Find Historic Hotels in Caribbean Islands from CA $117

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Top Caribbean Islands Historic Hotels

Hotel El Convento
Front of property
Hotel El Convento
4.5 star property
8.6 out of 10, Excellent, (1002)
"Absolutely stunning hotel. Very close to numerous wonderful cafes, restaurants and shops. Wish I spent my entire trip here- not just my last night. 10/10, way better than Fairmont. "
The price is CA $352
CA $460 total
includes taxes & fees
Nov 25 - Nov 26
Hotel El Convento
Boutique Hotel Palacio
Front of property
Boutique Hotel Palacio
3.5 star property
8.6 out of 10, Excellent, (1001)
"The area is about rough but safer than other areas. The hotel was secure and comfortable. "
The price is CA $117
CA $150 total
includes taxes & fees
Nov 25 - Nov 26
Boutique Hotel Palacio
Hotel Rumbao, a Tribute Portfolio Hotel
Exterior
Hotel Rumbao, a Tribute Portfolio Hotel
4.0 star property
9.0 out of 10, Wonderful, (506)
"Awesome location! "
The price is CA $266
CA $339 total
includes taxes & fees
Nov 24 - Nov 25
Hotel Rumbao, a Tribute Portfolio Hotel
CasaBlanca Hotel
Rooftop terrace
CasaBlanca Hotel
3.5 star property
8.8 out of 10, Excellent, (1250)
"Unique, close to port."
The price is CA $185
CA $214 total
includes taxes & fees
Dec 1 - Dec 2
CasaBlanca Hotel
The Gallery Inn
Outdoor pool
The Gallery Inn
3.0 star property
8.4 out of 10, Very good, (369)
"Un lugar muy diferente e interesante. La pasamos muy bien. "
The Gallery Inn
Villa Herencia Hotel
Hallway
Villa Herencia Hotel
3.5 star property
9.2 out of 10, Wonderful, (732)
"Lots of character and romantic vibe. Staff friendly but not on staff 24 hrs. Walking distance to r earthing in OSJ. Ac unit loud in our room so had to turn off . Overall lots of charm and for price would stay again . "
The price is CA $183
CA $208 total
includes taxes & fees
Nov 25 - Nov 26
Villa Herencia Hotel
La Terraza de San Juan
Terrace/patio
La Terraza de San Juan
3.5 star property
8.2 out of 10, Very good, (1008)
"I loved how close it was to all the restaurants and stores.. i didnt like the spotty internet"
The price is CA $226
CA $276 total
includes taxes & fees
Dec 23 - Dec 24
La Terraza de San Juan
Sanctuary Cap Cana, a Luxury Collection Resort, Dominican Republic, Adult All-Inclusive
Aerial view
Sanctuary Cap Cana, a Luxury Collection Resort, Dominican Republic, Adult All-Inclusive
5.0 star property
9.4 out of 10, Exceptional, (1004)
"The property is nice and clean but not enough entertainment and food quality and choice is overrated. One of the restaurants was closed for renovation, but nobody notified us about it. So out of 5 restaurants basically it was only 2 options, plus Stake House is closed on Fridays. "
The price is CA $817
CA $817 total
includes taxes & fees
Nov 25 - Nov 26
Sanctuary Cap Cana, a Luxury Collection Resort, Dominican Republic, Adult All-Inclusive
Admiral's Inn and Gunpowder Suites
Aerial view
Admiral's Inn and Gunpowder Suites
3.5 star property
9.4 out of 10, Exceptional, (151)
"The staff were particularly helpful storing some provisions and carrying all luggage to nearby location for our boat rental."
The price is CA $335
CA $440 total
includes taxes & fees
Nov 27 - Nov 28
Admiral's Inn and Gunpowder Suites
Fortaleza Suites
Presidential Suite | Balcony
Fortaleza Suites
3.5 star property
9.0 out of 10, Wonderful, (1006)
"Perfect place to stay with my son during my stay in PR! Helpful staff! Hotel is conveniently located at the Old San Juan!"
The price is CA $162
CA $173 total
includes taxes & fees
Nov 24 - Nov 25
Fortaleza Suites
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.
Don't see what you're looking for?
See all available properties in Caribbean Islands
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.
Unlock Black Friday deals