Holiday Vacation Packages
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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.
Top Holiday Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Captiva Beach Resort
South Village
CA $1,253
per person
Nov 6 - Nov 13
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,299 reviews)
Room super clean, we love it.
Parking ok
Kitchen ok
Staff, was ok, But we have some comments that may be helpful to the property.
1 - We had problems with the door lock, the staff should be able to show how it works, or give better instructions on the welcome paperwork.
2 - We asked if there was a restroom we could use after checkout, the lady(front desk) said: NO. Only a change room. And we found out that the property have a restroom outside, close to the change room.
Since we decided to stay a bit longer at the beach on Sunday the restroom would help us a lot before take 3 hours driving to final destination.
She could tell us about the restroom, but she did not.
Everything else was excelent! Location, quite place, clean and very confortable.
Thank you.
Reviewed on Aug 21, 2026
Tropical Breeze Resort
Siesta Key Village
CA $1,630
per person
Nov 6 - Nov 13
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,021 reviews)
The property looks like it’s from an episode of Three’s Company, which is great! Pool area is nice. Our room was recently renovated. May be some lackluster renovation quality going on there, but that isn’t the fault of the property owner. They try to make up in other areas. I think the house keeping staff needs to be more responsive, but they are probably overworked. Overall a good place. You can do a lot worse. The location is excellent. They probably get things right the majority of the time. I give it 3 stars, which is much better than the average. I would stay here again.
Reviewed on Aug 25, 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.
Holiday Lakes West
While Holiday Lakes West might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Anclote River Park and Tarpon Springs Sponge Docks.
Ready to book your vacation to Holiday?
Holiday Hotel Deals
Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
CA $289
CA $382 total
Aug 31 - Sep 1
includes taxes & fees
9.4/10 Exceptional! (3,767 reviews)
"Everyone was great and easy check-in/checkout. Need to do better on keeping the food fresh for breakfast. Also perhaps do more fish options. I had to take the smoked salmon off the bagels to get some protein that I actually eat."
Reviewed on Aug 26, 2026
The Westin Tampa Bay
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
CA $198
CA $225 total
Sep 3 - Sep 4
includes taxes & fees
8.6/10 Excellent! (1,523 reviews)
"Everything was excellent"
Reviewed on Aug 25, 2026
Hilton Clearwater Beach Resort & Spa
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
CA $226
CA $310 total
Sep 2 - Sep 3
includes taxes & fees
8.2/10 Very good! (2,951 reviews)
"Precio, verso propiedad no van acorde, un hotel muy viejo, el baño y muebles no estaban bien limpios, todo muy caro. Yo no se lo recomendo a nadie."
Reviewed on Aug 25, 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.
Stay near popular Holiday attractions
Anclote River Park
8.8/10 (48 reviews)
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.
Photo by Travel Ginger
Key Vista Nature Park
8.8/10 (33 reviews)
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.
Anclote Gulf Park
8.8/10 (32 reviews)
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.
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
CA $56
per adult
2 Hours Kayak Eco Tour in Tarpon Springs
CA $76
per adult
80% of travellers recommend
Audio Guide to New Port Richey's History and Quirky People
CA $10
per adult
Frequently asked questions
How much does a Holiday vacation package cost?
You can grab a vacation package to this popular destination from CA $875 on Expedia. But how much your vacation to Holiday costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Holiday?
If you'd like to score a cheap Holiday vacation package, consider travelling in August, October and November. You'll usually find better rates on hotels and airfares during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Holiday?
To fully enjoy your Holiday vacation, we recommend booking for 3 days. Divide your time between discovering Sunset Beach, St Nicholas Greek Orthodox Cathedral and other well-known attractions, as well as exploring neighbourhoods like New Port Richey Estates and Flor-a-mar. If you've got some time to spare, add a day trip to your Holiday vacation itinerary.
Is it worth booking a vacation package to Holiday?
It's easy to see why a Holiday vacation is on the to-do list of many travellers. Top attractions like Anclote River Park are just the start of things to see and do here.
How to find the best Holiday package deals?
Use Expedia's handy filters to help you find some great Holiday package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Holiday package deals in the off-peak 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 as early as possible.
Is it cheaper to book a Holiday vacation as a package?
You can enjoy significant savings on your Holiday getaway by booking a tailored vacation package. Check the "Package" heading, then select your destination and travel dates to see some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
How to plan a trip to Holiday?
- Choose your dates: What you plan to do in Holiday and your favourite season can help you decide when to travel.
- Work out your budget: Ensure you have enough money to pay for everything from meals and transportation to airfares and activities. Your accommodations will likely be the largest expense during your trip to Holiday.
- Determine how many days away: Start by making a list of all the attractions and activities you'd like to get to in Holiday. Then, estimate how long you'll need for each, as well as any travel time.
- Bundle your airfare and accommodations: After you've settled on your dates and duration, book the ideal Holiday vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
