Caribbean Islands Romantic Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Condado Vanderbilt Hotel

Condado Vanderbilt Hotel

5 out of 5
Condado
Save 100% on your flight
Price was S$1,594, price is now S$1,103 per person
S$1,103
per person
27 Sept - 2 Oct
found 1 day ago
Return direct flight included
Toronto (YTO) to San Juan (SJU)
9.2/10 Wonderful! (1,534 reviews)
Loved it!! Very Luxurious and staff was very nice and helpful, always provided a smile :)

Reviewed on 21 Aug, 2025

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

5 out of 5
Mameyes II
Price was S$1,326, price is now S$1,185 per person
S$1,185
per person
27 Sept - 2 Oct
found 1 day ago
Return direct flight included
Toronto (YTO) to San Juan (SJU)
8.6/10 Excellent! (2,138 reviews)
Amazing beachfront property, gardens and surrounding areas are well kept, rooms have been renovated. The hotel is going through renovations.

Reviewed on 22 Aug, 2025

Don't see what you're looking for?
See all available trips from Toronto to Caribbean Islands
View all trips
Price found within the past 48 hours. Click for updated prices.
Condado Vanderbilt Hotel

Condado Vanderbilt Hotel

5 out of 5
Condado
Save 100% on your flight
Price was S$1,594, price is now S$1,103 per person
S$1,103
per person
27 Sept - 2 Oct
found 1 day ago
Return direct flight included
Toronto (YTO) to San Juan (SJU)
9.2/10 Wonderful! (1,534 reviews)
Loved it!! Very Luxurious and staff was very nice and helpful, always provided a smile :)

Reviewed on 21 Aug, 2025

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

5 out of 5
Mameyes II
Price was S$1,326, price is now S$1,185 per person
S$1,185
per person
27 Sept - 2 Oct
found 1 day ago
Return direct flight included
Toronto (YTO) to San Juan (SJU)
8.6/10 Excellent! (2,138 reviews)
Amazing beachfront property, gardens and surrounding areas are well kept, rooms have been renovated. The hotel is going through renovations.

Reviewed on 22 Aug, 2025

Don't see what you're looking for?
See all available trips from Toronto to Caribbean Islands
View all trips
Majestic Elegance Punta Cana - All Inclusive

Majestic Elegance Punta Cana - All Inclusive

4.5 out of 5
Playa Bavaro - Punta Cana, Punta Cana, La Altagracia
  • 21 hours drive from Windward Islands
Stay at this 4.5-star luxury property in Punta Cana. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the restaurant in our ...
8.8/10 Excellent! (4,176 reviews)

Couples like: full-service spa, couples spa treatments, beachfront dining, hot tub

Travellers say...
"Amazing! Will come again"

Reviewed on 21 Aug, 2025

Majestic Elegance Punta Cana - All Inclusive
Excellence Punta Cana - Adults Only All Inclusive

Excellence Punta Cana - Adults Only All Inclusive

5 out of 5
Playas Uvero Alto - Punta Cana, Punta Cana, La Altagracia
  • 22 hours drive from Windward Islands
Stay at this 5-star luxury property in Punta Cana. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the pool and the restaurant in our reviews. ...
9.2/10 Wonderful! (2,393 reviews)

Couples like: adults-only property, full-service spa, couples spa treatments, hot tub

Travellers say...
"I absolutely loved my stay at Excellence Punta Cana! The resort has a beautiful, spacious layout with everything from the beach to the dining areas designed for comfort and relaxation. The service was excellent—truly above and beyond what I’m used to, whether I was lounging by the beach or enjoying ..."

Reviewed on 21 Aug, 2025

Excellence Punta Cana - Adults Only All Inclusive
JOIA Rose Hall by Iberostar - Adults Only - All Inclusive

JOIA Rose Hall by Iberostar - Adults Only - All Inclusive

5 out of 5
Rose Hall Main Road, Montego Bay, Saint James
  • 38 hours drive from Windward Islands
Stay at this 5-star luxury property in Montego Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,004 reviews)

Couples like: adults-only property, full-service spa, couples spa treatments, hot tub

Travellers say...
"Great place with great staff. Everything is very close to the rooms. Food was good overall in all the restaurants and buffet. 24 hr room service is always a +."

Reviewed on 22 Aug, 2025

JOIA Rose Hall by Iberostar - Adults Only - All Inclusive
See all 81,396 properties in Caribbean Islands
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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.