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Beachside Vacation Packages

Beachside Flight + Hotel packages

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 $1,157, price is now $814 per person
$814
per person
Jun 2 - Jun 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this 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.
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,475, price is now $1,716 per person
$1,716
per person
May 26 - May 31
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 breakfast, free WiFi, and parking (surcharge). Our guests praise the helpful staff and the property condition in our reviews. 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
Save 100% on your flight
Price was $1,568, price is now $1,106 per person
$1,106
per person
Jun 2 - Jun 6
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.
The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $1,800, price is now $1,283 per person
$1,283
per person
Jun 2 - Jun 6
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.
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 $1,807, price is now $1,317 per person
$1,317
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,456, price is now $1,072 per person
$1,072
per person
May 27 - Jun 1
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this B&B in Key West. Enjoy free breakfast, free WiFi, and a rooftop terrace. 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 Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Key West Historic District
Price was $1,297, price is now $981 per person
$981
per person
Jun 2 - Jun 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. 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 $3,070, price is now $2,323 per person
$2,323
per person
Jun 1 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.

3-4 Night Vacations in Beachside

Price found within the past 48 hours. Click for updated prices.
The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $1,448, price is now $1,077 per person
$1,077
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

3 out of 5
Old Town Key West
Price was $3,258, price is now $2,693 per person
$2,693
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Key West (EYW)
Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!

Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!

3 out of 5
Save 100% on your flight
Price was $2,247, price is now $1,786 per person
$1,786
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip non-stop 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
Price was $1,502, price is now $1,196 per person
$1,196
per person
Jun 5 - Jun 8
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.
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 $1,834, price is now $1,239 per person
$1,239
per person
May 26 - May 31
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 $2,770, price is now $2,029 per person
$2,029
per person
Jun 9 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $2,432, price is now $1,657 per person
$1,657
per person
May 26 - May 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,475, price is now $1,716 per person
$1,716
per person
May 26 - May 31
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
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
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
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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
Book a stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and South Beach ...
Opens in a new windowCasa Marina Key West, Curio Collection by Hilton
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Opens in a new windowSouthernmost Beach Resort and Guesthouses
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
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
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 ...
Opens in a new windowHilton Garden Inn Key West / The Keys Collection
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
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.
$104 Roundtrip, found 8 hours ago
$104
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Mon, Jun 15 from Tampa Intl. to Key West Intl., returning Wed, Jul 1, priced at $104 found 8 hours ago
Delta
Sun, May 24 - Thu, May 28
BOS
Logan Intl.
EYW
Key West Intl.
$217 Roundtrip, found 11 hours ago
$217
Roundtrip
found 11 hours ago
Select Delta flight, departing Sun, May 24 from Logan Intl. to Key West Intl., returning Thu, May 28, priced at $217 found 11 hours ago
United
Wed, Jun 3 - Wed, Jun 10
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$289 Roundtrip, found 1 hour ago
$289
Roundtrip
found 1 hour ago
Select United flight, departing Wed, Jun 3 from Newark Liberty Intl. Airport to Key West Intl., returning Wed, Jun 10, priced at $289 found 1 hour ago
American Airlines
Tue, Jul 7 - Wed, Jul 22
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$323 Roundtrip, found 2 hours ago
$323
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Jul 7 from Baltimore Washington Intl. Thurgood Marshall to Key West Intl., returning Wed, Jul 22, priced at $323 found 2 hours ago