Book Exclusive Caribbean Vacation Packages

Choose one or more items to build your trip:

Search vacation packages deals in Caribbean's top destinations

San Juan

Vacations
San Juan

Caribbean flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Ola Boutique Hotel

Ola Boutique Hotel

4.5 out of 5
Condado
per person
Feb. 5 - Feb. 12
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to San Juan (SJU)
Stay at this 4.5-star luxury hotel in San Juan. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Condado Beach and Pan American Pier are located nearby.
Princess Senses The Mangrove Resort - Adults Only

Princess Senses The Mangrove Resort - Adults Only

4 out of 5
per person
Jan. 24 - Jan. 31
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Montego Bay (MBJ)
Stay at this 4-star beach resort in Green Island. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Half Moon Beach and Samuel's Bay National Marine Park are located nearby.
Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

4.5 out of 5
per person
Feb. 4 - Feb. 11
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Montego Bay (MBJ)
Stay at this 4.5-star luxury resort in Green Island. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Half Moon Beach and Samuel's Bay National Marine Park are located nearby.
Sunset at the Palms Resort - Adults Only - All Inclusive

Sunset at the Palms Resort - Adults Only - All Inclusive

4.5 out of 5
per person
Jan. 24 - Jan. 31
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Montego Bay (MBJ)
Stay at this 4.5-star luxury property in Negril. Enjoy free breakfast, free WiFi, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Seven Mile Beach and Hedonism II are located nearby.
Alamanda Cottage at Serenity

Alamanda Cottage at Serenity

3 out of 5
per person
Jan. 6 - Jan. 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Montego Bay (MBJ)
Stay at this 3-star business-friendly cottage in Montego Bay. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Doctor's Cave Beach and Rose Hall Great House are located nearby.

Top Caribbean hotels deals

Hotel El Convento

Hotel El Convento

4.5 out of 5
100 Cristo St, San Juan
Free cancellation
Reserve now, pay when you stay
The price is CA $337 per night
CA $337
CA $441 total
includes taxes & fees
4 Dec - 5 Dec
Stay at this 4.5-star luxury hotel in San Juan. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of San Juan and Pan American Pier are located nearby.
Pool
Free WiFi
British Colonial - Nassau

British Colonial - Nassau

4 out of 5
Number One Bay St, Nassau
Free cancellation
Reserve now, pay when you stay
The price is CA $292 per night
CA $292
CA $413 total
includes taxes & fees
3 Dec - 4 Dec
Stay at this 4-star beach hotel in Nassau. Enjoy free WiFi, 2 outdoor pools, and 8 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Junkanoo Beach and Cable Beach are located nearby.
On private beach
Pool
Hotel Rumbao, a Tribute Portfolio Hotel

Hotel Rumbao, a Tribute Portfolio Hotel

4 out of 5
100 Brumbaugh Street, San Juan, Puerto Rico
Free cancellation
Reserve now, pay when you stay
The price is CA $296 per night
CA $296
CA $372 total
includes taxes & fees
4 Dec - 5 Dec
Stay at this 4-star business-friendly hotel in San Juan. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of San Juan and Pan American Pier are located nearby.
Pool
Hot tub
The Reef at Atlantis

The Reef at Atlantis

4.5 out of 5
Paradise Beach Drive, Paradise Island, New Providence
Get rates
Stay at this 4.5-star luxury resort in Paradise Island. Enjoy free WiFi, a full-service spa, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Junkanoo Beach and Cable Beach are located nearby.
On private beach
Pool
Boutique Hotel Palacio

Boutique Hotel Palacio

3.5 out of 5
Calle Duarte 106, Santo Domingo, Distrito Nacional
Free cancellation
Reserve now, pay when you stay
The price is CA $118 per night
CA $118
CA $151 total
includes taxes & fees
3 Dec - 4 Dec
Stay at this 3.5-star business-friendly hotel in Santo Domingo. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Malecon and Blue Mall are located nearby.
Pool
Breakfast included
Comfort Suites Paradise Island

Comfort Suites Paradise Island

4 out of 5
Paradise Island Drive, Paradise Island, New Providence
The price is CA $383 per night
CA $383
CA $594 total
includes taxes & fees
3 Dec - 4 Dec
Stay at this 4-star business-friendly hotel in Paradise Island. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Junkanoo Beach and Cable Beach are located nearby.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Caribbean
View all properties
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.

Photos of local treasures

Browse Caribbean vacation photos for more inspiration

Trunk Bay which includes island views
Emerald Bay showing sailing and a beach
Caribbean
Miami Beach which includes a beach and landscape views
Caribbean