Title: Book the Best ADVENTURE 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) ![Ponce de Leon\'s Fountain of Youth Archaeological Park featuring a park](https://images.trvl-media.com/place/6069637/dace87e2-b523-497f-957e-10f8e248dd29.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels & Resorts for Couples in Uptown, FL from CA $233 - ![](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 Hotels & Resorts for Couples Tonight [Nov 20 - Nov 21](https://www.expedia.ca/Hotel-Search?regionId=808446908111208448&startDate=2025-11-20&endDate=2025-11-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 21 - Nov 22](https://www.expedia.ca/Hotel-Search?regionId=808446908111208448&startDate=2025-11-21&endDate=2025-11-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=808446908111208448&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=808446908111208448&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Uptown Hotels & Resorts for Couples ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106120000/106118800/106118730/68d5c076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106120000/106118800/106118730/w905h683x60y0-ac0aae00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, computer monitors](https://images.trvl-media.com/lodging/107000000/106120000/106118800/106118730/f7b95bba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106120000/106118800/106118730/w1022h683x0y0-0bd51aae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downton Abbottry 2/2 House- 2 Blocks To The Fort Uptown 9.6/10 Exceptional (5) "Loved the quaint quiet location - perfect walkable place! Hope to be able to stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathy CA $300 CA $621 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/St-Augustine-Hotels-Downton-Abbottry-22-House-2-Blocks-To-The-Fort.h106118730.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/34000000/33510000/33508700/33508655/w1104h827x344y0-ef7c66fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33510000/33508700/33508655/w1609h828x91y0-ed5e85b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33510000/33508700/33508655/w828h621x0y586-cf64b217.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33510000/33508700/33508655/w1223h828x284y0-93e3fff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### COMFY DOWNTOWN SPACE Uptown 9.4/10 Exceptional (59) "Cozy clean property with 2 ply toilet paper! Great walking distance within all the sites. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Greg E. CA $147 CA $232 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/St-Augustine-Hotels-COMFY-DOWNTOWN-SPACE.h33508655.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96380000/96378200/96378107/72de2434.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96380000/96378200/96378107/w1890h1262x4y6-784f91d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96380000/96378200/96378107/8251a754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96380000/96378200/96378107/d74cd059.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Full House 2min walk to Historic Downtown with 75" 8K TV & Gas Grill Uptown 9.4/10 Exceptional (34) "Me and my wife loved this place its in walking distance to most of the activities and was very clean and cozy " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew A. CA $252 CA $569 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/St-Augustine-Hotels-Historic-Full-House-2min-Walk-To-Historic-Downtown-With-75-8K-TV-Gas-Grill.h96378107.Hotel-Information) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/34000000/33400000/33394000/33393991/1c78e657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33400000/33394000/33393991/0982aa1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33400000/33394000/33393991/b5523b04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33400000/33394000/33393991/5bee4867.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adorable Guest House walking distance to Historic St. Augustine! Uptown 10/10 Exceptional (182) "Property was very convenient to town, clean, and quiet. Very enjoyable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregg D. CA $250 CA $446 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/St-Augustine-Hotels-Adorable-Guest-House.h33393991.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83470000/83469900/83469857/2f91406f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83470000/83469900/83469857/e907ca08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83470000/83469900/83469857/382e604b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/84000000/83470000/83469900/83469857/94b63b40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet Friendly Oceanfront Retreats Unbeatable Discounts on Your Seaside Sanctuary! Uptown 9.0/10 Wonderful (11) "Totally enjoyed our stay and this house was perfect for our needs with its location and so comfy. Great , communicative host too. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph R. CA $421 CA $1,221 total includes taxes & fees Dec 6 - Dec 7 [](https://www.expedia.ca/St-Augustine-Hotels-Pet-Friendly-Oceanfront-Retreats-Unbeatable-Discounts-On-Your-Seaside-Sanctuary.h83469857.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107270000/107266400/107266395/ea8855b1.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/108000000/107270000/107266400/107266395/27916099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107270000/107266400/107266395/cfd8d2e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107270000/107266400/107266395/c792ec45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walker House c1888-Nat'l Reg of Historic Places Uptown 10/10 Exceptional (16) "This is a beautiful property. We really enjoyed staying here." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Corrine M. CA $517 CA $1,131 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/St-Augustine-Hotels-Walker-House-C1888-Natl-Reg-Of-Historic-Places.h107266395.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91740000/91737300/91737279/01fc1a5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91740000/91737300/91737279/142a7474.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/92000000/91740000/91737300/91737279/bfe1527c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/92000000/91740000/91737300/91737279/916d0416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet friendly Iconic Magnolia Ave, Fountain of Youth, 4 min to beach & Downtown Uptown 10/10 Exceptional (5) "Host was great ! I will come back again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kiley W. CA $420 CA $852 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/St-Augustine-Hotels-Iconic-Home-On-Magnolia-Ave.h91737279.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/117000000/116600000/116590300/116590244/16af954f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/117000000/116600000/116590300/116590244/73b11302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116600000/116590300/116590244/1ca819a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116600000/116590300/116590244/ba144b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5 Min Walk to St. George Street~Resort Access to Pool & Gym~King Beds~Grill~Wifi Uptown 10/10 Exceptional (3) "This place was fantastic. Beautiful home and in such a convenient area. We were able to walk to everything! Definitely recommend and would come back again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nate S. CA $755 CA $1,829 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/St-Augustine-Hotels-5-Min-Walk-To-St-George-StreetResort-Access-To-Pool-GymKing-BedsGrillWifi.h116590244.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) ![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) ![Game room](https://images.trvl-media.com/lodging/1000000/810000/809000/808920/3a47c465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/810000/809000/808920/0bdf76db.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 (651) "Great place to stay staff is very friendly and helpful. They have a nice kitchen and breakfast and the beach is in walking distance. Best place to stay in st Augustine." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jevon CA $102 CA $233 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/St-Augustine-Hotels-Ocean-Sands-Beach-Inn.h808920.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/580000/574400/574321/c4f69afc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/580000/574400/574321/f25915a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard, Two Queen Beds](https://images.trvl-media.com/lodging/1000000/580000/574400/574321/11bf299c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/580000/574400/574321/8d8c1bbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Regency Inn & Suites St. Augustine 8.6/10 Excellent (1117) "One of my favorite places to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Damon [](https://www.expedia.ca/St-Augustine-Hotels-Regency-Inn-Suites.h574321.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=2025-12-04&endDate=2025-12-05®ionId=808446908111208448&adults=2&nearby_group=recreation&sort=RECOMMENDED&openPlayBack=true) ## Top Uptown Hotel Reviews ![The Flagler Inn](https://images.trvl-media.com/lodging/1000000/10000/3600/3533/085c7f81_y.jpg) ### The Flagler Inn 10/10 Excellent "Room was pretty big very clean, air conditioning worked perfect. We were very pleased with our stay" [](https://expedia.ca/St-Augustine-Hotels-The-Flagler-Inn.h3533.Hotel-Information) ![Guy Harvey Resort on St Augustine Beach](https://images.trvl-media.com/lodging/1000000/10000/6500/6477/ae448125_y.jpg) ### Guy Harvey Resort on St Augustine Beach 10/10 Excellent "Room was clean. The staff was very friendly and always there to help!The pool is not heated. There are shuttles every hour to take you to town. Great beach access! Great place to stay. The only negative I have is the size of the bathroom ok for one person but small for two or a family. Still a great place to stay I would say there again!" [](https://expedia.ca/St-Augustine-Hotels-Guy-Harvey-Resort-On-St-Augustine-Beach.h6477.Hotel-Information) ![Days Inn by Wyndham St Augustine/Historic Downtown](https://images.trvl-media.com/lodging/1000000/30000/27100/27013/bdfd0a00_y.jpg) ### Days Inn by Wyndham St Augustine/Historic Downtown 10/10 Excellent "For the price its perfect for a nights stay" [](https://expedia.ca/St-Augustine-Hotels-Days-Inn-By-Wyndham-St-AugustineHistoric-Downtown.h27013.Hotel-Information) ![The Ponce St. Augustine Hotel](https://images.trvl-media.com/lodging/1000000/10000/7000/6922/26836a8d_y.jpg) ### The Ponce St. Augustine Hotel 10/10 Excellent "Staff was very welcoming and helpful. The outside of the hotel was clean and the inside was well designed and nice. Would stay again!" [](https://expedia.ca/St-Augustine-Hotels-The-Ponce-St-Augustine-Hotel.h6922.Hotel-Information) ![DoubleTree by Hilton Hotel St. Augustine Historic District](https://images.trvl-media.com/lodging/1000000/20000/14500/14483/135b7fed_y.jpg) ### DoubleTree by Hilton Hotel St. Augustine Historic District 10/10 Excellent "Had a great experience. Very sweet staff. Rooms always cleaned each day very well. Anything we asked for we received it quickly & with a smile. The lady that cleaned our room was so sweet & nice. Enjoyed our stay. " [](https://expedia.ca/St-Augustine-Hotels-DoubleTree-By-Hilton-Hotel-St-Augustine-Historic-District.h14483.Hotel-Information) ![Renaissance St. Augustine Historic Downtown Hotel](https://images.trvl-media.com/lodging/1000000/50000/41500/41440/6ca0284c_y.jpg) ### Renaissance St. Augustine Historic Downtown Hotel 10/10 Excellent "Large clean room, walking distance to everything " [](https://expedia.ca/St-Augustine-Hotels-Renaissance-St-Augustine-Historic-Downtown-Hotel.h41440.Hotel-Information) ![Southern Oaks Inn St. Augustine Historic District](https://images.trvl-media.com/lodging/1000000/20000/17600/17534/01d94618_y.jpg) ### Southern Oaks Inn St. Augustine Historic District 10/10 Excellent "Rooms were very clean and property was so cute! Highly recommend :) pool was large! Breakfast was light but overall the location and price is great!! :) " [](https://expedia.ca/St-Augustine-Hotels-Southern-Oaks-Inn.h17534.Hotel-Information) ![Casa Monica Resort & Spa, Autograph Collection](https://images.trvl-media.com/lodging/1000000/330000/329700/329630/186cf1c7_y.jpg) ### Casa Monica Resort & Spa, Autograph Collection 10/10 Excellent "Staff was very friendly. Room was spotless." 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