Cheap Flights to Monroe County from $36 (2026/2027)
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.
$86 Roundtrip, just found
$86
Roundtrip
just found
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$92 Roundtrip, just found
$92
Roundtrip
just found
LGA
LaGuardia
MIA
Miami Intl.
$144 Roundtrip, just found
$144
Roundtrip
just found
SFO
San Francisco Intl.
MIA
Miami Intl.
$173 Roundtrip, found 1 hour ago
$173
Roundtrip
found 1 hour ago
LGA
LaGuardia
MIA
Miami Intl.
$180 Roundtrip, found 12 hours ago
$180
Roundtrip
found 12 hours ago
LGA
LaGuardia
MIA
Miami Intl.
$180 Roundtrip, found 12 hours ago
$180
Roundtrip
found 12 hours ago
LGA
LaGuardia
EYW
Key West Intl.
$285 Roundtrip, found 2 days ago
$285
Roundtrip
found 2 days ago
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$286 Roundtrip, found 5 days ago
$286
Roundtrip
found 5 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| PHL | Miami | April 22 to April 22 | $66 |
| CLT | Miami | April 30 to May 3 | $81 |
| LGA | Miami | April 28 to May 9 | $86 |
| EWR | Miami | April 15 to April 18 | $92 |
| TPA | Miami | April 20 to April 25 | $124 |
| BOS | Miami | April 22 to April 29 | $135 |
| DTW | Miami | April 16 to April 24 | $159 |
| ATL | Key West | April 26 to May 1 | $235 |
| CLT | Key West | April 27 to April 30 | $256 |
| PHL | Key West | April 27 to April 30 | $265 |
| ORD | Key West | April 19 to April 24 | $279 |
| BWI | Key West | April 19 to April 23 | $281 |
| EWR | Key West | April 19 to April 23 | $292 |
| BOS | Key West | May 4 to May 7 | $318 |
| DTW | Key West | May 16 to May 20 | $336 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| MDW | Miami | April 4 to April 11 | $121 |
| PHL | Miami | April 4 to April 6 | $141 |
| DTW | Miami | April 5 to April 15 | $154 |
| BWI | Miami | April 3 to April 4 | $171 |
| CLT | Miami | April 5 to April 9 | $183 |
| TPA | Key West | April 5 to April 8 | $206 |
| TPA | Miami | April 4 to April 11 | $239 |
| EWR | Miami | April 5 to April 8 | $246 |
| BOS | Miami | April 5 to April 8 | $246 |
| DTW | Key West | April 5 to April 14 | $314 |
| ORD | Key West | April 5 to April 14 | $327 |
| ATL | Key West | April 5 to April 9 | $427 |
| CLT | Key West | April 5 to April 8 | $473 |
| JFK | Key West | April 4 to April 7 | $478 |
| BOS | Key West | April 5 to April 10 | $509 |
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.
8.2/10 Very Good! (2,020 reviews)
Awesome place to stay in the Keys. Enjoyed it very much.
Reviewed on Mar 31, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
Book a stay at this 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.
8.8/10 Excellent! (1,805 reviews)
Fun, clean and relaxing
Reviewed on Mar 31, 2026
Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
Book a stay at this luxury hotel in Key Largo. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John Pennekamp Coral Reef State Park and Caribbean Club Bar are located nearby.
9.4/10 Exceptional! (1,402 reviews)
Everything was very nice. Extra activities were right at the hotel too, so it made it so easy to do stuff. Pool, beach, drinks, room, everything was great.
Reviewed on Apr 1, 2026
Save an average of 15% on thousands of hotels when you're signed in
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! (2,102 reviews)
This was a wonderful stay. The property had a shuttle which provided transportation to two stops in the Key West area. The staff was wonderful and accommodating for any questions or problems. Only issues we had, elevators were broken so had to carry heavy suitcases up the stairs. Also the hot tub ...
Reviewed on Mar 31, 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.
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
Frequently asked questions
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)