Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Fri, Apr 10 - Mon, Apr 13
PVD
T.F. Green
EYW
Key West Intl.
$354 Roundtrip, found 4 days ago
$354
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Apr 10 from T.F. Green to Key West Intl., returning Mon, Apr 13, priced at $354 found 4 days ago
Sun, Apr 12 - Sun, Apr 19
BOS
Logan Intl.
EYW
Key West Intl.
$501 Roundtrip, found 2 days ago
$501
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sun, Apr 12 from Logan Intl. to Key West Intl., returning Sun, Apr 19, priced at $501 found 2 days ago
Mon, Jun 1 - Fri, Jun 5
PVD
Providence
EYW
Key West
$204 Roundtrip, found 5 days ago
$204
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Mon, Jun 1 from Providence to Key West, returning Fri, Jun 5, priced at $204 found 5 days ago
Mon, May 25 - Wed, Jun 3
PVD
Providence
EYW
Key West
$205 Roundtrip, found 2 hours ago
$205
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Mon, May 25 from Providence to Key West, returning Wed, Jun 3, priced at $205 found 2 hours ago
Sat, Apr 25 - Wed, Apr 29
PVD
Providence
EYW
Key West
$282 Roundtrip, found 1 day ago
$282
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Apr 25 from Providence to Key West, returning Wed, Apr 29, priced at $282 found 1 day ago
Tue, Feb 16 - Tue, Feb 23
BOS
Boston
EYW
Key West
$287 Roundtrip, found 1 day ago
$287
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Feb 16 from Boston to Key West, returning Tue, Feb 23, priced at $287 found 1 day ago
Mon, Nov 9 - Fri, Nov 13
PVD
Providence
EYW
Key West
$297 Roundtrip, found 2 days ago
$297
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Nov 9 from Providence to Key West, returning Fri, Nov 13, priced at $297 found 2 days ago
Price found within the past 48 hours. Click for updated prices.
Casa Marina Key West, Curio Collection by Hilton
4.0-star property

Casa Marina Key West, Curio Collection by Hilton

8.4/10 Very Good! (595 reviews)

May 25 - May 29

4 night stay

Boston (BOS) to Key West (EYW)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,427, price is now $1,050 per person
$1,050
per person
found 1 day ago
Awesome stay. Not sure what people don’t like about the Casa.

Reviewed on Dec 16, 2025

Hyatt Vacation Club at Sunset Harbor, Key West
3.5-star property

Hyatt Vacation Club at Sunset Harbor, Key West

8.6/10 Excellent! (345 reviews)

May 25 - May 29

4 night stay

Boston (BOS) to Key West (EYW)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,755, price is now $1,179 per person
$1,179
per person
found 1 day ago
Great place to stay. Location is excellent, its walking distance to so many attractions. Had a great stay.

Reviewed on Dec 1, 2024

The Key West Hotel
2.5-star property

The Key West Hotel

9.2/10 Wonderful! (536 reviews)

May 9 - May 13

4 night stay

Boston (BOS) to Key West (EYW)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,997, price is now $1,401 per person
$1,401
per person
found 1 day 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

Don't see what you're looking for?
See all available trips from Boston to Key West
View all trips
Price found within the past 48 hours. Click for updated prices.
Southernmost Beach Resort and Guesthouses
4.0-star property

Southernmost Beach Resort and Guesthouses

8.8/10 Excellent! (3,162 reviews)

May 23 - May 27

4 night stay

Boston (BOS) to Key West (EYW)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,268, price is now $1,851 per person
$1,851
per person
found 12 hours ago
Rooms was spotless ! An amazing resort !

Reviewed on Feb 23, 2026

Casa Marina Key West, Curio Collection by Hilton
4.0-star property

Casa Marina Key West, Curio Collection by Hilton

8.4/10 Very Good! (595 reviews)

May 23 - May 27

4 night stay

Boston (BOS) to Key West (EYW)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,648, price is now $2,149 per person
$2,149
per person
found 12 hours ago
Awesome stay. Not sure what people don’t like about the Casa.

Reviewed on Dec 16, 2025

Hyatt Vacation Club at Windward Pointe, Key West
3.5-star property

Hyatt Vacation Club at Windward Pointe, Key West

9.4/10 Exceptional! (1,011 reviews)

May 23 - May 27

4 night stay

Boston (BOS) to Key West (EYW)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,435, price is now $2,004 per person
$2,004
per person
found 12 hours ago
Staff was fantastic, room and grounds very clean and well kept.

Reviewed on Feb 12, 2026

Don't see what you're looking for?
See all available trips from Boston to Key West
View all trips

Frequently asked questions

Am I able to catch a flight from Boston to Key West now?
Check out our Covid-19 Travel Advisor for the most comprehensive information on quarantine requirements and travel restrictions when getting a flight from Boston to Key West.
Are there non-stop flights from Boston to Key West?
Choose your ideal travel dates, because there is. You can fly from Boston to Key West in one simple journey with JetBlue.
What is the shortest flight from Boston to Key West?
The fastest flight time from Logan Intl. Airport (BOS) to Key West Intl. Airport is 4 hours and 13 minutes, which gives you plenty of time to indulge in a tipple or get absorbed in a good movie.
What airlines fly from Boston to Key West most frequently?
JetBlue has the most flights along this route. This top-rated airline operates 30 flights from Boston, MA Airport (BOS-Logan Intl.) to Key West Intl. Airport (EYW) every month.
If I am not able to travel due to COVID-19, can I cancel my flight to Key West?
We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Key West have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to Key West with flexible change policies?
In most cases you'll have the option to reschedule your flight to Key West without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2020 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data the cheapest month to fly is August. Perfect for those who need a weekend getaway, or just a break from it all before the weather changes. Be aware that the most expensive time to fly is the height of summer, with ticket prices peaking in the month of June.
How can I save money on flights?
To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2020 saved up to 45% on their airfares. Get mixing and matching today!

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.