Home > Travel Deals > Vacations > Caribbean

Best Caribbean Vacation Deals*

 

$538 & up -- All-Inclusive Jamaica Trip w/Air & Tax, 60% Off

Spend three nights at a sprawling beachfront resort
Multiple departure cities available; travel through June
 

$949 -- Punta Cana Weeklong All-Incl. Beachfront Trip w/Air

Save $500 on a Junior Suite at an all-inclusive resort
Select departures April-May, some incl. Memorial Day weekend
 

$699 & up -- Aruba Vacations on Sale, up to $350 Off

Lounge beachfront with these air-&-hotel deals (incl. taxes)
Travel through August
 

$103 & up -- Puerto Rico Getaway: Deals up to 50% Off

No passport required to slip away to these beaches
Deals into August
 

$449 -- Puerto Rico 4-Star Escape w/Air & Tax, Half Off

This deal includes a $100 food & beverage credit
April 9 - June 30; +$40 Feb. 25 - April 8
 

$992 & up-- Weeklong Grand Cayman Trip w/Air (incl. tax)

Sale includes upscale resorts throughout the Cayman Islands
Available from multiple cities through September
 
 
 

More Deals on Caribbean Vacations *

 
 
Discounted pricing available through July
Delta Vacations
 
Discounted pricing available through September
Delta Vacations
 
Discounted pricing available through July
Delta Vacations
 
Discounted pricing available through June
Delta Vacations
 
Select dates through Dec. 28
Cruise & Land Travel
 
 
 
 
Includes airfare, tax; through March 29
Pleasant Holidays
 
Select March departures; fly from 18 cities
Apple Vacations
 
 
 
 
Depart May 20, Oct. 7 or Oct. 21 from Miami
Friendly Planet Travel
 
Depart Sundays April 15 - May 20
Puerto Rico Tourism Company
 
Select dates April 20 - May 31 (incl. Tax)
TravelByJen.com
 
May-June; +$70 March-April
CheapCaribbean.com
 
 
March-April; +$110 May-June
CheapCaribbean.com
 
 
Feb. 1 - March 18; April 8 - June 30
CheapCaribbean.com
 
 
 
 
 
 
 
Feb. 7-24; +$80 Feb. 25-March 14; April 15-June 20
CheapCaribbean.com
 

Compare Multiple Travel Sites in One Search

From: To:
Depart: Return:
Adults:
Children:
Rooms:
Click on the logos to search and compare top sites:

New: DOT Full Fare Rules

New U.S. government rules require airfare and air-inclusive packages to include all taxes and fees in the price.
Learn More »

Travelzoo Tips

Erin Rubin — Travel, Entertainment and Local Deal Expert
Angela Tablac — Travel, Entertainment and Local Deal Expert
Jaime Freedman — Travel, Entertainment and Local Deal Expert
When going all-inclusive, ask yourself these questions before booking. More »
Erin Rubin
Deal Expert, Toronto