Key West from Boston, Nov 27–30: round trip from $536
Round-trip flights from Boston to Key West cost $536 per person ($1,072 for two) for Nov 27–30, 2026, which is 3 nights, on JetBlue (B6) with 2 stops, so not nonstop. Expect typical highs of 75–77°F under mostly overcast skies. The best-value hotel, Blue Flamingo Resort Key West, is $837 for the stay.
The flight
$633 $536 per person, round trip
the highest fare we saw for these dates
$1,072 for two, taxes and fees included · JetBlue · 2 stops · 26h 16m
Out Fri, Nov 27, 8:00 AM – Fri, Nov 27, 11:55 AM · back Mon, Nov 30, 4:09 PM – Tue, Dec 1, 2:30 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| JetBlue | $536 | 2 stops | 26h 16m |
| B6 + MX | $551 | 2 stops | 31h 3m |
| JetBlue | $547 | 2 stops | 22h 4m |
Prices checked Oct 12, 2026, 2:16 PM EDT. Prices change; the binding price is the one on the booking site.
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Your trip for two
| For two | |
|---|---|
| Flights for two | $1,072 |
| Blue Flamingo Resort Key West, 3 nights | $837 |
| Trip total for two | $1,909 |
Regular: $2,103 You pay: $1,909 Saved: $194
the highest fare we saw for these dates.
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Why go now
$536 per person round trip is $97 below the highest fare we saw for these dates, or 15% less, across 12 offers we checked. That's $1,072 for two, all-in with taxes and fees as found when we checked, and fares can change at any time. Add Blue Flamingo Resort Key West at $837 for 3 nights and our rough budget for two comes to $3,049, with $1,140 of that set aside for food and fun. Late November is the tail end of hurricane season, and typical highs run 75–77°F with lows near 73°F. It works as a warm long weekend of sunsets, snorkeling and key lime pie, with no passport and no time change.
The kind of trip this is
This is an easy island long weekend: walkable streets, beach time, sunset crowds and bars with live music. It suits couples best, and also friends who want history by day and Duval Street by night. The pace is slow and loose, with room for one bigger day out if you want to snorkel the reef at Dry Tortugas or drive the Seven Mile Bridge.
Weather in Key West, Nov 27–30
Typical highs 75–77°F, lows near 73°F this time of year
| Day | Typical high | Typical low | Typical weather |
|---|---|---|---|
| Fri, Nov 27 | 77 °F | 74 °F | Overcast |
| Sat, Nov 28 | 75 °F | 71 °F | Overcast |
| Sun, Nov 29 | 76 °F | 72 °F | Overcast |
| Mon, Nov 30 | 76 °F | 73 °F | Drizzle |
Weather data by Open-Meteo.com · averages, not a forecast
Where to stay in Key West
Blue Flamingo Resort Key West is the best value: $837 for 3 nights ($279 a night) for a One Queen Bed room, 4 stars, rated 8.4 from 1,580 reviews. Hyatt Vacation Club at Beach House is the top rated at 9 from 380 reviews. It's $1,722 for the stay ($574 a night), and the Two-Bedroom Suite gives you room to spread out. Harborside Motel & Marina is the budget pick, 2 stars, at $916 ($305 a night) for a Deluxe Double Room, rated 8.6 from 1,343 reviews. It's the only one of the three with free cancellation. All three are room only. Old Town puts conch houses, Duval Street bars and most sights within walking distance. Truman Annex is quieter, with gated streets near Fort Zachary Taylor beach.
Blue Flamingo Resort Key West
$837 for 3 nights, two guests · $279 a night
See roomsHyatt Vacation Club at Beach House
$1,722 for 3 nights, two guests · $574 a night
See roomsHarborside Motel & Marina
$916 for 3 nights, two guests · $305 a night
See roomsAll hotels in Key West for these dates
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. How we earn
Where in Key West
- Old Town: Conch houses, Duval Street bars and most sights within walking distance.
- Duval Street: Right in the thick of the bars and live music.
- Truman Annex: Quiet gated streets steps from Old Town and Fort Zachary Taylor beach.
- New Town: Chain hotels near the airport and Smathers Beach at lower rates.
What to do in Key West
- Watch the sunset celebration in Mallory Square, the island's evening ritual.
- Tour the Ernest Hemingway Home and meet its six-toed cats.
- Snorkel or dive the reef at Dry Tortugas National Park for one full day out.
- Drive the Overseas Highway across the Seven Mile Bridge.
- Eat key lime pie on Duval Street, then stay for the live music.
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Getting there and around
| Airports in Boston | Boston Logan International (BOS) |
|---|---|
| Airports in Key West | Key West International (EYW), Miami International (MIA) |
| Flight time | 26h 16m (2 stops) |
| Distance | 1,374 miles each way |
| Time difference | same time zone |
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. How we earn
What 3 nights in Key West costs
| Estimate | |
|---|---|
| Flights for two | $1,072 |
| Hotel, 3 nights (Blue Flamingo Resort Key West) | $837 |
| Food, getting around and tickets, 3 days for two | $1,140 |
| Total for two | $3,049 |
Flights and hotel are the prices we found; spending is a planning estimate for a luxury destination, per person per day times two.
Price history: Boston to Key West
| Per person | |
|---|---|
| This trip | $536 per person |
| Lowest in the last 30 days | $469 (Oct 12, 2026) |
| Price checks | 2 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- Hurricane season; hotel rates drop in late summer
- No passport needed, the currency is the US dollar and Key West is on the same time as Boston.
- The fare has 2 stops and 26h 16m of total travel time. The return leaves Monday, Nov 30 at 4:09 PM and lands Tuesday, Dec 1 at 2:30 PM.
- Late November is still hurricane season, which runs June through November.
- All three hotels are room only, and only Harborside Motel & Marina offers free cancellation.
- You fly into Key West International (EYW). Miami International (MIA) is the other airport listed for this trip.
Questions readers ask
How much is the flight?
$536 per person round trip, $1,072 for two, on JetBlue (B6) with 2 stops. That's all-in with taxes and fees as of when we checked, and the price can change before you book.
What are the flight times?
You leave Friday, Nov 27 at 8:00 AM and land at 11:55 AM. The return leaves Monday, Nov 30 at 4:09 PM and doesn't land until Tuesday, Dec 1 at 2:30 PM, so plan for an overnight trip home.
What is the weather like?
Based on normals for this time of year, highs run 75–77°F with lows near 73°F. Most days look overcast, and Nov 30 shows drizzle.
Is 3 nights enough?
For Key West, mostly yes. Old Town is walkable, so 3 nights covers sunset at Mallory Square, the Hemingway Home and one big day out. The return leaves at 4:09 PM, which gives you most of Monday too.
What does the whole trip cost for two?
Our rough budget is $3,049 for two: $1,072 for flights, $837 for Blue Flamingo Resort Key West and $1,140 for spending, which works out to $190 per person per day.
Do I need a passport?
No. It's a domestic trip, you pay in US dollars and there's no time difference from Boston.
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Key West in pictures
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Image credits
- Photo: Vincent Gerbouin / Pexels, Pexels License
- Photo: Dominik Gryzbon / Pexels, Pexels License
- Photo: Mikhail Nilov / Pexels, Pexels License