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Vacation Deals From Philadelphia
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  • Grand Palladium Jamaica Resort & Spa - All Inclusive
    4 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Jamaica, Montego Bay
    Best Priced Departure Dates
    Feb 9, 2026
    4 Nights Includes Taxes + Fees
    $917 per person
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews

    Cocobay Resort - All Inclusive
    4 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Antigua
    Best Priced Departure Dates
    2025: Dec 15 - Dec 31 2026: Jan 1 - Nov 30
    4 Nights Includes Taxes + Fees
    Get Price
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews

    Galley Bay Resort and Spa - All Inclusive
    4 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Antigua
    Best Priced Departure Dates
    2025: Dec 15 - Dec 31 2026: Jan 1 - Nov 30
    4 Nights Includes Taxes + Fees
    Get Price
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews

    Pineapple Beach Club - All Inclusive
    4 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Antigua
    Best Priced Departure Dates
    2025: Dec 15 - Dec 31 2026: Jan 1 - Nov 30
    4 Nights Includes Taxes + Fees
    Get Price
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews

    St. James's Club - All Inclusive
    4 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Antigua
    Best Priced Departure Dates
    2025: Dec 15 - Dec 31 2026: Jan 1 - Nov 30
    4 Nights Includes Taxes + Fees
    Get Price
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews

    Divi Aruba - All Inclusive
    4 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Aruba
    Best Priced Departure Dates
    2025: Dec 15 - Dec 31 2026: Jan 1 - Nov 30
    4 Nights Includes Taxes + Fees
    Get Price
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews

    Grotto Bay Beach Resort - All Inclusive
    3.5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Bermuda
    Best Priced Departure Dates
    2025: Dec 15 - Dec 31 2026: Jan 1 - Nov 30
    4 Nights Includes Taxes + Fees
    Get Price
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews

    Grotto Bay Beach Resort - European Plan
    3.5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    Bermuda
    Best Priced Departure Dates
    2025: Dec 15 - Dec 31 2026: Jan 1 - Nov 30
    4 Nights Includes Taxes + Fees
    Get Price
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews

    Hamilton Princess & Beach Club, A Fairmont Managed Hotel
    4.5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    Bermuda
    Best Priced Departure Dates
    2025: Dec 15 - Dec 31 2026: Jan 1 - Nov 30
    4 Nights Includes Taxes + Fees
    Get Price
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Planning a getaway from Philadelphia has never been easier... or more exciting! With Apple Vacations, you can "Start Your Story" in stunning domestic and international cities where sun-drenched beaches, vibrant culture, and luxurious resorts feature in your most beautiful memories.

Flight deals from Philadelphia to incredible tropical destinations are surprisingly affordable. Pair these low fares with our vacation packages, and you have an all-encompassing escape that's ready to go. Whether it's a romantic retreat, family fun, or a special occasion, every trip from Philly sets the scene for meaningful experiences and joyous moments with the people you love.

Vacation Deals From Philadelphia FAQ

What destinations have the cheapest vacation deals from Philadelphia?

Our most affordable Philadelphia vacation packages often travel to Montego Bay and Hawaii. Montego Bay offers stunning beaches, rich culture, and all-inclusive resorts, while Hawaii provides lush nature and majestic beaches. These tropical locales combine affordability with unforgettable experiences—letting you focus on celebrating special moments with loved ones and creating lasting memories.

How far in advance should I book from Philadelphia for the best price?

For the best flight deals from Philadelphia, the optimal time to book is typically one to six months in advance. This timeframe balances low cost and availability. Scheduling more than six months out may result in higher prices. Late bookings can lead to limited options. The more popular the destination, the earlier you should book to secure your spot.

Are last minute vacation deals from Philadelphia worth it?

Yes! Last minute Philadelphia deals can be a unique way to enjoy a spontaneous getaway while saving as much as possible. With Apple Vacations, you can find vacation packages to various destinations with exclusive savings and flexible travel dates.

These bundles typically include round-trip airfare, accommodations, and more—making it easy and affordable to plan an impromptu escape.