Cheap Flights to Monroe County from $39 (2025/2026)
Wander Wisely with exceptional service, 24/7 supportOpens in a new window
Feel at ease with free flight cancellations within 24 hours of booking
Change your flight without a fee on select flights
Jet to one of Monroe County's top cities
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.
MCO
Orlando Intl.
MIA
Miami Intl.
$77 Roundtrip, found 3 days ago
$77
Roundtrip
found 3 days ago
TPA
Tampa Intl.
EYW
Key West Intl.
$85 Roundtrip, found 5 days ago
$85
Roundtrip
found 5 days ago
TPA
Tampa Intl.
EYW
Key West Intl.
$87 Roundtrip, found 4 days ago
$87
Roundtrip
found 4 days ago
MCO
Orlando Intl.
MIA
Miami Intl.
$91 Roundtrip, found 1 day ago
$91
Roundtrip
found 1 day ago
BOS
Logan Intl.
MIA
Miami Intl.
$97 Roundtrip, found 11 hours ago
$97
Roundtrip
found 11 hours ago
MCO
Orlando Intl.
MIA
Miami Intl.
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
BOS
Logan Intl.
MIA
Miami Intl.
$98 Roundtrip, found 2 hours ago
$98
Roundtrip
found 2 hours ago
MCO
Orlando Intl.
EYW
Key West Intl.
$122 Roundtrip, found 2 hours ago
$122
Roundtrip
found 2 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| TPA | Key West | August 18 to August 20 | $82 |
| BOS | Miami | August 30 to September 4 | $98 |
| DTW | Miami | September 2 to September 3 | $98 |
| CLT | Miami | June 30 to July 4 | $103 |
| ORD | Miami | July 8 to July 15 | $108 |
| PHL | Miami | August 18 to August 22 | $118 |
| TPA | Miami | August 21 to August 25 | $156 |
| BOS | Key West | September 6 to September 13 | $237 |
| EWR | Key West | September 3 to September 8 | $249 |
| EWR | Key West | September 3 to September 8 | $249 |
| BWI | Key West | July 14 to July 29 | $259 |
| MDW | Key West | August 14 to September 17 | $269 |
| ATL | Key West | August 16 to August 30 | $279 |
| DTW | Key West | August 12 to August 19 | $283 |
| CLT | Key West | August 11 to August 15 | $427 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Miami | June 22 to June 25 | $140 |
| BWI | Miami | June 22 to June 25 | $220 |
| EWR | Miami | June 20 to June 23 | $235 |
| ORD | Miami | June 20 to June 24 | $257 |
| CLT | Miami | June 20 to June 22 | $266 |
| PHL | Miami | June 21 to June 24 | $273 |
| TPA | Miami | June 20 to June 28 | $281 |
| BWI | Key West | June 21 to July 1 | $323 |
| DTW | Key West | June 21 to July 4 | $323 |
| ORD | Key West | June 21 to June 24 | $386 |
| ATL | Key West | June 21 to July 8 | $475 |
| JFK | Key West | June 20 to June 23 | $531 |
| BOS | Key West | June 22 to June 30 | $539 |
| EWR | Key West | June 20 to June 23 | $590 |
| CLT | Key West | June 22 to June 30 | $701 |
Best Monroe County Flight and Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from Boston to Monroe County
View all tripsTravelers ❤️ These Monroe County 🏨
Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Stay at this 3.5-star 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.
8.4/10 Very Good! (1,171 reviews)
"Great location"
Reviewed on Jun 13, 2025
Hawks Cay Resort
61 Hawks Cay Blvd, Marathon, FL
Book a stay at this beach hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Little Conch Key and Walkers Island are located nearby.
8/10 Very Good! (1,005 reviews)
"Great"
Reviewed on Jun 14, 2025
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Stay at this 4-star beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in our reviews. Popular attractions Duval Street and South Beach are located nearby.
8.6/10 Excellent! (2,506 reviews)
"Beautiful room, wonderful customer service, great location within walking distance to landmarks, and even a surprisingly well-rounded fitness center. Loved our stay! ❤️"
Reviewed on Jun 14, 2025
Save an average of 15% on thousands of hotels when you're signed in
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
Stay at this 4-star beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
8.6/10 Excellent! (1,719 reviews)
"The staff especially the waiter Alexander the front desk Chris and Agata the pool attendant gave us exceptional service and were very friendly and accommodating."
Reviewed on Jun 14, 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.
More Ways To Wander Monroe County
Destinations in Monroe County
Top Trending
Hotels
Cheap Hotels in ClearwaterCheap Hotels in KissimmeeCheap Hotels in St. PetersburgSouth Beach Beach Resorts & HotelsSt. Pete Beach Beach Resorts & HotelsCheap Hotels in HollywoodHotels in St. Augustine Historic DistrictHollywood Beach Resorts & HotelsHotels around Walt Disney World® ResortCheap Hotels in International DriveHotels in South BeachHotels around Hard Rock StadiumHotels in Downtown PensacolaCheap Hotels in Four CornersClearwater Beach Beach Resorts & HotelsHotels in Downtown Orlando
Cars