A tropical beach with clear turquoise waters, lush green hills, and a small red building on a hill.

Historic Hotels in Caribbean

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A beach with clear turquoise water, a sandy shore, and a city skyline with tall buildings including a Marriott hotel.
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San Juan

San Juan

Check availability on Caribbean Historic Hotels

This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Caribbean historic hotels

A yellow building with "EL CONVENTO" sign, columns, and a staircase leading to the entrance.

1. Hotel El Convento

Hotel El Convento
4.5 star property
Old San Juan
9.2 out of 10, Wonderful, (1,005 reviews)
"Great staff and great hotel, the location is the best!"
United States
Juan
The price is €403
includes taxes & fees
4 Oct - 5 Oct
Hotel El Convento
An outdoor patio area with multiple tables and chairs, surrounded by potted plants and a stone wall.

2. Boutique Hotel Palacio

Boutique Hotel Palacio
3.5 star property
Zona Colonial
8.6 out of 10, Excellent, (1,002 reviews)
"Wonderful place, friendly staff, close by to activities."
United States
Michael
The price is €72
includes taxes & fees
3 Oct - 4 Oct
Boutique Hotel Palacio
A modern kitchen with marble countertops, wooden shelves, and a variety of food items and kitchenware.

3. Hotel Rumbao, a Tribute Portfolio Hotel

Hotel Rumbao, a Tribute Portfolio Hotel
4.0 star property
Old San Juan
9.0 out of 10, Wonderful, (1,949 reviews)
"Excellent location, excellent and friendly staff."
United States
Daiza
The price is €159
includes taxes & fees
18 Oct - 19 Oct
Hotel Rumbao, a Tribute Portfolio Hotel
A rooftop deck with large tubs and a wooden deck, overlooking a cityscape.

4. CasaBlanca Hotel

CasaBlanca Hotel
3.5 star property
Old San Juan
8.8 out of 10, Excellent, (1,548 reviews)
"Clean rooms friendly staff and accommodating to restaurants and sight seeing in the area."
United States
Ray
The price is €99
includes taxes & fees
5 Oct - 6 Oct
CasaBlanca Hotel
An outdoor patio with wooden chairs and a table, surrounded by lush greenery and a rustic stone floor.

5. The Gallery Inn

The Gallery Inn
3.0 star property
Old San Juan
8.2 out of 10, Very good, (479 reviews)
"This hotel is a completely surreal world. My partner and I loved exploring all the rooms and appreciating the decorations and architecture of the house. Staff was extremely friendly and welcoming, and the live jazz music at night made this one of the best experiences I’ve had while traveling."
United States
Juan
The price is €202
includes taxes & fees
4 Oct - 5 Oct
The Gallery Inn
A bed with white linens and two hats, a glass-enclosed balcony with a view of greenery and buildings, and a wooden pergola structure.

6. Villa Herencia Hotel

Villa Herencia Hotel
3.5 star property
Old San Juan
9.2 out of 10, Wonderful, (885 reviews)
"Loved every aspect of this hotel. Will return in the future!"
United States
Kevin
The price is €151
includes taxes & fees
4 Oct - 5 Oct
Villa Herencia Hotel
A person relaxing by a pool with a drink and flowers, overlooking a cityscape.

7. La Terraza de San Juan

La Terraza de San Juan
3.5 star property
Old San Juan
8.4 out of 10, Very good, (1,004 reviews)
"The staff are great and the breakfast option on the terrace really adds a chefs kiss to the stay."
United States
Yanira
The price is €100
includes taxes & fees
4 Oct - 5 Oct
La Terraza de San Juan
A resort with a large pool, beachfront, and multiple buildings.

8. Sanctuary Cap Cana, a Luxury Collection Resort, Dominican Republic, Adult All-Inclusive

Sanctuary Cap Cana, a Luxury Collection Resort, Dominican Republic, Adult All-Inclusive
5.0 star property
Cap Cana
9.2 out of 10, Wonderful, (1,000 reviews)
"Amazing stay definitely coming back"
United States
camilo andres
The price is €402
includes taxes & fees
13 Oct - 14 Oct
Sanctuary Cap Cana, a Luxury Collection Resort, Dominican Republic, Adult All-Inclusive
A resort with a swimming pool, outdoor seating, and a view of the water and mountains.

9. Admiral's Inn and Gunpowder Suites

Admiral's Inn and Gunpowder Suites
3.5 star property
English Harbour
9.4 out of 10, Exceptional, (183 reviews)
"Loved this hotel in a lovely area of English Harbour. Lovely accommodations and very friendly staff "
United Kingdom
Wendy
The price is €300
includes taxes & fees
10 Oct - 11 Oct
Admiral's Inn and Gunpowder Suites
An open door with white curtains, a chair with a cushion, a small table with a cup and saucer, and a potted plant.

10. Fortaleza Suites

Fortaleza Suites
3.5 star property
Old San Juan
8.8 out of 10, Excellent, (1,459 reviews)
"Great stay"
United States
Laura
The price is €58
includes taxes & fees
14 Oct - 15 Oct
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.
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Top Caribbean Hotel Reviews

Hilton Aruba Caribbean Resort and Casino

Hilton Aruba Caribbean Resort and Casino

8/10 Good
"did not like the high resort fees"
robert 6-night trip
Posted less than an hour ago
Hilton Aruba Caribbean Resort and Casino

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