Title: Book the Best Kissimmee WINERY Hotels in 2025 | Expedia.ca [Kissimmee Travel Guide](https://expedia.ca/Kissimmee.dx7927)[Hotels in Kissimmee](https://expedia.ca/Kissimmee-Hotels.d7927.Travel-Guide-Hotels)[Vacation Rentals in Kissimmee](https://expedia.ca/Kissimmee-Vacation-Rentals.d7927.Travel-Guide-VacationRentals)[Flights to Kissimmee](https://expedia.ca/Cheap-Flights-To-Kissimmee.d7927.Travel-Guide-Flights)[Things to do in Kissimmee](https://expedia.ca/Things-To-Do-In-Kissimmee.d7927.Travel-Guide-Activities)[Kissimmee Car Rentals](https://expedia.ca/Car-Rentals-In-Kissimmee.d7927.Car-Rental-Guide)[Kissimmee Vacation Packages](https://expedia.ca/Kissimmee.d7927.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/553000/553963-kissimmee.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Kissimmee, FL from CA $90 ![](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 Kissimmee Winery Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=7927&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=7927&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7927&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=7927&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Kissimmee Winery Hotels ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/110000000/109920000/109917500/109917441/f9ab812e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109920000/109917500/109917441/891e0f52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/110000000/109920000/109917500/109917441/fe23c7c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball](https://images.trvl-media.com/lodging/110000000/109920000/109917500/109917441/6866cf08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Disney Universal Family Villa Resort with Elevator, Pool and many amenities! Kissimmee CA $137 CA $329 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Orlando-Hotels-Disney-Universal-Family-Villa-Resort-With-Elevator.h109917441.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22000/21968/8876466a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/22000/21968/64619b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22000/21968/0c26b09c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/22000/21968/c99ccb46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maingate Lakeside Resort Kissimmee 4.4/10 (2500) "The hotel celebrated our honeymoon!! It was awesome!!" CA $45 CA $90 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Orlando-Hotels-Maingate-Lakeside-Resort.h21968.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/110000000/109920000/109917000/109916919/e3e411c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109920000/109917000/109916919/c40e14f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109920000/109917000/109916919/91196b60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109920000/109917000/109916919/8f893913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more! Kissimmee CA $125 CA $312 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Orlando-Hotels-Charming-Cottage-10-Mins-To-Disney.h109916919.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/101000000/100890000/100880500/100880482/c1c5a336.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100890000/100880500/100880482/78f5bdf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100890000/100880500/100880482/9dabe4f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/101000000/100890000/100880500/100880482/c26fd60c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SPACIOUS 1 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 1377 Kissimmee CA $100 CA $283 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Orlando-Hotels-1-BEDROOM-DISNEY-AREA-VACATION-RENTAL-IN-AWARD-WINNING-MILL-CREEK-RESORT.h100880482.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/dcad85d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/25aafbc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/3ed7040c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/c31b3466.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family-Friendly Cottage Near Orlando’s Top Attractions Kissimmee CA $126 CA $285 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-Cottage-Near-Orlandos-Top-Attractions.h117622247.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/107000000/106550000/106541000/106540941/fab0abbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106550000/106541000/106540941/170d2c74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106550000/106541000/106540941/bff90ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106550000/106541000/106540941/7830aadc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern 3BR Home Near Disney – Perfect for Families! Kissimmee CA $89 CA $517 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Orlando-Hotels-3BR-Brand-New-Townhome-Near-Disney.h106540941.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105770000/105761400/105761338/d4ab4841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105770000/105761400/105761338/f3ec38a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/106000000/105770000/105761400/105761338/c93993fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105770000/105761400/105761338/2936714a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious condo near Walt Disney parks & AdventHealth - Kissimmee Florida Kissimmee 10/10 Exceptional (1) "Wonderful location and great accommodations." CA $139 CA $348 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Orlando-Hotels-Spacious-Family-Condo-Near-Walt-Disney-World-Kissimmee-Florida.h105761338.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/118000000/117400000/117394500/117394401/86179235.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/118000000/117400000/117394500/117394401/c7d12879.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117400000/117394500/117394401/9feb5b9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117400000/117394500/117394401/398b160b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene 4BR Waterfront Home • Pool, Grill & Perfect for Families! Bellavida CA $111 CA $581 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Orlando-Hotels-4BR-Bella-Vida-Resort-Private-Pool-BBQ.h117394401.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/101000000/100470000/100463800/100463789/9f065b1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100470000/100463800/100463789/428a2712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100470000/100463800/100463789/b6e53e30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100470000/100463800/100463789/3cdad547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SPACIOUS 2 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2763 Kissimmee 9.8/10 Exceptional (6) "Cozy and perfect for what we needed. Great location." CA $112 CA $305 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Orlando-Hotels-2-BEDROOM-DISNEY-AREA-VACATION-RENTAL-IN-AWARD-WINNING-MILL-CREEK-RESORT.h100463789.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/27000000/26690000/26685200/26685198/62ea5ab9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, Netflix, DVD player, books](https://images.trvl-media.com/lodging/27000000/26690000/26685200/26685198/df8828ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/27000000/26690000/26685200/26685198/e7278a58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/27000000/26690000/26685200/26685198/c882a453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Remodeled 3/2 condo minutes to Parks, shopping and entertainment Royal Palm Bay 9.4/10 Exceptional (44) "Property owner was very responsive to any and all questions and concerns. Location was ideal for convention center but you definitely need to leave time to deal with traffic. We stayed for volleyball tournament and had a lot of early morning games. " CA $125 CA $362 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Orlando-Hotels-Remodeled-32-Condo-Minutes-To-Parks.h26685198.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=2025-10-28&endDate=2025-10-29®ionId=7927&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Kissimmee Hotel Reviews ## Explore a world of travel with Expedia - Lodging - More ways to book - [Adults Only Resorts & in Central Florida](https://www.expedia.ca/Central-Florida-Hotels-Adults-Only-Resorts.0-0-d6048177-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Central Florida](https://www.expedia.ca/Central-Florida-Hotels-Beach-Hotel.0-0-d6048177-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Central Florida](https://www.expedia.ca/Central-Florida-Hotels-Boutique-Hotel.0-0-d6048177-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Central Florida](https://www.expedia.ca/Central-Florida-Hotels-Business-Hotel.0-0-d6048177-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Central Florida](https://www.expedia.ca/Central-Florida-Hotels-Casino-Hotel.0-0-d6048177-tCasinoHotel.Travel-Guide-Filter-Hotels) - 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[Hotels with Hot Tubs in Lake Buena Vista North](https://www.expedia.ca/Lake-Buena-Vista-North-Hotels-Hotels-With-Hot-Tubs.0-0-d553248625403845610-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Lake Buena Vista North](https://www.expedia.ca/Lake-Buena-Vista-North-Hotels-Hotels-With-Indoor-Pool.0-0-d553248625403845610-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Lake Buena Vista North](https://www.expedia.ca/Lake-Buena-Vista-North-Hotels-Hotels-With-Kitchenettes.0-0-d553248625403845610-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Hotels with Waterslides in Lake Buena Vista North](https://www.expedia.ca/Lake-Buena-Vista-North-Hotels-Hotels-With-Waterslides.0-0-d553248625403845610-tHotelswithWaterslides.Travel-Guide-Filter-Hotels) - [Lake Hotels in Lake Buena Vista North](https://www.expedia.ca/Lake-Buena-Vista-North-Hotels-Lake-Hotels.0-0-d553248625403845610-tLakeHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Lake Buena Vista North](https://www.expedia.ca/Lake-Buena-Vista-North-Hotels-Luxury-Hotel.0-0-d553248625403845610-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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