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

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Caribbean Accommodation: Most Popular Cities to Stay

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 Business Hotels

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Caribbean business-friendly hotels

A pool area with multiple white umbrellas and lounge chairs.

1. S Hotel Kingston

S Hotel Kingston
4.5 star property
New Kingston
9.4 out of 10, Exceptional, (1,815 reviews)
"Great stay with great food"
United States
Jodie
The price is ₹16,199
₹20,872 total
includes taxes & fees
8 Nov - 9 Nov
S Hotel Kingston
A modern restaurant with large windows offering a city view.

2. Dominican Fiesta Hotel

Dominican Fiesta Hotel
4.0 star property
Los Cacicazgos
8.2 out of 10, Very good, (2,869 reviews)
"Good location, friendly staff"
United States
Rosanna
The price is ₹7,144
₹9,144 total
includes taxes & fees
30 Nov - 1 Dec
Dominican Fiesta Hotel
An outdoor seating area with tables and chairs, palm trees, and a view of the ocean.

3. Hyatt Regency Trinidad

Hyatt Regency Trinidad
4.5 star property
Downtown Port of Spain
9.2 out of 10, Wonderful, (1,101 reviews)
"Its a great location"
United States
chiara
The price is ₹21,903
₹26,612 total
includes taxes & fees
15 Nov - 16 Nov
Hyatt Regency Trinidad
View from room

4. Knutsford Court Hotel

Knutsford Court Hotel
4.0 star property
New Kingston
7.6 out of 10, Good, (1,000 reviews)
"The property is just wonderfull."
United States
Neil
Knutsford Court Hotel
Beach

5. Radisson Aquatica Resort Barbados

Radisson Aquatica Resort Barbados
4.0 star property
Garrison Historic Area
7.6 out of 10, Good, (1,000 reviews)
"Perfect place to stay on one of the best beaches. Front desk staff and bell hop weren't the friendliest, but the waiters/and restaurant manager were amazing!!"
United States
Devri Ashanti
Radisson Aquatica Resort Barbados
A modern living room with a grey sofa, a coffee table, and a view of the beach through large windows.

6. Sheraton Santo Domingo Hotel

Sheraton Santo Domingo Hotel
4.0 star property
Gascue
8.8 out of 10, Excellent, (1,002 reviews)
"Excellent location and services"
United States
virgilio
The price is ₹11,332
₹14,505 total
includes taxes & fees
31 Oct - 1 Nov
Sheraton Santo Domingo Hotel
A modern living room with a large window, a sofa, a coffee table, and a TV on the wall.

7. Weston Suites & Hotel

Weston Suites & Hotel
3.5 star property
Downtown Santo Domingo
7.6 out of 10, Good, (1,000 reviews)
"Great place"
United States
julia
The price is ₹7,223
₹9,246 total
includes taxes & fees
31 Oct - 1 Nov
Weston Suites & Hotel
A luxurious dining area with round tables, white tablecloths, and gold chairs, featuring floral centerpieces and a view of the ocean.

8. TRYP by Wyndham Isla Verde

TRYP by Wyndham Isla Verde
3.5 star property
Isla Verde
8.4 out of 10, Very good, (1,819 reviews)
"Excellent place to stay highly recommend"
United States
Jose A
The price is ₹18,003
₹22,960 total
includes taxes & fees
18 Nov - 19 Nov
TRYP by Wyndham Isla Verde
A rooftop pool with a city view at dusk.

9. Embassy Suites by Hilton Santo Domingo

Embassy Suites by Hilton Santo Domingo
4.0 star property
Downtown Santo Domingo
9.4 out of 10, Exceptional, (1,076 reviews)
"I love everything about this resort"
United States
Rosa
The price is ₹14,327
₹18,339 total
includes taxes & fees
22 Nov - 23 Nov
Embassy Suites by Hilton Santo Domingo
A person seated at a wooden bar with a stone-tiled floor, holding a drink.

10. The Courtleigh Hotel and Suites

The Courtleigh Hotel and Suites
4.0 star property
New Kingston
9.2 out of 10, Wonderful, (1,002 reviews)
"Great location, excellent Food and Staff"
United States
Chantal
The price is ₹20,993
₹26,098 total
includes taxes & fees
6 Nov - 7 Nov
The Courtleigh Hotel and 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

Hotel El Convento

Hotel El Convento

10/10 Excellent
"I absolutely love this property. It’s historical and beautiful. The staff are amazing, and not just one person, the entire staff was wonderful. My family and I stay here every time we come to Puerto Rico. It’s wonderful for families with children. It’s close to so many restaurants, shops, food trucks, historical sites, and not far from beaches either. The only complaint I have is that they were working on expanding their rooftop pool so we were not able to enjoy that part of the property this time. Other than that, everything was wonderful."
Victoria 2-night trip
Posted 10 hours ago
Hotel El Convento

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Frequently asked questions

Why book your business-friendly hotel in Caribbean with Expedia?
At Expedia, our job is to help you track down the perfect stay at the right price. From deluxe, corporate-friendly escapes to affordable motor inns filled with conveniences, you'll have your next work trip organised in a few quick clicks.
How can I find cheap business-friendly hotels in Caribbean?
Click on the "business friendly" filter, listed under the "traveller experience" heading, to find cheap business-friendly hotels in Caribbean. Then refine your search by your budget and preferred hotel star rating. Looking for stays outside the city centre is another good way to save.