A beach with people standing and facing the ocean, with their arms raised. There are two suitcases on the sand.

Holiday Vacations from $524

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Your Holiday Vacation

Book a customized Holiday vacation package that has everything you need and nothing you don't. Great for shopping, walking and gift and craft shops, consider basing yourself in the neighborhood of Downtown Dunedin. If taking in sights is on the cards during your trip to Holiday, stop by leading attractions like Green Key Beach, Robert K Rees Memorial Park and James E. Grey Preserve. Whatever your travel plans or the size of your budget, putting together a tailored Holiday vacation is a walk in the park with Expedia.

The Latest Holiday Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 16 - Jan 22

    Little Harbor + Flight

    Ruskin
    6 nights
    3.0 star property
    8.2/10 - Very good (20 reviews)
    "Needs a kitchen sink or dishwasher, so you don’t have to wash your dishes in the bathtub. The balcony light was not working. We were told that no small dogs where not allowed, but there was a couple during our stay that had a small dog."
    Reviewed October 30, 2026
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - TPA • Nonstop TPA - BOS • Nonstop
    $824
    $524
    per traveler
    found 1 day ago
    Little Harbor
  • Jan 11 - Jan 16

    Ocean Club Treasure Island Hotel + Flight

    Sunshine Beach
    5 nights
    4.0 star property
    9.6/10 - Exceptional (1,323 reviews)
    "Gg"
    Reviewed November 8, 2026
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - TPA • Nonstop TPA - BOS • Nonstop
    $1,146
    $685
    per traveler
    found 1 day ago
    Ocean Club Treasure Island Hotel
  • Jan 28 - Feb 3

    Crystal Palms Beach Resort + Flight

    Sunshine Beach
    6 nights
    3.5 star property
    8.8/10 - Excellent (2,416 reviews)
    "It was amazing I felt like I got a whole apartment In one . It’s literally across the street from the beach 2-5 min walk you can see the water from hotel. It has a pool and hot tub .Everything was clean, the check in to get the keys in a lock box was different but I didn’t mind it . It felt like top secret underground location lol. 15/10 rating"
    Reviewed November 7, 2026
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - TPA • Nonstop TPA - BOS • Nonstop
    $1,207
    $751
    per traveler
    found 1 day ago
    Crystal Palms Beach Resort
  • Jan 22 - Jan 27

    CW Resort + Flight

    Clearwater Beach
    5 nights
    4.0 star property
    9.4/10 - Exceptional (300 reviews)
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $1,421
    $888
    per traveler
    found 1 day ago
    CW Resort
  • Jan 22 - Jan 27

    The Avalon Club + Flight

    Clearwater Beach
    5 nights
    4.0 star property
    9.4/10 - Exceptional (620 reviews)
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $1,328
    $845
    per traveler
    found 1 day ago
    The Avalon Club

Where to stay in and around Holiday

Holiday, Florida, offers a delightful mix of outdoor adventures and family-friendly fun. Explore the stunning beaches in Holiday or take a trip to nearby Clearwater Beach and Honeymoon Island. Enjoy the relaxing Gulf Coast atmosphere and discover more Florida attractions for an unforgettable vacation experience.

Tarpon Springs

Discover Tarpon Springs, a welcoming destination perfectly suited for travelers seeking a blend of cultural experiences and outdoor adventures. This charming city offers delightful attractions such as the beautiful Sunset Beach, the historic St. Nicholas Greek Orthodox Cathedral, and the renowned Innisbrook Golf Club, making it an ideal spot for family outings and relaxation. Located about 3 miles by car from Holiday, Tarpon Springs is an excellent choice for your vacation stay, providing a rich experience just a short drive away.

Anclote

Plan your stay in Anclote, a charming village in Holiday, Florida, ideal for families and nature enthusiasts eager to explore local attractions. With easy access to beautiful Sunset Beach, the scenic Anclote River Park, and the renowned Innisbrook Golf Club, visitors can enjoy a variety of outdoor activities year-round. Anclote’s convenient location makes it a smart choice for travelers looking to blend relaxation with adventure, ensuring a memorable getaway in this coastal haven.

Key Vista

If you are a family traveler or a couple seeking a relaxing getaway, look no further than Key Vista, a charming neighborhood around Holiday, Florida. Known for its beautiful beaches like Sunset Beach and the serene Anclote River Park, Key Vista offers a perfect mix of outdoor adventures and leisure activities. Enjoy the nearby recreational areas and shopping centers, all while being close to popular attractions like Innisbrook Golf Club. Booking your stay in Key Vista ensures a delightful vacation experience.

Holiday Lake Estates

Ideally situated for family travelers, Holiday Lake Estates provides a gateway to the stunning Sunset Beach and the beautiful Anclote River Park, offering ample opportunities for outdoor adventures and relaxation. With attractions like the renowned Innisbrook Golf Club nearby, visitors can indulge in both leisure and recreation. Located around Holiday, this neighborhood ensures easy access to local amenities and activities, making Holiday Lake Estates a smart choice for your vacation stay.

Colonial Hills

Travelers seeking a family-friendly vacation will find Colonial Hills to be the ideal base for their getaway, featuring easy access to outdoor adventures and local attractions. Just a short drive away, you can enjoy the stunning Sunset Beach, explore the lush trails of James E. Grey Preserve, or hit the links at the renowned Innisbrook Golf Club. Located around Holiday, Colonial Hills offers a relaxed atmosphere while keeping you close to vibrant activities and amenities, making it a smart choice for your next holiday.

Discover the most popular places to visit in Holiday

What to do in Holiday

Holiday Hotel Deals

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.

Frequently Asked Questions

How much does a Holiday vacation package cost?

You can pick up a vacation package to this destination from $524 on Expedia. But how much your vacation to Holiday costs will depend on factors like the season, hotel choice and length of stay.

What are the cheapest months to go to Holiday?

If you're hoping to snag a cheap Holiday vacation package, consider visiting in May, June and July. You'll typically find lower prices on hotels and airfares during these quieter months — perfect for travelers wishing to save money.

How many days is enough for Holiday?

Typically, a handful of days is enough for a Holiday vacation. With a well-organized itinerary, you can go to all the main attractions such as Anclote Gulf Park, as well as explore some hidden treasures along the way.

Is it worth booking a vacation package to Holiday?

It's no wonder a Holiday vacation is on the to-do list of many travelers. Top attractions like Anclote River Park are just the start of what you can explore here.

How to find the best Holiday package deals?

Use Expedia's filter tool to find some tempting Holiday package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Holiday package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.

Is it cheaper to book a Holiday vacation as a package?

An Expedia vacation package could save you hundreds of dollars when compared to booking stays and flights separately. Better still, you can tailor your Holiday getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.

When to book a vacation package to Holiday?

If you've got your Holiday travel dates finalized, book early to score some awesome deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for setting off on a whim.

How to plan a trip to Holiday?

  1. Choose when to go: Check your schedule and get packing. Your favorite season and the type of activities on offer will also help you decide when to visit Holiday.
  2. Set a budget: Factor in expenses such as flights, transportation and food when calculating how much to put aside for your trip to Holiday. Then, choose a property that suits your budget, whether that's a wallet-friendly option or a lavish retreat.
  3. Explore Holiday with our trip planning tool: Gain insights into the leading attractions and best hotels for your trip to Holiday. You can also save your must-visit places, collaborate with friends and family and manage your plans in one place.
  4. Decide how long to go away for: Now that you're more familiar with Holiday, you can figure out the right length of your break. Create a draft itinerary and allocate enough time to cover everything you want to see.
  5. Bundle your accommodations and airfare: After you've settled on your dates and duration, book the perfect Holiday vacation package for you.
  6. Book experiences or activities ahead of time: Whether it's entrance to a big attraction or a day trip, you won't have to worry about missing out on Holiday's highlights. Find all the exciting things to do in Holiday in Holiday with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Holiday vacation packages?

If you're like us, you love traveling but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Holiday trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.