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Beachside Vacation Packages

3-4 Night Vacations in Beachside

Price found within the past 48 hours. Click for updated prices.
Southwinds Motel

Southwinds Motel

2 out of 5
Key West Historic District
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
Key West Historic District
per person
Mar 30 - Apr 2
found 17 hours ago
Roundtrip non-stop flight included
Chicago (ORD) 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
Mar 7 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool

Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool

4 out of 5
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)

5-7 Night Vacations in Beachside

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
Save 100% on your flight
per person
Mar 4 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
The Grand Guesthouse

The Grand Guesthouse

2.5 out of 5
Key West Historic District
Save 100% on your flight
per person
Mar 4 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
Douglas House

Douglas House

3 out of 5
Key West Historic District
Save 100% on your flight
per person
Mar 21 - Mar 28
found 12 hours ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)
Southernmost Beach Resort

Southernmost Beach Resort

4 out of 5
Key West Historic District
Save 100% on your flight
per person
Mar 4 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)

Cheap Hotel Deals in Beachside

Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd, Key West, FL
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
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
7001 Shrimp Road, Key West, FL
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 ...
The Perry Hotel & Marina Key West
Southernmost Beach Resort

Southernmost Beach Resort

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
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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 golf 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
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
Havana Cabana at Key West - Adults Only

Havana Cabana at Key West - Adults Only

4 out of 5
3420 N. Roosevelt Blvd, Key West, FL
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 ...
Havana Cabana at Key West - Adults Only
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
24 North Hotel Key West - Newly Renovated

24 North Hotel Key West - Newly Renovated

4 out of 5
3820 North Roosevelt Boulevard, Key West, FL
Stay at this 4-star eco-certified hotel in Key West. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
24 North Hotel Key West - Newly Renovated
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.

Delta
Tue, Apr 15 - Wed, Apr 23
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$199 Roundtrip, found 5 days ago
$199
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Apr 15 from Baltimore Washington Intl. Thurgood Marshall to Key West Intl., returning Wed, Apr 23, priced at $199 found 5 days ago
Delta
Wed, Apr 16 - Wed, Apr 23
CLT
Charlotte-Douglas Intl.
EYW
Key West Intl.
$211 Roundtrip, found 4 days ago
$211
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Apr 16 from Charlotte-Douglas Intl. to Key West Intl., returning Wed, Apr 23, priced at $211 found 4 days ago
Delta
Tue, Mar 4 - Tue, Mar 4
ORD
O'Hare Intl.
EYW
Key West Intl.
$217 Roundtrip, found 3 days ago
$217
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Mar 4 from O'Hare Intl. to Key West Intl., returning Tue, Mar 4, priced at $217 found 3 days ago
Silver Airways
Fri, Feb 7 - Fri, Feb 7
TPA
Tampa Intl.
EYW
Key West Intl.
$229 Roundtrip, found 2 days ago
$229
Roundtrip
found 2 days ago
Select Silver Airways flight, departing Fri, Feb 7 from Tampa Intl. to Key West Intl., returning Fri, Feb 7, priced at $229 found 2 days ago