Beachside Vacation Packages for 2026
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
Price was $1,899, price is now $1,391 per person
$1,391
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Pensacola (PNS) to Key West (EYW)
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 attractions Duval Street and Smathers Beach are located nearby.
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,649, price is now $1,788 per person
$1,788
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Pensacola (PNS) 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.
The Marker Key West Harbor Resort
Key West Historic District
Price was $2,066, price is now $1,544 per person
$1,544
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Pensacola (PNS) 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.
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Price was $2,371, price is now $1,800 per person
$1,800
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Pensacola (PNS) 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.
Fitch Lodge - Key West Historic Inns
Key West Historic District
Price was $1,858, price is now $1,445 per person
$1,445
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Pensacola (PNS) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, daily housekeeping, and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Top Hotel Deals
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
0.68 km from Beachside
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 ...
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
3.31 km from Beachside
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 ...
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
3.41 km from Beachside
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. ...
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. ...
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
5.23 km from Beachside
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 ...
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
2.8 km from Beachside
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 ...
The Laureate Key West
3444 N Roosevelt Boulevard Key West FL
2.95 km from Beachside
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 ...
Parrot Key Hotel & Villas
2801 N Roosevelt Blvd Key West FL
1.76 km from Beachside
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. ...
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
1.23 km from Beachside
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 ...
The Perry Hotel & Marina Key West
7001 Shrimp Road Key West FL
4.29 km from Beachside
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Pier House Resort & Spa
1 Duval St Key West FL
2.98 km from Beachside
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff ...
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
3.05 km from Beachside
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Opal Key Resort & Marina, Key West
245 Front Street Key West FL
2.93 km from Beachside
Stay at this hotel in Key West. Enjoy a marina, 3 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
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.
Mon, Apr 6 - Fri, Apr 10
TPA
Tampa Intl.
EYW
Key West Intl.
$82 Roundtrip, found 2 days ago
$82
Roundtrip
found 2 days ago
Wed, May 6 - Tue, May 12
ORD
O'Hare Intl.
EYW
Key West Intl.
$319 Roundtrip, found 2 days ago
$319
Roundtrip
found 2 days ago
Sat, Aug 22 - Thu, Aug 27
ATL
Hartsfield-Jackson Atlanta Intl.
EYW
Key West Intl.
$319 Roundtrip, found 18 hours ago
$319
Roundtrip
found 18 hours ago
Tue, Apr 28 - Wed, May 20
BOS
Logan Intl.
EYW
Key West Intl.
$337 Roundtrip, found 4 days ago
$337
Roundtrip
found 4 days ago
Wed, May 6 - Tue, May 12
ORD
O'Hare Intl.
EYW
Key West Intl.
$366 Roundtrip, found 2 days ago
$366
Roundtrip
found 2 days ago