Title: Book the Best BOUTIQUE Hotels in Uptown in 2025 | Expedia.ca [Uptown Travel Guide](https://expedia.ca/St-Augustine-Uptown.dx808446908111208448)[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)[Uptown Car Rentals](https://expedia.ca/Car-Rentals-In-Uptown.d808446908111208448.Car-Rental-Guide)[Uptown Vacations](https://expedia.ca/Uptown.d808446908111208448.Destination-Travel-Guides) ![Mission of Nombre de Dios which includes a bridge and general coastal views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/109000/109472-Mission-Of-Nombre-De-Dios.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Boutique Hotels in Uptown, FL from CA $399 ![](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 Uptown Boutique Hotels Tonight [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=808446908111208448&startDate=2025-10-25&endDate=2025-10-26&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=808446908111208448&startDate=2025-10-26&endDate=2025-10-27&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=808446908111208448&startDate=2025-10-31&endDate=2025-11-02&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=808446908111208448&startDate=2025-11-07&endDate=2025-11-09&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Uptown Boutique Hotels ![View from property](https://images.trvl-media.com/lodging/3000000/2940000/2936900/2936880/9cd08ba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/3000000/2940000/2936900/2936880/98ac16c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/3000000/2940000/2936900/2936880/c1a92ddb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed | Terrace/patio](https://images.trvl-media.com/lodging/3000000/2940000/2936900/2936880/512fc1aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayfront Westcott House St Augustine B&B St. Augustine Historic District 9.8/10 Exceptional (260) "We enjoyed our stay. This is such a fun and relaxing place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $358 CA $399 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/St-Augustine-Hotels-Bayfront-Westcott-House-St-Augustine-BB.h2936880.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=808446908111208448&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top Uptown Hotel Reviews ![The Flagler Inn](//images.trvl-media.com/lodging/1000000/10000/3600/3533/085c7f81_y.jpg) ### The Flagler Inn 10/10 Excellent "The room was clean. The breakfast area was always clean. This is the third time staying here, we love the location and how close to the old part of town. The only issue with this stay the ac didn’t work very well in our room, we had to turn it down as low as it would go and it still barely blew. I didn’t say anything to the desk because this trip it was not as hot. If it was in the summer I would have told them about it. " [](https://expedia.ca/St-Augustine-Hotels-The-Flagler-Inn.h3533.Hotel-Information) ## Frequently asked questions ### What's there to see and do in Uptown? > Once you've decided where you'd like to stay, consider what to do for fun during your trip. Activities and attractions to experience around Uptown include St. Augustine Beach, Ripley's Believe It Or Not, and St. Augustine Pirate and Treasure Museum. You might also want to consider exploring Ponce de Leon's Fountain of Youth Archaeological Park, Mission of Nombre de Dios, and Old Jail Museum while you're here. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [5 Star Hotels in St. Augustine](https://www.expedia.ca/5Star-St-Augustine-Hotels.s50-0-d6047864.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Amelia Island](https://www.expedia.ca/Amelia-Island-Hotels-Hotel-With-Pool.0-0-d10814-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels near Castillo de San Marcos National Monument](https://www.expedia.ca/Castillo-De-San-Marcos-National-Monument-Hotels.0-l6068739-0.Travel-Guide-Filter-Hotels) - [Hotels near Cathedral Basilica of St. Augustine](https://www.expedia.ca/Cathedral-Basilica-Of-St-Augustine-Hotels.0-l6069643-0.Travel-Guide-Filter-Hotels) - [Best Western Hotels in Colonial Quarter](https://www.expedia.ca/Colonial-Quarter-St-Augustine-Hotels-Best-Western.0-n811713423814750208-0--bBestWestern.Travel-Guide-Filter-Hotels) - 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