$64 Cheap flight deals from Cleveland (CLE) to Rockland Key (EYW)

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This Weekend's Flight Deals from Cleveland to Rockland Key

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jan 2 - Thu, Jan 8
CAK
Akron-Canton
EYW
Key West Intl.
$254 Roundtrip, found 6 hours ago
$254
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Fri, Jan 2 from Akron-Canton to Key West Intl., returning Thu, Jan 8, priced at $254 found 6 hours ago
Sat, Jan 3 - Wed, Jan 7
CLE
Hopkins Intl.
EYW
Key West Intl.
$305 Roundtrip, found 4 days ago
$305
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Jan 3 from Hopkins Intl. to Key West Intl., returning Wed, Jan 7, priced at $305 found 4 days ago

Airfares from $64 One Way, $136 Round Trip from Cleveland to Rockland Key

Prices starting at $136 for return flights and $64 for one-way flights to Rockland Key were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Jan 25 - Thu, Feb 5
CAK
Akron
EYW
Key West
$136 Roundtrip, found 1 day ago
$136
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, Jan 25 from Akron to Key West, returning Thu, Feb 5, priced at $136 found 1 day ago
Mon, Jan 26 - Thu, Jan 29
CAK
Akron
EYW
Key West
$137 Roundtrip, found 15 hours ago
$137
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Mon, Jan 26 from Akron to Key West, returning Thu, Jan 29, priced at $137 found 15 hours ago
Sun, Feb 8 - Thu, Feb 12
CAK
Akron
EYW
Key West
$142 Roundtrip, found 3 hours ago
$142
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Sun, Feb 8 from Akron to Key West, returning Thu, Feb 12, priced at $142 found 3 hours ago
Sun, Jan 25 - Fri, Jan 30
CAK
Akron
EYW
Key West
$146 Roundtrip, found 14 hours ago
$146
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Sun, Jan 25 from Akron to Key West, returning Fri, Jan 30, priced at $146 found 14 hours ago
Mon, Jan 12 - Thu, Jan 15
CAK
Akron
EYW
Key West
$146 Roundtrip, found 1 day ago
$146
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Jan 12 from Akron to Key West, returning Thu, Jan 15, priced at $146 found 1 day ago

Rockland Key economy flight packages

Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina
4.0-star property

Oceans Edge Key West Resort, Hotel & Marina

9/10 Wonderful! (1,736 reviews)

Feb 10 - Feb 14

4 night stay

Cleveland (CLE) to Key West (EYW)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,494, price is now $962 per person
$962
per person
found 1 day ago
We LOVED the setting and the surrounding area! Absolutely beautiful! Be aware the hotel IS in the airport landing zone. If you like to watch/hear commercial planes you'll be very happy. Ask for a room on the top floor only - so you can (1) look over the marina AND (2) so you won't hear people moving chairs on their balcony above you. The max/min air conditioning is centrally controlled. If you want it colder than 67, you will not be able to. Not sure what the max heat was. Be extra vigilant about putting a thick towel on the floor to soak up any water that gets past the shower door. It WILL happen! Please do not slip on the wet tile floor! Be aware that if you want/need a later checkout, they will charge you an additional $50/hour past their usual checkout time of 11am. Be prepared for onsite meal expenses. They are very good, but they ARE on the pricy side. Our particular room smelled strongly of smoke on arrival. I'm nearly POSITIVE we asked for a nonsmoking room as we both have underlying medical problems that preclude exposre to smoke. Perhaps call ahead to ENSURE you get a nonsmoking on arrival. The entire hotel was booked so we did not have any other choice.

Reviewed on Dec 28, 2025

The Key West Hotel
2.5-star property

The Key West Hotel

9.2/10 Wonderful! (505 reviews)

Feb 10 - Feb 14

4 night stay

Cleveland (CLE) to Key West (EYW)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,838, price is now $1,634 per person
$1,634
per person
found 1 day ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.

Reviewed on Jan 5, 2025

Southernmost Beach Resort and Guesthouses
4.0-star property

Southernmost Beach Resort and Guesthouses

8.6/10 Excellent! (2,844 reviews)

Feb 10 - Feb 14

4 night stay

Cleveland (CLE) to Key West (EYW)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,827, price is now $1,194 per person
$1,194
per person
found 1 day ago
Billed me for parking when I didn’t have a car. Took several calls to try and resolve. Still haven’t received a refund. They were quick to take my money when I paid for the room but not so responsive in processing my refund.

Reviewed on Nov 1, 2025

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Rockland Key first class flight packages

Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina
4.0-star property

Oceans Edge Key West Resort, Hotel & Marina

9/10 Wonderful! (1,736 reviews)

Feb 2 - Feb 4

2 night stay

Cleveland (CLE) to Key West (EYW)

Delta • Non-stop roundtrip • FirstClass
Price was $1,781, price is now $1,559 per person
$1,559
per person
found 1 day ago
We LOVED the setting and the surrounding area! Absolutely beautiful! Be aware the hotel IS in the airport landing zone. If you like to watch/hear commercial planes you'll be very happy. Ask for a room on the top floor only - so you can (1) look over the marina AND (2) so you won't hear people moving chairs on their balcony above you. The max/min air conditioning is centrally controlled. If you want it colder than 67, you will not be able to. Not sure what the max heat was. Be extra vigilant about putting a thick towel on the floor to soak up any water that gets past the shower door. It WILL happen! Please do not slip on the wet tile floor! Be aware that if you want/need a later checkout, they will charge you an additional $50/hour past their usual checkout time of 11am. Be prepared for onsite meal expenses. They are very good, but they ARE on the pricy side. Our particular room smelled strongly of smoke on arrival. I'm nearly POSITIVE we asked for a nonsmoking room as we both have underlying medical problems that preclude exposre to smoke. Perhaps call ahead to ENSURE you get a nonsmoking on arrival. The entire hotel was booked so we did not have any other choice.

Reviewed on Dec 28, 2025

The Key West Hotel
2.5-star property

The Key West Hotel

9.2/10 Wonderful! (505 reviews)

Feb 2 - Feb 4

2 night stay

Cleveland (CLE) to Key West (EYW)

Delta • Non-stop roundtrip • FirstClass
Price was $2,248, price is now $1,829 per person
$1,829
per person
found 1 day ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.

Reviewed on Jan 5, 2025

Ella's Cottages - Key West Historic Inns
3.5-star property

Ella's Cottages - Key West Historic Inns

9.4/10 Exceptional! (390 reviews)

Feb 2 - Feb 4

2 night stay

Cleveland (CLE) to Key West (EYW)

Delta • Non-stop roundtrip • FirstClass
Price was $1,951, price is now $1,631 per person
$1,631
per person
found 1 day ago
We chose this historic inn based on central location to everything we wanted in less than 15 min. Front desk staff (Dwight and others) are fantastic and always willing to listen and provide assistance. Fort Zachary Taylor Beach Park is walkable - 25 min (beach water shoes recommended due to rocks). We didn't need to rent any transportation as it was easier for us to walk it out, so I can't comment on parking since I didn't use it (it is limited at most places). We felt very safe walking around, even at night. We used a taxi to and from Key West airport (both drivers familiar with this inn). Room is clean. Both night stands have power and USB charging outlets. Excellent daily room service and Sunshine Breakfast basket hand delivered to your room. Duval Loop bus stop 14 (free) in front of inn (bus route loop is an hour long and two buses running to ensure next bus in 30 min), so this is another convenient option if walking isn't your thing.

Reviewed on Dec 17, 2024

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More About Flying To Rockland Key from Cleveland

Route Information for Flights from Cleveland to Rockland Key

Origin Airport IATA Code
CLE
Destination Airport IATA Code
EYW
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Cleveland to Rockland Key

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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.