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Four-Night Beach Vacation in Hollywood, Florida, from $467 Per Person with Flights and Hotel
From $467
STEP TWO: FLIGHTSCheapest FlightsPirates, the Diplomat Beach Resort (4.7/5 on TripAdvisor & 2026 Travelers' Choice Winner) has been part of the South Florida resort scene for decades. Frank Sinatra performed here, Bob Hope stayed here, and in 2026, the property reopened as Signia by Hilton following a major renovation.
A 4-night vacation package with flights and hotel starts from $467 per person, which immediately caught our attention for a beachfront resort of this size and reputation.
Located between Miami and Fort Lauderdale, the resort offers direct beach access, multiple pools, a spa, and plenty of dining options. If you’re after the classic South Florida resort experience without paying Miami Beach prices, this one is worth a look.
🏴☠️ Pirate Tip: If you’re looking for a quieter afternoon by the pool, head to the adults-only Verandah Social Club and leave the family lagoon pool to everyone else.
We found some dates with the best rates for you, but many others are available.
You can also easily change the departure cities and dates.
🔻 Departing Atlanta
🔻 Departing Cincinnati
🔻 Departing Washington
🔻 Departing Houston
🔻 Departing Indianapolis
🔻 Departing Cleveland
🔻 Departing Philadelphia
🔻 Departing Raleigh
🔻 Departing Chicago
🔻 Departing New York
🔻 Departing New Orleans
🔻 Departing Charleston
🔻 Departing Nashville
🔻 Departing Los Angeles
🔻 Departing San Francisco
🔻 Departing Denver
*That's $390.50 per person!
Hotel Price per Person = $390.50
Flight Price = $76 Round-Trip
TOTAL = $467/Person [Based on Two Guests]