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 - ![](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 Santa Rosa Island Historic Hotels Tonight [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6341180&startDate=2025-11-01&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=6341180&startDate=2025-11-02&endDate=2025-11-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6341180&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6341180&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Santa Rosa Island Historic Hotels ![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 (352) "This home is absolutely wonderful! The views can’t be beat and Vic the owner could not have been more connected. Answered all questions immediately." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debbie D. CA $151 CA $516 total includes taxes & fees Nov 2 - Nov 3 [](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/66000000/65780000/65775600/65775536/02dededc.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) ![Outdoor pool](https://images.trvl-media.com/lodging/66000000/65780000/65775600/65775536/ed33fa8e.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) ### Directly on the Ocean! Beautiful Views! Free Beach Chairs and Umbrella sleeps 6 Pensacola Beach 9.6/10 Exceptional (93) "The view from the balcony was beautiful! The furniture and beds were very comfortable. The condo was very conveniently located. There was a corner store and restaurant right across the street. Just steps away from the beach. It was a great stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Justin R. CA $151 CA $659 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Pensacola-Hotels-Directly-On-The-Ocean-Beautiful-Views-Free-Beach-Chairs-And-Umbrella.h65775536.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) ![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/28000000/27140000/27132400/27132318/910bf5af.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 (64) "This is in a perfect location, close to the beach " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason S. CA $195 CA $574 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pensacola-Hotels-Huge-2-Story-Family-Home.h27132318.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) ![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) ![Smart TV, DVD player, books](https://images.trvl-media.com/lodging/21000000/20350000/20348600/20348570/caa0532b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Top floor! Complimentary beach chairs! Amazing view! Navarre 9.4/10 Exceptional (121) "What a perfect place to stay for our wedding anniversary!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $136 CA $388 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Pensacola-Hotels-Top-Floor-Complimentary-Beach-Chairs-Amazing-View.h20348570.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/43000000/42380000/42373900/42373848/a11bc751.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/43000000/42380000/42373900/42373848/1fdad28c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/43000000/42380000/42373900/42373848/1c4e3700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/43000000/42380000/42373900/42373848/f31b3524.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous beachfront condo w/ocean views, shared pool, and beach access Okaloosa Island 9.2/10 Wonderful (85) "This condo was great! Living room and kitchen were fantastic!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christie M. CA $122 CA $418 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Fort-Walton-Beach-Hotels-Gorgeous-Beachfront-Condo-Wocean-Views.h42373848.Hotel-Information) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/22000000/21390000/21385900/21385838/3a183a3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/22000000/21390000/21385900/21385838/b6beb6f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/22000000/21390000/21385900/21385838/0289af83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/22000000/21390000/21385900/21385838/1f2faccf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amazing Beach & Sunset Views, Free Lazy Days Beach Chairs/Umbrella provided Pensacola Beach 9.4/10 Exceptional (227) "Perfect location, amazing views and beach. Condo is perfect and comfy for our family of 4." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brenda T. CA $126 CA $624 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Pensacola-Hotels-Amazing-Beach-Sunset-Views.h21385838.Hotel-Information) ![On the beach, sun loungers](https://images.trvl-media.com/lodging/23000000/22130000/22125600/22125587/5c440e3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/23000000/22130000/22125600/22125587/002a996a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/23000000/22130000/22125600/22125587/w1150h1534x0y2-b82dc4a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22130000/22125600/22125587/0b3164d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Island Sands 109 -Beachfront Beauty- Corner Unit- Just WOW! Okaloosa Island 10/10 Exceptional (134) "Excellent location and beach. The walking distance Beachview restaurant was wonderful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melanie C. CA $149 CA $493 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Fort-Walton-Beach-Hotels-Island-Sands-109-Beachfront-Beauty-Corner-Unit-Just-WOW.h22125587.Hotel-Information) ![Beach nearby, sun loungers](https://images.trvl-media.com/lodging/19000000/18770000/18762300/18762231/57873cf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18770000/18762300/18762231/21593e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/19000000/18770000/18762300/18762231/203ad386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18770000/18762300/18762231/90-7eda358f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### BEACH SERVICE FREE WITH RENTAL🌴🐬SUNSET IN PARADISE 3B - HEATED POOL. Okaloosa Island 9.8/10 Exceptional (93) "Such a nice condo, has everything you need for a stay at the beach. We really enjoyed being able to head up from the beach, cook and relax, then head back down to enjoy some fun in the sun." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle T. CA $210 CA $490 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Fort-Walton-Beach-Hotels-BEACH-SERVICE-FREE-WITH-RENTALSUNSET-IN-PARADISE-3B-HEATED-POOL.h18762231.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33500000/33494700/33494674/eaf48aa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, blackout drapes, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/34000000/33500000/33494700/33494674/cd320ce0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33500000/33494700/33494674/d7d1841b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books, video library](https://images.trvl-media.com/lodging/34000000/33500000/33494700/33494674/df42c150.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Located high enough to have a beautiful view, low enough to hear the waves! Pensacola Beach 9.8/10 Exceptional (111) "Beautiful and convenient to everything, beach and shopping. Loved indoor and outdoor pools, adults and kiddos had the best time!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carla C. CA $1,189 CA $2,103 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Pensacola-Beach-Hotels-Located-High-Enough-To-Have-A-Beautiful-View.h33494674.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1730000/1724300/1724251/ec60f707.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) ### Village Inn Destin Destin 8.4/10 Very good (1517) "The hotel was cleane friendly staff the best were comfortable and it was in a great location I will definitely stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Felicia CA $88 CA $109 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Destin-Hotels-Village-Inn-Destin.h1724251.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=2025-11-15&endDate=2025-11-16®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 "The girl that checked me in was delightful. She was very efficient and very sweet. The room was nice and large and very clean.We did not have a balcony or beach view, but we did have a view of the Bay." [](https://expedia.ca/Pensacola-Hotels-Holiday-Inn-Resort-Pensacola-Beach.h537766.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 "Amazing view and loved to 2 pools and the hot tub. Along with being right on the water. " [](https://expedia.ca/Pensacola-Hotels-Wyndham-Garden-Fort-Walton-Beach-Destin.h10029.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 "The beach was wonderful and so relaxing. A quick reminder if you didn't bring any chairs you can rent them as well as umbrellas for $15 and up. The staff was wonderful. I will definitely be back. " [](https://expedia.ca/Pensacola-Hotels-Hampton-Inn-Pensacola-Beach.h24770.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 "Our room was incredible. It was an executive suite which was very big & had balcony with gulf & bay view. The swimming pool was really nice overlooking gulf & bay. Can’t wait to return again in future. " [](https://expedia.ca/Pensacola-Hotels-Margaritaville-Beach-Hotel.h16596.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 "As good a breakfast as any hotel. Wonderful beach view." [](https://expedia.ca/Pensacola-Hotels-Holiday-Inn-Express-Pensacola-Beach.h40611.Hotel-Information) ![Beal House Fort Walton Beach, Tapestry Collection by Hilton](//images.trvl-media.com/lodging/1000000/120000/118500/118444/735345df_y.jpg) ### Beal House Fort Walton Beach, Tapestry Collection by Hilton 10/10 Excellent "Austin at the front desk was just wonderful! Always helpful, always a smile and a greeting! He is an asset to the bell House." [](https://expedia.ca/Fort-Walton-Beach-Hotels-Beal-House-Fort-Walton-Beach.h118444.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [3 Star Hotels in Mary Esther](https://www.expedia.ca/3Star-Mary-Esther-Hotels.s30-0-d130507.Travel-Guide-Filter-Hotels) - [Cabin Rentals in Cinco Bayou](https://www.expedia.ca/Cinco-Bayou-Cabins.d553248634998723477-aaCabins.Travel-Guide-Accommodation) - [Cinco Bayou Hotels](https://www.expedia.ca/Cinco-Bayou-Hotels.d553248634998723477.Travel-Guide-Hotels) - [Hotels & Resorts for Couples in Destin](https://www.expedia.ca/Destin-Hotels-Couples-Resorts-Hotels.0-0-d6906-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in Destin](https://www.expedia.ca/Destin-Hotels-Hotels-With-Childcare.0-0-d6906-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Destin](https://www.expedia.ca/Destin-Hotels-Hotels-With-Free-Parking.0-0-d6906-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - 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