Cheap flights To Key West Intl. (EYW) from $42

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Cheap Flights to Key West Intl. from $42 One Way, $78 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sun, Jan 31 - Thu, Feb 4
SFB
Orlando Sanford Intl.
EYW
Key West Intl.
$78 Roundtrip, found 1 day ago
$78
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Sun, Jan 31 from Orlando Sanford Intl. to Key West Intl., returning Thu, Feb 4, priced at $78 found 1 day ago
Mon, Feb 1 - Fri, Feb 5
TYS
McGhee Tyson
EYW
Key West Intl.
$84 Roundtrip, found 2 hours ago
$84
Roundtrip
found 2 hours ago
Select Allegiant Air flight, departing Mon, Feb 1 from McGhee Tyson to Key West Intl., returning Fri, Feb 5, priced at $84 found 2 hours ago
Sat, Feb 20 - Fri, Feb 26
PIE
St. Petersburg-Clearwater Intl.
EYW
Key West Intl.
$86 Roundtrip, found 12 hours ago
$86
Roundtrip
found 12 hours ago
Select Allegiant Air flight, departing Sat, Feb 20 from St. Petersburg-Clearwater Intl. to Key West Intl., returning Fri, Feb 26, priced at $86 found 12 hours ago
Tue, Dec 22 - Thu, Dec 24
AVL
Asheville Regional
EYW
Key West Intl.
$92 Roundtrip, found 1 day ago
$92
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Tue, Dec 22 from Asheville Regional to Key West Intl., returning Thu, Dec 24, priced at $92 found 1 day ago
Wed, Dec 16 - Fri, Dec 25
TPA
Tampa Intl.
EYW
Key West Intl.
$102 Roundtrip, found 4 hours ago
$102
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Dec 16 from Tampa Intl. to Key West Intl., returning Fri, Dec 25, priced at $102 found 4 hours ago
Mon, Jan 4 - Wed, Jan 6
MCO
Orlando Intl.
EYW
Key West Intl.
$102 Roundtrip, just found
$102
Roundtrip
just found
Select Breeze Airways flight, departing Mon, Jan 4 from Orlando Intl. to Key West Intl., returning Wed, Jan 6, priced at $102 just found
Mon, Jan 25 - Fri, Jan 29
PIT
Pittsburgh Intl.
EYW
Key West Intl.
$102 Roundtrip, found 1 hour ago
$102
Roundtrip
found 1 hour ago
Select Allegiant Air flight, departing Mon, Jan 25 from Pittsburgh Intl. to Key West Intl., returning Fri, Jan 29, priced at $102 found 1 hour ago
Wed, Nov 25 - Fri, Dec 4
CVG
Cincinnati - Northern Kentucky Intl.
EYW
Key West Intl.
$108 Roundtrip, found 2 hours ago
$108
Roundtrip
found 2 hours ago
Select Allegiant Air flight, departing Wed, Nov 25 from Cincinnati - Northern Kentucky Intl. to Key West Intl., returning Fri, Dec 4, priced at $108 found 2 hours ago
Sun, Dec 13 - Tue, Dec 22
IND
Indianapolis Intl.
EYW
Key West Intl.
$114 Roundtrip, found 6 hours ago
$114
Roundtrip
found 6 hours ago
Select Allegiant Air flight, departing Sun, Dec 13 from Indianapolis Intl. to Key West Intl., returning Tue, Dec 22, priced at $114 found 6 hours ago
Wed, Dec 9 - Wed, Dec 16
CHS
Charleston Intl.
EYW
Key West Intl.
$123 Roundtrip, found 23 hours ago
$123
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Wed, Dec 9 from Charleston Intl. to Key West Intl., returning Wed, Dec 16, priced at $123 found 23 hours ago

Key West Intl. Flight Information

Traveling To
Key West Intl.
Destination Airport IATA Code
EYW
Number of Airlines Serving
Airlines
Allegiant Air, Breeze Airways
Flight Price
$78
Earliest Departing Flight
Latest Departing Flight

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Key West Intl. economy flight packages

Price found within the past 48 hours. Click for updated prices.
Orchid Key Inn - Adults Only
3.5-star property

Orchid Key Inn - Adults Only

Dec 18 - Dec 22

4 night stay

Boston (BOS) to Key West (EYW)

American Airlines • Non-stop • Coach

Key West (EYW) to Boston (BOS)

Allegiant Air • Non-stop • Coach
Price was $1,469, price is now $1,101 per person
$1,101
per person
found 1 day ago
The Key West Hotel
3.0-star property

The Key West Hotel

Dec 18 - Dec 22

4 night stay

Boston (BOS) to Key West (EYW)

American Airlines • Non-stop • Coach

Key West (EYW) to Boston (BOS)

Allegiant Air • Non-stop • Coach
Price was $2,148, price is now $1,492 per person
$1,492
per person
found 1 day ago
The Gardens Hotel
4.0-star property

The Gardens Hotel

Jan 3 - Jan 7

4 night stay

Boston (BOS) to Key West (EYW)

JetBlue Airways • Coach

Key West (EYW) to Boston (BOS)

American Airlines • Coach
Price was $3,058, price is now $2,213 per person
$2,213
per person
found 1 day ago
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Key West Intl. premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Southernmost House - Adult Exclusive
4.0-star property

Southernmost House - Adult Exclusive

9.4/10 Exceptional! (1,002 reviews)

Dec 17 - Dec 21

4 night stay

Boston (BOS) to Key West (EYW)

Allegiant Air • PremiumEconomy

Key West (EYW) to Boston (BOS)

Frontier Airlines • PremiumEconomy
Price was $1,509, price is now $1,139 per person
$1,139
per person
found 1 day ago
Stunning, I dont have to say anymore

Reviewed on Nov 10, 2026

The Key West Hotel
3.0-star property

The Key West Hotel

9.2/10 Wonderful! (564 reviews)

Dec 29 - Jan 5

7 night stay

Boston (BOS) to Key West (EYW)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $5,710, price is now $3,761 per person
$3,761
per person
found 1 day ago
Clean, clean, clean. Hidden! Elite Backyard Oasis. Top Tier bar and fantastic nightly entertainment. If your traveling with anyone under 25, choose different. Will be back, no doubt!

Reviewed on Oct 29, 2026

The Marker Key West Harbor Resort
4.0-star property

The Marker Key West Harbor Resort

9.2/10 Wonderful! (1,033 reviews)

Dec 29 - Jan 5

7 night stay

Boston (BOS) to Key West (EYW)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $5,010, price is now $3,726 per person
$3,726
per person
found 1 day ago

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See all available trips from Boston to Key West Intl.
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Key West Intl. first class flight packages

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

The Gardens Hotel

9.8/10 Exceptional! (1,006 reviews)

Dec 24 - Dec 28

4 night stay

Boston (BOS) to Key West (EYW)

American Airlines • Non-stop roundtrip • FirstClass
Price was $3,433, price is now $2,655 per person
$2,655
per person
found 20 hours ago
Wonderful location, great room, cozy property. Check in and out was very easy. Would definitely stay here again the next time Im in Key West

Reviewed on Nov 8, 2026

The Key West Hotel
3.0-star property

The Key West Hotel

9.2/10 Wonderful! (564 reviews)

Dec 27 - Jan 2

6 night stay

Boston (BOS) to Key West (EYW)

JetBlue Airways • FirstClass

Key West (EYW) to Boston (BOS)

American Airlines • FirstClass
Price was $6,522, price is now $4,581 per person
$4,581
per person
found 24 hours ago
Clean, clean, clean. Hidden! Elite Backyard Oasis. Top Tier bar and fantastic nightly entertainment. If your traveling with anyone under 25, choose different. Will be back, no doubt!

Reviewed on Oct 29, 2026

Southernmost House - Adult Exclusive
4.0-star property

Southernmost House - Adult Exclusive

9.4/10 Exceptional! (1,002 reviews)

Dec 27 - Jan 2

6 night stay

Boston (BOS) to Key West (EYW)

JetBlue Airways • FirstClass

Key West (EYW) to Boston (BOS)

American Airlines • FirstClass
Price was $6,066, price is now $4,712 per person
$4,712
per person
found 24 hours ago
Stunning, I dont have to say anymore

Reviewed on Nov 10, 2026

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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.