
Cheap Flights to Monroe County from $24 (2026/2027)
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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.
BWI
Baltimore Washington Intl. Thurgood Marshall
MIA
Miami Intl.
$66 Roundtrip, found 2 days ago
$66
Roundtrip
found 2 days ago
PHL
Philadelphia Intl.
MIA
Miami Intl.
$77 Roundtrip, found 3 hours ago
$77
Roundtrip
found 3 hours ago
BWI
Baltimore Washington Intl. Thurgood Marshall
MIA
Miami Intl.
$179 Roundtrip, found 3 days ago
$179
Roundtrip
found 3 days ago
SFO
San Francisco Intl.
MIA
Miami Intl.
$251 Roundtrip, found 11 hours ago
$251
Roundtrip
found 11 hours ago
BWI
Baltimore Washington Intl. Thurgood Marshall
AVT
Aventura Brightline Train Station
$320 Roundtrip, found 3 days ago
$320
Roundtrip
found 3 days ago
BWI
Baltimore Washington Intl. Thurgood Marshall
EKW
Miami Central Brightline Train Station
$320 Roundtrip, found 3 days ago
$320
Roundtrip
found 3 days ago
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$369 Roundtrip, found 1 day ago
$369
Roundtrip
found 1 day ago
SFO
San Francisco Intl.
EYW
Key West Intl.
$399 Roundtrip, found 4 days ago
$399
Roundtrip
found 4 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| CLT | Miami | December 7 to December 10 | $48 |
| ATL | Miami | November 17 to November 20 | $53 |
| PIE | Key West | December 2 to December 3 | $82 |
| PHL | Miami | January 8 to January 17 | $98 |
| TPA | Miami | December 30 to December 31 | $132 |
| EWR | Miami | January 27 to February 1 | $192 |
| BOS | Miami | January 12 to January 13 | $199 |
| SWF | Key West | January 13 to January 20 | $203 |
| CLT | Key West | December 7 to December 12 | $259 |
| BOS | Key West | February 1 to February 8 | $267 |
| BWI | Key West | January 21 to January 25 | $369 |
| ATL | Key West | December 12 to December 15 | $369 |
| EWR | Key West | December 17 to December 21 | $376 |
| DTW | Key West | December 16 to January 6 | $380 |
| PHL | Key West | February 6 to February 13 | $513 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Miami | November 6 to November 9 | $78 |
| PIE | Key West | November 7 to November 11 | $86 |
| CLT | Miami | November 8 to November 9 | $87 |
| BWI | Miami | November 6 to November 7 | $138 |
| PHL | Miami | November 7 to November 14 | $212 |
| DTW | Miami | November 6 to November 10 | $248 |
| TPA | Miami | November 7 to November 17 | $287 |
| MDW | Miami | November 7 to November 9 | $338 |
| LGA | Miami | November 7 to November 14 | $341 |
| BOS | Miami | November 8 to November 16 | $406 |
| BOS | Key West | November 6 to November 11 | $603 |
| EWR | Key West | November 8 to November 11 | $605 |
| EWR | Key West | November 8 to November 11 | $605 |
| ATL | Key West | November 6 to November 9 | $927 |
| PHL | Key West | November 8 to November 15 | $1,348 |
Best Monroe County Flight and Hotel Packages
Price found within the past 48 hours. Click for updated prices.



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Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Florida Keys Brewing Co. and Lorelei Restaurant & Cabana Bar are located nearby.
9.2/10 Wonderful! (1,499 reviews)
"Nice hotel, great service"
Reviewed on Nov 2, 2026

Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), a free airport shuttle, and room service. 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! (1,812 reviews)
"Kind and friendly service. Great pool, room was small but maximized its space. Free internet. Air conditioning worked well. No laundry service available unfortunately for longer stays."
Reviewed on Nov 2, 2026

Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
9/10 Wonderful! (1,901 reviews)
"The property closed for renovations and moved us to another hotel."
Reviewed on Nov 2, 2026
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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 Mallory Square are located nearby.
8.6/10 Excellent! (2,771 reviews)
"Very nice resort. Pool was great. Food was great as well. Bed was wonderful. Staff was very helpful and friendly. Shuttle made it excellent for getting to Old Town. The whole stay was the best…and we have traveled to all 50 states and 28 countries. Thank you!!"
Reviewed on Nov 2, 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.
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- Opal Key Resort & Marina Key West
- Orchid Key Inn - Adults Only
- Parrot Key Hotel & Villas
- Pet Friendly in Key West
- Pier House Resort & Spa
- Seashell Motel
- Silver Palms Inn & Historic Homes
- Simonton Court Historic Inn & Cottages
- Southernmost Beach Resort and Guesthouses
- Southwinds Motel
- Sunset Key Cottages
- The Cabana Inn Key West - Adults Only
- The Gardens Hotel
- The Laureate Key West
- The Marker Key West Harbor Resort
- The Marquesa Hotel
- The Perry Hotel & Marina Key West
- The Reach Key West Curio Collection by Hilton
- Southernmost House - Adult Exclusive
- The Southernmost Inn - Adults Only
- Westwinds Inn
- Wicker Guesthouse
- Hotels in Key West
- Houseboats in Key West
- Privatevacationhomes in Key West
- Resorts in Key West
- Hotels near Mallory Square
- Isla Bella Beach Resort & Spa
- Hotels in Marathon
- Old Town Key West Hotels
- Hotels near Southernmost Point
- Sugar Loaf Lodge
- Sugarloaf Key Hotel at KOA Resort
- Sunset Key Hotels
- Hotels in Big Pine Key
- Casa Marina Hotels
- Downtown Key West Hotels
- Hotels near Duval Street
- Hotels near Fort Zachary Taylor Historic State Park
- Bedandbreakfast in Key West
- Condos in Key West
- Key West Historic District Hotels
- Adults Only in Key West
- All-Inclusive in Key West
- Amsterdam's Curry Mansion Inn
- Beach in Key West
- Casa Marina Key West Curio Collection by Hilton
- Budget in Key West
- Coconut Beach Resort
- La Concha Key West Autograph Collection
- Duval House
- Family Friendly in Key West
- H2O Suites - Adults Only
- Havana Cabana at Key West
- Heron House - Adult Only
- The Independent Inn - Formerly Heron House Court
- Suites in Key West
- Island City House Hotel
- Beachside Resort & Residences
- Hilton Key West Resort & Marina
- Ocean Key Resort - A Noble House Resort
- NYAH Key West - Adults Only
- New Orleans House - Gay Men Adult Resort
- LA TE DA Hotel - Adults Only
- Winslow's Bungalows - Key West Historic Inns
- Lighthouse Hotel - Key West Historic Inns
- Ella's Cottages - Key West Historic Inns
- JetBlue Airways Jamaica (JFK) to Key West (EYW) flights
- Flights from Nashville (BNA) to Key West (EYW)
- Flights from Baltimore (BWI) to Key West (EYW)
- Flights from Dallas (DFW) to Key West (EYW)
- Flights from Detroit (DTW) to Key West (EYW)
- Flights from Newark (EWR) to Key West (EYW)
- Flights from Jacksonville (JAX) 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 New Orleans (MSY) to Key West (EYW)
- Flights from Chicago (ORD) to Key West (EYW)
- Flights from Philadelphia (PHL) to Key West (EYW)
- Flights from Pittsburgh (PIT) to Key West (EYW)
- Flights from Fort Myers (RSW) to Key West (EYW)
- Flights from St Louis (STL) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from Alcoa (TYS) to Key West (EYW)
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