Cheap Flights to Monroe County from $40 (2026/2027)
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Key West
Flights
How Much Does it Cost To Fly To Monroe County?
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
PHL
Philadelphia Intl.
MIA
Miami Intl.
$76 Roundtrip, just found
$76
Roundtrip
just found
DFW
Dallas-Fort Worth Intl.
MIA
Miami Intl.
$98 Roundtrip, found 5 hours ago
$98
Roundtrip
found 5 hours ago
DAL
Love Field
MIA
Miami Intl.
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
SFO
San Francisco Intl.
MIA
Miami Intl.
$245 Roundtrip, found 7 hours ago
$245
Roundtrip
found 7 hours ago
TTN
Mercer
MIA
Miami Intl.
$369 Roundtrip, found 3 days ago
$369
Roundtrip
found 3 days ago
DFW
Dallas-Fort Worth Intl.
AVT
Aventura Brightline Train Station
$391 Roundtrip, found 2 days ago
$391
Roundtrip
found 2 days ago
DFW
Dallas-Fort Worth Intl.
EKW
Miami Central Brightline Train Station
$392 Roundtrip, found 1 day ago
$392
Roundtrip
found 1 day ago
SFO
San Francisco Intl.
EYW
Key West Intl.
$419 Roundtrip, found 6 days ago
$419
Roundtrip
found 6 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| TPA | Key West | September 1 to September 2 | $82 |
| CLT | Miami | August 10 to August 12 | $116 |
| TPA | Miami | August 1 to August 4 | $151 |
| BOS | Miami | September 9 to September 15 | $157 |
| EWR | Miami | September 5 to September 12 | $167 |
| EWR | Miami | September 5 to September 12 | $167 |
| DTW | Miami | September 8 to September 12 | $167 |
| EWR | Key West | July 20 to July 29 | $296 |
| EWR | Key West | July 20 to July 29 | $296 |
| ATL | Key West | August 26 to August 29 | $306 |
| ORD | Key West | August 29 to September 1 | $309 |
| DTW | Key West | October 6 to October 14 | $323 |
| BOS | Key West | August 10 to August 14 | $327 |
| PHL | Key West | August 26 to September 2 | $443 |
| CLT | Key West | September 5 to September 12 | $505 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| TPA | Key West | July 5 to July 9 | $106 |
| BWI | Miami | July 4 to July 15 | $147 |
| CLT | Miami | July 4 to July 11 | $223 |
| TPA | Miami | July 4 to August 3 | $272 |
| LGA | Miami | July 4 to July 8 | $323 |
| DTW | Miami | July 4 to July 12 | $339 |
| BOS | Miami | July 4 to July 6 | $393 |
| PHL | Miami | July 4 to July 6 | $419 |
| JFK | Key West | July 4 to July 8 | $456 |
| EWR | Key West | July 4 to July 8 | $468 |
| EWR | Miami | July 5 to July 7 | $512 |
| PHL | Key West | July 4 to July 5 | $521 |
| CLT | Key West | July 4 to July 7 | $537 |
| BOS | Key West | July 5 to July 10 | $731 |
| ATL | Key West | July 5 to July 5 | $1,042 |
Best Monroe County Flight and Hotel Packages
Price found within the past 48 hours. Click for updated prices.
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Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
8.6/10 Excellent! (2,318 reviews)
"Good value for the price,Chicken Walk pool bar was great spot."
Reviewed on Jul 2, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
8.4/10 Very Good! (2,475 reviews)
"One of the best hotels I’ve had lately. Even better then Disney resorts"
Reviewed on Jul 2, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Southernmost Point and Duval Street are located nearby.
8.8/10 Excellent! (3,420 reviews)
"Beautiful resort ! Very clean ! The staff was amazing , everyone on the property was very friendly They always reached out from the front desk ( not a virtual assistant) to make sure you had all that you needed and to let you know about fun events they were having that day , thank you Frank ,Marilyn ..."
Reviewed on Jul 1, 2026
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Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Southernmost Point and Duval Street are located nearby.
8/10 Very Good! (1,259 reviews)
"To many extra charges"
Reviewed on Jul 2, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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- Old Town Key West Hotels
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- Flights from Key West Intl.
- Alaska Airlines Seattle (SEA) to Key West (EYW) flights
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- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Milwaukee (MKE) to Key West (EYW)
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- Flights from Knoxville (TYS) to Key West (EYW)