Title: Book the Best Vacation Village WINERY Hotels in 2025 | Expedia.ca [Vacation Rentals in Clermont](https://expedia.ca/Clermont-Vacation-Rentals.d7484.Travel-Guide-VacationRentals)[Flights to Clermont](https://expedia.ca/Cheap-Flights-To-Clermont.d7484.Travel-Guide-Flights)[Things to do in Clermont](https://expedia.ca/Things-To-Do-In-Clermont.d7484.Travel-Guide-Activities)[Vacation Village Car Rentals](https://expedia.ca/Car-Rentals-In-Vacation-Village.d553248635976472555.Car-Rental-Guide)[Vacation Village Vacations](https://expedia.ca/Vacation-Village.d553248635976472555.Destination-Travel-Guides) ![Lake Louisa State Park in the Fall in Clermont, a suburb of Orlando, Florida](https://images.trvl-media.com/place/553248635976472555/341bc3af-1486-4a76-965f-d330f9ae982c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Vacation Village, FL from CA $79 - ![](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 Vacation Village Winery Hotels Tonight [Nov 7 - Nov 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976472555&startDate=2025-11-07&endDate=2025-11-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 8 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976472555&startDate=2025-11-08&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976472555&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976472555&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Vacation Village Winery Hotels ![A heated pool](https://images.trvl-media.com/lodging/96000000/95110000/95108600/95108600/6b2125d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95110000/95108600/95108600/fb9c009d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/96000000/95110000/95108600/95108600/7cb09555.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/96000000/95110000/95108600/95108600/1acd73a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage-Pvt lake & pool access Near Disney w/porch Vacation Village 10/10 Exceptional (3) "I had employees working in the area who required lodging for 3 weeks. Amanda was great and easy to communicate with." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly B. CA $138 CA $482 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Clermont-Hotels-Cottage-Pvt-Lake-Pool-Access-Near-Disney-Wporch.h95108600.Hotel-Information) ![Smart TV, offices](https://images.trvl-media.com/lodging/96000000/95110000/95108600/95108591/7091da7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/96000000/95110000/95108600/95108591/w1430h912x4y7-1f9f0ce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95110000/95108600/95108591/62f91f86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95110000/95108600/95108591/a94c5d58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hook's Cabin- Lake & Pool near Disney A-frame Vacation Village 9.6/10 Exceptional (4) "Great location, very clean, and nicely decorated! The piil was closed for for a day, otherwise very satisfied. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leah F. CA $184 CA $545 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Clermont-Hotels-Relax-At-Hooks-Cabin-A-Frame-Lake-Louisa-Gated-Community-With-Pool-Near-Disney.h95108591.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/96000000/95110000/95108600/95108582/e6bc50f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/96000000/95110000/95108600/95108582/e70b12eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/96000000/95110000/95108600/95108582/9a431d60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/96000000/95110000/95108600/95108582/7a173069.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pumba's Place - FUN, Lake, Pool- NO Cleaning fees! Vacation Village 10/10 Exceptional (6) "We've rented several properties at Vacation Village. This unit is our absolute favorite. The hostess is ALWAYS super friendly & accommodating. This is a fantastic property for families with children." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Valerie L. CA $231 CA $464 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Clermont-Hotels-Pumbas-Place.h95108582.Hotel-Information) ![Outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/9a8a6f4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/08ef9167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/9512806c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/bf6ad209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Orlando at Flamingo Crossings Bay Lake 9.2/10 Wonderful (4872) "Very good place to stay." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Deval CA $146 CA $164 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Orlando-Hotels-Home2-Suites-By-Hilton-Orlando-Flamingo-Crossings.h58072517.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) ![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 (2485) "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 CA $51 CA $79 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Orlando-Hotels-Maingate-Lakeside-Resort.h21968.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236661/f518be97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236661/020e0b81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236661/dbc7ef18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236661/f7e25bdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites By Hilton Winter Garden Winter Garden 9.4/10 Exceptional (341) "Great hotel, grea" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michele CA $172 CA $194 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Winter-Garden-Hotels-Home2-Suites-By-Hilton-Winter-Garden.h102236661.Hotel-Information) ![Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/290000/281600/281522/271998df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/290000/281600/281522/7d2d1e3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/290000/281600/281522/4ff22d19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/290000/281600/281522/5ff401aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Orlando-International Drive/Convention Center International Drive District 8.4/10 Very good (1001) "Clean room and staff was friendly!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daija CA $122 CA $137 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Orlando-Hotels-Homewood-Suites-By-Hilton-Orlando-Intl-DriveConvention-Ctr.h281522.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/108000000/107130000/107122900/107122821/w2223h1482x0y93-820df345.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107130000/107122900/107122821/w2224h1482x0y93-9e10205f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/108000000/107130000/107122900/107122821/w2208h1480x8y0-606826f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107130000/107122900/107122821/ddabbab8_edited_42e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### FamilyFun: 4BR 3.5BA Townhouse near Disney Regal Palms 10/10 Exceptional (1) "Wow! What an amazing trip we had. The home was impeccable and communication with the hostess was instant! Where to start….The community is very clean and well maintained. Upon check in (which is easy) you receive parking tags and bracelets that you use for the pool and to get in and out of the gate. We just kept one in the car for that reason. We had three cars and they fit but you do have to park them like a T shape, 2 cars is really ideal but it is possible. If you have dogs, it’s a great spot... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer H. CA $146 CA $501 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Orlando-Hotels-Cozy-4-Bedroom-Townhome-In-Pleasant-Davenport-With-WiFi.h107122821.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114360000/114351000/114350903/9a30d0fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114360000/114351000/114350903/3a5b36d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/115000000/114360000/114351000/114350903/e44e1e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114360000/114351000/114350903/990ff193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private pool~Lazy River~Near Disney~Resort~Pool Table Kissimmee 9.4/10 Exceptional (6) "We had a wonderful stay at this VRBO property! The house was exactly as advertised—clean, spacious, and well stocked with supplies and kitchenware. The location was perfect for easy access to the theme parks and shopping. My whole family loved it, and we will definitely rent from these hosts again. They were very responsive and made sure we had everything we needed. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deidre M. CA $130 CA $895 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Orlando-Hotels-Private-PoolLazy-RiverNear-DisneyResortPool-Table.h114350903.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/96000000/95040000/95031200/95031190/171d03e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/96000000/95040000/95031200/95031190/d32257a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/96000000/95040000/95031200/95031190/16836968.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95040000/95031200/95031190/02517759.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Close to Disney and Universal! Family-sized condo with pool, balcony & game room Orlando 9.0/10 Wonderful (6) "If you love Star Wars and even if you don’t :) this place does not disappoint!!! Very clean and comfortable and plenty of room for the 5 of us. The Star Wars theme was a huge hit with my guys and the outlets directly next store that my daughter and I could walk to and shop all day was amazing! Communication was quick and when our key cards would not open the gym door, we had new ones within 30 minutes brought directly to us so we could get our work outs in. Loved the huge pool and deck side... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alex B. CA $141 CA $580 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Orlando-Hotels-Close-To-Disney-And-Universal-Family-Sized-Condo-With-Pool.h95031190.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. 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