Title: TOP Winery Hotels in Kissimmee, FL for 2025 | Expedia.co.uk [Kissimmee Travel Guide](https://expedia.co.uk/Kissimmee.dx7927)[Hotels in Kissimmee](https://expedia.co.uk/Kissimmee-Hotels.d7927.Travel-Guide-Hotels)[Holiday Rentals in Kissimmee](https://expedia.co.uk/Kissimmee-Holiday-Rentals.d7927.Travel-Guide-HolidayRentals)[Flights to Kissimmee](https://expedia.co.uk/Cheap-Flights-To-Kissimmee.d7927.Travel-Guide-Flights)[Things to do in Kissimmee](https://expedia.co.uk/Things-To-Do-In-Kissimmee.d7927.Travel-Guide-Activities)[Kissimmee Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Kissimmee.d7927.Car-Hire-Guide)[Kissimmee Holidays](https://expedia.co.uk/Kissimmee.d7927.Holidays-City-Breaks) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/553000/553963-kissimmee.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Winery Hotels in Kissimmee ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ![](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 [12 Oct - 13 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=7927&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [13 Oct - 14 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=7927&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [17 Oct - 19 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=7927&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [24 Oct - 26 Oct](https://www.expedia.co.uk/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 ![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) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/30000/22000/21968/6baee961.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) ### Maingate Lakeside Resort Kissimmee 4.4/10 (2493) "The hotel celebrated our honeymoon!! It was awesome!!" £48 includes taxes & fees 13 Oct - 14 Oct [](https://www.expedia.co.uk/Orlando-Hotels-Maingate-Lakeside-Resort.h21968.Hotel-Information) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109920000/109917500/109917441/cf74ec85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table football](https://images.trvl-media.com/lodging/110000000/109920000/109917500/109917441/6866cf08.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) ### Disney Universal Family Villa Resort with Elevator, Pool and many amenities! Kissimmee £180 includes taxes & fees 15 Oct - 16 Oct [](https://www.expedia.co.uk/Orlando-Hotels-Disney-Universal-Family-Villa-Resort-With-Elevator.h109917441.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) ![Smart TV, books](https://images.trvl-media.com/lodging/107000000/106550000/106541000/106540941/8641b9e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern 3BR Home Near Disney – Perfect for Families! Kissimmee £292 includes taxes & fees 13 Oct - 14 Oct [](https://www.expedia.co.uk/Orlando-Hotels-3BR-Brand-New-Townhome-Near-Disney.h106540941.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95690000/95687000/95686986/de63850d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95690000/95687000/95686986/10c8d10b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/96000000/95690000/95687000/95686986/d072900f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95690000/95687000/95686986/9dfd9fdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private 4 BDR Oasis in Kissimmee with Pool | BBQ Kissimmee [](https://www.expedia.co.uk/Orlando-Hotels-Private-4-BDR-Oasis-In-Kissimmee-With-Pool-BBQ.h95686986.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) ![Games room](https://images.trvl-media.com/lodging/101000000/100890000/100880500/100880482/c45a063b.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) ![Exterior](https://images.trvl-media.com/lodging/101000000/100890000/100880500/100880482/78f5bdf6.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 £161 includes taxes & fees 9 Nov - 10 Nov [](https://www.expedia.co.uk/Orlando-Hotels-1-BEDROOM-DISNEY-AREA-VACATION-RENTAL-IN-AWARD-WINNING-MILL-CREEK-RESORT.h100880482.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) ![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/c40e14f1.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 £170 includes taxes & fees 19 Oct - 20 Oct [](https://www.expedia.co.uk/Orlando-Hotels-Charming-Cottage-10-Mins-To-Disney.h109916919.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) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/3ed7040c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/948252d4.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) ### Family-Friendly Cottage Near Orlando’s Top Attractions Kissimmee £156 includes taxes & fees 12 Nov - 13 Nov [](https://www.expedia.co.uk/Orlando-Hotels-Family-Friendly-Cottage-Near-Orlandos-Top-Attractions.h117622247.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) ![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) ![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) ### Spacious condo near Walt Disney parks & AdventHealth - Kissimmee Florida Kissimmee 10/10 Exceptional (1) "Wonderful location and great accommodations." £189 includes taxes & fees 14 Oct - 15 Oct [](https://www.expedia.co.uk/Orlando-Hotels-Spacious-Family-Condo-Near-Walt-Disney-World-Kissimmee-Florida.h105761338.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/120000000/119830000/119822700/119822691/bb77415d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119830000/119822700/119822691/15cdf82f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/120000000/119830000/119822700/119822691/764767b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119830000/119822700/119822691/2f29b937.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wonderful apartment 10 minutes from Disney Kissimmee £212 includes taxes & fees 27 Oct - 28 Oct [](https://www.expedia.co.uk/Orlando-Hotels-Vrbo-Property.h119822691.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/110000000/109550000/109547200/109547155/49ff9093.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109550000/109547200/109547155/c0ae896b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109550000/109547200/109547155/bdba3121.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/110000000/109550000/109547200/109547155/a1628393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family-Friendly 3BR Getaway Minutes from Disney Kissimmee £308 includes taxes & fees 20 Oct - 21 Oct [](https://www.expedia.co.uk/Orlando-Hotels-3-Bedroom-Townhome-Close-To-Disney.h109547155.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.co.uk/Hotel-Search?startDate=2025-10-26&endDate=2025-10-27®ionId=7927&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Kissimmee Hotel Reviews ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - More ways to book - [Gay-Friendly Hotels in Celebration](https://www.expedia.co.uk/Celebration-Hotels-Gay-Friendly-Hotel.0-0-d602896-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Hotels with Breakfast in Celebration](https://www.expedia.co.uk/Celebration-Hotels-Hotel-With-Breakfast.0-0-d602896-thotelwithbreakfast.Travel-Guide-Filter-Hotels) - [Hotels with Gym in Celebration](https://www.expedia.co.uk/Celebration-Hotels-Hotel-With-Gym.0-0-d602896-thotelwithgym.Travel-Guide-Filter-Hotels) - [Lakeside Hotels in Celebration](https://www.expedia.co.uk/Celebration-Hotels-Lakeside-Hotel.0-0-d602896-tlakesidehotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Celebration](https://www.expedia.co.uk/Celebration-Hotels-Pet-Friendly-Hotel.0-0-d602896-tPetFriendlyHotel.Travel-Guide-Filter-Hotels) - 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[Hotels with Early Check-in in International Drive](https://www.expedia.co.uk/International-Drive-South-Hotels-Hotel-With-Early-Check-In.0-0-d553248625403852984-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with Entertainment in International Drive](https://www.expedia.co.uk/International-Drive-South-Hotels-Hotel-With-Entertainment.0-0-d553248625403852984-thotelwithentertainment.Travel-Guide-Filter-Hotels) - [Hotels with Parking in International Drive](https://www.expedia.co.uk/International-Drive-South-Hotels-Hotel-With-Free-Parking.0-0-d553248625403852984-thotelwithfreeparking.Travel-Guide-Filter-Hotels) - [Hotels with Gym in International Drive](https://www.expedia.co.uk/International-Drive-South-Hotels-Hotel-With-Gym.0-0-d553248625403852984-thotelwithgym.Travel-Guide-Filter-Hotels) - [Hotels with Parking in International Drive](https://www.expedia.co.uk/International-Drive-South-Hotels-Hotel-With-Parking.0-0-d553248625403852984-thotelwithparking.Travel-Guide-Filter-Hotels) - [Hotels with Balcony in International Drive](https://www.expedia.co.uk/International-Drive-South-Hotels-Hotels-With-Balcony.0-0-d553248625403852984-tHotelswithBalcony.Travel-Guide-Filter-Hotels) - [Hotels with Pool in International Drive](https://www.expedia.co.uk/International-Drive-South-Hotels-Hotels-With-Pool.0-0-d553248625403852984-tHotelswithPool.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in International Drive](https://www.expedia.co.uk/International-Drive-South-Hotels-Hotels-With-Smoking-Rooms.0-0-d553248625403852984-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Hotels with Waterslides in International Drive](https://www.expedia.co.uk/International-Drive-South-Hotels-Hotels-With-Waterslides.0-0-d553248625403852984-tHotelswithWaterslides.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in International Drive](https://www.expedia.co.uk/International-Drive-South-Hotels-Pet-Friendly-Hotel.0-0-d553248625403852984-tPetFriendlyHotel.Travel-Guide-Filter-Hotels) - [Hotels with Waterpark in International Drive South](https://www.expedia.co.uk/International-Drive-South-Hotels-Waterpark-Hotel.0-0-d553248625403852984-twaterparkhotel.Travel-Guide-Filter-Hotels) - [Hotels near Kissimmee Gateway](https://www.expedia.co.uk/Kissimmee-Gateway-Airport-Hotels.0-aISM-0.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Magic Landings](https://www.expedia.co.uk/Magic-Landings-Orlando-Hotels-Gay-Friendly-Hotel.0-n553248635976481189-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Montego Bay](https://www.expedia.co.uk/Montego-Bay-Orlando-Hotels-Gay-Friendly-Hotel.0-n553248635976472896-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Green Hotels in Orlando](https://www.expedia.co.uk/Orlando-Hotels-Green-Sustainable.0-0-d178294-tGreenSustainable.Travel-Guide-Filter-Hotels) - [Historic Hotels in Orlando](https://www.expedia.co.uk/Orlando-Hotels-Historic-Hotel.0-0-d178294-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with Babysitting Services in Orlando](https://www.expedia.co.uk/Orlando-Hotels-Hotel-With-Babysitting-Services.0-0-d178294-thotelwithbabysittingservices.Travel-Guide-Filter-Hotels) - 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[Car hire near Historic Downtown Kissimmee](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Historic-Downtown-Kissimmee.d800089.Car-Hire-Guide) - [Rental cars Kissimmee Gateway airport](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Kissimmee-Gateway.d6028687.Car-Hire-Guide) - [Book Winery Hotels in Kissimmee on Expedia.com](https://www.expedia.com/Kissimmee-Hotels-Winery-Hotel.0-0-d7927-tWineryHotel.Travel-Guide-Filter-Hotels)