Cheap Flights to Monroe County from $29 (2025/2026)
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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, found 1 hour ago
$58
Roundtrip
found 1 hour ago
BOS
Logan Intl.
MIA
Miami Intl.
$58 Roundtrip, just found
$58
Roundtrip
just found
ORD
O'Hare Intl.
MIA
Miami Intl.
$59 Roundtrip, found 1 hour ago
$59
Roundtrip
found 1 hour ago
ORD
O'Hare Intl.
MIA
Miami Intl.
$67 Roundtrip, just found
$67
Roundtrip
just found
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$71 Roundtrip, found 1 hour ago
$71
Roundtrip
found 1 hour ago
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$117 Roundtrip, found 1 hour ago
$117
Roundtrip
found 1 hour ago
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$118 Roundtrip, found 2 hours ago
$118
Roundtrip
found 2 hours ago
LGA
LaGuardia
MIA
Miami Intl.
$137 Roundtrip, found 6 hours ago
$137
Roundtrip
found 6 hours ago
LGA
LaGuardia
MIA
Miami Intl.
$157 Roundtrip, found 6 hours ago
$157
Roundtrip
found 6 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Miami | January 20 to January 23 | $50 |
| PHL | Miami | January 19 to January 31 | $58 |
| JFK | Miami | January 27 to February 7 | $58 |
| BOS | Miami | January 21 to January 29 | $58 |
| EWR | Miami | February 4 to February 10 | $71 |
| CLT | Miami | January 19 to January 23 | $72 |
| DTW | Miami | January 26 to January 30 | $72 |
| BWI | Miami | January 31 to February 7 | $107 |
| TPA | Key West | January 28 to February 4 | $110 |
| ATL | Key West | January 23 to January 30 | $110 |
| BOS | Key West | January 20 to January 21 | $140 |
| EWR | Key West | January 26 to February 5 | $157 |
| CLT | Key West | January 30 to February 2 | $194 |
| DTW | Key West | April 14 to April 28 | $215 |
| BWI | Key West | February 1 to February 9 | $215 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Miami | January 4 to January 14 | $130 |
| PHL | Miami | January 4 to January 15 | $141 |
| LGA | Miami | January 4 to January 14 | $154 |
| CLT | Miami | January 4 to January 7 | $181 |
| EWR | Miami | January 4 to January 17 | $185 |
| BWI | Miami | January 3 to January 15 | $192 |
| TPA | Miami | January 4 to January 8 | $272 |
| LGA | Key West | January 3 to January 22 | $319 |
| BOS | Key West | January 3 to January 6 | $332 |
| PHL | Key West | January 4 to January 8 | $337 |
| ORD | Key West | January 2 to February 2 | $370 |
| ATL | Key West | January 4 to January 7 | $375 |
| DTW | Key West | January 3 to January 15 | $384 |
| BOS | Downtown Miami | January 3 to January 15 | $412 |
| EWR | Key West | January 4 to January 11 | $444 |
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! (1,835 reviews)
Pool and hot tub were very nice,chicken walk was excellent! Great staff!!!!
Reviewed on Dec 26, 2025
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! (1,801 reviews)
Very clean
Reviewed on Dec 26, 2025
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! (1,761 reviews)
So many activities and amazing staff and service. The shuttle was very convenient. I would stay here again! Perfect for families. I felt safe. Very laid back environment.
Reviewed on Dec 26, 2025
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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! (2,957 reviews)
This is the most wonderful place to stay in all of Key West. It has a little bit of everything from multiple pool choices, poolside bars, onsite restaurant, beach access, live music, concierge and full service spa! It’s on the quiet end Duval Street, but still within walking distance of most everything, ...
Reviewed on Dec 29, 2025
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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