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Midtown Vacation Packages

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Midtown Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
New Town
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this 4-star 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 attractions Duval Street and Smathers Beach are located nearby.
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this 3.5-star hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this 4-star business-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 Smathers Beach are located nearby.
Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this 3.5-star business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Save 100% on your flight
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
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. Popular attractions Duval Street and South Beach are located nearby.
Bishop Hotel Key West

Bishop Hotel Key West

4 out of 5
Old Town Key West
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this 4-star guesthouse in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Stay at this 3.5-star hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.

3-4 Night Vacations in Midtown

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

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
per person
Jul 21 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
per person
Jul 21 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
per person
Jul 21 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
per person
Jul 21 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)

5-7 Night Vacations in Midtown

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)

Cheap Hotel Deals in Midtown

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
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. ...
Beachside Resort & Residences
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
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. ...
Southernmost Beach Resort and Guesthouses
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
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 ...
Margaritaville Beach House Key West
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Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue, Key West, FL
Stay at this 4-star 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 ...
Oceans Edge Key West Resort, Hotel & Marina
Fairfield Inn and Suites by Marriott Key West

Fairfield Inn and Suites by Marriott Key West

3 out of 5
2400 N Roosevelt Blvd, Key West, FL
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 ...
Fairfield Inn and Suites by Marriott Key West
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4 out of 5
601 Front St, Key West, FL
Book a stay at this beach resort in Key West. Enjoy free WiFi, a full-service spa, and a marina. Our guests praise the pool and the bar in our reviews. Popular ...
Hyatt Centric Key West Resort and Spa
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd, Key West, FL
Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and ...
Hilton Garden Inn Key West / The Keys Collection
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
525 United Street, Key West, FL
Stay at this 3-star hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
The Southernmost Inn - Adults Only
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.

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Silver Airways
Sun, Nov 30 - Tue, Dec 9
TPA
Tampa Intl.
EYW
Key West Intl.
$77 Roundtrip, found 4 days ago
$77
Roundtrip
found 4 days ago
Select Silver Airways flight, departing Sun, Nov 30 from Tampa Intl. to Key West Intl., returning Tue, Dec 9, priced at $77 found 4 days ago
Delta
Tue, Aug 19 - Tue, Aug 26
ORD
O'Hare Intl.
EYW
Key West Intl.
$249 Roundtrip, found 4 days ago
$249
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Aug 19 from O'Hare Intl. to Key West Intl., returning Tue, Aug 26, priced at $249 found 4 days ago
Delta
Wed, Nov 12 - Wed, Nov 19
LGA
LaGuardia
EYW
Key West Intl.
$249 Roundtrip, found 6 days ago
$249
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Nov 12 from LaGuardia to Key West Intl., returning Wed, Nov 19, priced at $249 found 6 days ago
Delta
Tue, Oct 14 - Tue, Oct 21
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$249 Roundtrip, found 1 day ago
$249
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 14 from Newark Liberty Intl. Airport to Key West Intl., returning Tue, Oct 21, priced at $249 found 1 day ago