$58 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $58 One Way, $108 Round Trip
$108 return flights and $58 one-way flights to Caribbean were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
JFK
New York
SJU
San Juan
$108 Roundtrip, found 2 days ago
$108
Roundtrip
found 2 days ago
JFK
New York
SJU
San Juan
$164 Roundtrip, found 14 hours ago
$164
Roundtrip
found 14 hours ago
JFK
New York
SJU
San Juan
$182 Roundtrip, found 3 days ago
$182
Roundtrip
found 3 days ago
JFK
New York
AUA
Oranjestad
$245 Roundtrip, found 1 hour ago
$245
Roundtrip
found 1 hour ago
JFK
New York
PUJ
Punta Cana
$264 Roundtrip, found 1 day ago
$264
Roundtrip
found 1 day ago
JFK
New York
STI
Santiago de los Caballeros
$270 Roundtrip, found 10 hours ago
$270
Roundtrip
found 10 hours ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | San Juan | December 7 to December 19 | $163 |
| JFK | Oranjestad | December 6 to December 11 | $335 |
| JFK | Oranjestad | December 6 to December 11 | $335 |
| JFK | Punta Cana | December 7 to December 10 | $343 |
| EWR | Piarco | December 7 to December 11 | $356 |
| JFK | Santiago de los Caballeros | December 7 to December 22 | $361 |
| LGA | Santo Domingo | December 6 to December 13 | $374 |
| EWR | Santo Domingo | December 6 to December 13 | $380 |
| EWR | Montego Bay | December 6 to December 8 | $422 |
| EWR | Montego Bay | December 6 to December 8 | $422 |
| JFK | Montego Bay | December 6 to December 11 | $423 |
| JFK | Santo Domingo | December 7 to December 14 | $449 |
| JFK | West End | December 7 to December 14 | $493 |
| JFK | Kingston | December 6 to December 13 | $533 |
| JFK | Piarco | December 6 to December 9 | $549 |
Find The Perfect Hotel For After Your Flight
Score Epic Caribbean Accommodation Deals
Comfort Suites Paradise Island
Paradise Island Drive Paradise Island New Providence
$327 nightly
The price is $352 total per night from Dec 7 to Dec 8
$352 total
Dec 7 - Dec 8
Total with taxes and fees
Book a stay at this business-friendly hotel in Paradise Island. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool ...
8.2/10 Very Good! (2,000 reviews)
The room was verry clean and the staff was fantastic! Really happy with my stay. Affordable no frills and get to take advantage of atlantis resort.
Reviewed on Dec 1, 2025
Coral by the Sea Hotel
Calle Rosa 2 Carolina
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $160 total per night from Dec 5 to Dec 6
$160 total
Dec 5 - Dec 6
Total with taxes and fees
Stay at this hotel in Carolina. Enjoy free WiFi, 2 restaurants, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
6/10 (1,976 reviews)
All ok!!
Reviewed on Nov 30, 2025
Breezes Resort Bahamas All Inclusive
1 Breezes Lane, Cable Beach Nassau New Providence
Book a stay at this beach hotel in Nassau. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
7.4/10 Good! (1,994 reviews)
What an absolute amazing experience! I highly recommend this resort due to ALL of the amenities. The staff members went above and beyond. Not only did they all provide superlative service, they were very personable, professional and kind. The grounds were extremely well maintained. The food AND drinks ...
Reviewed on Nov 30, 2025
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Meridian Inn
Dover St. Lawrence Gap Christ Church
Stay at this hotel in St. Lawrence Gap. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.4/10 Very Good! (829 reviews)
As mentioned by others, the staff was excellent, easy to speak with, unpretentious. Looking for a quiet getaway with a beach sans crowd steps away to public beach access, eateries and small grocery store within walking distance, then Meridian is the place.
Reviewed on Nov 30, 2025
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.
Our Top Caribbean Apartment Hotels
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
$160 nightly
The price is $167 total per night from Dec 15 to Dec 16
$167 total
Dec 15 - Dec 16
Total with taxes and fees
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our ...
8.8/10 Excellent! (1,497 reviews)
Beach was amazing, our room was on the first floor facing the parking.. therfore did not really like that. Tried to change but they said no other availability. Restaurants are close by. Roads around the complex need some major repairs. We rented a car which made it easier to get around. Rooms were ...
Reviewed on Nov 29, 2025
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
Book a stay at this beach hotel in Noord. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9.4/10 Exceptional! (1,014 reviews)
I really liked staying at Amsterdam Manor Beach Resort. The resort is cozy and quiet. We don't have small kids, and I didn't feel like having little kids running and splashing around nonstop. Our two-bedroom suite was absolutely fantastic, with an ocean view and a balcony with chairs and an umbrella. ...
Reviewed on Dec 3, 2025
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
$463 nightly
The price is $524 total per night from Dec 16 to Dec 17
$524 total
Dec 16 - Dec 17
Total with taxes and fees
Book a stay at this beach resort in Noord. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.8/10 Excellent! (1,007 reviews)
Newly renovated rooms. Right on the beach. Staff wonderful
Reviewed on Nov 23, 2025
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Eagle Aruba Resort
J. E. Irausquin Boulevard 248 Oranjestad
Fully refundableReserve now, pay when you stay
$271 nightly
The price is $306 total per night from Dec 14 to Dec 15
$306 total
Dec 14 - Dec 15
Total with taxes and fees
Book a stay at this beach hotel in Oranjestad. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
8.8/10 Excellent! (2,267 reviews)
Excellent spot if you don't want to eat all of your meals in restaurants. Easy walking distance to an excellent grocery store and enough of a kitchen to prepare meals. The three pools offer a lot of options and it is a short walk to an excellent sandy beach.
Reviewed on Dec 2, 2025
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.
Score Epic Caribbean Accommodation Deals
Hotel El Convento
100 Cristo St San Juan
Fully refundableReserve now, pay when you stay
$305 nightly
The price is $333 total per night from Dec 10 to Dec 11
$333 total
Dec 10 - Dec 11
Total with taxes and fees
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 ...
8.8/10 Excellent! (1,005 reviews)
Excellent location; walkable to everything imaginable. The staff at the Patio restaurant were great. The character of the hotel was quaint and aligned with its boutique nature. If you want to avoid the commercial nature of big chain hotels, this is a good one.
Reviewed on Dec 2, 2025
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
$340 nightly
The price is $372 total per night from Dec 18 to Dec 19
$372 total
Dec 18 - Dec 19
Total with taxes and fees
Book a stay at this beach hotel in Nassau. Enjoy free WiFi, 2 outdoor pools, and 8 restaurants. Our guests praise the helpful staff and the clean rooms in our ...
8.6/10 Excellent! (2,062 reviews)
Clean and nice staff
Reviewed on Dec 3, 2025
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
$190 nightly
The price is $207 total per night from Dec 17 to Dec 18
$207 total
Dec 17 - Dec 18
Total with taxes and fees
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 ...
9/10 Wonderful! (1,329 reviews)
Bay view room was spacious. Location was convenient for the cruise port and also for sightseeing.
Reviewed on Nov 29, 2025
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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 ...
8.8/10 Excellent! (1,425 reviews)
Another great stay at Atlantis. 4th time for my wife and I. Kids really enjoyed it this time around as they were older and couldn’t stay out of water park. First time at The Reef and room was good. Enjoyed being able to do breakfast and lunch in house. Only recommendation is rooms are too dark and ...
Reviewed on Dec 2, 2025
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.
Family Friendly Hotels in Caribbean
Barceló Bávaro Palace - All Inclusive
Carretera Bávaro Km. 1 Punta Cana La Altagracia
$275 nightly
The price is $352 total per night from Dec 5 to Dec 6
$352 total
Dec 5 - Dec 6
Total with taxes and fees
Book a stay at this luxury property in Punta Cana. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our ...
8/10 Very Good! (5,416 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
Good for a quick getaway.
Reviewed on Dec 3, 2025
Majestic Colonial Punta Cana - All Inclusive
Carretera El Macao Punta Cana La Altagracia
$416 nightly
The price is $416 total per night from Dec 10 to Dec 11
$416 total
Dec 10 - Dec 11
Total with taxes and fees
Book a stay at this beach property in Punta Cana. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
8.8/10 Excellent! (6,386 reviews)
The staff was incredible. The beach was incredible! I cannot wait to come back
Reviewed on Dec 1, 2025
Dreams Rose Hall Resort & Spa - All Inclusive
Rose Hall Montego Bay Saint James
Book a stay at this luxury resort in Montego Bay. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our ...
8.4/10 Very Good! (1,963 reviews)
Families like: Outdoor pools, free waterpark access, kids club, playground
Travelers say...
Pool was enjoyable and not crowded. Food excellent. Would spend a whole week there and i dont really like all inclusive hotels.
Reviewed on Nov 25, 2025
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Majestic Elegance Punta Cana - All Inclusive
Playa Bavaro - Punta Cana Punta Cana La Altagracia
$424 nightly
The price is $424 total per night from Dec 9 to Dec 10
$424 total
Dec 9 - Dec 10
Total with taxes and fees
Book a stay at this luxury property in Punta Cana. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the restaurant in our reviews. ...
8.8/10 Excellent! (4,583 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
Good
Reviewed on Nov 30, 2025
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.
Need a Car For After Your Flight?
Economy
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Compact
Ford Focus or similar
Midsize
Toyota Corolla or similar
SUV
Jeep Compass or similar
Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.