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Beachside Vacation Packages

Beachside Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,996, price is now $1,477 per person
$1,477
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, parking (surcharge), and concierge services. Popular attractions Duval Street and Mallory Square are located nearby.
Contra House Key West

Contra House Key West

3 out of 5
Old Town Key West
Price was $5,778, price is now $4,450 per person
$4,450
per person
May 17 - May 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this vacation home in Key West. Enjoy free WiFi, free parking, and a garden. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $3,127, price is now $2,101 per person
$2,101
per person
May 3 - May 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, room service, and daily housekeeping. Popular attractions Duval Street and Mallory Square are located nearby.
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

3 out of 5
Save 100% on your flight
Price was $2,173, price is now $1,603 per person
$1,603
per person
May 8 - May 13
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this cottage in Key West. Enjoy a beach locale, balconies, and in-room washers/dryers. Popular attractions Duval Street and Smathers 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
Save 100% on your flight
Price was $2,152, price is now $1,607 per person
$1,607
per person
May 3 - May 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this 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.
Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool

Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool

3 out of 5
Save 100% on your flight
Price was $2,663, price is now $2,016 per person
$2,016
per person
May 26 - May 31
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Stay at this 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.
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
Save 100% on your flight
Price was $2,517, price is now $1,917 per person
$1,917
per person
May 1 - May 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Book a stay at this 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. 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.
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,104, price is now $819 per person
$819
per person
May 8 - May 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $2,077, price is now $1,378 per person
$1,378
per person
May 13 - May 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Price was $1,144, price is now $830 per person
$830
per person
May 13 - May 16
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.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,894, price is now $1,272 per person
$1,272
per person
May 3 - May 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Old Town Key West
Price was $2,315, price is now $1,488 per person
$1,488
per person
May 7 - May 12
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $3,127, price is now $2,101 per person
$2,101
per person
May 3 - May 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)

Cheap Hotel Deals in Beachside

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Opens in a new windowBlue Flamingo Resort Key West
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
Opens in a new windowMargaritaville Beach House Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Book a stay at this 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. ...
Opens in a new windowBeachside Resort & Residences
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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. ...
Opens in a new windowIbis Bay Beach Resort
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Book a stay at this 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 ...
Opens in a new windowOceans Edge Key West Resort, Hotel & Marina
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
Opens in a new windowHavana Cabana at Key West
The Laureate Key West

The Laureate Key West

3.5 out of 5
3444 N Roosevelt Boulevard Key West FL
Book a stay at this beach hotel in Key West. Enjoy a 24-hour front desk, a 24-hour business center, and daily housekeeping. Our guests praise the pool and the ...
Opens in a new windowThe Laureate Key West
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

4 out of 5
2801 N Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 4 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. ...
Opens in a new windowParrot Key Hotel & Villas
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
Mon, Jun 15 - Wed, Jul 1
TPA
Tampa Intl.
EYW
Key West Intl.
$97 Roundtrip, found 9 hours ago
$97
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Mon, Jun 15 from Tampa Intl. to Key West Intl., returning Wed, Jul 1, priced at $97 found 9 hours ago
Bargain Flight
Tue, Apr 14 - Tue, Apr 21
BOS
Logan Intl.
EYW
Key West Intl.
$280 Roundtrip, found 2 days ago
$280
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Tue, Apr 14 from Logan Intl. to Key West Intl., returning Tue, Apr 21, priced at $280 found 2 days ago
Spirit Airlines
Thu, Apr 16 - Sun, Apr 19
ATL
Hartsfield-Jackson Atlanta Intl.
EYW
Key West Intl.
$292 Roundtrip, found 2 days ago
$292
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Apr 16 from Hartsfield-Jackson Atlanta Intl. to Key West Intl., returning Sun, Apr 19, priced at $292 found 2 days ago
Delta
Wed, Aug 26 - Wed, Sep 2
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$309 Roundtrip, just found
$309
Roundtrip
just found
Select Delta flight, departing Wed, Aug 26 from Newark Liberty Intl. Airport to Key West Intl., returning Wed, Sep 2, priced at $309 just found