Beachside Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Beachside Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina
per person
Jul 11 - Jul 15
found 1 day ago
Roundtrip flight included
Washington (DCA) 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.
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
per person
Jul 11 - Jul 15
found 1 day ago
Roundtrip flight included
Washington (DCA) 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.
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
per person
Jul 11 - Jul 15
found 1 day ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
Stay at this 4-star hotel in Key West. Enjoy free breakfast, free WiFi, and 3 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Orchid Key Inn - Adults Only
Old Town Key West
Save 100% on your flight
per person
Jul 11 - Jul 15
found 1 day ago
Roundtrip flight included
Washington (DCA) 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.
Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
per person
Jul 11 - Jul 15
found 1 day ago
Roundtrip flight included
Washington (DCA) 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 helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Perry Hotel & Marina Key West
per person
Jul 11 - Jul 15
found 1 day ago
Roundtrip flight included
Washington (DCA) 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.
Top Hotel Deals
Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
3.41 km from Beachside
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. ...
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
1.85 km from Beachside
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. ...
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
5.25 km from Beachside
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 ...
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
0.68 km from Beachside
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 ...
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd, Key West, FL
2.11 km from Beachside
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. ...
The Perry Hotel & Marina Key West
7001 Shrimp Road, Key West, FL
4.29 km from Beachside
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 ...
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd, Key West, FL
3.34 km from Beachside
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 ...
Fairfield Inn and Suites by Marriott Key West
2400 N Roosevelt Blvd, Key West, FL
1.24 km from Beachside
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 ...
Havana Cabana at Key West
3420 N. Roosevelt Blvd, Key West, FL
2.8 km from Beachside
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 ...
Pier House Resort & Spa
1 Duval St, Key West, FL
2.98 km from Beachside
Stay at this 4-star beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
The Reach Key West, Curio Collection by Hilton
1435 Simonton Street, Key West, FL
1.64 km from Beachside
Stay at this 4-star beach resort in Key West. Enjoy a full-service spa, a private beach, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Hyatt Centric Key West Resort and Spa
601 Front St, Key West, FL
2.8 km from Beachside
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 ...
La Concha Key West, Autograph Collection
430 Duval St, Key West, FL
2.54 km from Beachside
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff ...
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
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Jun 24 - Wed, Jul 2
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$249 Roundtrip, found 3 days ago
$249
Roundtrip
found 3 days ago
Thu, Sep 11 - Mon, Sep 15
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$259 Roundtrip, found 5 days ago
$259
Roundtrip
found 5 days ago
Mon, Aug 18 - Tue, Aug 19
LGA
LaGuardia
EYW
Key West Intl.
$262 Roundtrip, found 5 days ago
$262
Roundtrip
found 5 days ago
Fri, Jun 20 - Tue, Jun 24
JFK
John F. Kennedy Intl.
EYW
Key West Intl.
$312 Roundtrip, found 5 days ago
$312
Roundtrip
found 5 days ago
Best points of interest in Key West
- Smathers Beach Vacations
- Duval Street Vacations
- Southernmost Point Vacations
- Mallory Square Vacations
- Ernest Hemingway Home and Museum Vacations
- Fort Zachary Taylor Historic State Park Vacations
- South Beach Vacations
- Key West Golf Club Vacations
- Stock Island Yacht Club & Marina Vacations
- Clarence S. Higgs Memorial Beach Park Vacations
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