Holiday Vacations from $496

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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.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was $704, price is now $496 per person
$496
per person
Jun 13 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (976 reviews)
The property was super clean and modern and everything we thought it would be

Reviewed on May 12, 2026

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,962, price is now $1,303 per person
$1,303
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (3,211 reviews)
We had a fabulous Mother’s Day weekend at Wyndham Grand Clearwater Beach. It also happened to be Country Weekend, which made the experience even more fun and memorable. The entertainment was a huge plus and created such an amazing atmosphere throughout the weekend. The lobby bar staff and pool staff were absolutely amazing. Everyone was so attentive, friendly, and welcoming, especially on Mother’s Day. They truly went above and beyond to make all the moms feel special and taken care of. From the beautiful property to the great energy and outstanding customer service, the entire experience exceeded our expectations. Thank you to the whole team for making our Mother’s Day celebration so enjoyable and unforgettable. We will definitely be back!

Reviewed on May 12, 2026

East Gulf Dockside Beach Homes

East Gulf Dockside Beach Homes

2.5 out of 5
Save 100% on your flight
Price was $1,300, price is now $893 per person
$893
per person
Jul 18 - Jul 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
No reviews
Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

2.5 out of 5
Save 100% on your flight
Price was $1,172, price is now $805 per person
$805
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,005 reviews)
Really enjoyed our stay. This is convenient to the beach and boardwalk.

Reviewed on May 10, 2026

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,742, price is now $1,219 per person
$1,219
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (534 reviews)
Great experience! The staff is very kind. The only issue was the living room sofa was very noisy. Would definitely stay again!

Reviewed on May 12, 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
Dramatic cloudy sunrise viewed on a tropical sandy beach at the Atlantic Ocean Shore. Plantation Key, Florida Keys, Florida, United States.

Key Vista

If you're looking for some top things to see and do in Key Vista and surrounding area, you can visit Key Vista Nature Park and Anclote River Park.

Find hotels in Key Vista

Discover the most popular places to visit in Holiday

The landscape photo of a boat at the Anclote River Park the ripples of the water provide a timeless feel

Anclote River Park

Why not spend a carefree afternoon at Anclote River Park during your travels in Holiday? While you're in the area, wander around the parks.

Anclote River Park
Key Vista Nature Park

Key Vista Nature Park

Commune with nature and explore the great outdoors at Key Vista Nature Park during your travels in Holiday. Stroll along the waterfront in this family-friendly area, or seek out the golf courses.

Key Vista Nature Park

Anclote Gulf Park

Anclote Gulf Park is just one of the places to see in Holiday, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's waterfront, or seek out the golf courses.

Anclote Gulf Park

What to do in Holiday

2 Hours Kayak Eco Tour in Tarpon Springs

2 Hours Kayak Eco Tour in Tarpon Springs

$54
per adult
80% of travellers recommend
2 Hours Kayak Eco Tour in Tarpon Springs
Tarpon Springs Ghost Tour — Haunted History & True Crime

Tarpon Springs Ghost Tour — Haunted History & True Crime

$40
per adult
Tarpon Springs Ghost Tour — Haunted History & True Crime
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
$340 nightly
The price is $385 total per night from May 21 to May 22
$385 total
May 21 - May 22
Total with taxes and fees
9.4/10 Exceptional! (3,220 reviews)
Amazing

Reviewed on May 12, 2026

Wyndham Grand Clearwater Beach
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundable
$143 nightly
The price is $163 total per night from May 25 to May 26
$163 total
May 25 - May 26
Total with taxes and fees
8.6/10 Excellent! (1,295 reviews)
Pool was under construction, Bathroom has no fan. We ordered breakfast from the menu 1 day and got the buffet another morning and it was delicious. Aj and staff were very helpful and friendly!

Reviewed on May 12, 2026

The Westin Tampa Bay
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$204 nightly
The price is $230 total per night from May 25 to May 26
$230 total
May 25 - May 26
Total with taxes and fees
8/10 Very Good! (2,625 reviews)
Room had food and womens hair scrunchies on the floor. Needed a better cleaning and vacuuming. Limited view was air conditioning units!

Reviewed on May 12, 2026

Hilton Clearwater Beach Resort & Spa
See all 6,056 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 $496 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.