Title: Book the Best Englewood South WINERY Hotels in 2026 | Expedia.ca [Vacation Rentals in Englewood](https://expedia.ca/Englewood-Vacation-Rentals.d7839.Travel-Guide-VacationRentals)[Flights to Englewood](https://expedia.ca/Cheap-Flights-To-Englewood.d7839.Travel-Guide-Flights)[Things to do in Englewood](https://expedia.ca/Things-To-Do-In-Englewood.d7839.Travel-Guide-Activities)[Englewood South Car Rentals](https://expedia.ca/Car-Rentals-In-Englewood-South.d553248635976471930.Car-Rental-Guide)[Englewood South Vacations](https://expedia.ca/Englewood-South.d553248635976471930.Destination-Travel-Guides) ![Parking lot at Blind Pass beach on Manasota Key in Englewood. Tourists cars in front of ocean beach with soft white sand in Florida. Popular vacation spot at sunset](https://images.trvl-media.com/place/553248635976471930/54c59b74-93fd-435f-898d-1f04ba2e7c57.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Englewood South, FL from CA $445 - ![](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 Englewood South Winery Hotels Tonight [Dec 30 - Dec 31](https://www.expedia.ca/Hotel-Search?regionId=553248635976471930&startDate=2025-12-30&endDate=2025-12-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 31 - Jan 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976471930&startDate=2025-12-31&endDate=2026-01-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976471930&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976471930&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Englewood South hotels with winery ![Property grounds](https://images.trvl-media.com/lodging/91000000/90950000/90941200/90941170/cc7b55fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90950000/90941200/90941170/8fd731b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90950000/90941200/90941170/dea0fba8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/91000000/90950000/90941200/90941170/e0a0c7e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palm-lined waterfront retreat with enclosed pool, inviting patio, & central AC [](https://www.expedia.ca/Rotonda-West-Hotels-Palm-Lined-Waterfront-Retreat-W-Enclosed-Pool.h90941170.Hotel-Information) Pebble Beach 9.2/10 Wonderful (5) "We had an amazing time. Would definately come back!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia V. CA $180 CA $804 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Rotonda-West-Hotels-Palm-Lined-Waterfront-Retreat-W-Enclosed-Pool.h90941170.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76590000/76584800/76584797/5bfa2b25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/77000000/76590000/76584800/76584797/a2cd42a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76590000/76584800/76584797/224f0e2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76590000/76584800/76584797/4c4d818f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Turtle Cay at The Beach Shack! Come On Down! [](https://www.expedia.ca/Englewood-Hotels-Turtle-Cay-At-The-Beach-Shack-Come-On-Down.h76584797.Hotel-Information) Manasota Key 10/10 Exceptional (43) "This was such a cute place to stay rhat is conveniently located via walking diatance to the beach and local restaurants. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Renay S. CA $199 CA $450 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Englewood-Hotels-Turtle-Cay-At-The-Beach-Shack-Come-On-Down.h76584797.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/57000000/56840000/56833500/56833487/2473d6b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/57000000/56840000/56833500/56833487/396ffa8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/57000000/56840000/56833500/56833487/abcbeb48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/57000000/56840000/56833500/56833487/f4d7dece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Flamingo's Nest at the Beach Shack. Just one block from the beach! [](https://www.expedia.ca/Englewood-Hotels-Flamingos-Nest-At-The-Beach-Shack-Just-One-Block-From-The-Beach.h56833487.Hotel-Information) Manasota Key 10/10 Exceptional (40) "Location was great, property condition is excellent!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mabel CA $196 CA $445 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Englewood-Hotels-Flamingos-Nest-At-The-Beach-Shack-Just-One-Block-From-The-Beach.h56833487.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/45000000/44350000/44343900/44343827/1cb07875.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/45000000/44350000/44343900/44343827/18a5bd92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/45000000/44350000/44343900/44343827/a77faa00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/45000000/44350000/44343900/44343827/ffd86bd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heated Pool Oasis • 3BR Family Escape w/ Fire Pit & Near Beaches! [](https://www.expedia.ca/Englewood-Hotels-New-Listing-Englewood-Retreat.h44343827.Hotel-Information) Englewood East 8.8/10 Excellent (5) "Everything was clean and beautiful at this property! The owner was very responsive to my messages and answered all of my questions right away. I will definitely rent this property again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa S. CA $191 CA $751 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Englewood-Hotels-New-Listing-Englewood-Retreat.h44343827.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76590000/76584800/76584800/3a125d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/77000000/76590000/76584800/76584800/e60f8ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76590000/76584800/76584800/edb2ba1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/77000000/76590000/76584800/76584800/2d646a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seashell Shanty at The Beach Shack! Come On Down! [](https://www.expedia.ca/Englewood-Hotels-Seashell-Shanty-At-The-Beach-Shack-Come-On-Down.h76584800.Hotel-Information) Manasota Key 10/10 Exceptional (43) "We had a wonderful experience. We 100% recommend this property and hosts. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christian S. [](https://www.expedia.ca/Englewood-Hotels-Seashell-Shanty-At-The-Beach-Shack-Come-On-Down.h76584800.Hotel-Information) ![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/107000000/106200000/106198700/106198627/b9465af5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106200000/106198700/106198627/w1179h1565x0y0-61ec8ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/107000000/106200000/106198700/106198627/c229aff3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/107000000/106200000/106198700/106198627/e74385d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Retreat 4 BR, 3 BA screened & heated pool, gorgeous canal views [](https://www.expedia.ca/Rotonda-West-Hotels-This-Will-Show-Up-In-Searches-And-At-The-Top-Of-Your-Listing-Use-This-Space-To.h106198627.Hotel-Information) Oakland Hills 8.8/10 Excellent (3) "Was great time, the salt water pool was perfect and the house was very relaxing. No real complaints! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SaraKay S. CA $285 CA $866 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Rotonda-West-Hotels-This-Will-Show-Up-In-Searches-And-At-The-Top-Of-Your-Listing-Use-This-Space-To.h106198627.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130409/606882ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130409/b204bf1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130409/39e44603.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130409/1dee68e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene 2 BR/ 2 BA house with AC and private yard in North Port [](https://www.expedia.ca/North-Port-Hotels-Serene-2-BR-2-BA-House-With-AC-And-Private-Yard-In-North-Port.h123130409.Hotel-Information) Warm Mineral Springs CA $241 CA $637 total includes taxes & fees Jan 10 - Jan 11, 2026 [](https://www.expedia.ca/North-Port-Hotels-Serene-2-BR-2-BA-House-With-AC-And-Private-Yard-In-North-Port.h123130409.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/111000000/110660000/110652700/110652676/5aafe435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110660000/110652700/110652676/ebd1c985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/111000000/110660000/110652700/110652676/0142ad9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110660000/110652700/110652676/5b90c78e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 4BR Escape with Heated Saltwater Pool & Hot Tub – Near Beaches & Golf [](https://www.expedia.ca/Rotonda-West-Hotels-Florida-Paradise-Newly-Build-4-BR3-BA.h110652676.Hotel-Information) Long Meadow 10/10 Exceptional (3) "The house was just what we wanted. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Keith L. CA $373 CA $1,066 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Rotonda-West-Hotels-Florida-Paradise-Newly-Build-4-BR3-BA.h110652676.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/56000000/55030000/55022200/55022187/9220dadb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/56000000/55030000/55022200/55022187/00d4e656.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/56000000/55030000/55022200/55022187/5b6487af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/56000000/55030000/55022200/55022187/3742725c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pineapple Express at the Beach Shack Just one block from the beach! [](https://www.expedia.ca/Englewood-Hotels-Pineapple-Express-At-The-Beach-Shack-Just-One-Block-From-The-Beach.h55022187.Hotel-Information) Manasota Key 10/10 Exceptional (37) "Great place with snacks!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy N. CA $303 CA $637 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Englewood-Hotels-Pineapple-Express-At-The-Beach-Shack-Just-One-Block-From-The-Beach.h55022187.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/93000000/92860000/92851200/92851110/9e5d0283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/93000000/92860000/92851200/92851110/625b61d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92860000/92851200/92851110/1fe99d4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92860000/92851200/92851110/8bf14e2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax, Fish, Golf, Dine, Shop in Punta Gorda! [](https://www.expedia.ca/Punta-Gorda-Hotels-Relax.h92851110.Hotel-Information) Downtown Punta Gorda 10/10 Exceptional (2) "amazing host, amazing home" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zane H. [](https://www.expedia.ca/Punta-Gorda-Hotels-Relax.h92851110.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=2026-01-13&endDate=2026-01-14®ionId=553248635976471930&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Englewood South Hotel Reviews ## Explore a world of travel with Expedia - Lodging - More ways to book - [Hotels with Childcare in Clearwater Beach ](https://www.expedia.ca/Clearwater-Beach-Hotels-Hotels-With-Childcare.0-0-d10759-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Golf Hotels in Clearwater ](https://www.expedia.ca/Clearwater-Hotels-Golf-Hotel.0-0-d6033-tGolfHotel.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Clearwater ](https://www.expedia.ca/Clearwater-Hotels-Hotel-With-Early-Check-In.0-0-d6033-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in Clearwater ](https://www.expedia.ca/Clearwater-Hotels-Hotels-With-Childcare.0-0-d6033-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Clearwater ](https://www.expedia.ca/Clearwater-Hotels-Hotels-With-Smoking-Rooms.0-0-d6033-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - 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