The BEST Offers in the Islands
Reduced rates, kids stay FREE offers, added values and more!
Book by 8/7/16 for travel through 12/15/16

All Deals Include: Round-trip airfare, Hotel accommodations, Taxes and more

Caribbean Vacation Packages

 from $555
 

Aruba

3 nights with air from $1,045

Book Now
 
 

Bahamas

3 nights with air from $855

Book Now
 
 

Dominican Republic

3 nights with air from $599

Book Now
 
 

Grand Cayman

3 nights with air from $1,079

Book Now
 
 

Jamaica

3 nights with air from $1,029

Book Now
 
 

Puerto Rico

3 nights with air from $555

Book Now
 
 

Saint Lucia

3 nights with air from $1,515

Book Now
 
 

St. Martin and Sint Maarten

3 nights with air from $1,245

Book Now
 
 

Turks & Caicos

3 nights with air from $1,239

Book Now
 
 

US Virgin Islands

4 nights with air from $715

Book Now
 
Share With
Rates are based on roundtrip air travel to/from Boston (BOS) for Jamaica, St. Lucia, Turks & Caicos and US Virgin Islands, Los Angeles (LAX) for Dominican Republic and Puerto Rico, Manchester (MHT) for Grand Cayman and St. Martin, Pittsburgh (PIT) for Bahamas and Providence (PVD) for Aruba, and are per person, based on double occupancy. Advertised vacation rate(s) valid for departures 8/25/16 for Bahamas, 10/17/16 for St. Lucia, 10/5/16 for Dominican Republic and Puerto Rico and 10/6/16 for all other destinations. Dominican Republic: Rates do not include a $10 per person Tourist Card fee payable upon arrival in the Dominican Republic.
Caribbean - Best Offers: Valid on new bookings at participating resorts made 6/20 - 8/7/16 for travel 6/20 - 12/15/16. Minimum night stay may be required and varies by participating resort. Blackout dates apply. All offers subject to change or cancellation without notice.
Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]