Update: Some offers mentioned below are no longer available. View the current offers here.Airfare deals are typically only available on limited dates. We recommend that you use Google Flights to find dates to fly, then book through an online travel agency, such as Orbitz, which allows you to cancel flights without penalty by 11pm Eastern Time within one day of booking. Remember: Fares may disappear quickly, so book right away and take advantage of Orbitz’s courtesy cancellation if you’re unable to travel. Additionally, keep in mind that discounted partner fares may not earn miles with US-based carriers.Looking to score an awesome deal on an off-season trip to the Caribbean? JetBlue is currently offering discounted fares from New York (JFK) to Barbados (BGI) from $254 round-trip for departures in June and from New York (JFK) to Grand Cayman (GCM) from $262 round-trip for departures in September. Note that you can also earn at least 9x points for JetBlue flights in June — be sure to register before you book. We’re seeing somewhat limited availability for these itineraries, but if your travel dates are flexible there are great deals to be had!Airlines: JetBlueRoutes: JFK to BGI and GCMCost: $254+ round-trip in economyDates: June 2016 and September 2016Booking Link: OrbitzPay With: Premier Rewards Gold Card from American Express, Citi Prestige or Chase Sapphire PreferredHere are a few examples of what you can book:New York (JFK) to Barbados (BGI) for $254 round-trip on JetBlue in June:Sign up for our daily newsletterEmail addressSign upI would like to subscribe to The Points Guy newsletters and special email promotions. The Points Guy will not share or sell your email. See privacy policy.New York (JFK) to Barbados (BGI) for $254 round-trip on Jetblue.New York (JFK) to Grand Cayman (GCM) for $262 round-trip on JetBlue in September:New York (JFK) to Grand Cayman (GCM) for $262 round-trip on JetBlue.Maximize Your PurchaseDon’t forget to use a credit card that earns additional points on airfare purchases, such as the American Express Premier Rewards Gold or Citi Prestige (3x on airfare) or the Chase Sapphire Preferred Card (2x on all travel purchases). Check out this post for more on maximizing airfare purchases.H/T: Scott’s Cheap FlightsIf you’re able to score one of these tickets, please share the good news in the comments below!