Pinellas County Vacations & Trips 2026 from CA $1,245

Name: Wyndham Grand Clearwater Beach
Price range: CA $292

Your Pinellas County Vacation

Head off on your next exciting adventure with a Pinellas County vacation package, and leave knowing all the details are taken care of. And with the ability to customize your getaway, it'll be one you won't forget. Start your trip to Pinellas County with a couple of nights in Clearwater visiting popular sights like Honeymoon Island State Park and Clearwater Marine Aquarium. Tierra Verde is another city that draws travellers from far and wide. John's Pass Village & Boardwalk and Tropicana Field are two of the leading places to see here. Start packing your suitcase, because your Pinellas County vacation is only a few clicks away with Expedia.

Top vacation destinations in Pinellas County

A modern building with large glass windows and a sign reading "Museum of Fine Arts".

Top Pinellas County Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Ocean Club Treasure Island Hotel

Sunshine Beach

CA $1,245

per person

Jan 17 - Jan 24

found 7 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Tampa (TPA)

9.6/10 Exceptional! (1,282 reviews)

CW Resort

CA $1,508

per person

Jan 17 - Jan 24

found 7 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Tampa (TPA)

9.4/10 Exceptional! (255 reviews)

New construction, clean everywhere. Great staff. Very happy have already rebooked

Reviewed on Nov 13, 2026

FUSION Resort Waterfront Suites

CA $1,310

per person

Jan 30 - Feb 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Tampa (TPA)

9.2/10 Wonderful! (1,266 reviews)

Not happy about cleaning. As scheduled every 3 days but no where to empty trash or get clean towels. Cleaning carts always in hallway by elevator Balcony was amazing. Great view. Love the suite. Very accommodating for the four of us.

Reviewed on Nov 13, 2026

Crystal Palms Beach Resort

Sunshine Beach

CA $1,323

per person

Feb 1 - Feb 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

8.8/10 Excellent! (2,409 reviews)

It was amazing I felt like I got a whole apartment In one . It’s literally across the street from the beach 2-5 min walk you can see the water from hotel. It has a pool and hot tub .Everything was clean, the check in to get the keys in a lock box was different but I didn’t mind it . It felt like top secret underground location lol. 15/10 rating

Reviewed on Nov 7, 2026

Provident Oceana Beachfront Suites

Save 100% on your flight

CA $1,552

per person

Jan 24 - Jan 31

found 8 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

9.4/10 Exceptional! (686 reviews)

At the rate paid I was surprised to not be provided with at least on coffee pod or free bottle of water. Location was wonderful, we enjoyed the hot tub.

Reviewed on Nov 12, 2026

Pinellas County Hotel Deals

Wyndham Grand Clearwater Beach

100 Coronado Drive Clearwater Beach FL

Fully refundableReserve now, pay when you stay

CA $292

CA $387 total

Dec 13 - Dec 14

includes taxes & fees

Hyatt Regency Clearwater Beach Resort and Suites

301 S Gulfview Blvd Clearwater Beach FL

Fully refundableReserve now, pay when you stay

CA $331

CA $430 total

Dec 8 - Dec 9

includes taxes & fees

Hilton Clearwater Beach Resort & Spa

400 Mandalay Ave Clearwater Beach FL

Fully refundableReserve now, pay when you stay

CA $268

CA $359 total

Nov 29 - Nov 30

includes taxes & fees

See all 14,047 properties in Pinellas County

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.

Frequently asked questions

How much does a Pinellas County vacation package cost?

Much less than you might think — from as low as CA $1,245, in fact! By bundling flights, hotels and car rentals into your own customized package, your trip to Pinellas County is just clicks away.

How do I get a cheap travel package to Pinellas County?

Bundle your bookings with Expedia to save big bucks on your next getaway. With more than 550 air carriers and 1,000,000 hotels around the globe, your Pinellas County vacation package can be customized exactly to suit your travel style. With all that extra money, why not throw in one or more fun experiences and tours? It's an easy way to unlock even more bargains. Your dream getaway to Pinellas County is closer than you thought!

Where should I stay in Pinellas County?

If you've always wanted to visit Clearwater Marine Aquarium and Sand Key Park, the city of Clearwater Beach is the place to head.

What are the top hotels in Pinellas County?

For properties in Clearwater Beach with cozy beds and friendly service, look up Hilton Clearwater Beach Resort & Spa and Wyndham Grand Clearwater Beach. If you plan to visit St. Pete Beach as well, you'll get a good night's sleep at Sirata Beach Resort or Dolphin Beach Resort.

How far in advance should I book my Pinellas County vacation?

While prices change from time to time, we generally suggest reserving your seat as early as possible. Most international airfares can be compared on Expedia up to a year in advance. If you're booking last minute, you might still be in luck. Low prices to Pinellas County sometimes appear only weeks before departure.

What does an Expedia Pinellas County travel package include?

Flights, hotels and rental cars — we've got them all. With Expedia, you can create your Pinellas County package just how you like it. All you have to do is decide what you need. Once you've made your booking, you can add on fun things like experiences and activities. The more you bundle, the greater your savings!

What should I know before booking a Pinellas County travel package?

Bundling your bookings into a Pinellas County vacation package is the most convenient way to organize your trip. Not only that, you'll save when you combine your hotels, flights and car rentals. Once you've booked, why not add on a day tour or an activity?

Can I choose my airline with a Pinellas County Expedia vacation package?

Yes, you're in charge. We offer more than 550 airlines around the world, so you can customize your Pinellas County getaway according to your style and budget.

If I'm not able to travel, can I cancel my Pinellas County vacation package?

We get it — life sometimes gets in the way of your plans. If you've booked a Pinellas County vacation package and need to change or cancel it, we can help. We suggest having a look at our Customer Service Portal first for information. But generally speaking, if you've taken out your package within 24 hours, you may be able to cancel and rebook at no cost. If it's more than 24 hours, your airline, hotel or car rental company may impose a charge.

Stay near popular Pinellas County attractions

An aerial view of a coastal city with a long sandy beach, a marina, and a bridge connecting the mainland to an island.

John's Pass Village & Boardwalk

9.2/10 (5,191 reviews)

You can do some window-shopping at John's Pass Village & Boardwalk during your stay in Madeira Beach. Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.

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