Holiday Vacations from $601

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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
Price was $902, price is now $601 per person
$601
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (2,374 reviews)

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,801, price is now $1,021 per person
$1,021
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (1,096 reviews)
Great

Reviewed on Jul 31, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,277, price is now $1,362 per person
$1,362
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (561 reviews)
The central location on the island is perfect. We stayed in Wildflower cottage. Bed was comfortable. Kitchen was minimally equipped but functional. Western facing deck was amazing. Bikes and beach towels available for free.

Reviewed on Jul 30, 2026

CW Hotel

CW Hotel

4 out of 5
Save 100% on your flight
Price was $1,635, price is now $989 per person
$989
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.8/10 Exceptional! (16 reviews)
Our stay was great with very nice and clean rooms.

Reviewed on Jul 31, 2026

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $942, price is now $634 per person
$634
per person
Sep 24 - Sep 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,158 reviews)
tHEY CHARGE YOU CREDIT CARD WITHOUT AUTHORIZATION FOR BREAkfast / never used and still charged / staff not friendly to respond and assist / very rude / manager never called / i called x 5 / Receptionist did not want to connect to a manager / They were raising voice / I spend thousands of dollars for business transaction / I am very reputable businessman and do not deserve for such a treatment American Express helped to clarify and refunded money / It is not money it is principles . Management is terrible / no communication Everyone can make a mistake but nobody bothered to resolve it and call back and talk and apologize and refund it I believe somebody did not pay for a breakfast and They grabbed first available card on file and applied my signature I signed at the end when checked out to the breakfast bill / it is fraud

Reviewed on Jul 30, 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 beach with rocks in the foreground and a sunset over the ocean.

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.

Find hotels in Key Vista

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.
See properties

What to do in Holiday

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
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
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
$263 nightly
The price is $297 total per night from Aug 9 to Aug 10
$297 total
Aug 9 - Aug 10
Total with taxes and fees
Wyndham Grand Clearwater Beach
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
$143 nightly
The price is $163 total per night from Aug 23 to Aug 24
$163 total
Aug 23 - Aug 24
Total with taxes and fees
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
$198 nightly
The price is $224 total per night from Aug 11 to Aug 12
$224 total
Aug 11 - Aug 12
Total with taxes and fees
Hilton Clearwater Beach Resort & Spa
See all 6,138 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 $601 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.