Search Deals onBeachside Vacation Packages
Beachside Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Grand Guesthouse
Old Town Key West
Save 100% on your flight
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and South Beach are located nearby.
New Waterfront Home - Sunray House
Save 100% on your flight
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Key West (EYW)
Stay at this vacation home in Key West. Enjoy free parking and a garden. Popular attractions Duval Street and Smathers Beach are located nearby.
Aquaria House by Brightwild Pool Boat Dock
Save 100% on your flight
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Key West (EYW)
Stay at this vacation home in Key West. Enjoy free parking. Popular attractions Duval Street and Smathers Beach are located nearby.
Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool
Key West Historic District
per person
Sep 29 - Oct 4
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy patios, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool
per person
Sep 20 - Sep 26
found 24 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Key West (EYW)
Stay at this 4-star villa in Key West. Enjoy free parking, a beach locale, and a garden. Popular attractions Duval Street and Smathers Beach are located nearby.
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Save 100% on your flight
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy balconies, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Smathers Beach are located nearby.
Hyatt Vacation Club at Beach House, Key West
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Key West (EYW)
Stay at this 3.5-star eco-certified hotel in Key West. Enjoy free WiFi, free parking, and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
3-4 Night Vacations in Beachside
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Beachside
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Beachside
Beachside Resort & Residences
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. ...
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard, Key West, FL
Stay at this 4-star eco-certified hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
Oceans Edge Key West Resort, Hotel & Marina
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 ...
Save an average of 15% on thousands of hotels when you're signed in
Southernmost Beach Resort and Guesthouses
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. ...
Margaritaville Beach House Key West
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 ...
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street, Key West, FL
Stay at this 4-star beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and South Beach ...
Hyatt Centric Key West Resort and Spa
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 Vacation Club at Windward Pointe, Key West
3675 South Roosevelt Boulevard, Key West, FL
Stay at this 3.5-star eco-certified hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool 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
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Sep 9 - Wed, Sep 10
TPA
Tampa Intl.
EYW
Key West Intl.
$123 Roundtrip, found 6 days ago
$123
Roundtrip
found 6 days ago
Mon, Sep 8 - Fri, Sep 12
BOS
Logan Intl.
EYW
Key West Intl.
$192 Roundtrip, just found
$192
Roundtrip
just found
Wed, Oct 29 - Wed, Nov 5
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$229 Roundtrip, found 3 days ago
$229
Roundtrip
found 3 days ago
Fri, Oct 31 - Thu, Nov 13
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$259 Roundtrip, found 17 hours ago
$259
Roundtrip
found 17 hours ago
Discover Other Travel Deals
- Smathers Beach Vacations
- Duval Street Vacations
- Southernmost Point Vacations
- Mallory Square Vacations
- South Beach Vacations
- Ernest Hemingway Home and Museum Vacations
- Fort Zachary Taylor Historic State Park Vacations
- Stock Island Yacht Club & Marina Vacations
- Key West Golf Club Vacations
- Clarence S. Higgs Memorial Beach Park Vacations
- Harry S. Truman Little White House Vacations