
Cheap Flights to Caribbean (2026/2027)
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Punta Cana
Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | San Juan | August 30 to September 2 | $237 |
| JFK | San Juan | August 30 to September 2 | $237 |
| JFK | Nassau | June 21 to June 27 | $301 |
| JFK | Montego Bay | July 7 to July 23 | $317 |
| EWR | San Juan | July 4 to July 9 | $320 |
| JFK | Oranjestad | June 21 to June 24 | $337 |
| JFK | Oranjestad | June 21 to June 24 | $337 |
| JFK | Punta Cana | August 23 to August 27 | $337 |
| JFK | Piarco | August 18 to August 28 | $350 |
| JFK | Kingston | August 25 to September 8 | $395 |
| JFK | Kingston | August 25 to September 8 | $395 |
| JFK | Santo Domingo | June 15 to June 25 | $403 |
| EWR | Kingston | September 8 to September 22 | $415 |
| JFK | West End | July 13 to July 21 | $952 |
| JFK | West End | July 13 to July 21 | $952 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | San Juan | June 7 to June 17 | $297 |
| JFK | San Juan | June 7 to June 17 | $297 |
| JFK | Montego Bay | June 6 to June 10 | $337 |
| EWR | San Juan | June 7 to June 17 | $342 |
| JFK | Oranjestad | June 6 to June 11 | $363 |
| JFK | Nassau | June 6 to June 13 | $363 |
| LGA | Piarco | June 6 to June 13 | $371 |
| JFK | Santiago de los Caballeros | June 7 to June 14 | $383 |
| EWR | Santo Domingo | June 5 to June 18 | $391 |
| EWR | Montego Bay | June 7 to June 13 | $403 |
| JFK | Santo Domingo | June 7 to June 10 | $403 |
| EWR | Punta Cana | June 7 to June 11 | $409 |
| EWR | Santiago de los Caballeros | June 7 to June 13 | $410 |
| JFK | Kingston | June 6 to June 20 | $415 |
| JFK | Piarco | June 7 to June 17 | $490 |
Best Caribbean Flight and Hotel Packages
Price found within the past 48 hours. Click for updated prices.



Travelers ❤️ These Caribbean 🏨

Hotel El Convento
100 Cristo St San Juan
Book a stay at this 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 Condado Beach are located nearby.
9/10 Wonderful! (1,003 reviews)
"Excellent location, walkable to all the things in old San Juan that you would want to see! Staff was helpful and kind. They had cold bottled water available at all times. Nice wine and cheese reception in the evening. Cool building with a lot of history."
Reviewed on May 28, 2026

British Colonial - Nassau
Number One Bay St Nassau
Book a stay at this beach hotel in Nassau. Enjoy free WiFi, 2 outdoor pools, and 6 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cable Beach and Pirates of Nassau Museum are located nearby.
8.6/10 Excellent! (2,605 reviews)
"On-site beach and proximity to many Nassau attractions"
Reviewed on May 30, 2026

Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Book a stay at this 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 Condado Beach are located nearby.
9/10 Wonderful! (1,694 reviews)
"La comida sobre todo tiene muy buena calidad ,esta situado en un lugar estrategico buena vista y facil acceso,muy buen trato del personal,es mi segunda vez en este hotel lastima que como somos familia de cinco tuvimos que rentar dos habitaciones,solo eso por lo demas un poquito mejorar el detalle ..."
Reviewed on May 31, 2026
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The Reef at Atlantis
Paradise Beach Drive Paradise Island New Providence
Book a stay at this 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 Cable Beach and Aquaventure are located nearby.
9/10 Wonderful! (1,494 reviews)
"The room was very clean but the water smells like sewer. Taking a bath isn’t exactly appealing when the water stinks and I certainly wasn’t drinking it. It would be nice if there was a restaurant inside the reef or a bar but there is not. The privacy of the beach and pool makes it all worth it. Our ..."
Reviewed on May 31, 2026
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.



