Title: Book the Best St. Augustine South WINERY Hotels in 2025 | Expedia.ca [Vacation Rentals in St. Augustine](https://expedia.ca/St-Augustine-Vacation-Rentals.d6047864.Travel-Guide-VacationRentals)[Flights to St. Augustine](https://expedia.ca/Cheap-Flights-To-St-Augustine.d6047864.Travel-Guide-Flights)[Things to do in St. Augustine](https://expedia.ca/Things-To-Do-In-St-Augustine.d6047864.Travel-Guide-Activities)[St. Augustine South Car Rentals](https://expedia.ca/Car-Rentals-In-St-Augustine-South.d553248623743419702.Car-Rental-Guide)[St. Augustine South Vacations](https://expedia.ca/St-Augustine-South.d553248623743419702.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in St. Augustine South, FL from CA $103 ![](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 St. Augustine South Winery Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=553248623743419702&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=553248623743419702&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248623743419702&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248623743419702&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top St. Augustine South Winery Hotels ![Beach nearby](https://images.trvl-media.com/lodging/114000000/113910000/113905600/113905523/2525d6b1_edited_22bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113910000/113905600/113905523/d271defa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113910000/113905600/113905523/w1125h840x0y1-b5b2d3ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113910000/113905600/113905523/75633dfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming house with free WiFi, AC min from hospital min from historical downtown St. Augustine South 10/10 Exceptional (1) "Very nice, recently update house. We came down just for the weekend, had a great time sightseeing and took in a show at the amphitheater. Very nice quiet neighborhood, and a short uber ride to the theatre.The host was very kind and responsive. Would definitely recommend this place." CA $202 CA $491 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/St-Augustine-Hotels-Charming-House-With-Free-WiFi.h113905523.Hotel-Information) ![Private beach, white sand, beach cabanas, sun loungers](https://images.trvl-media.com/lodging/1000000/810000/809000/808920/65d99be5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/1000000/810000/809000/808920/3a47c465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/810000/809000/808920/f1ca7ae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/809000/808920/b6ab9541.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Sands Beach Boutique Inn - 1 Acre Private Beach Vilano Beach 8.8/10 Excellent (594) "such a beautiful Inn it has so much to do or you can do nothing we stayed on the beach view side and it was very pretty breakfast every morning was hot and fresh, super delicious " CA $94 CA $105 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/St-Augustine-Hotels-Ocean-Sands-Beach-Inn.h808920.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1050000/1047500/1047488/91aa9fcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 9:00 AM to 7:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1050000/1047500/1047488/fbd8aa99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 9:00 AM to 7:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1050000/1047500/1047488/3eeb13eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1050000/1047500/1047488/d7395ed9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort St. Augustine 9.0/10 Wonderful (1204) "Room was clean, staff was very nice, beach access great, balcony view outstanding. " CA $218 CA $277 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/St-Augustine-Hotels-Embassy-Suites-By-Hilton-St-Augustine-Beach-Oceanfront-Resor.h1047488.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/880000/871300/871240/de55622b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/880000/871300/871240/075d5961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/880000/871300/871240/e15165b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/880000/871300/871240/f7578bed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn St. Augustine Downtown Historic District Uptown 9.2/10 Wonderful (551) "Great accommodations.Clean and quiet rooms." CA $160 CA $178 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/St-Augustine-Hotels-Holiday-Inn-St-Augustine-Historic.h871240.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17600/17534/01d94618.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/17600/17534/03008a62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually furnished, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/20000/17600/17534/c561c60f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17600/17534/93e1dcc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southern Oaks Inn Greater Fullerwood 8.8/10 Excellent (1960) "Loved staying here for a weekend get away. The shuttle service to downtown was so nice and the front desk staff and shuttle drivers were so kind and helpful " CA $100 CA $111 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/St-Augustine-Hotels-Southern-Oaks-Inn.h17534.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340806/3acc747d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340806/b6a8e672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340806/69c34e1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340806/c92b8747.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton St. Augustine San Sebastian Oyster Creek 8.8/10 Excellent (1009) "The entire prolerty was extremly clean. Staff was professional and welcoming. Location is very convenient to all shops and restaurants. " CA $160 CA $178 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/St-Augustine-Hotels-Homewood-Suites-By-Hilton-St-Augustine-San-Sebastian.h61340806.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/93000000/92420000/92418500/92418478/9f85a766.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92420000/92418500/92418478/83f4b199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/93000000/92420000/92418500/92418478/42c86566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/93000000/92420000/92418500/92418478/b24ba2d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites St. Augustine Historic District Area Greater Fullerwood 9.4/10 Exceptional (1259) "Great staff, clean rooms" CA $130 CA $145 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/St-Augustine-Hotels-Comfort-Suites.h92418478.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/27000000/26970000/26960600/26960599/3fbd4ad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/26970000/26960600/26960599/042c7b13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/27000000/26970000/26960600/26960599/6b743eb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/27000000/26970000/26960600/26960599/3b87577f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### voco St. Augustine Historic Area by IHG Davis Shores 9.0/10 Wonderful (1005) "Great staff and hotel" CA $179 CA $199 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/St-Augustine-Hotels-Voco-St-Augustine-Historic-Area.h26960599.Hotel-Information) ![Beach nearby, white sand, 3 beach bars](https://images.trvl-media.com/lodging/1000000/900000/898100/898020/8a55c4b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/900000/898100/898020/42b60f14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/900000/898100/898020/d6e702e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/898100/898020/aa1052dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Breeze Inn St. Augustine 8.0/10 Very good (1055) "Nice stay close to beach " CA $92 CA $103 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/St-Augustine-Hotels-Ocean-Breeze-Inn.h898020.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119110000/119107800/119107716/a279ea6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119110000/119107800/119107716/f832544f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/120000000/119110000/119107800/119107716/42661f01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119110000/119107800/119107716/b88f0f17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AC Hotel St. Augustine Downtown Historic District CA $189 CA $211 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/St-Augustine-Hotels-Ac-Hotel-St-Augustine.h119107716.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=2025-10-28&endDate=2025-10-29®ionId=553248623743419702&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top St. Augustine South Hotel Reviews ![Casa Monica Resort & Spa, Autograph Collection](//images.trvl-media.com/lodging/1000000/330000/329700/329630/186cf1c7_y.jpg) ### Casa Monica Resort & Spa, Autograph Collection 10/10 Excellent "This hotel is centrally located and we had an awesome experience. 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