$88 Cheap flight deals from Boston (BOS) to Stock Island (EYW)
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This Weekend's Flight Deals from Boston to Stock Island
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
BOS
Logan Intl.
EYW
Key West Intl.
$339 Roundtrip, found 3 days ago
$339
Roundtrip
found 3 days ago
MHT
Manchester-Boston Regional
EYW
Key West Intl.
$382 Roundtrip, found 4 days ago
$382
Roundtrip
found 4 days ago
PVD
T.F. Green
EYW
Key West Intl.
$635 Roundtrip, found 3 days ago
$635
Roundtrip
found 3 days ago
Airfares from $88 One Way, $153 Round Trip from Boston to Stock Island
Prices starting at $153 for return flights and $88 for one-way flights to Stock Island were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
BOS
Boston
EYW
Key West
$153 Roundtrip, found 4 days ago
$153
Roundtrip
found 4 days ago
PVD
Providence
EYW
Key West
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
BOS
Boston
EYW
Key West
$182 Roundtrip, found 5 days ago
$182
Roundtrip
found 5 days ago
PVD
Providence
EYW
Key West
$184 Roundtrip, found 2 days ago
$184
Roundtrip
found 2 days ago
PVD
Providence
EYW
Key West
$185 Roundtrip, found 2 days ago
$185
Roundtrip
found 2 days ago
Stock Island economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Hyatt Vacation Club at Beach House, Key West
9.4/10 Exceptional! (1,002 reviews)
Mar 5 - Mar 8
3 night stay
Boston (BOS) to Key West (EYW)
JetBlue Airways • Coach
Key West (EYW) to Boston (BOS)
Spirit Airlines • Coach
Price was $1,680, price is now $1,268 per person
$1,268
per person
found 2 days ago
The property was truly amazing. We.rented a 2 bedroom villa and it was comfortable and very well decorated and equipped. The only complaint would be the " complimentary breakfast" needs to be better. It was only a selection of cruisants with water and orange juice. For the price spent, please add eggs, meat and coffee at least. Other than that, it was very nice
Reviewed on Sep 7, 2025
2.5-star property
The Key West Hotel
9.2/10 Wonderful! (505 reviews)
Feb 23 - Feb 27
4 night stay
Boston (BOS) to Key West (EYW)
JetBlue Airways • Coach
Key West (EYW) to Boston (BOS)
Spirit Airlines • Coach
Price was $3,212, price is now $2,263 per person
$2,263
per person
found 2 days ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.
Reviewed on Jan 5, 2025
4.0-star property
The Reach Key West, Curio Collection by Hilton
8.4/10 Very Good! (1,001 reviews)
Feb 15 - Feb 20
5 night stay
Boston (BOS) to Key West (EYW)
Delta • Coach
Key West (EYW) to Boston (BOS)
Southwest Airlines • Coach
Save 100% on your flight
Price was $3,403, price is now $2,615 per person
$2,615
per person
found 2 days ago
Relaxing, beach area was kept clean but sadly water was not what my husband expected.
Reviewed on Jun 28, 2025
Stock Island packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Oceans Edge Key West Resort, Hotel & Marina
9/10 Wonderful! (1,736 reviews)
Feb 23 - Feb 26
3 night stay
Boston (BOS) to Key West (EYW)
Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,254, price is now $921 per person
$921
per person
found 1 hour ago
We LOVED the setting and the surrounding area! Absolutely beautiful!
Be aware the hotel IS in the airport landing zone. If you like to watch/hear commercial planes you'll be very happy.
Ask for a room on the top floor only - so you can (1) look over the marina AND (2) so you won't hear people moving chairs on their balcony above you.
The max/min air conditioning is centrally controlled. If you want it colder than 67, you will not be able to. Not sure what the max heat was.
Be extra vigilant about putting a thick towel on the floor to soak up any water that gets past the shower door. It WILL happen! Please do not slip on the wet tile floor!
Be aware that if you want/need a later checkout, they will charge you an additional $50/hour past their usual checkout time of 11am.
Be prepared for onsite meal expenses. They are very good, but they ARE on the pricy side.
Our particular room smelled strongly of smoke on arrival. I'm nearly POSITIVE we asked for a nonsmoking room as we both have underlying medical problems that preclude exposre to smoke. Perhaps call ahead to ENSURE you get a nonsmoking on arrival. The entire hotel was booked so we did not have any other choice.
Reviewed on Dec 28, 2025
2.5-star property
The Key West Hotel
9.2/10 Wonderful! (505 reviews)
Feb 23 - Feb 26
3 night stay
Boston (BOS) to Key West (EYW)
Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,473, price is now $1,513 per person
$1,513
per person
found 1 hour ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.
Reviewed on Jan 5, 2025
4.0-star property
Southernmost Beach Resort and Guesthouses
8.6/10 Excellent! (2,844 reviews)
Feb 23 - Feb 26
3 night stay
Boston (BOS) to Key West (EYW)
Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,753, price is now $1,365 per person
$1,365
per person
found 1 hour ago
Billed me for parking when I didn’t have a car. Took several calls to try and resolve. Still haven’t received a refund. They were quick to take my money when I paid for the room but not so responsive in processing my refund.
Reviewed on Nov 1, 2025
Stock Island first class flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Lighthouse Hotel - Key West Historic Inns
9/10 Wonderful! (831 reviews)
Feb 15 - Feb 19
4 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Roundtrip • FirstClass
Price was $2,608, price is now $1,969 per person
$1,969
per person
found 9 hours ago
This place is a much better place to stay than places closer to the cruise ship pier or off or whitehead or duval
Reviewed on Sep 22, 2024
4.0-star property
Oceans Edge Key West Resort, Hotel & Marina
9/10 Wonderful! (1,736 reviews)
Feb 15 - Feb 19
4 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Roundtrip • FirstClass
Price was $3,304, price is now $2,288 per person
$2,288
per person
found 9 hours ago
We LOVED the setting and the surrounding area! Absolutely beautiful!
Be aware the hotel IS in the airport landing zone. If you like to watch/hear commercial planes you'll be very happy.
Ask for a room on the top floor only - so you can (1) look over the marina AND (2) so you won't hear people moving chairs on their balcony above you.
The max/min air conditioning is centrally controlled. If you want it colder than 67, you will not be able to. Not sure what the max heat was.
Be extra vigilant about putting a thick towel on the floor to soak up any water that gets past the shower door. It WILL happen! Please do not slip on the wet tile floor!
Be aware that if you want/need a later checkout, they will charge you an additional $50/hour past their usual checkout time of 11am.
Be prepared for onsite meal expenses. They are very good, but they ARE on the pricy side.
Our particular room smelled strongly of smoke on arrival. I'm nearly POSITIVE we asked for a nonsmoking room as we both have underlying medical problems that preclude exposre to smoke. Perhaps call ahead to ENSURE you get a nonsmoking on arrival. The entire hotel was booked so we did not have any other choice.
Reviewed on Dec 28, 2025
4.0-star property
Winslow's Bungalows - Key West Historic Inns
9.2/10 Wonderful! (1,044 reviews)
Feb 15 - Feb 19
4 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Roundtrip • FirstClass
Price was $2,669, price is now $1,999 per person
$1,999
per person
found 9 hours ago
Great place! Great staff!
Reviewed on Dec 26, 2025
More About Flying To Stock Island from Boston
Route Information for Flights from Boston to Stock Island
Origin Airport IATA Code | BOS |
|---|---|
Destination Airport IATA Code | EYW |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Boston to Stock Island
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Stock Island Airports
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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.