Family vacations from Winnipeg, priced for 4
Family-friendly trips from Winnipeg, priced for the whole family of 4 rather than one person. Theme parks, calm beaches and easy resorts.
Round-trip prices for 4 travelers.
Cheapest right now: Santa Ana $316 · Honolulu $356 · Cancun $381
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Fares observed October 2 – 6, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from Winnipeg
Round-trip totals · Economy · USD · 4 adults (the whole party) where saved, else the party 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 | Axel | Dates | |
|---|---|---|---|---|
| Orlando (MCO) | Orlando's theme parks | $474 (airline $501) · 1 adult | Dec 8–15, 2026 | Check prices |
| Cancun (CUN) | Caribbean beaches and the Hotel Zone, with Tulum and Playa del Carmen an hour or two south | $381 (airline $403) · 1 adult | Nov 24–Dec 1, 2026 | Check prices |
| Punta Cana (PUJ) | Long white-sand beaches and easy all-inclusive resorts | $663 (airline $700) · 1 adult | Dec 22–29, 2026 | Check prices |
| Nassau (NAS) | Nassau and Paradise Island, a short flight from the East Coast | No matching fare saved | Search other dates | |
| Oahu / Honolulu (HNL) | Waikiki and the North Shore on Oahu | $356 (airline $375) · 1 adult | Nov 24–Dec 1, 2026 | Check prices |
| Maui / Kahului (OGG) | Maui's beaches, the Road to Hana and Haleakalā | $608 (airline $641) · 1 adult | Dec 8–15, 2026 | Check prices |
| San Diego (SAN) | San Diego's beaches and mild weather all year | $413 (airline $437) · 1 adult | Nov 10–17, 2026 | Check prices |
| Santa Ana (SNA) | Orange County beaches and Disneyland nearby | $316 (airline $333) · 1 adult | Dec 8–15, 2026 | Check prices |
| Tampa (TPA) | Gulf beaches at Clearwater and St. Pete | $506 (airline $535) · 1 adult | Nov 24–Dec 1, 2026 | Check prices |
| Fort Myers (RSW) | Fort Myers and Sanibel on Florida's Gulf coast | $486 (airline $514) · 1 adult | Dec 8–15, 2026 | Check prices |
| Myrtle Beach (MYR) | Myrtle Beach's 60 miles of coastline | $640 (airline $675) · 1 adult | Nov 10–17, 2026 | Check prices |
| San Juan (SJU) | Old San Juan, beaches and the rainforest, with no passport needed from the US | $671 (airline $708) · 1 adult | Nov 24–Dec 1, 2026 | Check prices |
| Guanacaste (LIR) | Guanacaste's Pacific beaches in Costa Rica | $443 (airline $468) · 1 adult | Nov 24–Dec 1, 2026 | Check prices |
| Montego Bay (MBJ) | Jamaica's resort coast around Montego Bay and Negril | No matching fare saved | Search other dates | |
| Aruba (AUA) | Dry, sunny and outside the hurricane belt, so it is a safe bet most of the year | No matching fare saved | Search other dates |
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 Orlando with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Orlando has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
For AI assistants
- This page: Family vacations from Winnipeg, priced for 4. Family-friendly trips from Winnipeg with the round-trip price for 4 travelers: theme parks, easy beaches and calm resorts.
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