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) ![Moment Open](https://images.trvl-media.com/place/7927/b63b8a82-d8e7-4936-9033-5b5daf0dfa65.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 [27 Nov - 28 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=7927&startDate=2025-11-27&endDate=2025-11-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [28 Nov - 29 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=7927&startDate=2025-11-28&endDate=2025-11-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [28 Nov - 30 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=7927&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [5 Dec - 7 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=7927&startDate=2025-12-05&endDate=2025-12-07&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) ![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) ![2 outdoor pools, pool umbrellas, pool 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 (2504) "I had a very great stay everyone was absolutely nice and very well mannered and my room was amazing very clean and spacious." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sirya £45 includes taxes & fees 22 Dec - 23 Dec [](https://www.expedia.co.uk/Orlando-Hotels-Maingate-Lakeside-Resort.h21968.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/122000000/121740000/121733800/121733762/9cfc6887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/122000000/121740000/121733800/121733762/5ebb4f84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/122000000/121740000/121733800/121733762/ddba817c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121740000/121733800/121733762/fe3fdbf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful 3BR Family Condo ✧ Minutes to Disney – Caribe Cove Resort! Kissimmee £296 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Orlando-Hotels-Peaceful-3BR-Family-Condo-Minutes-To-Disney-Caribe-Cove-Resort.h121733762.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/122000000/121930000/121924300/121924285/a9a63d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/122000000/121930000/121924300/121924285/6603be6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/122000000/121930000/121924300/121924285/056c3e23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel cot, free WiFi](https://images.trvl-media.com/lodging/122000000/121930000/121924300/121924285/46d7bd72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bella Vida 4BR Townhouse w/Private Pool, BBQ & Themed Rooms ☆ close to Disney! Bellavida £341 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Orlando-Hotels-Bella-Vida-4BR-Townhouse-WPrivate-Pool.h121924285.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/122000000/121930000/121924300/121924284/89242869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/122000000/121930000/121924300/121924284/9c9ba056.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/122000000/121930000/121924300/121924284/fc490e5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/122000000/121930000/121924300/121924284/9972e795.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family-Friendly 4BR Townhome Near Disney – Private Pool, BBQ & Themed Rooms! Bellavida £338 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Orlando-Hotels-Family-Friendly-4BR-Townhome-Near-Disney-Private-Pool.h121924284.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/123000000/122130000/122121400/122121338/5ee430e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/123000000/122130000/122121400/122121338/b6b4d0c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122130000/122121400/122121338/e3a5804c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122130000/122121400/122121338/d78e5f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Enchanting 6BR Lakefront Villa Near Disney • Private Pool, BBQ & Much more! Kissimmee £370 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Orlando-Hotels-Enchanting-6BR-Lakefront-Villa-Near-Disney-Private-Pool.h122121338.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) ![Dining](https://images.trvl-media.com/lodging/110000000/109920000/109917500/109917441/fe23c7c6.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) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109920000/109917500/109917441/891e0f52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Disney Universal Family Villa Resort with Elevator, Pool and many amenities! Kissimmee £175 includes taxes & fees 9 Dec - 10 Dec [](https://www.expedia.co.uk/Orlando-Hotels-Disney-Universal-Family-Villa-Resort-With-Elevator.h109917441.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70290000/70286400/70286316/fe821527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/71000000/70290000/70286400/70286316/994d0a0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/71000000/70290000/70286400/70286316/6cc6586b_edited_e804.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/71000000/70290000/70286400/70286316/676c3433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect Place for a Perfect Vacation Kissimmee 10/10 Exceptional (1) £148 includes taxes & fees 5 Dec - 6 Dec [](https://www.expedia.co.uk/Orlando-Hotels-Perfect-Place-For-A-Perfect-Vacation.h70286316.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) ![Sports court](https://images.trvl-media.com/lodging/101000000/100890000/100880500/100880482/c26fd60c.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) ![Games room](https://images.trvl-media.com/lodging/101000000/100890000/100880500/100880482/c45a063b.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 £156 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Orlando-Hotels-1-BEDROOM-DISNEY-AREA-VACATION-RENTAL-IN-AWARD-WINNING-MILL-CREEK-RESORT.h100880482.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/95000000/94950000/94949600/94949516/24fec395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/95000000/94950000/94949600/94949516/990a1f3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/95000000/94950000/94949600/94949516/8f1240d6.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/95000000/94950000/94949600/94949516/60338bac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Remodeled Studio by Disney-Resort- New Listing Reunion £174 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Orlando-Hotels-Remodeled-Studio-By-Disney-Resort-New-Listing.h94949516.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112340000/112332800/112332774/34f15ac8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112340000/112332800/112332774/7c0d787d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports court](https://images.trvl-media.com/lodging/113000000/112340000/112332800/112332774/0f29506b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, ping pong](https://images.trvl-media.com/lodging/113000000/112340000/112332800/112332774/0515f855.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pool + Tennis/B-Ball Courts + Game Room + Mins to Disney! Indian Wells £217 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Orlando-Hotels-Spacious-Family-Retreat-In-Kissimmee.h112332774.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=2025-12-11&endDate=2025-12-12®ionId=7927&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_FR-DE-MX-UK_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Save up to 40% on select hotels. [Book now](https://expedia.co.uk/cheap-deals?rfrr=AFFINITY_BF_PROMO_7927) ## 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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[Boutique Hotels in International Drive](https://www.expedia.co.uk/International-Drive-South-Hotels-Boutique-Hotel.0-0-d553248625403852984-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in International Drive](https://www.expedia.co.uk/International-Drive-South-Hotels-Business-Hotel.0-0-d553248625403852984-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Historic Hotels in International Drive](https://www.expedia.co.uk/International-Drive-South-Hotels-Historic-Hotel.0-0-d553248625403852984-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels Suites in International Drive](https://www.expedia.co.uk/International-Drive-South-Hotels-Hotel-Suites.0-0-d553248625403852984-thotelsuites.Travel-Guide-Filter-Hotels) - [Hotels with Breakfast in International Drive](https://www.expedia.co.uk/International-Drive-South-Hotels-Hotel-With-Breakfast.0-0-d553248625403852984-thotelwithbreakfast.Travel-Guide-Filter-Hotels) - [Hotels with Connecting Rooms in International Drive](https://www.expedia.co.uk/International-Drive-South-Hotels-Hotel-With-Connecting-Rooms.0-0-d553248625403852984-thotelwithconnectingrooms.Travel-Guide-Filter-Hotels) - [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)