Title: Book the Best Downtown Pensacola WINERY Hotels in 2025 | Expedia.ca [Vacation Rentals in Pensacola](https://expedia.ca/Pensacola-Vacation-Rentals.d6023331.Travel-Guide-VacationRentals)[Flights to Pensacola](https://expedia.ca/Cheap-Flights-To-Pensacola.d6023331.Travel-Guide-Flights)[Downtown Pensacola Car Rentals](https://expedia.ca/Car-Rentals-In-Downtown-Pensacola.d553248635976468629.Car-Rental-Guide)[Downtown Pensacola Vacations](https://expedia.ca/Downtown-Pensacola.d553248635976468629.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/498000/498469-tt-wentworth-jr-florida-state-museum.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Downtown Pensacola, FL from CA $495 ![](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 Downtown Pensacola Winery Hotels Tonight [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976468629&startDate=2025-10-24&endDate=2025-10-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976468629&startDate=2025-10-25&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976468629&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976468629&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Downtown Pensacola Winery Hotels ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76650000/76641900/76641806/de85c57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, printers](https://images.trvl-media.com/lodging/77000000/76650000/76641900/76641806/745719ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76650000/76641900/76641806/d697e27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76650000/76641900/76641806/83fbd9f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ice hockey & Baseball fans we have a place for you! Downtown Pensacola 9.2/10 Wonderful (22) "We had a wonderful stay…lots of room! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cooking Keto S. CA $301 CA $647 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Pensacola-Hotels-Walk-To-Palafox-Restaurants.h76641806.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/119000000/118840000/118833100/118833037/4288f538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/119000000/118840000/118833100/118833037/6acd39b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/119000000/118840000/118833100/118833037/4bbc3f99.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/119000000/118840000/118833100/118833037/b58b76f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Santa Rosa Dunes | Olympic Size Pool & More | My Beach Getaways Pensacola Beach CA $119 CA $843 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Pensacola-Beach-Hotels-Santa-Rosa-Dunes-Olympic-Size-Pool-More-My-Beach-Getaways.h118833037.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89840000/89833700/89833605/475dcd90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89840000/89833700/89833605/ed1fde73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89840000/89833700/89833605/df7961a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/90000000/89840000/89833700/89833605/4e3069dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet-Friendly, Luxurious Modern Home ✨5 min to Downtown✨ Southeast Pensacola 9.6/10 Exceptional (8) "The property was super clean and was very accessible for my 2 dogs. We made it our own home for a few days as I celebrated my 40th birthday." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles G. CA $203 CA $496 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pensacola-Hotels-Pet-Friendly.h89833605.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89840000/89835000/89834917/24b66b60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, travel crib, free WiFi](https://images.trvl-media.com/lodging/90000000/89840000/89835000/89834917/5460c42b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89840000/89835000/89834917/dc5df529.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89840000/89835000/89834917/b12f6f9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet-Friendly, Contemporary Home ✨5 min to Downtown✨ Southeast Pensacola 9.4/10 Exceptional (8) "We thoroughly enjoyed our stay here. The property manager was prompt and polite. The neighborhood is safe and clean, with lots of places within walking distance. The house was updated and comfortable. The mattresses were like sleeping on a cloud. We would definitely come back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cody K. CA $205 CA $495 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Pensacola-Hotels-Pet-Friendly.h89834917.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/103000000/102560000/102554100/102554077/30debfac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/103000000/102560000/102554100/102554077/518fe9c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102560000/102554100/102554077/1294be84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/103000000/102560000/102554100/102554077/2ec39c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Heated Pool | Dog Friendly | My Beach Getaways Villa Segunda 8.8/10 Excellent (8) "We loved staying at the house. The beds were so comfort" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kacie C. CA $306 CA $1,182 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Pensacola-Beach-Hotels-Private-Heated-Pool-Dog-Friendly-My-Beach-Getaways.h102554077.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/108000000/107170000/107165200/107165127/53f4b39e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107170000/107165200/107165127/b4a76983.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107170000/107165200/107165127/2cc7d0d3.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/108000000/107170000/107165200/107165127/dfb00d4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog Friendly | Saltwater Pool | Fire Pit | Beach Getaways Oak Court 9.8/10 Exceptional (22) "Definite kid friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathy S. CA $210 CA $1,140 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Pensacola-Hotels-Dog-Friendly-Saltwater-Pool-Fire-Pit-Beach-Getaways.h107165127.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/54000000/53710000/53708700/53708658/76f73e55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/54000000/53710000/53708700/53708658/4a785b59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/54000000/53710000/53708700/53708658/e944cb31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/54000000/53710000/53708700/53708658/e77f0ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Updated 2 br/2ba in Emerald Isle Villa Primera 9.8/10 Exceptional (55) "We enjoyed our first trip to the Pensacola Beach area. The condo was great and we would stay there again. Enjoyed all of the restaurants and shops within walking distance. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karma K. CA $1,010 CA $1,385 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Pensacola-Hotels-Newly-Updated-2-Br2ba-In-Emerald-Isle.h53708658.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/114000000/113330000/113329100/113329090/32c8c39c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113330000/113329100/113329090/5464ae2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/114000000/113330000/113329100/113329090/b76c71ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113330000/113329100/113329090/3035315c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Downtown Cottage 10 Mins to Pcola Beach South Pensacola 2.0/10 (1) "My family & I stayed here while driving my brother’s car down to Pensacola, hoping to make a vacation out of it. The location was great, and the pictures looked decent—but the reality was very disappointing.Upon check in, the place seemed decent but then we started noticing the floors were filthy & sticky, grease splatter on the appliances, old coffee grounds left in the coffee maker. The “curtains” were literally folded pieces of paper taped to the window-no rod, couldn’t pull them up. The... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica G. CA $359 CA $837 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Pensacola-Hotels-Cozy-Downtown-Cottage-10-Mins-To-Pcola-Beach.h113329090.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=2025-11-08&endDate=2025-11-09®ionId=553248635976468629&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Downtown Pensacola Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [5 Star Hotels in Pensacola](https://www.expedia.ca/5Star-Pensacola-Hotels.s50-0-d6023331.Travel-Guide-Filter-Hotels) - [Aparthotels in Brent](https://www.expedia.ca/Brent-Apart-Hotels.d553248635975871623-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Brent](https://www.expedia.ca/Brent-Bed-And-Breakfast.d553248635975871623-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels & Resorts for Couples in Destin](https://www.expedia.ca/Destin-Hotels-Couples-Resorts-Hotels.0-0-d6906-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in Destin](https://www.expedia.ca/Destin-Hotels-Hotels-With-Childcare.0-0-d6906-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - 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[Bayview Dog Beach Park](https://www.expedia.ca/Bayview-Dog-Beach-Park-Southeast-Pensacola.d553248621561885451.Vacation-Attraction) - [Brent Athletic Park](https://www.expedia.ca/Brent-Athletic-Park-Northwest-Pensacola.d553248621558033332.Vacation-Attraction) - [Visit Escambia County](https://www.expedia.ca/Escambia-County.dx553248635976433617) - [Historic Pensacola Village](https://www.expedia.ca/Historic-Pensacola-Village-Downtown-Pensacola.d6063677.Vacation-Attraction) - [Visit East Pensacola Heights](https://www.expedia.ca/Pensacola-East-Pensacola-Heights.dx553248635976477162) - [Visit Old East Hill](https://www.expedia.ca/Pensacola-Old-East-Hill.dx553248635976475054) - [Pensacola Vacations](https://www.expedia.ca/Pensacola.d6023331.Destination-Travel-Guides) - [Visit Pensacola](https://www.expedia.ca/Pensacola.dx6023331) - [Seville Square](https://www.expedia.ca/Seville-Square-Seville-Historic-District.d553248621557934532.Vacation-Attraction) - [Budget Rental Cars in Pensacola](https://www.expedia.ca/Budget-Car-Rentals-In-Pensacola.d6023331-c39.Car-Rental-Guide-Suppliers) - 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