Holiday Vacations from $502
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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.
CW Hotel
$863
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (48 reviews)
Everyone was friendly. Great views from our room. Amazing location, walkable to pier/beach. Parking was $40 I think, reasonable for the area. Resort fee of $40, had access to pool we didn’t use. Didn’t really get any value out of resort fee. $300 security deposit seems a bit high but was removed from credit card in a couple days. Just one elevator for 8 floors so sometimes a wait/full. Would stay there again.
Reviewed on Aug 18, 2026
Where to stay in Holiday
Find the best Holiday areas and neighborhoods for the activities you enjoy most. Learn more about Holiday
Key Vista
If you're looking for some top things to see and do in Key Vista and surrounding area, you can visit Anclote River Park and Tarpon Springs Sponge Docks.
Holiday Lake Estates
Holiday Lake Estates might not have many top sights, but Tarpon Springs Sponge Docks and Anclote River Park are two attractions nearby that you can check out.
Aloha Gardens
If you're looking for some top things to see and do in Aloha Gardens and surrounding area, you can visit Anclote River Park and Tarpon Springs Sponge Docks.
Baileys Bluff Estates
When in Baileys Bluff Estates, you can plan a visit to Anclote River Park and Green Key Beach, some noteworthy sights in the nearby area.
Buena Vista
While Buena Vista isn't home to many top sights, Tarpon Springs Sponge Docks and Anclote River Park are some notable places to visit nearby.
Stay near popular Holiday attractions
Anclote River Park
8.8/10 (48 reviews)
This 31-acre waterfront haven offers a sandy beach, fishing pier, and six-lane boat launch on the Anclote River. Arrive early on weekends to secure prime picnic spots near the water.
Photo by Travel Ginger
Key Vista Nature Park
8.8/10 (33 reviews)
This coastal preserve offers panoramic Gulf views from its observation tower after a gentle hike through diverse habitats. Bring binoculars to spot ospreys and bald eagles along the mangrove-lined shores.
Anclote Gulf Park
8.8/10 (32 reviews)
Anclote Gulf Park offers a 500-foot fishing pier extending into the Gulf's tranquil waters. Watch the legendary sunsets from the boardwalk or bring your dog to enjoy the dedicated pet-friendly areas.
Lake Conley
Commune with nature and explore the great outdoors at Lake Conley during your travels in Holiday.
What to do in Holiday
Tarpon Springs Ghost Tour — Haunted History & True Crime
$40
per adult
2 Hours Kayak Eco Tour in Tarpon Springs
$54
per adult
80% of travellers recommend
3-Hour Private Clearwater Beach Adventure – Dolphins & Sandbars
$375
per traveler
Holiday Hotel Deals
Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$250 nightly
$282 total
Aug 23 - Aug 24
Total with taxes and fees
9.4/10 Exceptional! (3,750 reviews)
"Poolside Entertainment was 👍 Dislike was over housekeeping rooms aren't cleaned properly 😑 And taking hours to do it."
Reviewed on Aug 18, 2026
The Westin Tampa Bay
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
$143 nightly
$163 total
Aug 31 - Sep 1
Total with taxes and fees
8.6/10 Excellent! (1,516 reviews)
"Excellent service, room, breakfast, staff"
Reviewed on Aug 16, 2026
Hilton Clearwater Beach Resort & Spa
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$198 nightly
$224 total
Aug 25 - Aug 26
Total with taxes and fees
8.2/10 Very Good! (2,940 reviews)
"Beautiful clean hotel close to airport"
Reviewed on Aug 18, 2026
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.
Find the Best Holiday Vacation Packages
Holiday Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Tampa Intl. Airport (TPA) |
Population | 22,400 |
Max Temp Winter | 70ºF |
Max Temp Summer | 90ºF |
Top Sights | Werner Boyce Salt Springs State Park, Richey Suncoast Theater and West Pasco Historical Society Museum and Library |
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Frequently asked questions
How much does a Holiday vacation package cost?
You can pick up a vacation package to this destination from $502 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?
- 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.
- 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.
- 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.
- 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.
- Bundle your accommodations and airfare: After you've settled on your dates and duration, book the perfect Holiday vacation package for you.
- 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.
