Title: Book the Best Southeast 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)[Southeast Pensacola Car Rentals](https://expedia.ca/Car-Rentals-In-Southeast-Pensacola.d553248635976472746.Car-Rental-Guide)[Southeast Pensacola Vacations](https://expedia.ca/Southeast-Pensacola.d553248635976472746.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/a58fefda928b9b8b45afa388e31d287b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Cody Trimm # Find Winery Hotels in Southeast Pensacola, FL from CA $398 - ![](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 Southeast Pensacola Winery Hotels Tonight [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976472746&startDate=2025-11-04&endDate=2025-11-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=553248635976472746&startDate=2025-11-05&endDate=2025-11-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976472746&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=553248635976472746&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Southeast Pensacola Winery Hotels ![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) ![Smart TV, books](https://images.trvl-media.com/lodging/90000000/89840000/89833700/89833605/46fce65e.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 $165 CA $448 total includes taxes & fees Nov 6 - Nov 7 [](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) ![Interior](https://images.trvl-media.com/lodging/90000000/89840000/89835000/89834917/b12f6f9d.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) ![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) ### Pet-Friendly, Contemporary Home ✨5 min to Downtown✨ Southeast Pensacola 9.4/10 Exceptional (8) "Super clean and beautifully decorated. Back bedroom bed was very comfortable. Great having a washer and dryer. Every amenity like home. Would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gerald T. CA $128 CA $398 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Pensacola-Hotels-Pet-Friendly.h89834917.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/105000000/104060000/104055100/104055095/w904h683x60y0-d4ec182e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, computer monitors](https://images.trvl-media.com/lodging/105000000/104060000/104055100/104055095/f15fbacc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104060000/104055100/104055095/cd80c824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/105000000/104060000/104055100/104055095/2596fe05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Home 4mil to Beach • Fenced Yard•Full Kitchen & Grill• Easy 14-Day Cancel Navarre 10/10 Exceptional (3) "We enjoyed our stay so much that we actually extended our trip! Very pleasant, clean and comfortable house with all needed amenities. Great location, very close to the beach. The owners made communication simple and were lovely to deal with. We loved our stay and would return the next time we're in Navarre. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy W. CA $164 CA $553 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Navarre-Hotels-New-Host-Special-Newly-Renovated-House-By-Navarre-Beach.h104055095.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99280000/99271200/99271136/08a6b0f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, music library, offices](https://images.trvl-media.com/lodging/100000000/99280000/99271200/99271136/7a70fe48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99280000/99271200/99271136/93c2cbb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, music library, offices](https://images.trvl-media.com/lodging/100000000/99280000/99271200/99271136/f490d3bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super Fun Family Bungalow - Hot Tub - Yard Games - Seasonal Cowboy pool Pensacola 10/10 Exceptional (8) "We had a wonderful and comfortable stay ! So cute !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Murphy C. [](https://www.expedia.ca/Pensacola-Hotels-Hip-Mermaid-House-King-Bed-Close-To-Beaches-And-Downtown-Snowbirds-Welcome.h99271136.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) ![Exterior](https://images.trvl-media.com/lodging/119000000/118840000/118833100/118833037/dfec6ad5.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) ![Beach nearby](https://images.trvl-media.com/lodging/119000000/118840000/118833100/118833037/6acd39b4.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 $782 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Pensacola-Beach-Hotels-Santa-Rosa-Dunes-Olympic-Size-Pool-More-My-Beach-Getaways.h118833037.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) ![Interior](https://images.trvl-media.com/lodging/108000000/107170000/107165200/107165127/21bf602d.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) ### Dog Friendly | Saltwater Pool | Fire Pit | Beach Getaways Oak Court 9.8/10 Exceptional (22) "Beautiful house that was well equipped with everything you needed. Beds were super comfy. Enjoyed the pool and house was located in good area. Maintenance responded to any issues we had." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Phoebe W. CA $210 CA $1,142 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Pensacola-Hotels-Dog-Friendly-Saltwater-Pool-Fire-Pit-Beach-Getaways.h107165127.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) ![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/103000000/102560000/102554100/102554077/518fe9c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102560000/102554100/102554077/616fda94.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 really enjoyed our stay. The pool was great, I loved the backyard. The house had everything we needed. We could drive over to the beach entrance and park or let people out and walk straight down to the beach. Be sure to call and have your 2 chairs and umbrella set up for each day, that was really nice.My only complaint is that the fitted sheet on the king size beds would not stay on, they need a bigger sheet. Other than that I couldn’t ask for more!Also I took 3 of my granddaughters to an... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mrs.Kimberly B. CA $308 CA $1,182 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Pensacola-Beach-Hotels-Private-Heated-Pool-Dog-Friendly-My-Beach-Getaways.h102554077.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105770000/105769400/105769326/a4bf8115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/106000000/105770000/105769400/105769326/792cef32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/106000000/105770000/105769400/105769326/c3b55bce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105770000/105769400/105769326/3cfaa653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunshine Oasis | Private Pool | Dog-Friendly | My Beach Getaways Gulf Breeze 8.2/10 Very good (31) "The size of the house was great for us. Loved the fenced in backyard with the large pool." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jamie H. CA $307 CA $1,199 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Pensacola-Beach-Hotels-Private-Pool-Hot-Tub-3-BR-2-BA-Sunshine-Oasis-Pensacola-Beach.h105769326.Hotel-Information) ![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) ![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) ![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) ### 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 $641 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Pensacola-Hotels-Walk-To-Palafox-Restaurants.h76641806.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) ![TV](https://images.trvl-media.com/lodging/54000000/53710000/53708700/53708658/e944cb31.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/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) "The condo was perfect for our family vacation to Pensacola. The location was perfect, the rooms were well appointed and the kitchen had everything we needed. Great place ti stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Don C. CA $910 CA $1,290 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Pensacola-Hotels-Newly-Updated-2-Br2ba-In-Emerald-Isle.h53708658.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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