Cheap flights from EVV to EYW (Evansville Regional to Key West Intl.)
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Cheap Flights from EVV to EYW starting at $335 One Way, $407 Round Trip
Prices starting at $407 for return flights and $335 for one-way flights to Key West Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
EVV
Evansville
EYW
Key West
$407 Roundtrip, found 2 days ago
$407
Roundtrip
found 2 days ago
EVV
Evansville
EYW
Key West
$417 Roundtrip, found 2 days ago
$417
Roundtrip
found 2 days ago
EVV
Evansville
EYW
Key West
$419 Roundtrip, found 2 days ago
$419
Roundtrip
found 2 days ago
EVV
Evansville
EYW
Key West
$427 Roundtrip, found 2 days ago
$427
Roundtrip
found 2 days ago
EVV
Evansville
EYW
Key West
$429 Roundtrip, found 2 days ago
$429
Roundtrip
found 2 days ago
Hotel Ideas near Key West Intl.
Airport Hotels near Key West Intl.
Hyatt Vacation Club at Windward Pointe, Key West
3675 South Roosevelt Boulevard Key West FL
$495 nightly
The price is $557 total per night from Feb 21 to Feb 22
$557 total
Feb 21 - Feb 22
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (1,007 reviews)
Great view, clean property. Beds were very comfortable. Having a telescope to view the stars is a nice touch
Reviewed on Jan 16, 2026
Hampton Inn Key West FL
3755 S Roosevelt Blvd Key West FL
$467 nightly
The price is $525 total per night from Feb 2 to Feb 3
$525 total
Feb 2 - Feb 3
Total with taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
9/10 Wonderful! (1,301 reviews)
The staff is excellent especially Sam who always helps me when I stay there.
Reviewed on Jan 16, 2026
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
$369 nightly
The price is $416 total per night from Jan 25 to Jan 26
$416 total
Jan 25 - Jan 26
Total with taxes and fees
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8/10 Very Good! (1,001 reviews)
Very clean. The pool area is fantastic. Good food and bar. Just a heads up though, the planes are extremely loud!
Reviewed on Jan 14, 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.
Hotels In Key West
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
$511 nightly
The price is $574 total per night from Jan 26 to Jan 27
$574 total
Jan 26 - Jan 27
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.6/10 Excellent! (3,009 reviews)
Great location! The rooms were updated. (We had a few problems that we brought to the attention of the staff and they were quickly addressed.) We paid extra for a balcony view, however it looked over the roof of another part of the hotel... No street view, no pool view, no beach view. With that said, ...
Reviewed on Jan 20, 2026
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
$551 nightly
The price is $620 total per night from Feb 2 to Feb 3
$620 total
Feb 2 - Feb 3
Total with taxes and fees
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 ...
8.8/10 Excellent! (1,776 reviews)
The entire resort was absolutely beautiful. It was also very welcoming. Not just in appearance but the staff were all so friendly and wonderful to work with!
Reviewed on Jan 16, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
$400 nightly
The price is $450 total per night from Jan 25 to Jan 26
$450 total
Jan 25 - Jan 26
Total with taxes and fees
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 ...
8/10 Very Good! (1,881 reviews)
I emailed Blue Flamingo asking for an early check in as our flight got in at 10:00am and check in was at 4:00pm. The email was not reponded to, when we arrived they did offer to hold our bags there and text when room was ready. Rooms were very clean and inviting. The staff was very friendly and ...
Reviewed on Jan 20, 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.
Key West Hotels With Airport Transportation
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
$369 nightly
The price is $416 total per night from Jan 25 to Jan 26
$416 total
Jan 25 - Jan 26
Total with taxes and fees
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8/10 Very Good! (1,001 reviews)
Very clean. The pool area is fantastic. Good food and bar. Just a heads up though, the planes are extremely loud!
Reviewed on Jan 14, 2026
Hampton Inn Key West FL
3755 S Roosevelt Blvd Key West FL
$467 nightly
The price is $525 total per night from Feb 2 to Feb 3
$525 total
Feb 2 - Feb 3
Total with taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
9/10 Wonderful! (1,301 reviews)
The staff is excellent especially Sam who always helps me when I stay there.
Reviewed on Jan 16, 2026
Eden House
1015 Fleming St Key West FL
$398 nightly
The price is $448 total per night from Jan 26 to Jan 27
$448 total
Jan 26 - Jan 27
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free WiFi, in-room massages, and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. ...
9/10 Wonderful! (1,001 reviews)
I will definitely be back.
Reviewed on Jan 15, 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.
Low Priced Key West Hotels
Southwinds Motel
1321 Simonton Street Key West FL
$349 nightly
The price is $393 total per night from Jan 26 to Jan 27
$393 total
Jan 26 - Jan 27
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
8.6/10 Excellent! (1,269 reviews)
Everyone was nice and courteous. Quiet place. Really enjoyed our weekend
Reviewed on Jan 20, 2026
Seashell Motel
718 South Street Key West FL
$285 nightly
The price is $321 total per night from Jan 26 to Jan 27
$321 total
Jan 26 - Jan 27
Total with taxes and fees
Stay at this hostel in Key West. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
7.8/10 Good! (1,001 reviews)
Check in was great and friendly. Walking distance to the beach. Air conditioning froze out my husband. Hotel was under construction but still very clean and kept. Would definitely stay again.
Reviewed on Jan 17, 2026
Duval House
815 Duval St Key West FL
$351 nightly
The price is $392 total per night from Jan 26 to Jan 27
$392 total
Jan 26 - Jan 27
Total with taxes and fees
Stay at this B&B in Key West. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the breakfast and the pool in our reviews. Popular ...
9.4/10 Exceptional! (1,001 reviews)
Yes
Reviewed on Jan 17, 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.
Family Friendly Hotels in Key West
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
$511 nightly
The price is $574 total per night from Jan 26 to Jan 27
$574 total
Jan 26 - Jan 27
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.6/10 Excellent! (3,009 reviews)
Great location! The rooms were updated. (We had a few problems that we brought to the attention of the staff and they were quickly addressed.) We paid extra for a balcony view, however it looked over the roof of another part of the hotel... No street view, no pool view, no beach view. With that said, ...
Reviewed on Jan 20, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free parking, 2 restaurants, and breakfast (surcharge). Popular attractions Duval Street and Smathers Beach ...
8.2/10 Very Good! (999 reviews)
Families like: Outdoor pool, babysitting, close to beach, bicycle rentals
Travelers say...
Room was clean and comfortable but after first day towels were shorted. Had to ask for more twice Desk staff were very nice and helpful. Concierge was helpful with rentals Restaurant was not as good as past stays when Sheraton. Food even pancakes were tough and overcooked. Shuttle drivers were very ...
Reviewed on Dec 4, 2025
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
$400 nightly
The price is $450 total per night from Jan 25 to Jan 26
$450 total
Jan 25 - Jan 26
Total with taxes and fees
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 ...
8/10 Very Good! (1,881 reviews)
Families like: Outdoor pools, miniature golf, game room, bicycle rentals
Travelers say...
I emailed Blue Flamingo asking for an early check in as our flight got in at 10:00am and check in was at 4:00pm. The email was not reponded to, when we arrived they did offer to hold our bags there and text when room was ready. Rooms were very clean and inviting. The staff was very friendly and ...
Reviewed on Jan 20, 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.
EVV to EYW Route Info
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EVV Address & GPS
Address:
7801 Bussing Drive
Evansville IN, 47725
United States
IATA Code:
EVV
Longitude:
-87.527965
Latitude:
38.046164
Time Zone:
America/Chicago
EYW Address & GPS
Address:
3491 South Roosevelt Boulevard
Key West FL, 33040-5260
United States
IATA Code:
EYW
Longitude:
-81.75501
Latitude:
24.553574
Time Zone:
America/New_York
Other Flights from Evansville Regional Airport (EVV)
Other Flights to Key West Intl. Airport (EYW)
- Owensboro-Daviess County Regional Airport (OWB)
- Williamson County Regional Airport (MWA)
- Barkley Regional Airport (PAH)
- Louisville Intl. Airport (SDF)
- Bowman Field Airport (LOU)
- Cairo Regional Airport (CIR)
- Cape Girardeau Municipal Airport (CGI)
- Indianapolis Intl. Airport (IND)
- Nashville Intl. Airport (BNA)
- University Of Illinois Urbana-Champaign Williard Airport (CMI)
Top Trending
Flights
- DCA to MCO
- BOS to MCO
- BDL to MCO
- LGA to MIA
- LGA to FLL
- MCO to LAX
- DTW to MCO
- DCA to MIA
- MCO to LGA
- BWI to MIA
- JFK to FLL
- LAX to MCO
- EWR to MCO
- ATL to MCO
- LGA to MCO
- MSP to MCO
- BWI to FLL
- MCO to JFK
- MCO to EWR
- ORD to MCO
- MCO to SJU
- DTW to MIA
- PHL to MCO
- BWI to MCO
- JFK to MCO
- JFK to MIA
- FLL to JFK
- DCA to FLL
- RDU to MCO
- JFK to TPA
Frequently asked questions
Map To Nearby Hotels
Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.