Historic Hotels in Caribbean Islands
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Featured Caribbean Islands Historic Hotels

Hotel El Convento
100 Cristo St San Juan
Free Cancellation
Reserve now, pay when you stay
$290 nightly
The price is $316 total per night
$316 total
Dec 25 - Dec 26
Total with taxes and fees
At Hotel El Convento, guests enjoy features like an outdoor pool, a gym, and free WiFi in public areas. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, tours or tickets, and luggage storage. Other amenities at this luxury hotel include meeting rooms, free use of bicycles, and a library.
Pool
Free WiFi

Boutique Hotel Palacio
Calle Duarte 106 Santo Domingo Distrito Nacional
Free Cancellation
Reserve now, pay when you stay
$68 nightly
The price is $88 total per night
$88 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Boutique Hotel Palacio features an outdoor pool, free WiFi in public areas, and meeting rooms. You can take advantage of free parking, along with an airport shuttle (available 24 hours) for USD 40 per vehicle one-way. Multilingual staff at the 24-hour front desk can assist with luggage storage, tours or tickets, and dry cleaning/laundry. Additional amenities include conference space, coffee/tea in a common area, and a library.
Pool
Breakfast included

Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Free Cancellation
Reserve now, pay when you stay
$248 nightly
The price is $270 total per night
$270 total
Dec 24 - Dec 25
Total with taxes and fees
At Hotel Rumbao, a Tribute Portfolio Hotel, guests enjoy an outdoor pool, a 24-hour gym, and free WiFi in public areas. Valet parking is available for USD 36.00 per night. Multilingual staff at the 24-hour front desk can assist with tours or tickets, securing valuables, and luggage storage. Additional amenities include meeting rooms, conference space, and a computer station.
Pool
Pet friendly

CasaBlanca Hotel
316 Calle Fortaleza San Juan
$139 nightly
The price is $152 total per night
$152 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Guests of CasaBlanca Hotel enjoy a rooftop terrace, free WiFi in public areas, and microwave in a common area. Offsite parking is offered for a fee. The 24-hour front desk has multilingual staff ready to assist with securing valuables, luggage storage, and concierge services. Additional amenities include a refrigerator in a common area, express check-out, and a terrace.
Free WiFi
Air conditioning

The Gallery Inn
204-206 Norzagaray San Juan
$232 nightly
The price is $253 total per night
$253 total
Jan 19 - Jan 20, 2026
Total with taxes and fees
The Gallery Inn features an outdoor pool, a rooftop terrace, and microwave in a common area. Self parking is offered for USD 25 per night. The front desk has multilingual staff that can help with luggage storage, and offer advice about sights and eateries nearby. Additional amenities include a terrace, wedding services, and a garden.
Pool
Restaurant

Villa Herencia Hotel
23 Cll Caleta Las Monjas San Juan
$245 nightly
The price is $263 total per night
$263 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
Villa Herencia Hotel features free WiFi in public areas, a library, and express check-in. The front desk has multilingual staff that can help with dry cleaning/laundry, concierge services, and luggage storage. Other amenities at this boutique hotel include express check-out, a terrace, and a picnic area.
Free WiFi
Air conditioning

La Terraza de San Juan
262 Calle del Sol San Juan
Free Cancellation
Reserve now, pay when you stay
$165 nightly
The price is $180 total per night
$180 total
Jan 20 - Jan 21, 2026
Total with taxes and fees
At La Terraza de San Juan, guests have access to an outdoor pool, a rooftop terrace, and free WiFi in public areas. The 24-hour front desk has multilingual staff ready to assist with luggage storage and concierge services. Additional amenities include express check-in, express check-out, and laundry facilities.
Pool
Free WiFi

Sanctuary Cap Cana, a Luxury Collection Resort, Dominican Republic, Adult All-Inclusive
Blvd Zona Hotelera, Playa Juanillo Punta Cana La Altagracia
$710 nightly
The price is $710 total per night
$710 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
Sanctuary Cap Cana, a Luxury Collection Resort, Dominican Republic, Adult All-Inclusive features a private beach, a full-service spa, and 6 outdoor pools. There's free parking if you drive. The front desk has multilingual staff on hand 24/7 to help with securing valuables, concierge services, and luggage storage. Other amenities at this adults-only resort include a nightclub, karaoke, and a gym.
On private beach
Pool

Admiral's Inn and Gunpowder Suites
Nelson's Dockyard English Harbour Antigua
$336 nightly
The price is $397 total per night
$397 total
Dec 27 - Dec 28
Total with taxes and fees
Guests of Admiral's Inn and Gunpowder Suites enjoy an outdoor pool, free WiFi in public areas, and spa treatment rooms. You can take advantage of free parking, along with an airport shuttle (available 24 hours) for USD 50 per vehicle one-way. The front desk has multilingual staff that can help with luggage storage and tours/tickets. Other amenities at this beach hotel include a meeting room, a terrace, and laundry facilities.
Pool
Spa

Fortaleza Suites
315 Calle Fortaleza San Juan
Free Cancellation
Reserve now, pay when you stay
$163 nightly
The price is $175 total per night
$175 total
Dec 30 - Dec 31
Total with taxes and fees
Fortaleza Suites features free WiFi in public areas, coffee in a common area, and microwave in a common area. Multilingual staff at the front desk are standing by 24/7 to help with concierge services, dry cleaning/laundry, and luggage storage. Additional amenities include a refrigerator in a common area, express check-in, and express check-out.
Free WiFi
Laundry

Caribe Hilton
1 San Geronimo Street San Juan
Free Cancellation
Reserve now, pay when you stay
$355 nightly
The price is $387 total per night
$387 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Guests of Caribe Hilton have access to a full-service spa, 3 outdoor pools, and a children's pool. Valet parking is available for USD 32 per day. The 24-hour front desk has multilingual staff ready to assist with securing valuables, concierge services, and dry cleaning/laundry. Other amenities at this beach resort include a gym, a sauna, and outdoor tennis courts.
Pool
Hot Tub

Copper and Lumber Store Hotel
Nelsons Dockyard English Harbour Antigua
Guests staying at Copper and Lumber Store Hotel enjoy a marina, free WiFi in public areas, and laundry facilities. A stay here includes free parking. Front-desk staff can assist with tours or tickets, securing valuables, and dry cleaning/laundry. Other amenities at this historic hotel include wedding services, an ATM, and a hair salon.
Parking included
Free WiFi

Luca Hotel by Heritage Residences Signature Collection
Calle 19 de Marzo No. 164 Santo Domingo Distrito Nacional
Guests staying at Luca Hotel by Heritage Residences Signature Collection enjoy a 24-hour gym, a rooftop terrace, and free WiFi in public areas. There's free offsite parking, and an airport shuttle (available 24 hours) for USD 50 per vehicle one way. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, tours or tickets, and dry cleaning/laundry. Additional amenities include a hot tub, a meeting room, and a terrace.
Hot Tub
Breakfast included

Ponce Plaza Hotel & Casino
Reina Street Ponce
Free Cancellation
Reserve now, pay when you stay
$186 nightly
The price is $204 total per night
$204 total
Dec 28 - Dec 29
Total with taxes and fees
Guests of Ponce Plaza Hotel & Casino enjoy a casino, an outdoor pool, and a gym. Self parking is offered for USD 11.15 per night. The front desk has multilingual staff on hand 24/7 to help with luggage storage, dry cleaning/laundry, and concierge services. Other amenities at this historic hotel include free WiFi in public areas, a library, and express check-out.
Pool
Pet friendly

Condado Vanderbilt Hotel
1055 Ashford Avenue San Juan
Free Cancellation
Reserve now, pay when you stay
$587 nightly
The price is $651 total per night
$651 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
A local mainstay since 1919, Condado Vanderbilt Hotel offers a full-service spa, 4 outdoor pools, and a children's pool. Valet parking is offered for USD 30 per day. Front-desk staff can answer questions 24/7, and assist with luggage storage, securing valuables, and tours or tickets. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach hotel include a 24-hour gym, a sauna, and free WiFi in public areas.
Pool
Hot Tub
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See all available properties in Caribbean Islands
View all propertiesLowest 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.
Caribbean Islands hotels essential information
Accommodation | 84,901 hotels |
|---|---|
Lowest Price | $88 |
Highest Price | $710 |
Popular hotels | Hotel El Convento, Boutique Hotel Palacio, Hotel Rumbao, a Tribute Portfolio Hotel, CasaBlanca Hotel, The Gallery Inn, Villa Herencia Hotel, La Terraza de San Juan, Sanctuary Cap Cana, a Luxury Collection Resort, Dominican Republic, Adult All-Inclusive, Admiral's Inn and Gunpowder Suites, Fortaleza Suites, Caribe Hilton, Copper and Lumber Store Hotel , Luca Hotel by Heritage Residences Signature Collection, Ponce Plaza Hotel & Casino, Condado Vanderbilt Hotel |
Recent Historic Hotels Reviews

Grand Hyatt Baha Mar
5/5 Excellent
"We stayed as a multigenerational family of nine—adult children with spouses and three kids—and the resort handled it effortlessly. From check-in to checkout, the operation is tight, professional, and built for families who want both energy and comfort.
The property itself is expansive, immaculately maintained, and intelligently designed. There’s enough variety that everyone finds their lane—kids stay engaged, adults relax, and no one feels boxed in. That’s not easy to execute at this size, but Baha Mar gets it right.
The water activities were a standout. Jet skiing was pure adrenaline and a definite crowd-pleaser across generations. The boat tour and snorkeling were equally impressive—well organized, safe, and genuinely enjoyable, not the usual tourist filler. Clear waters, great guides, and memorable moments all around.
What really seals the deal is how family-friendly the resort is without feeling chaotic. Staff are polished, responsive, and clearly trained to manage large groups smoothly. You feel taken care of without being hovered over.
This is old-school hospitality executed with modern scale and ambition. Grand Hyatt Baha Mar isn’t just a resort—it’s a well-run ecosystem that knows exactly what it’s doing.
Strong recommendation. We had a blast, and it’s a place we’d confidently return to with the entire family"
A verified traveler from Oakville stayed at Grand Hyatt Baha Mar
Posted 3 days ago


