Cheap flights from TUP to EYW (Tupelo Regional to Key West Intl.)
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Cheap Flights from TUP to EYW starting at One Way, $653 Round Trip
Prices starting at $653 for return flights and 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.
TUP
Tupelo
EYW
Key West
$653 Roundtrip, found 1 day ago
$653
Roundtrip
found 1 day ago
TUP
Tupelo
EYW
Key West
$815 Roundtrip, found 1 day ago
$815
Roundtrip
found 1 day ago
TUP
Tupelo
EYW
Key West
$977 Roundtrip, found 1 day ago
$977
Roundtrip
found 1 day ago
TUP
Tupelo
EYW
Key West
$1,238 Roundtrip, found 1 day ago
$1,238
Roundtrip
found 1 day 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
$317 nightly
The price is $357 total per night from Aug 3 to Aug 4
$357 total
Aug 3 - Aug 4
Total includes taxes and fees
Stay at this 3.5-star eco-certified hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff ...
9.4/10 Exceptional! (1,018 reviews)
"The check in is to late at 4pm and the check out to early at 10 am, basically you lost a whole day. It’s not fear for customers."
Reviewed on Jul 1, 2025
Hampton Inn Key West FL
3755 S Roosevelt Blvd, Key West, FL
$199 nightly
The price is $224 total per night from Jul 6 to Jul 7
$224 total
Jul 6 - Jul 7
Total includes taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,183 reviews)
"Would definitely recommend. Clean, great staff, complimentary breakfast and water bottles. We enjoyed exploring the city on a golf cart we rented from the concierge."
Reviewed on Jun 30, 2025
Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
$197 nightly
The price is $222 total per night from Jul 8 to Jul 9
$222 total
Jul 8 - Jul 9
Total includes taxes and fees
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. ...
8.4/10 Very Good! (1,272 reviews)
"I recently stayed at this hotel and was impressed by how beautiful all the areas were – from the well-maintained grounds to the elegant interiors. The overall atmosphere was relaxing and enjoyable. However, the pool area and bar could use some improvement. Both seemed understaffed during my stay, ..."
Reviewed on Jun 30, 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.
Hotels In Key West
Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
$197 nightly
The price is $222 total per night from Jul 8 to Jul 9
$222 total
Jul 8 - Jul 9
Total includes taxes and fees
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. ...
8.4/10 Very Good! (1,272 reviews)
"I recently stayed at this hotel and was impressed by how beautiful all the areas were – from the well-maintained grounds to the elegant interiors. The overall atmosphere was relaxing and enjoyable. However, the pool area and bar could use some improvement. Both seemed understaffed during my stay, ..."
Reviewed on Jun 30, 2025
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
$285 nightly
The price is $321 total per night from Jul 16 to Jul 17
$321 total
Jul 16 - Jul 17
Total includes taxes and fees
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 ...
8.6/10 Excellent! (1,736 reviews)
"Amazing!"
Reviewed on Jun 27, 2025
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
$274 nightly
The price is $308 total per night from Jul 16 to Jul 17
$308 total
Jul 16 - Jul 17
Total includes taxes and fees
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. ...
8.6/10 Excellent! (2,593 reviews)
"The amenities on the property were great! We enjoyed the shores pool and pool bar during our stay. However, we did not enjoy the pigeons and roosters roaming everywhere or their waste all over the property. There was pigeon poop all outside our room and down the steps leading to the pool area. We ..."
Reviewed on Jul 1, 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.
Key West Hotels With Airport Transportation
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd, Key West, FL
$189 nightly
The price is $213 total per night from Jul 6 to Jul 7
$213 total
Jul 6 - Jul 7
Total includes taxes and fees
Stay at this 4-star business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
7.8/10 Good! (1,002 reviews)
"No comment"
Reviewed on Jun 25, 2025
Hampton Inn Key West FL
3755 S Roosevelt Blvd, Key West, FL
$199 nightly
The price is $224 total per night from Jul 6 to Jul 7
$224 total
Jul 6 - Jul 7
Total includes taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,183 reviews)
"Would definitely recommend. Clean, great staff, complimentary breakfast and water bottles. We enjoyed exploring the city on a golf cart we rented from the concierge."
Reviewed on Jun 30, 2025
Eden House
1015 Fleming St, Key West, FL
$202 nightly
The price is $227 total per night from Jul 7 to Jul 8
$227 total
Jul 7 - Jul 8
Total includes taxes and fees
Stay at this 3.5-star 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 ...
9/10 Wonderful! (1,001 reviews)
Great Guest House
"Excellent. Great people"
Reviewed on Jul 1, 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.
Low Priced Key West Hotels
Southwinds Motel
1321 Simonton Street, Key West, FL
$170 nightly
The price is $191 total per night from Aug 3 to Aug 4
$191 total
Aug 3 - Aug 4
Total includes taxes and fees
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and a 24-hour front desk. Our guests praise the breakfast and the pool in our reviews. ...
8.6/10 Excellent! (1,125 reviews)
"Always stay at Southwinds. Like the location"
Reviewed on Jul 1, 2025
Seashell Motel & Key West Hostel
718 South Street, Key West, FL
$131 nightly
The price is $147 total per night from Jul 6 to Jul 7
$147 total
Jul 6 - Jul 7
Total includes 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 ...
7.6/10 Good! (1,003 reviews)
"Great choice"
Reviewed on Jun 23, 2025
Duval House
815 Duval St, Key West, FL
$151 nightly
The price is $167 total per night from Jul 6 to Jul 7
$167 total
Jul 6 - Jul 7
Total includes taxes and fees
Stay at this 3-star B&B in Key West. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (1,022 reviews)
"The best place to stay in Key West. Staff is uber friendly, rooms are terrific. Clean, Location cannot be beat."
Reviewed on Jun 30, 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.
Family Friendly Hotels in Key West
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
$274 nightly
The price is $308 total per night from Jul 16 to Jul 17
$308 total
Jul 16 - Jul 17
Total includes taxes and fees
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. ...
8.6/10 Excellent! (2,593 reviews)
"The amenities on the property were great! We enjoyed the shores pool and pool bar during our stay. However, we did not enjoy the pigeons and roosters roaming everywhere or their waste all over the property. There was pigeon poop all outside our room and down the steps leading to the pool area. We ..."
Reviewed on Jul 1, 2025
Margaritaville Beach House Key West
2001 South Roosevelt Blvd, Key West, FL
Stay at this 4-star 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! (1,000 reviews)
Families like: Outdoor pool, babysitting, close to beach, bicycle rentals
Travelers say...
"Everything was was great"
Reviewed on May 9, 2025
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard, Key West, FL
$184 nightly
The price is $207 total per night from Jul 6 to Jul 7
$207 total
Jul 6 - Jul 7
Total includes taxes and fees
Stay at this 4-star eco-certified hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
7.6/10 Good! (1,447 reviews)
Families like: Outdoor pools, miniature golf, game room, bicycle rentals
Travelers say...
"Clean, comfortable well kept property and grounds. Friendly staff."
Reviewed on Jul 1, 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.
TUP to EYW Route Info
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TUP Address & GPS
Address:
Lemons Drive
Tupelo MS, 38801-7024
United States
IATA Code:
TUP
Longitude:
-88.767222
Latitude:
34.258889
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 Tupelo Regional Airport (TUP)
Other Flights to Key West Intl. Airport (EYW)
- Roscoe Turner Field Airport (CRX)
- Golden Triangle Regional Airport (GTR)
- Northwest Alabama Regional Airport (MSL)
- Memphis Intl. Airport (MEM)
- McKellar-Sipes Regional Airport (MKL)
- Tunica Municipal Airport (UTM)
- Huntsville Intl. Airport (HSV)
- Birmingham Intl. Airport (BHM)
- Meridian Regional Airport (MEI)
- Mid Delta Regional Airport (GLH)
Top Trending
Flights
DCA to MCOBOS to MCOBDL to MCOLGA to MIALGA to FLLMCO to LAXDTW to MCODCA to MIAMCO to LGABWI to MIAJFK to FLLLAX to MCOEWR to MCOATL to MCOLGA to MCOMSP to MCOBWI to FLLMCO to JFKMCO to EWRORD to MCOMCO to SJUDTW to MIAPHL to MCOBWI to MCOJFK to MCOJFK to MIAFLL to JFKDCA to FLLRDU to MCOJFK 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.