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 ![](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 Caribbean Islands Historic Hotels Tonight [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-10-11&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Caribbean Islands Historic Hotels ![Horseback riding](https://images.trvl-media.com/lodging/5000000/4680000/4675500/4675477/438a5d23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Suite | Balcony view](https://images.trvl-media.com/lodging/5000000/4680000/4675500/4675477/070c0873.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/5000000/4680000/4675500/4675477/d9e16d0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4680000/4675500/4675477/9f09ebef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sea Gate Hotel Isabel II 9.4/10 Exceptional (1003) "Love love love this place. Perfect island vacation " CA $111 CA $130 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Vieques-Hotels-Sea-Gate-Hotel.h4675477.Hotel-Information) ![Private beach, white sand, beach cabanas, beach massages](https://images.trvl-media.com/lodging/120000000/119900000/119898600/119898585/809b99d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, City View | Private kitchen](https://images.trvl-media.com/lodging/120000000/119900000/119898600/119898585/ba74fa99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/120000000/119900000/119898600/119898585/9f5e6143.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/120000000/119900000/119898600/119898585/bf9c5f81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LAS PALMAS STUDIOS playa LOS CORALES Bávaro 9.6/10 Exceptional (10) "Beautiful location, very peaceful and relaxing. The pool area was my favorite spot, with plenty of loungers and a great vibe." CA $162 CA $216 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Punta-Cana-Hotels-LAS-PALMAS-STUDIOS-Playa-LOS-CORALES.h119898585.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/107000000/106900000/106890800/106890772/fd679681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/107000000/106900000/106890800/106890772/e8351447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/107000000/106900000/106890800/106890772/a204e4b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed with Sofa bed, City View | Bathroom](https://images.trvl-media.com/lodging/107000000/106900000/106890800/106890772/69fbcf72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AC Hotel Santiago de los Caballeros La Zurza 9.2/10 Wonderful (220) "Very nice stay near downtown " CA $156 CA $199 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Santiago-De-Los-Caballeros-Hotels-AC-Hotel-Santiago-De-Los-Caballeros.h106890772.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/11000000/10560000/10552400/10552354/3d6b1909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/11000000/10560000/10552400/10552354/4299a1ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/11000000/10560000/10552400/10552354/9a1f70d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superieure](https://images.trvl-media.com/lodging/11000000/10560000/10552400/10552354/f2b804e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel L'Imperatrice Fort-de-France 7.6/10 Good (338) "Within easy walking distance of various tourist sites in Fort-de-France, shops, restaurants and Ferry Station to beaches at Les Trois-Ilets." [](https://www.expedia.ca/Fort-De-France-Hotels-Hotel-LImperatrice.h10552354.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/17000000/16210000/16203100/16203001/w3837h2563x3y0-43f4ccce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/17000000/16210000/16203100/16203001/4527ccfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/17000000/16210000/16203100/16203001/w3837h2560x3y3-371b08fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/17000000/16210000/16203100/16203001/bbfbafdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hodelpa Nicolas de Ovando Zona Colonial 9.2/10 Wonderful (1007) "Beautiful hotel for history lovers. Excellent accommodations, bedding was very comfortable. I loved it and will stay again " CA $148 CA $190 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Santo-Domingo-Hotels-Hodelpa-Nicolas-De-Ovando.h16203001.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/60000000/59950000/59946400/59946372/5a877fe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Jimmy Buffett)](https://images.trvl-media.com/lodging/60000000/59950000/59946400/59946372/28963f22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/60000000/59950000/59946400/59946372/cde82baa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/60000000/59950000/59946400/59946372/80f6a272.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Margaritaville Beach Resort - Nassau Downtown Nassau 8.4/10 Very good (2200) "Beautiful resort and staff was nice. " CA $352 CA $548 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Nassau-Hotels-Margaritaville-Beach-Resort-Nassau.h59946372.Hotel-Information) ![Superior Room, 1 King Bed, Balcony, Hill View | View from room](https://images.trvl-media.com/lodging/1000000/530000/526800/526796/dac174f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/530000/526800/526796/5a5a4257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/530000/526800/526796/f81eb0d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner served; Caribbean cuisine, alfresco dining ](https://images.trvl-media.com/lodging/1000000/530000/526800/526796/0fe77622.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bunker Hill Hotel St. Thomas 8.0/10 Very good (1054) "Great location local to everything " CA $146 CA $179 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/St-Thomas-Hotels-Bunker-Hill-Hotel.h526796.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/190000/185600/185536/33a91132.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/190000/185600/185536/913e95c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/190000/185600/185536/61eeb430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/190000/185600/185536/b0fd3807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Company House Hotel St. Croix Christiansted Historic District 9.0/10 Wonderful (229) "Overall awesome experience. The staff was great friendly and helpful. I’ll stay there again in my next trip" CA $175 CA $215 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Christiansted-Hotels-Company-House-Hotel.h185536.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/19000/18948/a32a17a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Caribbean cuisine, alfresco dining ](https://images.trvl-media.com/lodging/1000000/20000/19000/18948/16ba6ca5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/20000/19000/18948/1251b6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/1000000/20000/19000/18948/4b16b150.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fort Young Hotel Roseau 8.8/10 Excellent (769) "Visit was good. I always stay at Fort Young when I visit Dominica. I enjoyed the room service menu better than the restaurant menu" CA $272 CA $333 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Roseau-Hotels-Fort-Young-Hotel.h18948.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/9000000/8290000/8283200/8283142/cfdba44f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/9000000/8290000/8283200/8283142/5316e8b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave](https://images.trvl-media.com/lodging/9000000/8290000/8283200/8283142/e89937e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave](https://images.trvl-media.com/lodging/9000000/8290000/8283200/8283142/3cbf06bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dream's Hotel Puerto Rico Río Piedras 7.6/10 Good (955) "Great staff " CA $117 CA $140 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/San-Juan-Hotels-Dreams-Hotel-Puerto-Rico.h8283142.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=2025-10-25&endDate=2025-10-26®ionId=3000652683&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Caribbean Islands Hotel Reviews ![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 "My stay at this hotel was truly exceptional. The staff was warm, welcoming and always ready to help with a smile. The room was spotless, beautifully maintained, and very comfortable, making me feel right at home with an amazing ocean view. the location was perfect, easy valet parking. I would highly recommend this hotel to anyone looking for comfort, quality and outstanding service. I look forward to returning" [](https://expedia.ca/San-Juan-Hotels-La-Concha-Renaissance-San-Juan-Resort.h1760259.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 "Balcony view beautiful!" [](https://expedia.ca/San-Juan-Hotels-Hyatt-Regency-Grand-Reserve-Puerto-Rico.h979694.Hotel-Information) ![Hotel Riu Palace Antillas - Adults Only - All Inclusive](//images.trvl-media.com/lodging/1000000/30000/28700/28648/c1474878_y.jpg) ### Hotel Riu Palace Antillas - Adults Only - All Inclusive 10/10 Excellent "I rated it excellent " [](https://expedia.ca/Noord-Hotels-Riu-Palace-Antillas-All-Inclusive-Adult-Only.h28648.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 "Great view from the room" [](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 really enjoyed the service and the food " [](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 "Everything was amazing! Practically a private beach" [](https://expedia.ca/San-Juan-Hotels-Royal-Sonesta-San-Juan.h289099.Hotel-Information) ![Grand Hyatt Baha Mar](//images.trvl-media.com/lodging/8000000/7780000/7779300/7779293/8fc5fb82_y.jpg) ### Grand Hyatt Baha Mar 10/10 Excellent "Ocean view room wss amazing. The food at Stix was quite tasty. There are several pools...all are great. The Baha Mar hotels are extremely nice." [](https://expedia.ca/Nassau-Hotels-Grand-Hyatt-Baha-Mar.h7779293.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 "Location location location Friendly staff Gorgeous beach" [](https://expedia.ca/Noord-Hotels-Holiday-Inn-Resort-Aruba-Beach-Resort-And-Casino.h5956.Hotel-Information)