$106 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $106 One Way, $193 Round Trip
$193 return flights and $106 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.
EWR
New York
SJU
San Juan
$193 Roundtrip, found 5 days ago
$193
Roundtrip
found 5 days ago
EWR
New York
SJU
San Juan
$212 Roundtrip, found 11 hours ago
$212
Roundtrip
found 11 hours ago
EWR
New York
MBJ
Montego Bay
$241 Roundtrip, found 5 days ago
$241
Roundtrip
found 5 days ago
EWR
New York
SJU
San Juan
$257 Roundtrip, found 5 hours ago
$257
Roundtrip
found 5 hours ago
EWR
New York
SJU
San Juan
$257 Roundtrip, found 9 hours ago
$257
Roundtrip
found 9 hours ago
EWR
New York
PUJ
Punta Cana
$277 Roundtrip, found 6 days ago
$277
Roundtrip
found 6 days ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | San Juan | May 9 to May 14 | $306 |
| EWR | Montego Bay | May 8 to May 12 | $337 |
| JFK | Nassau | May 9 to May 15 | $363 |
| JFK | Punta Cana | May 9 to May 16 | $393 |
| JFK | Oranjestad | May 9 to May 12 | $403 |
| JFK | Oranjestad | May 9 to May 12 | $403 |
| JFK | Piarco | May 8 to May 11 | $404 |
| EWR | Oranjestad | May 9 to May 16 | $413 |
| EWR | San Juan | May 10 to May 17 | $426 |
| JFK | Santiago de los Caballeros | May 9 to May 17 | $435 |
| JFK | Santo Domingo | May 9 to May 13 | $459 |
| JFK | Kingston | May 9 to May 16 | $471 |
| EWR | Kingston | May 9 to May 16 | $476 |
| EWR | Santo Domingo | May 10 to May 17 | $482 |
| EWR | Punta Cana | May 10 to May 17 | $493 |
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 May 5 to May 6
$352 total
May 5 - May 6
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 ...
8.4/10 Very Good! (2,242 reviews)
The staff are very professional respectful and friendly. They are ready to help.
Reviewed on May 3, 2026
Coral by the Sea Hotel
Calle Rosa 2 Carolina
Fully refundableReserve now, pay when you stay
$214 nightly
The price is $233 total per night from May 4 to May 5
$233 total
May 4 - May 5
Total with taxes and fees
Stay at this hotel in Carolina. Enjoy free WiFi, 2 restaurants, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.2/10 (2,357 reviews)
La ubicación la mejor Cerca de todo a pie
Reviewed on May 2, 2026
Breezes Resort Bahamas All Inclusive
1 Breezes Lane, Cable Beach Nassau New Providence
$339 nightly
The price is $376 total per night from May 7 to May 8
$376 total
May 7 - May 8
Total with taxes and fees
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 ...
7.6/10 Good! (2,270 reviews)
The food was outstanding enjoyed every bit of it. The staff was not friendly at all. I've visited several all inclusive resorts and the customer service at this resort is horrible. Know one seems to smile or greet you and say hello. It was a very unwelcome experience for me.
Reviewed on May 3, 2026
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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 ...
8.6/10 Excellent! (861 reviews)
Stayed 2 nights while waiting for flights after a cruise. Wonderful place on the Ocean. Great pool and friendly staff. Comfortable bed. Would certainly stay here again as it’s a great price when you do not want an all inclusive resort. I gave cleanliness a 5* even though the bathroom had tiny ants ...
Reviewed on Apr 25, 2026
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
$239 nightly
The price is $250 total per night from May 14 to May 15
$250 total
May 14 - May 15
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 ...
9/10 Wonderful! (1,690 reviews)
We had a fantastic time at this resort! Our room was in the perfect location in the marina building, ocean front and also beside a pool and bar. We had the breakfast buffet every morning, it was delicious with fresh fruit and a mix of different items every day. Service here was great and the staff ...
Reviewed on May 3, 2026
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
$324 nightly
The price is $364 total per night from May 11 to May 12
$364 total
May 11 - May 12
Total with taxes and fees
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. ...
9.6/10 Exceptional! (1,002 reviews)
Great stay! We will book here for our next Aruba trip. Hotel, restaurants, private beach were top notch.
Reviewed on May 2, 2026
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
$473 nightly
The price is $536 total per night from May 9 to May 10
$536 total
May 9 - May 10
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! (1,002 reviews)
Beach tower room was great. Only down issue was soap dispensers were way to high up on wall in bathrooms. A5ft 6 person has tough time reaching pump that is about 5& 1/2 ft high on wall with 22” counter top to reach over. Do not like liquid soap dispenser in shower . Need bar soap. Still loved divi ...
Reviewed on Apr 28, 2026
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Eagle Aruba Resort
J. E. Irausquin Boulevard 248 Oranjestad
Fully refundableReserve now, pay when you stay
$332 nightly
The price is $377 total per night from May 28 to May 29
$377 total
May 28 - May 29
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. ...
9/10 Wonderful! (2,027 reviews)
The rooms need a deep cleaning. The couch made of material smelled of dust
Reviewed on Apr 30, 2026
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
$299 nightly
The price is $326 total per night from Jun 1 to Jun 2
$326 total
Jun 1 - Jun 2
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 ...
9.2/10 Wonderful! (1,003 reviews)
Take thr history tour.
Reviewed on Apr 30, 2026
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
$303 nightly
The price is $332 total per night from Jun 1 to Jun 2
$332 total
Jun 1 - Jun 2
Total with taxes and fees
Book a stay at this beach hotel in Nassau. Enjoy free WiFi, 2 outdoor pools, and 6 restaurants. Our guests praise the helpful staff and the clean rooms in our ...
8.6/10 Excellent! (2,539 reviews)
Property well maintained and beautiful. Easy access to downtown for shopping. Staff very helpful and attentive. Would have liked more options for dinner restaurant in house
Reviewed on May 2, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
$228 nightly
The price is $249 total per night from May 24 to May 25
$249 total
May 24 - May 25
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! (1,666 reviews)
This place was absolutely beautiful and the stuff where all amazing.
Reviewed on May 2, 2026
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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 ...
9/10 Wonderful! (1,463 reviews)
Had
Reviewed on May 2, 2026
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
$348 nightly
The price is $445 total per night from May 19 to May 20
$445 total
May 19 - May 20
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 ...
8.2/10 Very Good! (5,579 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
Rooms were AMAZING. Staff were very friendly and helpful. Food was decent but the entertainment was very good as well. I would definitely recommend and come back.
Reviewed on May 3, 2026
Majestic Colonial Punta Cana - All Inclusive
Carretera El Macao Punta Cana La Altagracia
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. ...
9/10 Wonderful! (6,677 reviews)
The staff was really kind. VIP area was also very nice! I enjoyed my stay and I would definitely come back. The beach area was also at a really good point on the island which was gorgeous.
Reviewed on May 1, 2026
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! (1,764 reviews)
Families like: Outdoor pools, free waterpark access, kids club, playground
Travelers say...
All was good
Reviewed on Jan 15, 2026
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Majestic Elegance Punta Cana - All Inclusive
Playa Bavaro - Punta Cana Punta Cana La Altagracia
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. ...
9/10 Wonderful! (4,852 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
everything was amazing
Reviewed on May 3, 2026
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.
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Caribbean
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Mix and Match
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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.