Cheap Flights to Monroe County from $40 (2025/2026)

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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.

OriginDestinationTravel DatesFlights From*
TPAKey WestAugust 18 to August 20$82
BWIMiamiJune 29 to July 8$88
LGAMiamiAugust 25 to August 27$91
DTWMiamiAugust 20 to August 26$98
PHLMiamiJune 30 to July 4$100
BOSMiamiSeptember 4 to September 7$108
TPAMiamiSeptember 12 to September 29$154
BOSKey WestSeptember 6 to September 13$237
EWRKey WestAugust 20 to August 27$249
EWRKey WestAugust 20 to August 27$249
BWIKey WestJuly 14 to July 29$259
MDWKey WestAugust 14 to September 17$269
ATLKey WestAugust 16 to August 30$279
DTWKey WestAugust 12 to August 19$283
CLTKey WestAugust 13 to August 20$405
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
CLTMiamiJune 22 to June 28$161
DTWMiamiJune 22 to July 7$170
ORDMiamiJune 21 to June 28$185
JFKMiamiJune 21 to June 25$191
BOSMiamiJune 21 to June 30$290
BWIKey WestJune 21 to July 1$323
DTWKey WestJune 21 to July 4$323
TPAMiamiJune 22 to July 1$336
EWRKey WestJune 22 to June 28$344
EWRKey WestJune 22 to June 28$344
ORDKey WestJune 21 to June 24$386
ATLKey WestJune 21 to July 8$475
BOSKey WestJune 22 to June 30$539
PHLKey WestJune 21 to June 24$575
CLTKey WestJune 22 to July 8$639
*Prices include taxes and fees

Best Monroe County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Henrosa Hotel
Cavalier Hotel South Beach
The Retreat Collection at 1 Hotel & Homes South Beach
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Travelers ❤️ These Monroe County 🏨

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
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

Beachside Resort & Residences
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
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

Southernmost Beach Resort and Guesthouses
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
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! (1,003 reviews)
"Property is nice and beautiful"

Reviewed on Jun 12, 2025

Hawks Cay Resort
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Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
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

Margaritaville Beach House Key West
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.
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.