Title: Book the Best Anna Maria WINERY Hotels in 2025 | Expedia.ca [Hotels in Anna Maria](https://expedia.ca/Anna-Maria-Hotels.d74028.Travel-Guide-Hotels)[Vacation Rentals in Anna Maria](https://expedia.ca/Anna-Maria-Vacation-Rentals.d74028.Travel-Guide-VacationRentals)[Flights to Anna Maria](https://expedia.ca/Cheap-Flights-To-Anna-Maria.d74028.Travel-Guide-Flights)[Anna Maria Car Rentals](https://expedia.ca/Car-Rentals-In-Anna-Maria.d74028.Car-Rental-Guide)[Anna Maria Vacation Packages](https://expedia.ca/Anna-Maria.d74028.Destination-Travel-Guides) ![The day comes to a close over the Gulf of Mexico. Bean Point Beach is at the Northwest end of Anna Maria Island. A nice wide beach with fine white sand. A little more secluded than some of the other beaches nearby.](https://images.trvl-media.com/place/74028/8bf298b4-fe4b-49ec-a6ce-565760a5baca.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by throwingsofas # Find Winery Hotels in Anna Maria, FL from CA $249 - ![](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 Anna Maria Winery Hotels Tonight [Nov 12 - Nov 13](https://www.expedia.ca/Hotel-Search?regionId=74028&startDate=2025-11-12&endDate=2025-11-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 13 - Nov 14](https://www.expedia.ca/Hotel-Search?regionId=74028&startDate=2025-11-13&endDate=2025-11-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=74028&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=74028&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Anna Maria Winery Hotels ![Smart TV, foosball](https://images.trvl-media.com/lodging/74000000/73530000/73528000/73527928/cfe099c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/74000000/73530000/73528000/73527928/0bd3cb15.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/74000000/73530000/73528000/73527928/2633890b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73530000/73528000/73527928/e99c97be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Home with Pool and Hot Tub, just 5 Houses to the Water! Anna Maria 9.4/10 Exceptional (29) "Wow!! This place had everything we needed for the perfect beach vacation! The management company was amazing! We loved everything about the property! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carrie J. CA $281 CA $641 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Anna-Maria-Hotels-Private-Home-With-Pool-And-Hot-Tub.h73527928.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/74000000/73530000/73527800/73527715/fd0b5dbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73530000/73527800/73527715/ffc0d99e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73530000/73527800/73527715/406e8f84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73530000/73527800/73527715/53fdb072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adorable Cottage with Covered Balconies and Private Pool Anna Maria 9.6/10 Exceptional (41) "The location was perfect with close beach access and surrounded by a lot of fun businesses. We loved being over the pizza shop, could go down there and grab food or drinks! We enjoyed our stay very much!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah E. CA $307 CA $715 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Anna-Maria-Hotels-Adorable-Cottage-With-Covered-Balconies-And-Private-Pool.h73527715.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/74000000/73530000/73528000/73527934/c6c6c94a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/74000000/73530000/73528000/73527934/1a4de489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/74000000/73530000/73528000/73527934/f667a3aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73530000/73528000/73527934/01024c08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Home with Pool and Spa, 2 Blocks to Beach and Guest Suite! Anna Maria 9.4/10 Exceptional (35) "Seamless process and beautiful property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) K S. CA $272 CA $634 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Anna-Maria-Hotels-Private-Home-With-Pool-And-Hot-Tub.h73527934.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73530000/73527400/73527399/9dcdc0d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/74000000/73530000/73527400/73527399/95b0d9c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis](https://images.trvl-media.com/lodging/74000000/73530000/73527400/73527399/883388c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/74000000/73530000/73527400/73527399/b74c7f16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Canal Home with Pool & Dock Near Beach Anna Maria 9.6/10 Exceptional (8) "The only negative I can say is that my trip wasn't longer. This property is fantastic. Great location and had everything we needed. I would highly recommend it and can't wait to book it again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela R. CA $301 CA $665 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Anna-Maria-Hotels-Canal-Home-With-Private-Dock.h73527399.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/74000000/73530000/73527600/73527575/29a41ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73530000/73527600/73527575/326f581a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73530000/73527600/73527575/95b97511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73530000/73527600/73527575/dcb3e56d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Guest House Near the Beach with Private Pool! Anna Maria 8.6/10 Excellent (29) "The house is above 2 restaurants. But that did not cause us problems. There had been a huge storm on day of arrival and the pool got trashed. I called and had someone out next morning. There was an annoying fire beeping alarming going off everyday and that really didn't get addressed during our stay despite my calls. I had to shut it off multiple times. Overall it was a great stay. Beds so comfortable I miss them! Plenty of room for us ladies. Would consider coming back if the alarm was... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn H. CA $271 CA $638 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Anna-Maria-Hotels-Beautiful-Guest-House-Near-The-Beach-With-Private-Pool.h73527575.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/22000000/21710000/21709700/21709690/fc5c24d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21710000/21709700/21709690/7a09bc4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/22000000/21710000/21709700/21709690/4b7dc0d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/22000000/21710000/21709700/21709690/89c47d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Do you love the beach? Anna Maria 10/10 Exceptional (149) "This place is just wonderful - location is outstanding, with less than a minute's walk to the beach, everything was well set up, and was simply a lovely place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter W. CA $322 CA $757 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Anna-Maria-Hotels-Memories-Are-Made-In-Flip-Flops.h21709690.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73530000/73528000/73527932/e04ab158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73530000/73528000/73527932/bd191bf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73530000/73528000/73527932/47de7b6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73530000/73528000/73527932/791b4f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Home with Pool and Game Room, 1 Block to Beach! - Dolphin Pointe Anna Maria 9.6/10 Exceptional (28) "The location is great—just a short walk to the beach. We do wish there were easier access to the pool and grill from the upstairs area. The rooms were clean, and we really appreciated that each one had its own bathroom. Communication was excellent; all of our questions were answered promptly.With the amount of money we spent I would have like to see more than two laundry and dishwasher pods along with dish soap. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Meghan Z. CA $459 CA $938 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Anna-Maria-Hotels-Private-Home-With-Pool-And-Game-Room.h73527932.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73060000/73055700/73055690/ff1f5349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73060000/73055700/73055690/16109961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73060000/73055700/73055690/4e8bf2d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/74000000/73060000/73055700/73055690/3fd7ae52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vintage Cottage: Pool and Walk to Beach, Pine Ave Shops Anna Maria 8.4/10 Very good (7) "Property is centrally located, nicely furnished (cute and beachey with good quality furniture and linens) and geared to family groups. The online photos do not do justice to how generously sized the rooms are. The porches, front and back, were pleasantly shaded with ceiling fans and comfy seating. The pool is quite small - which was not a surprise, but it did get quite warm in the late afternoon. Water temperature was pleasant in the mornings. We were able to easily. walk to either the bay or... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lori C. CA $468 CA $919 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Anna-Maria-Hotels-Adorable-Cottage-With-Heated-Pool-Fantastic-Location.h73055690.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/74000000/73530000/73527500/73527476/0c6f0343.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73530000/73527500/73527476/38ed99de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73530000/73527500/73527476/aa563736.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool, sun loungers](https://images.trvl-media.com/lodging/74000000/73530000/73527500/73527476/3e6b24ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private, Remodeled Home with Pool! 1 Block to Beach, Great for Families! Anna Maria 9.6/10 Exceptional (29) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wilson CA $350 CA $773 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Anna-Maria-Hotels-Private-Home-With-Caged-Pool.h73527476.Hotel-Information) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/68000000/67270000/67267100/67267071/c4bda2e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool views ](https://images.trvl-media.com/lodging/68000000/67270000/67267100/67267071/fcf39d35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, memory foam beds, in-room safe](https://images.trvl-media.com/lodging/68000000/67270000/67267100/67267071/addd8edf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/68000000/67270000/67267100/67267071/ff1b03fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Saint Hotel St. Pete Beach 9.6/10 Exceptional (474) "Great hotel and staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan Elizabeth CA $171 CA $249 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-The-Saint-Hotel.h67267071.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=2025-11-26&endDate=2025-11-27®ionId=74028&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Anna Maria Hotel Reviews ## Explore a world of travel with Expedia - Lodging - More ways to book - [Beach Hotel Hotels in Anna Maria Island](https://www.expedia.ca/Anna-Maria-Island-Hotels-Beach-Hotel.0-0-d553248622847118534-tBeachHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Anna Maria Island](https://www.expedia.ca/Anna-Maria-Island-Hotels-Casino-Hotel.0-0-d553248622847118534-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Anna Maria Island](https://www.expedia.ca/Anna-Maria-Island-Hotels-Cheap-Hotels.0-0-d553248622847118534-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Anna Maria Island](https://www.expedia.ca/Anna-Maria-Island-Hotels-Family-Hotel.0-0-d553248622847118534-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Anna Maria Island](https://www.expedia.ca/Anna-Maria-Island-Hotels-Golf-Hotel.0-0-d553248622847118534-tGolfHotel.Travel-Guide-Filter-Hotels) - 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[Oceanfront Hotels in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Oceanfront-Hotels.0-n553248635976473287-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Pet-Friendly-Hotel.0-n553248635976473287-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Waterpark-Hotels.0-n553248635976473287-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Business Hotels in Sarasota](https://www.expedia.ca/Sarasota-Hotels-Business-Hotel.0-0-d602719-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Green Hotels in Sarasota](https://www.expedia.ca/Sarasota-Hotels-Green-Sustainable.0-0-d602719-tGreenSustainable.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Sarasota](https://www.expedia.ca/Sarasota-Hotels-Hotel-With-Pool.0-0-d602719-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Sarasota](https://www.expedia.ca/Sarasota-Hotels-Hotels-With-Smoking-Rooms.0-0-d602719-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - 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