Cheap Flights to Monroe County from $29 (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.
LGA
LaGuardia
MIA
Miami Intl.
$58 Roundtrip, just found
$58
Roundtrip
just found
ORD
O'Hare Intl.
MIA
Miami Intl.
$59 Roundtrip, just found
$59
Roundtrip
just found
BOS
Logan Intl.
MIA
Miami Intl.
$60 Roundtrip, found 1 hour ago
$60
Roundtrip
found 1 hour ago
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$63 Roundtrip, just found
$63
Roundtrip
just found
BOS
Logan Intl.
MIA
Miami Intl.
$128 Roundtrip, just found
$128
Roundtrip
just found
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$137 Roundtrip, just found
$137
Roundtrip
just found
BOS
Logan Intl.
EYW
Key West Intl.
$153 Roundtrip, found 7 hours ago
$153
Roundtrip
found 7 hours ago
BOS
Logan Intl.
MIA
Miami Intl.
$160 Roundtrip, found 1 hour ago
$160
Roundtrip
found 1 hour ago
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$160 Roundtrip, found 1 hour ago
$160
Roundtrip
found 1 hour ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Miami | February 10 to February 18 | $57 |
| PHL | Miami | February 3 to February 5 | $58 |
| LGA | Miami | January 31 to February 12 | $58 |
| CLT | Miami | February 16 to February 19 | $59 |
| BOS | Miami | February 4 to February 11 | $61 |
| EWR | Miami | January 24 to January 31 | $63 |
| DTW | Miami | February 2 to February 10 | $84 |
| TPA | Key West | April 13 to April 16 | $110 |
| TPA | Miami | February 10 to February 10 | $130 |
| BOS | Key West | February 5 to February 14 | $153 |
| PHL | Key West | February 15 to February 26 | $166 |
| EWR | Key West | February 5 to February 12 | $187 |
| EWR | Key West | February 5 to February 12 | $187 |
| CLT | Key West | February 26 to March 2 | $197 |
| DTW | Key West | January 26 to January 29 | $219 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Miami | January 18 to January 27 | $75 |
| CLT | Miami | January 18 to January 26 | $81 |
| PHL | Miami | January 18 to January 24 | $87 |
| EWR | Miami | January 17 to January 29 | $91 |
| EWR | Miami | January 17 to January 29 | $91 |
| BOS | Miami | January 18 to January 31 | $107 |
| TPA | Key West | January 18 to January 22 | $145 |
| DTW | Miami | January 18 to January 21 | $164 |
| TPA | Miami | January 18 to January 21 | $226 |
| ATL | Key West | January 18 to January 25 | $273 |
| PHL | Key West | January 18 to January 23 | $321 |
| CLT | Key West | January 18 to January 26 | $322 |
| EWR | Key West | January 18 to January 22 | $381 |
| BWI | Key West | January 17 to January 21 | $467 |
| DTW | Key West | January 17 to January 21 | $475 |
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 Smathers Beach are located nearby.
8.6/10 Excellent! (1,879 reviews)
Front desk staff was excellent as was the breakfast staff. Only had breakfast and it was excellent. Room could’ve been cleaner because that was disappointing. Two out of three soaps didn’t work in the shower. Overall a nice stay.
Reviewed on Jan 7, 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 Smathers Beach are located nearby.
8/10 Very Good! (1,829 reviews)
Clean decent place
Reviewed on Jan 8, 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 Duval Street and Southernmost Point are located nearby.
8.6/10 Excellent! (2,994 reviews)
The room were clean and well appointed. Support staff was very friendly and ready to assist when asked for help. The views were amazing, pools clean and lots of activities each day. The food at the cafe was excellent. Everything you need all in one location, while being in the heart of Duvall ...
Reviewed on Jan 9, 2026
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Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
8.8/10 Excellent! (1,771 reviews)
Friendly staff
Reviewed on Jan 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
- Beach Resorts & in Midtown
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