Cheap Flights to Monroe County from $32 (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.
LGA
LaGuardia
MIA
Miami Intl.
$63 Roundtrip, just found
$63
Roundtrip
just found
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$63 Roundtrip, just found
$63
Roundtrip
just found
JFK
John F. Kennedy Intl.
MIA
Miami Intl.
$68 Roundtrip, just found
$68
Roundtrip
just found
LGA
LaGuardia
MIA
Miami Intl.
$68 Roundtrip, just found
$68
Roundtrip
just found
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$127 Roundtrip, just found
$127
Roundtrip
just found
JFK
John F. Kennedy Intl.
MIA
Miami Intl.
$127 Roundtrip, found 1 hour ago
$127
Roundtrip
found 1 hour ago
LGA
LaGuardia
EYW
Key West Intl.
$170 Roundtrip, found 5 days ago
$170
Roundtrip
found 5 days ago
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$191 Roundtrip, just found
$191
Roundtrip
just found
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Miami | December 1 to December 5 | $55 |
| EWR | Miami | December 10 to December 16 | $63 |
| EWR | Miami | December 10 to December 16 | $63 |
| DTW | Miami | December 8 to December 12 | $69 |
| CLT | Miami | December 2 to December 9 | $75 |
| BOS | Miami | January 13 to January 16 | $98 |
| TPA | Key West | December 2 to December 5 | $110 |
| TPA | Miami | December 3 to December 11 | $120 |
| PHL | Key West | February 2 to February 6 | $157 |
| ATL | Key West | January 23 to January 26 | $169 |
| EWR | Key West | December 11 to December 13 | $184 |
| BWI | Key West | January 22 to January 25 | $189 |
| BOS | Key West | December 7 to December 13 | $191 |
| CLT | Key West | December 23 to December 27 | $209 |
| DTW | Key West | January 12 to January 16 | $215 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| CLT | Miami | November 22 to November 24 | $87 |
| PHL | Miami | November 22 to November 22 | $91 |
| DTW | Miami | November 21 to November 24 | $96 |
| ATL | Miami | November 22 to November 23 | $96 |
| JFK | Miami | November 22 to November 27 | $106 |
| EWR | Miami | November 22 to November 27 | $168 |
| TPA | Key West | November 23 to December 5 | $180 |
| ATL | Key West | November 23 to November 27 | $255 |
| CLT | Key West | November 23 to December 6 | $265 |
| EWR | Key West | November 22 to December 4 | $270 |
| DTW | Key West | November 23 to November 27 | $346 |
| BOS | Key West | November 23 to November 26 | $365 |
| ORD | Key West | November 23 to November 27 | $366 |
| PHL | Key West | November 22 to November 29 | $375 |
| TPA | Miami | November 23 to November 24 | $427 |
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 🏨
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.
7.8/10 Good! (1,671 reviews)
The star was outstanding and the experience was overall great. Only caveat is the resort fees and taxes not being very crystal clear with Expedia pricing and what they hold at the resort and charge.
Reviewed on Nov 8, 2025
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! (1,680 reviews)
Staff was horrible on directions to room. We had to give directions to 4 different sets of new guests as well as getting lost ourselves. Place was great. Nice location.
Reviewed on Nov 13, 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! (1,732 reviews)
Excellent
Reviewed on Nov 7, 2025
Save an average of 15% on thousands of hotels when you're signed in
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! (2,849 reviews)
Air conditioning was very loud which prevented a higher rating
Reviewed on Nov 10, 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
Monroe County Hotels
Find the perfect hotel after your flight
Monroe County Vacation Rentals
Great Deals on alternative accommodations
Monroe County Car Rentals
Affordable cars to get you around town
Monroe County Vacations
Save more by combining flights, hotels and cars
Things to do in Monroe County
Activities, attractions and tours
Explore More Ways to Travel with Travelocity
- Old Town Key West Hotels
- Beach Resorts & in Midtown
- Pet Friendly Hotels in Midtown
- Midtown Hotels
- Beach Resorts & in New Town
- Convention Center Hotels in New Town
- Gay Friendly Hotels in New Town
- Hotels with Pools in New Town
- Luxury Hotels in New Town
- Pet Friendly Hotels in New Town
- New Town Hotels
- Condos in Key West
- All Inclusive Resorts & in Key West
- Beach Resorts & in Key West
- Key West Hotels
- Houseboats in Key West
- Hotels near Duval Street
- Hotels near Smathers Beach
- Flights to Goodland
- Flights to Lower Arsnicker Keys
- Flights to Long Key
- Flights to Chokoloskee
- Flights to Raccoon Key
- Flights to Kice Island
- Flights to Lower Matecumbe Key
- Flights to Everglades City
- Flights to Key Colony Beach
- Flights to Islamorada
- Flights to Sugarloaf Key
- Flights to Tavernier
- Flights to Marco Island
- Flights to Miami
- Flights to Marathon
- Flights to Summerland Key
- Flights to Key West
- Flights to Key Largo
- Flights to Conch Key
- Flights to Layton
- Flights to Grassy Key
- Flights to Big Pine Key
- Flights to Florida Keys Marathon
- Flights to Little Torch Key
- Flights to Stock Island
- Flights to Cudjoe Key
- Flights to Ten Thousand Islands
- Flights to Duck Key
- Flights from Key West Intl.
- Alaska Airlines Seattle (SEA) to Key West (EYW) flights
- American Airlines Miami (MIA) to Key West (EYW) flights
- Delta Atlanta (ATL) to Key West (EYW) flights
- Jetblue Airways Albany (ALB) to Key West (EYW) flights
- Jetblue Airways Charleston (CHS) to Key West (EYW) flights
- Jetblue Airways New York (JFK) to Key West (EYW) flights
- Jetblue Airways Boston (BOS) to Key West (EYW) flights
- Jetblue Airways Sarasota (SRQ) to Key West (EYW) flights
- Silver Airways Tampa (TPA) to Key West (EYW) flights
- Flights from Atlanta (ATL) to Key West (EYW)
- Flights from Austin (AUS) to Key West (EYW)
- Flights from Hartford (BDL) to Key West (EYW)
- Flights from Nashville (BNA) to Key West (EYW)
- Flights from Boston (BOS) to Key West (EYW)
- Flights from Baltimore (BWI) to Key West (EYW)
- Flights from Cleveland (CLE) to Key West (EYW)
- Flights from Charlotte (CLT) to Key West (EYW)
- Flights from Columbus (CMH) to Key West (EYW)
- Flights from Cincinnati (CVG) to Key West (EYW)
- Flights from Washington (DCA) to Key West (EYW)
- Flights from Denver (DEN) to Key West (EYW)
- Flights from Dallas (DFW) to Key West (EYW)
- Flights from Detroit (DTW) to Key West (EYW)
- Flights from Newark Liberty Intl. Airport (EWR) to Key West (EYW)
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Flights from Grand Rapids (GRR) to Key West (EYW)
- Flights from Washington (IAD) to Key West (EYW)
- Flights from Houston (IAH) to Key West (EYW)
- Flights from Indianapolis (IND) to Key West (EYW)
- Flights from Jacksonville (JAX) to Key West (EYW)
- Flights from New York (JFK) to Key West (EYW)
- Flights from Kansas City (MCI) to Key West (EYW)
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Milwaukee (MKE) to Key West (EYW)
- Flights from Minneapolis (MSP) to Key West (EYW)
- Flights from New Orleans (MSY) to Key West (EYW)
- Flights from Myrtle Beach (MYR) to Key West (EYW)
- Flights from Chicago (ORD) to Key West (EYW)
- Flights from Norfolk (ORF) to Key West (EYW)
- Flights from West Palm Beach (PBI) to Key West (EYW)
- Flights from Philadelphia (PHL) to Key West (EYW)
- Flights from Pittsburgh (PIT) to Key West (EYW)
- Flights from Pensacola (PNS) to Key West (EYW)
- Flights from Providence (PVD) to Key West (EYW)
- Flights from Raleigh (RDU) to Key West (EYW)
- Flights from Richmond (RIC) to Key West (EYW)
- Flights from Fort Myers (RSW) to Key West (EYW)
- Flights from Louisville (SDF) to Key West (EYW)
- Flights from St. Louis (STL) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from Knoxville (TYS) to Key West (EYW)