Cheap flights from TUP to EYW (Tupelo Regional to Key West Intl.)

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Hotel Ideas near Key West Intl.

Airport Hotels near Key West Intl.

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
3675 South Roosevelt Boulevard Key West FL
$203 nightly
The price is $228 total per night from Sep 1 to Sep 2
$228 total
Sep 1 - Sep 2
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! (1,235 reviews)
"The property itself was very nice and well kept. The maintenance and cleaning staff were very creepy men and made me feel very uncomfortable during my stay. It’s something to think about if you are solo traveling. The area was nice, amenities were great, but I would not return here."

Reviewed on Aug 17, 2026

Hyatt Vacation Club at Windward Pointe, Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

2.5 out of 5
3755 S Roosevelt Blvd Key West FL
$118 nightly
The price is $133 total per night from Aug 31 to Sep 1
$133 total
Aug 31 - Sep 1
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! (1,473 reviews)
"The free breakfast every morning was filling. They also shuttle you to a designated area that is walking distance from lots of shops and activities. They also pick you up from the same designated spot as at scheduled times. Definitely save money on the UBERING."

Reviewed on Aug 18, 2026

Hampton Inn Key West FL
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
$144 nightly
The price is $162 total per night from Sep 1 to Sep 2
$162 total
Sep 1 - Sep 2
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 ...
8.4/10 Very Good! (1,083 reviews)
"No complaints."

Reviewed on Aug 18, 2026

DoubleTree Resort by Hilton Grand Key - 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.

Hotels In Key West

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$203 nightly
The price is $228 total per night from Sep 1 to Sep 2
$228 total
Sep 1 - Sep 2
Total with taxes and fees
Book a stay at this spa 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 ...
8.8/10 Excellent! (3,536 reviews)
"X"

Reviewed on Aug 18, 2026

Southernmost Beach Resort and Guesthouses
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
$136 nightly
The price is $153 total per night from Aug 19 to Aug 20
$153 total
Aug 19 - Aug 20
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. ...
Ibis Bay Beach Resort
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
$200 nightly
The price is $225 total per night from Sep 2 to Sep 3
$225 total
Sep 2 - Sep 3
Total with taxes and fees
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 ...
Havana Cabana at 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.

Key West Hotels With Airport Transportation

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
$144 nightly
The price is $162 total per night from Sep 1 to Sep 2
$162 total
Sep 1 - Sep 2
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 ...
8.4/10 Very Good! (1,083 reviews)
"No complaints."

Reviewed on Aug 18, 2026

DoubleTree Resort by Hilton Grand Key - Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

2.5 out of 5
3755 S Roosevelt Blvd Key West FL
$118 nightly
The price is $133 total per night from Aug 31 to Sep 1
$133 total
Aug 31 - Sep 1
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! (1,473 reviews)
"The free breakfast every morning was filling. They also shuttle you to a designated area that is walking distance from lots of shops and activities. They also pick you up from the same designated spot as at scheduled times. Definitely save money on the UBERING."

Reviewed on Aug 18, 2026

Hampton Inn Key West FL
Eden House

Eden House

4 out of 5
1015 Fleming St Key West FL
$145 nightly
The price is $163 total per night from Aug 19 to Aug 20
$163 total
Aug 19 - Aug 20
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. ...
Eden House
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

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$155 nightly
The price is $175 total per night from Sep 2 to Sep 3
$175 total
Sep 2 - Sep 3
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! (1,384 reviews)
"Duty"

Reviewed on Aug 18, 2026

Southwinds Motel
Seashell Motel

Seashell Motel

1.5 out of 5
718 South Street Key West FL
$96 nightly
The price is $108 total per night from Aug 24 to Aug 25
$108 total
Aug 24 - Aug 25
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 ...
8/10 Very Good! (1,000 reviews)
"The room itself was very nice, clean, and comfortable, and the location was great because it was very close to everything. My main disappointment was that the listing mentioned a shared area, but when we arrived, it was under construction. There appeared to be a new pool that was already filled with ..."

Reviewed on Aug 13, 2026

Seashell Motel
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$124 nightly
The price is $136 total per night from Aug 19 to Aug 20
$136 total
Aug 19 - Aug 20
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 ...
9.6/10 Exceptional! (1,087 reviews)
"The location, the rooms, and the whole hotel was wonderful!! So relaxing. I will absolutely staying there whenever I'm back in Key West."

Reviewed on Aug 18, 2026

Duval House
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

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$203 nightly
The price is $228 total per night from Sep 1 to Sep 2
$228 total
Sep 1 - Sep 2
Total with taxes and fees
Book a stay at this spa 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 ...
8.8/10 Excellent! (3,536 reviews)
"X"

Reviewed on Aug 18, 2026

Southernmost Beach Resort and Guesthouses
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
$166 nightly
The price is $187 total per night from Sep 1 to Sep 2
$187 total
Sep 1 - Sep 2
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 ...
8.6/10 Excellent! (2,633 reviews)

Families like: Outdoor pools, playground, miniature golf, game room

Travelers say...
"This resort is amazing. We have stayed here for the past 3 years and plan to go back again next year. The only thing that I would have a small complaint is there is no microwave in the rooms. We wasted alot of leftover food from restaurants because there was no way to heat it back up. After the first ..."

Reviewed on Aug 18, 2026

Blue Flamingo Resort Key West
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
$188 nightly
The price is $211 total per night from Aug 25 to Aug 26
$211 total
Aug 25 - Aug 26
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 ...
9/10 Wonderful! (1,838 reviews)
"The room was clean and smells clean. Staffs are very helpful and greeted me enthusiastically. It was a place that I was expecting to be in and relax after a long drive. The pool was nice, heated and relaxing. Highly recommended."

Reviewed on Aug 17, 2026

Hilton Key West Resort & Marina
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

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
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

Frequently asked questions

What airlines have the most flights from TUP to Key West Intl. Airport (EYW)?
Do a little shopping, pick up a doughnut, chat with a stranger ... Airport stopovers don't have to be a bore! If you're planning to head from Tupelo to Key West, you can't fly direct. Be prepared to make at least one stop somewhere.

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.

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