$50 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $50 One Way, $88 Round Trip
$88 return flights and $50 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.
MIA
Miami
SJU
San Juan
$88 Roundtrip, found 1 day ago
$88
Roundtrip
found 1 day ago
JFK
New York
SJU
San Juan
$252 Roundtrip, just found
$252
Roundtrip
just found
MIA
Miami
SDQ
Santo Domingo
$263 Roundtrip, found 1 hour ago
$263
Roundtrip
found 1 hour ago
EWR
New York
SJU
San Juan
$266 Roundtrip, just found
$266
Roundtrip
just found
MIA
Miami
PUJ
Punta Cana
$270 Roundtrip, found 1 day ago
$270
Roundtrip
found 1 day ago
MIA
Miami
POS
Trinidad
$291 Roundtrip, found 2 hours ago
$291
Roundtrip
found 2 hours ago
MIA
Miami
NAS
Nassau
$293 Roundtrip, just found
$293
Roundtrip
just found
JFK
New York
MBJ
Montego Bay
$318 Roundtrip, found 1 hour ago
$318
Roundtrip
found 1 hour ago
JFK
New York
PUJ
Punta Cana
$323 Roundtrip, found 1 hour ago
$323
Roundtrip
found 1 hour ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | San Juan | September 5 to September 15 | $317 |
| JFK | San Juan | September 5 to September 15 | $317 |
| EWR | Montego Bay | September 6 to September 13 | $410 |
| EWR | Nassau | September 6 to September 12 | $413 |
| EWR | Santo Domingo | September 5 to October 27 | $451 |
| JFK | Punta Cana | September 6 to September 24 | $471 |
| JFK | Montego Bay | September 6 to September 10 | $507 |
| EWR | Piarco | September 4 to September 7 | $513 |
| JFK | Santo Domingo | September 6 to September 26 | $521 |
| EWR | Kingston | September 6 to September 10 | $558 |
| EWR | Kingston | September 6 to September 10 | $558 |
| JFK | Santiago de los Caballeros | September 6 to September 18 | $575 |
| JFK | Kingston | September 5 to September 19 | $590 |
| JFK | Oranjestad | September 6 to September 13 | $621 |
| JFK | Piarco | September 5 to September 6 | $685 |
Find The Perfect Hotel For After Your Flight
Score Epic Caribbean Accommodation Deals
Comfort Suites Paradise Island
Paradise Island Drive Paradise Island New Providence
$317 nightly
The price is $345 total per night from Sep 6 to Sep 7
$345 total
Sep 6 - Sep 7
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! (2,424 reviews)
"The rooms were adequate and mostly clean. The staff was friendly and helpful. The breakfast was pretty good with a few decent options daily. The swim up bar was ok. The hotel is close to everything."
Reviewed on Aug 29, 2026
Coral by the Sea Hotel
Calle Rosa 2 Carolina
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $140 total per night from Aug 30 to Aug 31
$140 total
Aug 30 - Aug 31
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. ...
6.4/10 (2,436 reviews)
"Very friendly accommodating staff!"
Reviewed on Aug 29, 2026
Breezes Resort Bahamas All Inclusive
1 Breezes Lane, Cable Beach Nassau New Providence
$314 nightly
The price is $349 total per night from Sep 3 to Sep 4
$349 total
Sep 3 - Sep 4
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 ...
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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
Fully refundableReserve now, pay when you stay
$162 nightly
The price is $170 total per night from Sep 13 to Sep 14
$170 total
Sep 13 - Sep 14
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! (1,980 reviews)
"N/A"
Reviewed on Aug 29, 2026
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
$312 nightly
The price is $350 total per night from Aug 30 to Aug 31
$350 total
Aug 30 - Aug 31
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. ...
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
$541 nightly
The price is $612 total per night from Aug 30 to Aug 31
$612 total
Aug 30 - Aug 31
Total with taxes and fees
Book a stay at this spa 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! (1,006 reviews)
"Overall everything was great. The resort could just use a bit of a spruce up. The signage is very faded, the pool and beach chairs are a bit worn. The room was very nice and clean. The staff was helpful. Dining options were fine. Location is great."
Reviewed on Aug 29, 2026
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Eagle Aruba Resort
J. E. Irausquin Boulevard 248 Oranjestad
$288 nightly
The price is $335 total per night from Sep 29 to Sep 30
$335 total
Sep 29 - Sep 30
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! (1,869 reviews)
"Loved the pools and the short walk to Eagle beach !"
Reviewed on Aug 29, 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
$247 nightly
The price is $270 total per night from Sep 7 to Sep 8
$270 total
Sep 7 - Sep 8
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 ...
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
$205 nightly
The price is $228 total per night from Sep 8 to Sep 9
$228 total
Sep 8 - Sep 9
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 ...
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
$183 nightly
The price is $203 total per night from Sep 13 to Sep 14
$203 total
Sep 13 - Sep 14
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! (1,891 reviews)
"Very accommodating and lovely staff:)"
Reviewed on Aug 29, 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 ...
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
$230 nightly
The price is $295 total per night from Sep 3 to Sep 4
$295 total
Sep 3 - Sep 4
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 ...
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. ...
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! (1,531 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! (4,946 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
"Enjoyed our stay everything was great!"
Reviewed on Aug 29, 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.
Need a Car For After Your Flight?
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Caribbean
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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.