Title: Book the Best HISTORIC Hotels in Santa Rosa Island in 2025 | Expedia.ca [Santa Rosa Island Travel Guide](https://expedia.ca/Santa-Rosa-Island.dx6341180)[Hotels in Santa Rosa Island](https://expedia.ca/Santa-Rosa-Island-Hotels.d6341180.Travel-Guide-Hotels)[Vacation Rentals in Santa Rosa Island](https://expedia.ca/Santa-Rosa-Island-Vacation-Rentals.d6341180.Travel-Guide-VacationRentals)[Flights to Santa Rosa Island](https://expedia.ca/Cheap-Flights-To-Santa-Rosa-Island.d6341180.Travel-Guide-Flights)[Things to do in Santa Rosa Island](https://expedia.ca/Things-To-Do-In-Santa-Rosa-Island.d6341180.Travel-Guide-Activities)[Santa Rosa Island Car Rentals](https://expedia.ca/Car-Rentals-In-Santa-Rosa-Island.d6341180.Car-Rental-Guide)[Santa Rosa Island Vacation Packages](https://expedia.ca/Santa-Rosa-Island.d6341180.Destination-Travel-Guides) ![Okaloosa Island featuring general coastal views and views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/107000/107604-Okaloosa-Island.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Santa Rosa Island, FL ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Santa Rosa Island Historic Hotels Tonight [Sep 27 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=6341180&startDate=2025-09-27&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 28 - Sep 29](https://www.expedia.ca/Hotel-Search?regionId=6341180&startDate=2025-09-28&endDate=2025-09-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6341180&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6341180&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Santa Rosa Island Historic Hotels ![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15990000/15981000/15980967/ad00a8b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/16000000/15990000/15981000/15980967/73bf8827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/16000000/15990000/15981000/15980967/4b02f928.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15990000/15981000/15980967/61657bf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Pensacola Downtown by IHG Downtown Pensacola 9.2/10 Wonderful (814) "It was the right location and good accommodations." CA $206 CA $232 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Pensacola-Hotels-Holiday-Inn-Express-Pensacola-Downtown.h15980967.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/2000000/1730000/1724300/1724251/b175877b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1730000/1724300/1724251/3215ecf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1730000/1724300/1724251/a04d4f92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1730000/1724300/1724251/34324546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Village Inn Destin Destin 8.4/10 Very good (1513) "I stayed a couple of nights and my stay was great at The Inn." CA $88 CA $109 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Destin-Hotels-Village-Inn-Destin.h1724251.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/78000000/77130000/77124300/77124234/27b0e79f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/78000000/77130000/77124300/77124234/0f2aba79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/78000000/77130000/77124300/77124234/3f06a823.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/78000000/77130000/77124300/77124234/0664c9b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oyster Bay Boutique Hotel Downtown Pensacola 9.4/10 Exceptional (17) "Clean, quiet and absolutely beautiful inside and out! Staff was super friendly! Would definitely stay there again!" CA $652 CA $734 total includes taxes & fees Oct 3 - Oct 4 [](https://www.expedia.ca/Pensacola-Hotels-Oyster-Bay-Boutique-Hotel.h77124234.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/66000000/65780000/65775600/65775536/02dededc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/66000000/65780000/65775600/65775536/fa69d77a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/66000000/65780000/65775600/65775536/f2df6033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/66000000/65780000/65775600/65775536/19cd74e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Directly on the Ocean! Beautiful Views! Free Beach Chairs and Umbrella sleeps 6 Pensacola Beach 9.6/10 Exceptional (91) "This condo is perfect. It is clean.The location is great and the beach is so close!" CA $167 CA $677 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Pensacola-Hotels-Directly-On-The-Ocean-Beautiful-Views-Free-Beach-Chairs-And-Umbrella.h65775536.Hotel-Information) ![On the beach, sun loungers](https://images.trvl-media.com/lodging/21000000/20350000/20348600/20348570/f72d5840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/21000000/20350000/20348600/20348570/39baea75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/21000000/20350000/20348600/20348570/85a32a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books](https://images.trvl-media.com/lodging/21000000/20350000/20348600/20348570/b5fae50f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Top floor! Complimentary beach chairs! Amazing view! Navarre 9.4/10 Exceptional (119) "We had a wonderful time with the best views of the ocean and the gulf! Everything was just as described and pictured on the site, with added bonuses. " [](https://www.expedia.ca/Pensacola-Hotels-Top-Floor-Complimentary-Beach-Chairs-Amazing-View.h20348570.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27140000/27132400/27132318/31db3d8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/28000000/27140000/27132400/27132318/67f7e8c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27140000/27132400/27132318/e31622d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27140000/27132400/27132318/1cd1bfd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Huge Home In A Fantastic Location ~ Game Room ~ Foosball Pensacola Beach 9.8/10 Exceptional (62) "This" CA $249 CA $629 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Pensacola-Hotels-Huge-2-Story-Family-Home.h27132318.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/22000000/21460000/21456000/21455955/50be4de5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/22000000/21460000/21456000/21455955/3fff1d4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, stereo](https://images.trvl-media.com/lodging/22000000/21460000/21456000/21455955/21e1dfd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21460000/21456000/21455955/041cb5b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spectacular Beach Front Views! Free Lazy Days Beach Chairs & Umbrella Included! Pensacola Beach 9.6/10 Exceptional (348) "Excellent " CA $150 CA $500 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Pensacola-Hotels-Spectacular-Beach-Front-Views-Free-Lazy-Days-Beach-Chairs-Umbrella-Included.h21455955.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/68000000/67190000/67181300/67181299/2a718429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/68000000/67190000/67181300/67181299/c8ca35cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67190000/67181300/67181299/bb9912a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books, music library](https://images.trvl-media.com/lodging/68000000/67190000/67181300/67181299/b6d0ddde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Front Penthouse Suite Panoramic Views of Gulf,Pensacola Beach,Pier, & Bay Pensacola Beach 9.8/10 Exceptional (293) "Repeat visitor to the area and this property with family. Property is always well kept in an excellent location with access to the beach and other entertainment. Will be back soon." CA $174 CA $483 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Pensacola-Hotels-Gorgeous-Panoramic-Views-Of-Gulf.h67181299.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/34000000/33950000/33949000/33948932/66508fec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33950000/33949000/33948932/a66c8f84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33950000/33949000/33948932/8bf82c39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33950000/33949000/33948932/d1c3afa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ultimate Family Home! Game Porch / No Stairs / Pets / Pool / Tesla Charger Villa Segunda 9.8/10 Exceptional (157) "Trip was perfect. We had 21 people and everyone was comfortable-plenty of room for all of us. House was great -very convenient to get to beach or town for activities. " CA $298 CA $416 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Pensacola-Hotels-Ultimate-Family-Vacation-House-Heated-Pool-Game-Room-On-Sand-Level.h33948932.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/22000000/21340000/21336400/21336328/aec8fae1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/22000000/21340000/21336400/21336328/651b02a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books](https://images.trvl-media.com/lodging/22000000/21340000/21336400/21336328/69dd9972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/22000000/21340000/21336400/21336328/9540b189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spectacular Unobstructed 10th Floor Views - Free Beach Chairs and Umbrellas Pensacola Beach 9.6/10 Exceptional (232) "Had a 3 night stay and everything was clean and organized. Great view of the gulf as well with an easy check in." CA $314 CA $1,001 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Pensacola-Beach-Hotels-Spectacular-Unobstructed-10th-Floor-Views-Free-Beach-Chairs-And-Umbrellas.h21336328.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=2025-10-12&endDate=2025-10-13®ionId=6341180&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Santa Rosa Island Hotel Reviews ![Holiday Inn Resort Pensacola Beach by IHG](//images.trvl-media.com/lodging/1000000/540000/537800/537766/214fc1d2_y.jpg) ### Holiday Inn Resort Pensacola Beach by IHG 10/10 Excellent "This hotel is great! Can't wait to go back " [](https://expedia.ca/Pensacola-Hotels-Holiday-Inn-Resort-Pensacola-Beach.h537766.Hotel-Information) ![ The Pensacola Beach Resort](//images.trvl-media.com/lodging/1000000/20000/16600/16596/3512c628_y.jpg) ### The Pensacola Beach Resort 10/10 Excellent "The bed was firm but comfortable. Spacious. Quiet. Everything you’d want for a quick getaway. " [](https://expedia.ca/Pensacola-Hotels-Margaritaville-Beach-Hotel.h16596.Hotel-Information) ![Wyndham Garden Fort Walton Beach Destin](//images.trvl-media.com/lodging/1000000/20000/10100/10029/46cb556a_y.jpg) ### Wyndham Garden Fort Walton Beach Destin 10/10 Excellent "We were very impressed with everything the facility had to offer and the staff was very nice and professional. Our room was AWESOME and housekeeping was extra sweet! We will definite be back! Great location to the beach and very nice swimming pools that were spotless :)" [](https://expedia.ca/Pensacola-Hotels-Wyndham-Garden-Fort-Walton-Beach-Destin.h10029.Hotel-Information) ![Holiday Inn Express Pensacola Beach by IHG](//images.trvl-media.com/lodging/1000000/50000/40700/40611/929ed2b0_y.jpg) ### Holiday Inn Express Pensacola Beach by IHG 10/10 Excellent "Everything was amazing! The room, hospitality, location, everything" [](https://expedia.ca/Pensacola-Hotels-Holiday-Inn-Express-Pensacola-Beach.h40611.Hotel-Information) ![Hampton Inn Pensacola Beach](//images.trvl-media.com/lodging/1000000/30000/24800/24770/e16914ac_y.jpg) ### Hampton Inn Pensacola Beach 10/10 Excellent "Perfect weather, perfect beach, friendly staff. 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