Holiday Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was CA $1,676, price is now CA $1,114 per person
CA $1,114
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8.8/10 Excellent! (2,471 reviews)
What a great little place to stay! The stay was exceptional. The room was located next to everything. Super clean and cute. There were lots of extra amenities to enjoy in your stay as wall. Only 5 minutes from the best beaches. And great restaurants and entertainment just around the corner. Highly recommend!

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 CA $3,321, price is now CA $1,708 per person
CA $1,708
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,282 reviews)

CW Resort

CW Resort

4 out of 5
Save 100% on your flight
Price was CA $2,060, price is now CA $1,256 per person
CA $1,256
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.4/10 Exceptional! (255 reviews)
Had a wonderful stay for a girls weekend! We got a bigger room, 3 bedrooms, 3 full baths, so we were all out of each other’s way and had perfect space! Did not really feel like a hotel, but more a condo feel. Large TV’s in all rooms, extremely clean, although this is a newer property. We definitely return, especially if we want a larger room compared to a standard hotel room. Location also close to everything and beach!

Reviewed on Oct 28, 2026

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was CA $2,380, price is now CA $1,583 per person
CA $1,583
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (1,260 reviews)
Amazing hotel

Reviewed on Oct 26, 2026

Stylish Treasure Island Escape

Stylish Treasure Island Escape

3 out of 5
Sunshine Beach
Save 100% on your flight
Price was CA $11,544, price is now CA $7,944 per person
CA $7,944
per person
Jan 1 - Jan 7
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
No reviews

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

Ready to book your vacation to Holiday?

 

Choose your dates

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
The price is CA $332 per night from Nov 9 to Nov 10
CA $332
CA $431 total
Nov 9 - Nov 10
includes taxes & fees
9.4/10 Exceptional! (4,017 reviews)
"It would be helpful to understand what is included or not included when travelling to the beach ... on windy days or calm days."

Reviewed on Oct 28, 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
The price is CA $331 per night from Nov 11 to Nov 12
CA $331
CA $430 total
Nov 11 - Nov 12
includes taxes & fees
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
The price is CA $218 per night from Nov 22 to Nov 23
CA $218
CA $247 total
Nov 22 - Nov 23
includes taxes & fees
The Westin Tampa Bay
See all 6,241 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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)
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.
See properties

What to do in Holiday

Tarpon Springs: Evening Dolphin Cruise

Tarpon Springs: Evening Dolphin Cruise

CA $41
per adult
90% of travellers recommend
Tarpon Springs: Evening Dolphin Cruise
Tarpon Springs Ghost Tour: Haunted History & True Crime

Tarpon Springs Ghost Tour: Haunted History & True Crime

CA $56
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

CA $76
per adult
86% of travellers recommend
2 Hours Kayak Eco Tour in Tarpon Springs
See all activities in Holiday

Frequently asked questions

How much does a Holiday vacation package cost?
You can grab a vacation package to this popular destination from CA $1,114 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?

  1. Choose your dates: What you plan to do in Holiday and your favourite season can help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.