Home > Travel Deals > Vacations > Caribbean

Best Caribbean Vacation Deals*

*Some taxes, fees additional.
$369 & up -- Puerto Rico 4-Star Escape w/Air, Save $410

$369 & up -- Puerto Rico 4-Star Escape w/Air, Save $410

Source: CheapCaribbean.com | By Kelsie Ozamiz

Sand and sun are the backdrop to a relaxing day dipping into the lagoon-style pool with swim-up bar
July 1 - Oct. 31

$2999 -- Cuba: 8-Nt. Vacation w/Air, Hotel & Tours, $300 Off

$2999 -- Cuba: 8-Nt. Vacation w/Air, Hotel & Tours, $300 Off
Source: Friendly Planet Travel

Highlights include Havana, Cienfuegos, Trinidad, Cojimar and Santa Clara
Depart Sept. 17, 28; Oct. 1; +$200 Aug. 13

Go to site »
 

$489 & up -- Jamaica 3-Nt. All-Incl. Trip; Kids Stay Free

$489 & up -- Jamaica 3-Nt. All-Incl. Trip; Kids Stay Free
Source: Vacation Express

Kick back at a family-friendly resort this summer or fall; kids ages 2-16 to stay, play and eat for free.
Select dates through September

Go to site »
 

$599 & up -- Caribbean All-Incl. Spring & Summer Trips w/Air

$599 & up -- Caribbean All-Incl. Spring & Summer Trips w/Air
Source: Featured Destination: Dominican Republic

Sale features top-rated beaches and luxury resorts like Iberostar and Dreams
Travel select dates through September

More »
 

More Deals on Caribbean Vacations *

 
August-October
CheapCaribbean.com
 
Select dates through June
Vacation Express
 
Aug. 20 - Nov. 3
CheapCaribbean.com
 
Select dates through October
CheapCaribbean.com
 
August-October
CheapCaribbean.com
 
Select dates through December
Cruise & Land Travel
 
Select June-August dates
TravelByBob.com
 
May 23-June 24
CheapCaribbean.com
 
May 6 - June 30
CheapCaribbean.com
 
June 23-Aug. 17
CheapCaribbean.com
 
Select dates through August
Apple Vacations
 
Through June 27
CheapCaribbean.com
 
Aug. 18 - Sept. 30
CheapCaribbean.com
 
Through June
CheapCaribbean.com
 
Sept. 2 - Nov. 15; +$100 May 1 - Sept. 1
Grand Lucayan exclusively through Jet Luxury Resorts
 
From Miami; select August-Sept. dates
Last Moment Discount Travel Club
 
From FLL; other cities more; select May-June dates
TravelByBob.com
 
From NYC; other cities more; select Sept.-Oct.
Last Moment Discount Travel Club
 
From Dallas; May 30; +$30 June 1, 2, 5
Last Moment Discount Travel Club
 
Select dates through 2013; book by May 15
Sunny Land Tours
 

Compare Multiple Travel Sites in One Search

From: To: Travelers:
Depart: Return: One-way
Round-trip   
Enter city: Guests:
Check-in: Check-out: Rooms:
From: To: Travelers:
Depart: Return: Rooms:
Enter city: Pick-up Time:
Pick-up Date: Return Date: Return Time:

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

From Our 250+ Deal Experts Around the World
Andrew Young — Travel, Entertainment and Local Deal Expert
Andrew Young
Deal Expert, New York
For when you're looking for a trip that’s a little more "wow" than "woo-hoo." More »