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Beachside Vacation Packages

Beachside Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
per person
Sep 28 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
per person
Sep 28 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Grand Guesthouse

The Grand Guesthouse

2.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Oct 13 - Oct 17
found 1 hour 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.
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
Old Town Key West
per person
Sep 28 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
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 are located nearby.
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
per person
Sep 17 - Sep 21
found 16 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Key West (EYW)
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 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
per person
Sep 28 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
per person
Sep 28 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
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. Popular attractions Duval Street and Mallory Square are located nearby.
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
per person
Sep 17 - Sep 21
found 15 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
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
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)

5-7 Night Vacations in Beachside

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
Sep 17 - Sep 22
found 2 days ago
Roundtrip non-stop flight included
Austin (AUS) 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
Sep 28 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
per person
Sep 28 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
Old Town Key West
per person
Sep 28 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)

Cheap Hotel Deals in Beachside

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
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

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 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
Blue Flamingo Resort Key West
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
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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
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
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 ...
Casa Marina Key West, Curio Collection by Hilton
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
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
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 ...
Hyatt Vacation Club at Windward Pointe, Key West
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.

Breeze Airways
Fri, Oct 3 - Tue, Oct 14
TPA
Tampa Intl.
EYW
Key West Intl.
$133 Roundtrip, found 1 hour ago
$133
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Fri, Oct 3 from Tampa Intl. to Key West Intl., returning Tue, Oct 14, priced at $133 found 1 hour ago
American Airlines
Mon, Sep 8 - Fri, Sep 12
BOS
Logan Intl.
EYW
Key West Intl.
$192 Roundtrip, found 3 hours ago
$192
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Mon, Sep 8 from Logan Intl. to Key West Intl., returning Fri, Sep 12, priced at $192 found 3 hours ago
Delta
Wed, Oct 29 - Wed, Nov 5
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$249 Roundtrip, found 3 hours ago
$249
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Oct 29 from Newark Liberty Intl. Airport to Key West Intl., returning Wed, Nov 5, priced at $249 found 3 hours ago
American Airlines
Fri, Oct 31 - Thu, Nov 13
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$259 Roundtrip, found 3 hours ago
$259
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Fri, Oct 31 from Baltimore Washington Intl. Thurgood Marshall to Key West Intl., returning Thu, Nov 13, priced at $259 found 3 hours ago