Holiday Vacations from $544

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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.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $857, price is now $544 per person
$544
per person
Dec 6 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (2,471 reviews)
Property had a grateful kitchen with just enough utensils, frying pans things that you would need if you prepare your own food during your stay. The property does not have a lot of amenities, but if you’re not into amenities, it doesn’t matter. It’s in a great location central to all things Sarasota and Siesta key.

Reviewed on Oct 29, 2026

CW Resort

CW Resort

4 out of 5
Price was $1,589, price is now $972 per person
$972
per person
Jan 17 - Jan 22
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (255 reviews)

Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Price was $1,519, price is now $954 per person
$954
per person
Jan 6 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,006 reviews)

The Avalon Club

The Avalon Club

4 out of 5
Price was $1,303, price is now $828 per person
$828
per person
Jan 17 - Jan 22
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (615 reviews)
The room was spacious for my family and I. A close walk to the beach. Close to shopping and eating, great location.

Reviewed on Oct 28, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,107, price is now $705 per person
$705
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (1,282 reviews)
clean

Reviewed on Oct 29, 2026

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Where to stay in Holiday

Find the best Holiday areas and neighborhoods for the activities you enjoy most. Learn more about Holiday
A waterfront with a marina, palm trees, and buildings reflecting on the water.

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.

Find hotels in Holiday Lake Estates

Stay near popular Holiday attractions

A calm body of water with a sailboat, a distant shoreline, and a clear sky.

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.
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What to do in Holiday

Tarpon Springs: Evening Dolphin Cruise

Tarpon Springs: Evening Dolphin Cruise

$29
per adult
90% of travellers recommend
Tarpon Springs: Evening Dolphin Cruise
2 Hours Kayak Eco Tour in Tarpon Springs

2 Hours Kayak Eco Tour in Tarpon Springs

$54
per adult
86% of travellers recommend
2 Hours Kayak Eco Tour in Tarpon Springs
Audio Guide to New Port Richey's History and Quirky People

Audio Guide to New Port Richey's History and Quirky People

$7
per adult
Audio Guide to New Port Richey's History and Quirky People
See all activities in Holiday

Holiday Hotel Deals

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$272 nightly
The price is $307 total per night from Nov 18 to Nov 19
$307 total
Nov 18 - Nov 19
Total with taxes and fees
9.4/10 Exceptional! (4,019 reviews)
"Breakfast was on the top spot"

Reviewed on Oct 29, 2026

Wyndham Grand Clearwater Beach
Hyatt Regency Clearwater Beach Resort and Suites

Hyatt Regency Clearwater Beach Resort and Suites

4 out of 5
301 S Gulfview Blvd Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$259 nightly
The price is $293 total per night from Nov 11 to Nov 12
$293 total
Nov 11 - Nov 12
Total with taxes and fees
9.4/10 Exceptional! (2,471 reviews)
"Location was nice. Could petty much walk to anywhere we wanted. Food close by. Cvs a block away. Beack and entertainment all right there."

Reviewed on Oct 29, 2026

Hyatt Regency Clearwater Beach Resort and Suites
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $176 total per night from Nov 22 to Nov 23
$176 total
Nov 22 - Nov 23
Total with taxes and fees
The Westin Tampa Bay
See all 6,245 properties in Holiday
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 $544 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.