Title: Book the Best HISTORIC Hotels in Caribbean Islands in 2025 | Expedia.ca [Caribbean Islands Travel Guide](https://expedia.ca/Caribbean-Islands.dx3000652683)[Hotels in Caribbean Islands](https://expedia.ca/Caribbean-Islands-Hotels.d3000652683.Travel-Guide-Hotels)[Vacation Rentals in Caribbean Islands](https://expedia.ca/Caribbean-Islands-Vacation-Rentals.d3000652683.Travel-Guide-VacationRentals)[Flights to Caribbean Islands](https://expedia.ca/Cheap-Flights-To-Caribbean-Islands.d3000652683.Travel-Guide-Flights)[Caribbean Islands Car Rentals](https://expedia.ca/Car-Rentals-In-Caribbean-Islands.d3000652683.Car-Rental-Guide)[Caribbean Islands Vacation Packages](https://expedia.ca/Caribbean-Islands.d3000652683.Destination-Travel-Guides) ![Anguilla featuring rocky coastline, a beach and tropical scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/25000/25736-Anguilla.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Caribbean Islands from CA $134 ![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 Caribbean Islands Historic Hotels Tonight [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-10-01&endDate=2025-10-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-10-02&endDate=2025-10-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Caribbean Islands Historic Hotels ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/23200/23106/12be56a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/23200/23106/c974117d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/23200/23106/930895ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/1000000/30000/23200/23106/0881e27c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel El Convento Old San Juan 9.0/10 Wonderful (1000) "Beautiful hotel! Was a fantastic place to stay for a first time in San Juan " CA $274 CA $359 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/San-Juan-Hotels-Hotel-El-Convento.h23106.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1820000/1817700/1817661/66551567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1820000/1817700/1817661/e52d10de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1820000/1817700/1817661/071394f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1820000/1817700/1817661/27a7e0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Boutique Hotel Palacio Zona Colonial 8.6/10 Excellent (1000) "We enjoyed our stay in this beautiful hotel " CA $104 CA $134 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Santo-Domingo-Hotels-Boutique-Hotel-Palacio.h1817661.Hotel-Information) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/50000/48900/48823/c16aa94e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/50000/48900/48823/43d29c38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/50000/48900/48823/683e6f98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/48900/48823/d4485e52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Rumbao, a Tribute Portfolio Hotel Old San Juan 9.0/10 Wonderful (1181) "Great location with amazing activities near by" CA $220 CA $298 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/San-Juan-Hotels-Sheraton-Old-San-Juan-Hotel.h48823.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/4000000/3010000/3009200/3009193/b767937c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/4000000/3010000/3009200/3009193/47eefe4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 2 Queen Beds](https://images.trvl-media.com/lodging/4000000/3010000/3009200/3009193/d4c28615.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/4000000/3010000/3009200/3009193/ed9dec27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CasaBlanca Hotel Old San Juan 8.8/10 Excellent (1439) "Great stay!" CA $128 CA $148 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/San-Juan-Hotels-CasaBlanca-Hotel.h3009193.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/3000000/2600000/2595400/2595374/caedc206.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/3000000/2600000/2595400/2595374/964d4a33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room](https://images.trvl-media.com/lodging/3000000/2600000/2595400/2595374/71361506.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Building design](https://images.trvl-media.com/lodging/3000000/2600000/2595400/2595374/d94a3a1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Gallery Inn Old San Juan 8.4/10 Very good (369) "Un lugar muy diferente e interesante. La pasamos muy bien. " CA $249 CA $302 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/San-Juan-Hotels-The-Gallery-Inn.h2595374.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/5000000/4010000/4002600/4002581/b755fcd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![19-inch flat-screen TV with satellite channels, TV](https://images.trvl-media.com/lodging/5000000/4010000/4002600/4002581/28557bcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/5000000/4010000/4002600/4002581/b472c664.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed](https://images.trvl-media.com/lodging/5000000/4010000/4002600/4002581/c84957a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Herencia Hotel Old San Juan 9.2/10 Wonderful (816) "Beautiful place to stay. " CA $148 CA $168 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/San-Juan-Hotels-Villa-Herencia-Hotel.h4002581.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/5000000/4260000/4258000/4257992/187ba09f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room](https://images.trvl-media.com/lodging/5000000/4260000/4258000/4257992/da3bb9cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4260000/4258000/4257992/0452fab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room](https://images.trvl-media.com/lodging/5000000/4260000/4258000/4257992/1d066a5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Terraza de San Juan Old San Juan 8.2/10 Very good (1012) "AN OVERALL GREAT STAY!!" CA $136 CA $167 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/San-Juan-Hotels-La-Terraza-De-San-Juan.h4257992.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1960000/1950600/1950513/38527439.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1960000/1950600/1950513/2621e310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/2000000/1960000/1950600/1950513/594a0063.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bars/lounges, swim-up bar, poolside bar, beach bar](https://images.trvl-media.com/lodging/2000000/1960000/1950600/1950513/f5652bb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sanctuary Cap Cana, a Luxury Collection Resort, Dominican Republic, Adult All-Inclusive Cap Cana 9.4/10 Exceptional (1002) "Great staff and great stay!" CA $863 CA $863 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Punta-Cana-Hotels-Sanctuary-Cap-Cana.h1950513.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/10000000/9400000/9394800/9394742/4a516aa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/10000000/9400000/9394800/9394742/w4000h2995x0y0-56ecd5d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/10000000/9400000/9394800/9394742/cfe20db8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Loft, Harbour View | Living area](https://images.trvl-media.com/lodging/10000000/9400000/9394800/9394742/dd7cce99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Admiral's Inn and Gunpowder Suites English Harbour 9.4/10 Exceptional (166) "Beautiful and relaxing" CA $296 CA $390 total includes taxes & fees Oct 11 - Oct 12 [](https://www.expedia.ca/English-Harbour-Hotels-Admirals-Inn-And-Gunpowder-Suites.h9394742.Hotel-Information) ![Presidential Suite | Balcony](https://images.trvl-media.com/lodging/9000000/8130000/8123500/8123414/c4bdef4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/9000000/8130000/8123500/8123414/7144df13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite | Living room](https://images.trvl-media.com/lodging/9000000/8130000/8123500/8123414/ec18a684.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite | Private kitchen](https://images.trvl-media.com/lodging/9000000/8130000/8123500/8123414/1093ce92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fortaleza Suites Old San Juan 9.0/10 Wonderful (1162) "Great place to stay. " CA $135 CA $144 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/San-Juan-Hotels-Fortaleza-Suites.h8123414.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=2025-10-15&endDate=2025-10-16®ionId=3000652683&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Caribbean Islands Hotel Reviews ![Grand Hyatt Baha Mar](//images.trvl-media.com/lodging/8000000/7780000/7779300/7779293/8fc5fb82_y.jpg) ### Grand Hyatt Baha Mar 10/10 Excellent "Best vacation, the food was delicious. I do wish the pol would close at a later time but overall it was great. " [](https://expedia.ca/Nassau-Hotels-Grand-Hyatt-Baha-Mar.h7779293.Hotel-Information) ![Hyatt Regency Grand Reserve Puerto Rico](//images.trvl-media.com/lodging/1000000/980000/979700/979694/08d6d09c_y.jpg) ### Hyatt Regency Grand Reserve Puerto Rico 10/10 Excellent "Great view" [](https://expedia.ca/San-Juan-Hotels-Hyatt-Regency-Grand-Reserve-Puerto-Rico.h979694.Hotel-Information) ![Hotel Riu Palace Paradise Island - Adults Only - All Inclusive](//images.trvl-media.com/lodging/1000000/10000/1100/1039/9adb12c0_y.jpg) ### Hotel Riu Palace Paradise Island - Adults Only - All Inclusive 10/10 Excellent "The good beach" [](https://expedia.ca/Nassau-Hotels-Riu-Palace-Paradise-Island-All-Inclusive-Adults-Only.h1039.Hotel-Information) ![Hotel Riu Montego Bay - Adults Only - All Inclusive](//images.trvl-media.com/lodging/3000000/2070000/2062100/2062016/5bbbc6e7_y.jpg) ### Hotel Riu Montego Bay - Adults Only - All Inclusive 10/10 Excellent "I enjoy the stay at the hotel" [](https://expedia.ca/Montego-Bay-Hotels-Riu-Montego-Bay-Adults-Only-All-Inclusive.h2062016.Hotel-Information) ![The Royal Sonesta San Juan](//images.trvl-media.com/lodging/1000000/290000/289100/289099/110d1700_y.jpg) ### The Royal Sonesta San Juan 10/10 Excellent "The property is excellent very convenient for people that likes the pool and the beach. Suggestion: don’t charge too much for parking for the guest. " [](https://expedia.ca/San-Juan-Hotels-Royal-Sonesta-San-Juan.h289099.Hotel-Information) ![La Concha Resort, Puerto Rico, Autograph Collection](//images.trvl-media.com/lodging/2000000/1770000/1760300/1760259/22470d47_y.jpg) ### La Concha Resort, Puerto Rico, Autograph Collection 10/10 Excellent "Room service was great staff was awesome " [](https://expedia.ca/San-Juan-Hotels-La-Concha-Renaissance-San-Juan-Resort.h1760259.Hotel-Information) ![Holiday Inn Resort Aruba - Beach Resort & Casino by IHG](//images.trvl-media.com/lodging/1000000/10000/6000/5956/6f50ef2e_y.jpg) ### Holiday Inn Resort Aruba - Beach Resort & Casino by IHG 10/10 Excellent "Best location! Resort is a little dated, but comfortable." [](https://expedia.ca/Noord-Hotels-Holiday-Inn-Resort-Aruba-Beach-Resort-And-Casino.h5956.Hotel-Information)