai #beaches #lifeatexpedia #sunrise](https://images.trvl-media.com/place/183151/9c7f26bf-0c4c-476a-b85b-af4b460da07a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Lisa A Schmidt # Find Winery Hotels in Kailua, HI from CA $532 - ![](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 availability on Kailua Winery Hotels Tonight [Dec 16 - Dec 17](https://www.expedia.ca/Hotel-Search?regionId=183151&startDate=2025-12-16&endDate=2025-12-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 17 - Dec 18](https://www.expedia.ca/Hotel-Search?regionId=183151&startDate=2025-12-17&endDate=2025-12-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=183151&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=183151&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Kailua hotels with winery ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/45000000/44060000/44050500/44050416/70358899.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/45000000/44060000/44050500/44050416/8a038d41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/45000000/44060000/44050500/44050416/02bfd628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/45000000/44060000/44050500/44050416/a8b533c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1-bedroom apartment just 5minutes walk to Ala Moana Center [](https://www.expedia.ca/Honolulu-Hotels-1-Bedroom-Apartment-Just-11-Minutes-Walk-To-Ala-Moana-Center.h44050416.Hotel-Information) Waikiki 9.8/10 Exceptional (27) "Clean room, good location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CHING FEN CA $186 CA $612 total includes taxes & fees Jan 10 - Jan 11, 2026 [](https://www.expedia.ca/Honolulu-Hotels-1-Bedroom-Apartment-Just-11-Minutes-Walk-To-Ala-Moana-Center.h44050416.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/91000000/90560000/90559200/90559180/0a46ce7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90560000/90559200/90559180/c094cad7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/90560000/90559200/90559180/124a671b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/91000000/90560000/90559200/90559180/bffb2db4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### All Access! | Pool + Fitness Center [](https://www.expedia.ca/Honolulu-Hotels-All-Access-Pool-Fitness-Center.h90559180.Hotel-Information) Waikiki 8.6/10 Excellent (4) "Great Location, good value, responsive owners." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen A. CA $342 CA $745 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Honolulu-Hotels-All-Access-Pool-Fitness-Center.h90559180.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/116000000/115080000/115077000/115076949/06a2cc5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/116000000/115080000/115077000/115076949/d30cb757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/116000000/115080000/115077000/115076949/393ba18e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115080000/115077000/115076949/4432ce24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renovated Waikiki Suite, Walk to Beach + Parking [](https://www.expedia.ca/Honolulu-Hotels-Renovated-Waikiki-Suite.h115076949.Hotel-Information) Waikiki 8.0/10 Very good (1) "I loved that parking came with the VRBO. I have stayed at Waikiki many times and it is nice to be in a central location and not having to pay for parking. It was in a safe area and there is lots to do. There was a small issue that the property manager gave us the wrong internet code but they worked with us to help us troubleshoot to find out the problem. It was resolved within 24 hours. They accidently gave us the wrong information but corrected it. There was construction going on right... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lila R. CA $217 CA $706 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Honolulu-Hotels-Renovated-Waikiki-Suite.h115076949.Hotel-Information) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/108000000/107720000/107713900/107713895/w1277h850x3y3-e6d98847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107720000/107713900/107713895/63090755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/108000000/107720000/107713900/107713895/c9720105.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games](https://images.trvl-media.com/lodging/108000000/107720000/107713900/107713895/w1277h850x3y3-75ab6b77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luana Waikiki Oceanview High Floor Condo [](https://www.expedia.ca/Honolulu-Hotels-Luana-Waikiki-Oceanview-High-Floor-Condo.h107713895.Hotel-Information) Waikiki 6.0/10 (1) CA $198 CA $544 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Honolulu-Hotels-Luana-Waikiki-Oceanview-High-Floor-Condo.h107713895.Hotel-Information) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120360000/120352300/120352276/dca11c99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120360000/120352300/120352276/72d29733.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Stovetop, cookware/dishes/utensils](https://images.trvl-media.com/lodging/121000000/120360000/120352300/120352276/5b5db966.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120360000/120352300/120352276/2db3fd80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW Studio with 2 Queen Beds in Waikiki [](https://www.expedia.ca/Honolulu-Hotels-NEW-Studio-With-2-Queen-Beds-In-Waikiki.h120352276.Hotel-Information) Waikiki CA $231 CA $532 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Honolulu-Hotels-NEW-Studio-With-2-Queen-Beds-In-Waikiki.h120352276.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19420000/19417600/19417586/a9ba3f6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/20000000/19420000/19417600/19417586/5c255223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/20000000/19420000/19417600/19417586/3b5cd86c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/20000000/19420000/19417600/19417586/fbd2012a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### High Rise Deluxe Ocean View Free Parking/Wifi in Waikiki 3204 [](https://www.expedia.ca/Honolulu-Hotels-High-Rise-Deluxe-Ocean-View-Free-ParkingWifi-In-Waikiki-3204.h19417586.Hotel-Information) Waikiki 9.4/10 Exceptional (69) "Quiet location, clean, onlocation with free security parking, convenient location close to everything, and all we needed for our 4 day stay before going on a 7 day islands cruise. We were pleased and this particular place had 1 king and 1 queen bed plus a pull out so there would be plenty of room for a family. Loved the evening lights and could not have been pleased anymore than we were. Thank you for making it a vacation to remember." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $337 CA $875 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Honolulu-Hotels-High-Rise-Deluxe-Ocean-View-Free-ParkingWifi-In-Waikiki-3204.h19417586.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/112000000/111760000/111758300/111758271/e9ded46f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/112000000/111760000/111758300/111758271/w5474h3648x3y0-2de5ba75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111760000/111758300/111758271/fb1aac8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/112000000/111760000/111758300/111758271/b94fc995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Remodeled Ocean View Steps to Waikiki Beach [](https://www.expedia.ca/Honolulu-Hotels-Diamond-Head-Ocean-View-Stay-W-Free-Parking.h111758271.Hotel-Information) Waikiki 10/10 Exceptional (1) "This unit was very clean and the views from the windows and lanai are amazing. Short walk to the beach. The unit is also equipped with beach chairs and all other items in the kitchen and bathroom. Communication with the host was timely. The staff was very helpful and kind! We appreciated the option for a late checkout. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Irene C. CA $282 CA $777 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Honolulu-Hotels-Diamond-Head-Ocean-View-Stay-W-Free-Parking.h111758271.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/74000000/73640000/73632000/73631916/0358641a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73640000/73632000/73631916/ac1c5cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/74000000/73640000/73632000/73631916/633c410e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/74000000/73640000/73632000/73631916/b8c550cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lovely condo at Waikiki beach 2 Bedrooms & 2 Baths, with 1 free parking space. [](https://www.expedia.ca/Honolulu-Hotels-Lovely-Condo-At-Waikiki-Beach-2-Beds-2-Bath-With-Free-Parking.h73631916.Hotel-Information) Waikiki 9.6/10 Exceptional (28) "Nice condo in great a location. AC was cold, water was pressure good, beds were comfortable and the owner was responsive. Eazy check in and out. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric M. CA $843 CA $1,578 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Honolulu-Hotels-Lovely-Condo-At-Waikiki-Beach-2-Beds-2-Bath-With-Free-Parking.h73631916.Hotel-Information) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/20000000/19400000/19394300/19394275/397c6999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/20000000/19400000/19394300/19394275/fc98e5b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19400000/19394300/19394275/cdf835e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player](https://images.trvl-media.com/lodging/20000000/19400000/19394300/19394275/bb7d9f97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### High Rise Deluxe Ocean View Free Parking/Wifi in Waikiki 3106 [](https://www.expedia.ca/Honolulu-Hotels-High-Rise-Deluxe-Ocean-View-Free-ParkingWifi-In-Waikiki-3106.h19394275.Hotel-Information) Waikiki 9.2/10 Wonderful (66) "Nice place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thai CA $337 CA $877 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Honolulu-Hotels-High-Rise-Deluxe-Ocean-View-Free-ParkingWifi-In-Waikiki-3106.h19394275.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=2025-12-31&endDate=2026-01-01®ionId=183151&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Kailua Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - More ways to book - [Adults Only Resorts & in Coconut Grove ](https://www.expedia.ca/Coconut-Grove-Kailua-Hotels-Adults-Only-Resorts.0-n553248635976481454-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Coconut Grove ](https://www.expedia.ca/Coconut-Grove-Kailua-Hotels-Beach-Hotel.0-n553248635976481454-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Coconut Grove ](https://www.expedia.ca/Coconut-Grove-Kailua-Hotels-Boutique-Hotel.0-n553248635976481454-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Coconut Grove ](https://www.expedia.ca/Coconut-Grove-Kailua-Hotels-Cheap-Hotels.0-n553248635976481454-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Coconut Grove ](https://www.expedia.ca/Coconut-Grove-Kailua-Hotels-Hotels-With-Free-Parking.0-n553248635976481454-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - 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