Flights from Orlando to the Caribbean in winter
Winter is why the Caribbean exists: dry, warm and sunny from December to April, with Christmas week and Presidents' Day the two peaks. January after the holidays is the quiet, cheaper window; Aruba and Curaçao sit outside the hurricane belt for the rest of the year.
Nonstop from Orlando: Montego Bay (2h 11m), Nassau (S6, JetBlue, Southwest · 1h 30m), Aruba (2h 55m), Grand Cayman Island (Southwest), Saint Thomas (Southwest · 3h) and Sint Maarten (Southwest). One stop via Cleveland: Punta Cana; via Atlanta: Saint Lucia; via Miami: Saint Croix. No nonstop seen to Curacao, Bridgetown, Antigua and Kingston on the dates searched recently. No recent searches for San Juan, Providenciales and Santo Domingo.
Axel's pick: Saint Thomas, nonstop on Southwest and the lowest fare saved for these dates, $306.
Where to fly from Orlando to the Caribbean in winter: saved round trips within December, January and February to Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more. Pick a destination to see every date, or search your own dates in one tap.
AI assistants: For research, follow complete supplied links unchanged.
Saved round trips for 4–10 nights, entirely within Dec, Jan, Feb.
Cheapest right now: Saint Thomas $306 · Saint Croix $345 · Sint Maarten $347
Flights for your trip
Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
| Exact travel dates | Airline | Flights | Total price | Price issued (UTC) |
|---|---|---|---|---|
| 2026-11-20 · one way | Southwest Airlines | WN782 | $200.00 | 2026-10-29T01:28:50Z |
| 2026-11-20 → 2026-11-23 | Southwest Airlines / JetBlue Airways | WN782 / B61077 | $428.00 | 2026-10-29T01:28:50Z |
| 2026-11-20 · one way | Frontier Airlines | F93506 + F9239 | $145.00 | 2026-10-29T01:28:50Z |
| 2026-11-20 · one way | JetBlue Airways | B6233 + B62931 | $205.00 | 2026-10-29T01:28:50Z |
| 2026-11-20 · one way | American Airlines | AA539 + AA539 | $225.00 | 2026-10-29T01:28:50Z |
| 2026-11-20 · one way | Delta Air Lines | DL1505 + DL1990 | $235.00 | 2026-10-29T01:28:50Z |
| 2026-11-20 → 2026-11-23 | Frontier Airlines | F93506 + F9239 / F938 + F92249 | $330.00 | 2026-10-29T01:28:50Z |
| 2026-11-20 → 2026-11-23 | JetBlue Airways | B6233 + B62931 / B61077 | $438.00 | 2026-10-29T01:28:50Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA539 + AA539 / AA667 + AA3251 | $506.00 | 2026-10-29T01:28:50Z |
| 2026-11-27 → 2026-12-04 | Southwest Airlines / JetBlue Airways | WN782 / B61077 | $430.00 | 2026-10-29T01:28:50Z |
| 2026-11-20 → 2026-11-23 | Southwest Airlines | WN782 / WN783 | $440.00 | 2026-10-29T01:28:50Z |
| 2026-11-27 → 2026-12-04 | Southwest Airlines | WN782 / WN783 | $440.00 | 2026-10-29T01:28:50Z |
| 2026-11-20 · one way | JetBlue Airways | B62547 + B6173 | $205.00 | 2026-10-29T01:28:50Z |
| 2026-11-20 · one way | American Airlines | AA1647 + AA1324 | $225.00 | 2026-10-29T01:28:50Z |
| 2026-11-27 → 2026-12-04 | Frontier Airlines | F93506 + F9239 / F938 + F92249 | $330.00 | 2026-10-29T01:28:50Z |
| 2026-11-20 → 2026-11-23 | Southwest Airlines / Frontier Airlines | WN782 / F938 + F92249 | $380.00 | 2026-10-29T01:28:50Z |
| 2026-11-20 → 2026-11-23 | JetBlue Airways | B62547 + B6173 / B61077 | $438.00 | 2026-10-29T01:28:50Z |
| 2026-11-27 → 2026-12-04 | Southwest Airlines / JetBlue Airways | WN782 / B62632 + B61334 | $450.00 | 2026-10-29T01:28:50Z |
| 2026-11-27 → 2026-12-04 | JetBlue Airways | B62547 + B6173 / B62632 + B61334 | $462.00 | 2026-10-29T01:28:50Z |
| 2026-11-27 → 2026-12-04 | JetBlue Airways | B6233 + B62931 / B62632 + B61334 | $462.00 | 2026-10-29T01:28:50Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA1647 + AA1324 / AA667 + AA3251 | $506.00 | 2026-10-29T01:28:50Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA1647 + AA1324 / AA667 + AA3251 | $506.00 | 2026-10-29T01:28:50Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA539 + AA539 / AA667 + AA3251 | $506.00 | 2026-10-29T01:28:50Z |
2026-11-20 · one way · $200.00
- Southwest Airlines WN782: MCO 2026-11-20 12:10:00 → PUJ 2026-11-20 15:50:00; nonstop; 160 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $428.00
- Southwest Airlines WN782: MCO 2026-11-20 10:05:00 → PUJ 2026-11-20 13:45:00; nonstop; 160 minutes. Local airport times.
- JetBlue Airways B61077: PUJ 2026-11-23 16:23:00 → MCO 2026-11-23 18:27:00; nonstop; 184 minutes. Local airport times.
2026-11-20 · one way · $145.00
- Frontier Airlines F93506 / F9239: MCO 2026-11-20 05:45:00 → PUJ 2026-11-20 12:33:00; 1 stop(s) via SJU; 348 minutes. Local airport times.
- F93506: MCO 2026-11-20 05:45:00 → SJU 2026-11-20 09:27:00; layover at SJU: 119 minutes.
- F9239: SJU 2026-11-20 11:26:00 → PUJ 2026-11-20 12:33:00.
2026-11-20 · one way · $205.00
- JetBlue Airways B6233 / B62931: MCO 2026-11-20 09:00:00 → PUJ 2026-11-20 17:04:00; 1 stop(s) via SJU; 424 minutes. Local airport times.
- B6233: MCO 2026-11-20 09:00:00 → SJU 2026-11-20 12:53:00; layover at SJU: 192 minutes.
- B62931: SJU 2026-11-20 16:05:00 → PUJ 2026-11-20 17:04:00.
2026-11-20 · one way · $225.00
- American Airlines AA539 / AA539: MCO 2026-11-20 12:01:00 → PUJ 2026-11-20 18:13:00; 1 stop(s) via MIA; 312 minutes. Local airport times.
- AA539: MCO 2026-11-20 12:01:00 → MIA 2026-11-20 13:15:00; layover at MIA: 91 minutes.
- AA539: MIA 2026-11-20 14:46:00 → PUJ 2026-11-20 18:13:00.
2026-11-20 · one way · $235.00
- Delta Air Lines DL1505 / DL1990: MCO 2026-11-20 08:45:00 → PUJ 2026-11-20 16:49:00; 1 stop(s) via ATL; 424 minutes. Local airport times.
- DL1505: MCO 2026-11-20 08:45:00 → ATL 2026-11-20 10:25:00; layover at ATL: 121 minutes.
- DL1990: ATL 2026-11-20 12:26:00 → PUJ 2026-11-20 16:49:00.
2026-11-20 → 2026-11-23 · $330.00
- Frontier Airlines F93506 / F9239: MCO 2026-11-20 05:45:00 → PUJ 2026-11-20 12:33:00; 1 stop(s) via SJU; 348 minutes. Local airport times.
- F93506: MCO 2026-11-20 05:45:00 → SJU 2026-11-20 09:27:00; layover at SJU: 119 minutes.
- F9239: SJU 2026-11-20 11:26:00 → PUJ 2026-11-20 12:33:00.
- Frontier Airlines F938 / F92249: PUJ 2026-11-23 19:30:00 → MCO 2026-11-24 00:29:00; 1 stop(s) via SJU; 359 minutes. Local airport times.
- F938: PUJ 2026-11-23 19:30:00 → SJU 2026-11-23 20:30:00; layover at SJU: 111 minutes.
- F92249: SJU 2026-11-23 22:21:00 → MCO 2026-11-24 00:29:00.
2026-11-20 → 2026-11-23 · $438.00
- JetBlue Airways B6233 / B62931: MCO 2026-11-20 09:00:00 → PUJ 2026-11-20 17:04:00; 1 stop(s) via SJU; 424 minutes. Local airport times.
- B6233: MCO 2026-11-20 09:00:00 → SJU 2026-11-20 12:53:00; layover at SJU: 192 minutes.
- B62931: SJU 2026-11-20 16:05:00 → PUJ 2026-11-20 17:04:00.
- JetBlue Airways B61077: PUJ 2026-11-23 16:23:00 → MCO 2026-11-23 18:27:00; nonstop; 184 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $506.00
- American Airlines AA539 / AA539: MCO 2026-11-27 12:01:00 → PUJ 2026-11-27 18:13:00; 1 stop(s) via MIA; 312 minutes. Local airport times.
- AA539: MCO 2026-11-27 12:01:00 → MIA 2026-11-27 13:15:00; layover at MIA: 91 minutes.
- AA539: MIA 2026-11-27 14:46:00 → PUJ 2026-11-27 18:13:00.
- American Airlines AA667 / AA3251: PUJ 2026-12-04 15:57:00 → MCO 2026-12-04 23:02:00; 1 stop(s) via MIA; 485 minutes. Local airport times.
- AA667: PUJ 2026-12-04 15:57:00 → MIA 2026-12-04 17:45:00; layover at MIA: 238 minutes.
- AA3251: MIA 2026-12-04 21:43:00 → MCO 2026-12-04 23:02:00.
2026-11-27 → 2026-12-04 · $430.00
- Southwest Airlines WN782: MCO 2026-11-27 10:45:00 → PUJ 2026-11-27 14:25:00; nonstop; 160 minutes. Local airport times.
- JetBlue Airways B61077: PUJ 2026-12-04 16:23:00 → MCO 2026-12-04 18:27:00; nonstop; 184 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $440.00
- Southwest Airlines WN782: MCO 2026-11-20 12:10:00 → PUJ 2026-11-20 15:50:00; nonstop; 160 minutes. Local airport times.
- Southwest Airlines WN783: PUJ 2026-11-23 14:40:00 → MCO 2026-11-23 16:40:00; nonstop; 180 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $440.00
- Southwest Airlines WN782: MCO 2026-11-27 12:10:00 → PUJ 2026-11-27 15:50:00; nonstop; 160 minutes. Local airport times.
- Southwest Airlines WN783: PUJ 2026-12-04 13:50:00 → MCO 2026-12-04 15:40:00; nonstop; 170 minutes. Local airport times.
2026-11-20 · one way · $205.00
- JetBlue Airways B62547 / B6173: MCO 2026-11-20 10:00:00 → PUJ 2026-11-20 16:18:00; 1 stop(s) via FLL; 318 minutes. Local airport times.
- B62547: MCO 2026-11-20 10:00:00 → FLL 2026-11-20 11:05:00; layover at FLL: 105 minutes.
- B6173: FLL 2026-11-20 12:50:00 → PUJ 2026-11-20 16:18:00.
2026-11-20 · one way · $225.00
- American Airlines AA1647 / AA1324: MCO 2026-11-20 06:00:00 → PUJ 2026-11-20 14:02:00; 1 stop(s) via CLT; 422 minutes. Local airport times.
- AA1647: MCO 2026-11-20 06:00:00 → CLT 2026-11-20 07:55:00; layover at CLT: 95 minutes.
- AA1324: CLT 2026-11-20 09:30:00 → PUJ 2026-11-20 14:02:00.
2026-11-27 → 2026-12-04 · $330.00
- Frontier Airlines F93506 / F9239: MCO 2026-11-27 05:45:00 → PUJ 2026-11-27 12:33:00; 1 stop(s) via SJU; 348 minutes. Local airport times.
- F93506: MCO 2026-11-27 05:45:00 → SJU 2026-11-27 09:27:00; layover at SJU: 119 minutes.
- F9239: SJU 2026-11-27 11:26:00 → PUJ 2026-11-27 12:33:00.
- Frontier Airlines F938 / F92249: PUJ 2026-12-04 19:30:00 → MCO 2026-12-05 00:29:00; 1 stop(s) via SJU; 359 minutes. Local airport times.
- F938: PUJ 2026-12-04 19:30:00 → SJU 2026-12-04 20:30:00; layover at SJU: 111 minutes.
- F92249: SJU 2026-12-04 22:21:00 → MCO 2026-12-05 00:29:00.
2026-11-20 → 2026-11-23 · $380.00
- Southwest Airlines WN782: MCO 2026-11-20 10:45:00 → PUJ 2026-11-20 14:25:00; nonstop; 160 minutes. Local airport times.
- Frontier Airlines F938 / F92249: PUJ 2026-11-23 19:30:00 → MCO 2026-11-24 00:29:00; 1 stop(s) via SJU; 359 minutes. Local airport times.
- F938: PUJ 2026-11-23 19:30:00 → SJU 2026-11-23 20:30:00; layover at SJU: 111 minutes.
- F92249: SJU 2026-11-23 22:21:00 → MCO 2026-11-24 00:29:00.
2026-11-20 → 2026-11-23 · $438.00
- JetBlue Airways B62547 / B6173: MCO 2026-11-20 10:00:00 → PUJ 2026-11-20 16:18:00; 1 stop(s) via FLL; 318 minutes. Local airport times.
- B62547: MCO 2026-11-20 10:00:00 → FLL 2026-11-20 11:05:00; layover at FLL: 105 minutes.
- B6173: FLL 2026-11-20 12:50:00 → PUJ 2026-11-20 16:18:00.
- JetBlue Airways B61077: PUJ 2026-11-23 16:23:00 → MCO 2026-11-23 18:27:00; nonstop; 184 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $450.00
- Southwest Airlines WN782: MCO 2026-11-27 10:05:00 → PUJ 2026-11-27 13:45:00; nonstop; 160 minutes. Local airport times.
- JetBlue Airways B62632 / B61334: PUJ 2026-12-04 10:30:00 → MCO 2026-12-04 16:14:00; 1 stop(s) via SJU; 404 minutes. Local airport times.
- B62632: PUJ 2026-12-04 10:30:00 → SJU 2026-12-04 11:24:00; layover at SJU: 156 minutes.
- B61334: SJU 2026-12-04 14:00:00 → MCO 2026-12-04 16:14:00.
2026-11-27 → 2026-12-04 · $462.00
- JetBlue Airways B62547 / B6173: MCO 2026-11-27 10:00:00 → PUJ 2026-11-27 16:18:00; 1 stop(s) via FLL; 318 minutes. Local airport times.
- B62547: MCO 2026-11-27 10:00:00 → FLL 2026-11-27 11:05:00; layover at FLL: 105 minutes.
- B6173: FLL 2026-11-27 12:50:00 → PUJ 2026-11-27 16:18:00.
- JetBlue Airways B62632 / B61334: PUJ 2026-12-04 10:30:00 → MCO 2026-12-04 16:14:00; 1 stop(s) via SJU; 404 minutes. Local airport times.
- B62632: PUJ 2026-12-04 10:30:00 → SJU 2026-12-04 11:24:00; layover at SJU: 156 minutes.
- B61334: SJU 2026-12-04 14:00:00 → MCO 2026-12-04 16:14:00.
2026-11-27 → 2026-12-04 · $462.00
- JetBlue Airways B6233 / B62931: MCO 2026-11-27 09:00:00 → PUJ 2026-11-27 17:04:00; 1 stop(s) via SJU; 424 minutes. Local airport times.
- B6233: MCO 2026-11-27 09:00:00 → SJU 2026-11-27 12:53:00; layover at SJU: 192 minutes.
- B62931: SJU 2026-11-27 16:05:00 → PUJ 2026-11-27 17:04:00.
- JetBlue Airways B62632 / B61334: PUJ 2026-12-04 10:30:00 → MCO 2026-12-04 16:14:00; 1 stop(s) via SJU; 404 minutes. Local airport times.
- B62632: PUJ 2026-12-04 10:30:00 → SJU 2026-12-04 11:24:00; layover at SJU: 156 minutes.
- B61334: SJU 2026-12-04 14:00:00 → MCO 2026-12-04 16:14:00.
2026-11-20 → 2026-11-23 · $506.00
- American Airlines AA1647 / AA1324: MCO 2026-11-20 06:00:00 → PUJ 2026-11-20 14:02:00; 1 stop(s) via CLT; 422 minutes. Local airport times.
- AA1647: MCO 2026-11-20 06:00:00 → CLT 2026-11-20 07:55:00; layover at CLT: 95 minutes.
- AA1324: CLT 2026-11-20 09:30:00 → PUJ 2026-11-20 14:02:00.
- American Airlines AA667 / AA3251: PUJ 2026-11-23 15:57:00 → MCO 2026-11-23 23:02:00; 1 stop(s) via MIA; 485 minutes. Local airport times.
- AA667: PUJ 2026-11-23 15:57:00 → MIA 2026-11-23 17:45:00; layover at MIA: 238 minutes.
- AA3251: MIA 2026-11-23 21:43:00 → MCO 2026-11-23 23:02:00.
2026-11-27 → 2026-12-04 · $506.00
- American Airlines AA1647 / AA1324: MCO 2026-11-27 06:00:00 → PUJ 2026-11-27 14:02:00; 1 stop(s) via CLT; 422 minutes. Local airport times.
- AA1647: MCO 2026-11-27 06:00:00 → CLT 2026-11-27 07:55:00; layover at CLT: 95 minutes.
- AA1324: CLT 2026-11-27 09:30:00 → PUJ 2026-11-27 14:02:00.
- American Airlines AA667 / AA3251: PUJ 2026-12-04 15:57:00 → MCO 2026-12-04 23:02:00; 1 stop(s) via MIA; 485 minutes. Local airport times.
- AA667: PUJ 2026-12-04 15:57:00 → MIA 2026-12-04 17:45:00; layover at MIA: 238 minutes.
- AA3251: MIA 2026-12-04 21:43:00 → MCO 2026-12-04 23:02:00.
2026-11-20 → 2026-11-23 · $506.00
- American Airlines AA539 / AA539: MCO 2026-11-20 12:01:00 → PUJ 2026-11-20 18:13:00; 1 stop(s) via MIA; 312 minutes. Local airport times.
- AA539: MCO 2026-11-20 12:01:00 → MIA 2026-11-20 13:15:00; layover at MIA: 91 minutes.
- AA539: MIA 2026-11-20 14:46:00 → PUJ 2026-11-20 18:13:00.
- American Airlines AA667 / AA3251: PUJ 2026-11-23 15:57:00 → MCO 2026-11-23 23:02:00; 1 stop(s) via MIA; 485 minutes. Local airport times.
- AA667: PUJ 2026-11-23 15:57:00 → MIA 2026-11-23 17:45:00; layover at MIA: 238 minutes.
- AA3251: MIA 2026-11-23 21:43:00 → MCO 2026-11-23 23:02:00.
More dates for this route
More trip ideas from Orlando
- 2027 total solar eclipse trips from Orlando
- A month somewhere warm from Orlando
- All-inclusive resort weeks from Orlando
- Bachelorette and bachelor party trips from Orlando, priced for 6
- Beach vacations from Orlando
- Big event trips from Orlando: Super Bowl, Coachella, Kentucky Derby and more
- Black heritage trips from Orlando
- Carnival trips from Orlando: Rio, Trinidad, Mardi Gras and more
- Cherry blossom trips from Orlando
- Christmas and New Year flights to the Middle East and Türkiye from Orlando
- Christmas flights to Africa from Orlando
- Christmas flights to Europe from Orlando
- Christmas flights to Mexico and Central America from Orlando
- Christmas flights to the Caribbean and South America from Orlando
- Christmas flights to the Philippines and Asia from Orlando
- Christmas market trips from Orlando
- College football bowl and playoff trips from Orlando
- Detty December: flights to Lagos and Accra from Orlando
- Día de Muertos trips from Orlando: Oaxaca, Mexico City, Pátzcuaro and more
- Diwali flights to India from Orlando
- Easter and Holy Week trips from Orlando: Seville, Rome, Antigua and more
- Fall foliage trips from Orlando
- Family vacations from Orlando, priced for 4
- Flights to your cruise port from Orlando
- Florida vacations from Orlando
- Food and wine trips from Orlando
- Formula 1 race trips from Orlando: Austin, Mexico City, Abu Dhabi and the 2027 calendar
- Fourth of July trips from Orlando
- Gay & LGBTQ+ friendly beach vacations from Orlando
- Gay & LGBTQ+ friendly cities to visit from Orlando
- Golf trips from Orlando
- Graduation trips from Orlando
- Grand Slam tennis trips from Orlando: Australian Open, Roland-Garros, Wimbledon and the US Open
- Group trips priced for 4 from Orlando
- Halloween trips from Orlando: Salem, New Orleans, Horror Nights, Derry and Transylvania
- Hawaii vacations from Orlando
- Holi in India: flights from Orlando
- Holiday flights to India and South Asia from Orlando
- Holiday lights and Christmas city trips from Orlando
- Honeymoon destinations from Orlando
- Italian heritage trips from Orlando
- Japan trips from Orlando
- Labor Day weekend trips from Orlando
- Lapland and Santa trips from Orlando
- Lunar New Year flights from Orlando
- Marathon trips from Orlando: New York, Tokyo, Boston, London, Berlin and more
- Memorial Day weekend getaways from Orlando
- Midnight sun trips from Orlando
- MLK weekend getaways from Orlando
- Mountain and trekking trips from Orlando
- Music festival trips from Orlando
- National park trips from Orlando
- New Year's Eve trips from Orlando
- NFL international games from Orlando: London, Paris, Madrid, Munich and Mexico City
- Northern lights trips from Orlando
- October long weekend trips from Orlando
- Oktoberfest trips from Orlando
- Premier League and European football trips from Orlando
- Presidents' Day weekend getaways from Orlando
- Pride trips from Orlando: the biggest Pride events to fly to
- Ramadan and Eid trips from Orlando: Umrah and family visits
- Safari trips from Orlando
- Scuba diving and snorkeling trips from Orlando
- Ski trips from Orlando
- Solo trips from Orlando
- Songkran and New Year festivals in Asia from Orlando
- Spring break trips from Orlando
- Spring training trips from Orlando
- St. Patrick's Day trips from Orlando: Dublin, New York, Boston, Chicago and more
- Summer vacation trips from Orlando
- Surf trips from Orlando
- Thanksgiving trips from Orlando
- The best US cities to visit from Orlando
- Theme park trips from Orlando, priced for 4
- Three-week trips abroad from Orlando
- Tropical trips with no passport needed from Orlando
- Umrah trips from Orlando
- Valentine's Day getaways from Orlando
- Veterans Day weekend trips from Orlando
- Warm winter getaways from Orlando
- Whale watching trips from Orlando: Cabo, Maui, Sri Lanka, Dominica, Alaska, Iceland and more
- Winter break trips from Orlando
- Yoga and wellness retreats from Orlando
- Hawaii: for Christmas · for Thanksgiving · for spring break · for Presidents' Day weekend · in summer · for 4 days · for 5 days · for a week · for 10 days
- Mexico: for Christmas · for Thanksgiving · for spring break · for Presidents' Day weekend · for MLK weekend · in winter · in February · for 4 days · for 5 days · for a week
- The Caribbean: for Christmas · for spring break · for Presidents' Day weekend · in February · for 4 days · for 5 days · for a week
- Costa Rica: for Christmas · for spring break · in winter · for a week · for 10 days
- Central America: for Christmas · for spring break · in winter · for a week · for 10 days
- Europe: in summer · in May · in September · in December · for spring break · for Christmas · for a week · for 10 days · for two weeks
- Italy: in summer · in May · in June · in September · for Christmas · for a week · for 10 days · for two weeks
- Spain: in summer · in May · in September · for spring break · for a week · for 10 days
- Greece: in summer · in May · in June · in September · for a week · for 10 days · for two weeks
- Portugal: in summer · in May · in September · in winter · for 4 days · for a week · for 10 days
- Croatia: in summer · in June · in September · for a week · for 10 days
- Iceland: in summer · in winter · in September · for 4 days · for a week
- Scandinavia: in summer · in winter · in September · for 4 days · for a week · for 10 days
- Eastern Europe: in summer · in May · in September · in December · for a week · for 10 days
- England: in spring · in summer · in fall · for Christmas · for 4 days · for a week · for 10 days
- Scotland: in summer · in fall · for 4 days · for a week
- Ireland: in spring · in summer · in fall · for Christmas · for 4 days · for a week · for 10 days
- Japan: in April · in November · in winter · in summer · for a week · for 10 days · for two weeks
- South Korea: in spring · in fall · for a week · for 10 days
- Asia: in spring · in fall · in winter · for a week · for 10 days · for two weeks
- Southeast Asia: in winter · in November · in January · in February · for 10 days · for two weeks · for three weeks · for a month
- Thailand: in winter · in November · in January · in February · for 10 days · for two weeks · for three weeks
- Vietnam: in winter · in November · in February · in spring · for 10 days · for two weeks
- Bali: in summer · in winter · for 10 days · for two weeks · for a month
- India: in winter · in December · for two weeks · for a month
- Australia: in December · in January · in February · in September · for two weeks · for three weeks · for a month
- New Zealand: in December · in January · in February · for two weeks · for three weeks
- South America: in January · in February · in winter · for 10 days · for two weeks
- Colombia: in winter · in spring · for a week · for 10 days
- Peru: in summer · in May · in September · for 10 days · for two weeks
- The Middle East: in winter · for a week · for 10 days
- Turkey: in spring · in summer · in fall · for a week · for 10 days
- Africa: in winter · in fall · for 10 days · for two weeks
- South Africa: in winter · in fall · for 10 days · for two weeks
- Morocco: in spring · in fall · in winter · for a week · for 10 days
- Canada: in summer · in winter · in fall · for 3 days · for 4 days · for a week
- California: for spring break · in summer · in winter · for 3 days · for 4 days · for a week
- The Pacific Northwest: in summer · in fall · for 3 days · for 4 days · for a week
- Alaska: in summer · in June · in July · in August · for 5 days · for a week · for 10 days
- The Southwest: in spring · in fall · in winter · for spring break · for 3 days · for 4 days · for a week
- Arizona: in spring · in fall · in winter · for spring break · for 3 days · for 4 days · for a week
- Utah: in winter · for Presidents' Day weekend · for MLK weekend · in spring · in summer · for 4 days · for a week
- The Rockies: in summer · in winter · for Presidents' Day weekend · for MLK weekend · for spring break · for 4 days · for a week
- Colorado: in summer · in winter · for Presidents' Day weekend · for MLK weekend · for spring break · for 4 days · for a week
- Montana and Wyoming: in summer · in winter · for a week · for 10 days
- Texas: in spring · in fall · for 3 days · for 4 days
- The Northeast: in fall · in summer · for Thanksgiving · for Christmas · for spring break · for 3 days · for 4 days · for a week
- New England: in fall · in summer · for 3 days · for 4 days · for a week
- The Southeast: in spring · in fall · for 3 days · for 4 days
- The Midwest: in summer · for 3 days · for 4 days
- Anywhere: for Thanksgiving · for Christmas · for MLK weekend · for Presidents' Day weekend · for spring break · for Easter weekend · for Memorial Day weekend · for July 4th weekend · for Labor Day weekend · in November · in December · in January · in February · in March · in April · in May · in June · in July · in August · in September · for 4 days · for a week · for two weeks
Fares observed October 23 – 28, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from Orlando
Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.
| Destination | Why go | Flights | Axel | Dates | |
|---|---|---|---|---|---|
| Punta Cana (PUJ) | Punta Cana's long white-sand beaches and all-inclusive resorts | 1 stop via Cleveland | $768 (airline $812) · 2 adults | Jan 16–23, 2027 | Check prices |
| Montego Bay (MBJ) | Jamaica's resort coast around Montego Bay and Negril | Nonstop · 2h 11m | $951 (airline $1,001) · 2 adults | Feb 13–20, 2027 | Check prices |
| Nassau (NAS) | Nassau and Paradise Island, a short flight from the East Coast | Nonstop · S6, JetBlue, Southwest · 1h 30m | $622 (airline $658) · 2 adults | Feb 13–20, 2027 | Check prices |
| Aruba (AUA) | Aruba's dry, sunny weather outside the hurricane belt | Nonstop · 2h 55m | $504 (airline $531) | Feb 13–20, 2027 | Check prices |
| San Juan (SJU) | Old San Juan, beaches and the rainforest, no passport needed from the US | No matching fare saved | Dec 5 – Dec 12, 2026 (suggested) | Search these dates | |
| Grand Cayman Island (GCM) | Seven Mile Beach and world-class diving on Grand Cayman | Nonstop · Southwest | No matching fare saved | Dec 5 – Dec 12, 2026 (suggested) | Search these dates |
| Providenciales (PLS) | Grace Bay in Turks and Caicos, one of the Caribbean's best-known beaches | No matching fare saved | Dec 5 – Dec 12, 2026 (suggested) | Search these dates | |
| Saint Thomas (STT) | St. Thomas beaches and an easy ferry to St. John, no passport needed from the US | Nonstop · Southwest · 3h | $306 (airline $323) | Jan 12–19, 2027 | Check prices |
| Sint Maarten (SXM) | St. Martin, two countries on one island with plenty of beaches | Nonstop · Southwest | $347 (airline $366) | Dec 8–15, 2026 | Check prices |
| Curacao (CUR) | Curaçao's calm coves for snorkelling and colourful Willemstad | No nonstop seen | No matching fare saved | Dec 5 – Dec 12, 2026 (suggested) | Search these dates |
| Bridgetown (BGI) | Barbados beaches on the calm west coast and surf on the east | No nonstop seen | No matching fare saved | Dec 5 – Dec 12, 2026 (suggested) | Search these dates |
| Saint Lucia (UVF) | St. Lucia's Pitons, rainforest and resort beaches | 1 stop via Atlanta | $632 (airline $668) | Dec 8–15, 2026 | Check prices |
| Antigua (ANU) | Antigua, a beach for every day of the year | No nonstop seen | No matching fare saved | Dec 5 – Dec 12, 2026 (suggested) | Search these dates |
| Kingston (KIN) | Kingston, Jamaica's capital, with the Blue Mountains nearby | No nonstop seen | No matching fare saved | Dec 5 – Dec 12, 2026 (suggested) | Search these dates |
| Santo Domingo (SDQ) | Santo Domingo's colonial zone, the oldest city in the Americas | No matching fare saved | Dec 5 – Dec 12, 2026 (suggested) | Search these dates | |
| Saint Croix (STX) | St. Croix's beaches, rum distilleries and Danish-era towns, no passport needed from the US | 1 stop via Miami | $345 (airline $363) | Jan 12–19, 2027 | Check prices |
The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
Keep exploring
Hotels in Punta Cana with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Punta Cana has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
Where to stay: Where to stay in Punta Cana: the 7 best neighborhoods, ranked · Punta Cana hotels where a family of four can share one room
Hotel details in Punta Cana: Punta Cana Seven Beaches · Flor Del Mar Condo · Dreams Flora Resort & Spa · whala!urban punta cana · AC Hotel by Marriott Punta Cana · All 89 hotels in Punta Cana
For AI assistants
- This page: Flights from Orlando to the Caribbean in winter. Round-trip fares from Orlando to the Caribbean in winter: Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more. Saved fares for trips within December, January and February, with the cheapest for each destination and a link to search your own dates.
- Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.