$74 Cheap flight deals from Key West (EYW) to Southeast Massachusetts (BOS)

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Airfares from $74 One Way, $270 Round Trip from Key West to Southeast Massachusetts

Prices starting at $270 for return flights and $74 for one-way flights to Southeast Massachusetts were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Jul 8 - Sun, Jul 12
EYW
Key West
PVD
Providence
$270 Roundtrip, found 5 days ago
$270
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Jul 8 from Key West to Providence, returning Sun, Jul 12, priced at $270 found 5 days ago
Mon, Jul 20 - Sun, Jul 26
EYW
Key West
PVD
Providence
$275 Roundtrip, found 4 days ago
$275
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Mon, Jul 20 from Key West to Providence, returning Sun, Jul 26, priced at $275 found 4 days ago
Wed, Jul 8 - Sun, Jul 12
EYW
Key West
PVD
Providence
$277 Roundtrip, found 5 days ago
$277
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Jul 8 from Key West to Providence, returning Sun, Jul 12, priced at $277 found 5 days ago
Fri, Jul 24 - Thu, Jul 30
EYW
Key West
PVD
Providence
$302 Roundtrip, found 4 days ago
$302
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jul 24 from Key West to Providence, returning Thu, Jul 30, priced at $302 found 4 days ago
Thu, Jul 16 - Mon, Jul 20
EYW
Key West
PVD
Providence
$304 Roundtrip, found 4 days ago
$304
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jul 16 from Key West to Providence, returning Mon, Jul 20, priced at $304 found 4 days ago

Southeast Massachusetts economy flight packages

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer
4.0-star property

Eurostars The Boxer

8.8/10 Excellent! (1,524 reviews)

Aug 17 - Aug 21

4 night stay

Key West (EYW) to Boston (BOS)

Delta • Non-stop roundtrip • Coach
Price was $975, price is now $775 per person
$775
per person
found 1 day ago
Quiet Clean Location Good Stay 👍

Reviewed on Jul 4, 2026

The Colonnade Hotel Back Bay
4.0-star property

The Colonnade Hotel Back Bay

9.2/10 Wonderful! (2,381 reviews)

Aug 17 - Aug 21

4 night stay

Key West (EYW) to Boston (BOS)

Delta • Non-stop roundtrip • Coach
Price was $1,204, price is now $940 per person
$940
per person
found 1 day ago
We drove from Connecticut and arrived around 11:30AM At check-in, the front desk said no rollaway beds were available and our room was not ready. When my wife explained that she had just confirmed it that morning, the same employee said she must have spoken to housekeeping and that housekeeping did not have authority to reserve one. So the hotel can confirm something, put it on your reservation, then later say it does not exist?!? The rooftop pool was NOT family-friendly! It felt like a college/frat pool party: packed with adults drinking, socializing, sitting on all sides of the pool edge, filling the pool, all chairs, all tables, and the bar. There was nowhere for my wife, me, or our three young daughters to sit or put our belongings. One kind guest offered us one beach chair. The pool was so crowded there was barely room for kids to swim safely! My wife felt unsafe going in or leaving our things unattended. The deck boards were so hot they burned our daughters’ feet; we had to put a towel down for them to stand on. As we left, we saw a mom tell her two small daughters they could not swim because it was too crowded, and the youngest (approx 3YO) began crying. It was sad to watch, but I totally understood! This hotel was one failure after another: no early check-in, no rollaway despite being requested and confirmed, overcrowded alcohol-heavy rooftop pool, unsafe hot decking, poor staff interactions, dirty room, clogged sink, dirty toilet, missing basic supplies, dirty/brok

Reviewed on Jul 6, 2026

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,002 reviews)

Aug 17 - Aug 21

4 night stay

Key West (EYW) to Boston (BOS)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,919, price is now $1,543 per person
$1,543
per person
found 1 day ago
Great health club

Reviewed on Jul 6, 2026

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More About Flying To Southeast Massachusetts from Key West

Route Information for Flights from Key West to Southeast Massachusetts

Origin Airport IATA Code
EYW
Destination Airport IATA Code
BOS
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Key West to Southeast Massachusetts

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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.