Pinellas County Vacation Packages

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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

FlightsFlightsHotelsHotels

St. Petersburg - Clearwater

St. Petersburg - Clearwater

Top Pinellas County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton St. Petersburg Bayfront

Hilton St. Petersburg Bayfront

4 out of 5
Downtown St. Petersburg
Price was CA $1,267, price is now CA $962 per person
CA $962
per person
Jul 20 - Jul 27
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
7.8/10 Good! (1,030 reviews)
The only concern was some people smoking marihuana in the pool area and people screaming in the middle of the night.

Reviewed on May 12, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $1,519, price is now CA $996 per person
CA $996
per person
Jul 28 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (506 reviews)
The staff was so sweet and accommodating. Everything you could need for an overnight at the beach. Room by the road had traffic noise but we didn’t mind at all!

Reviewed on May 7, 2026

Captiva Beach Resort

Captiva Beach Resort

3 out of 5
South Village
Price was CA $1,635, price is now CA $1,143 per person
CA $1,143
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,245 reviews)
The 2 bedroom condo was very clean and updated. The walk to the beach was short and we didn't have to cross any busy streets just walked the small roads within the complex of other resort condos.

Reviewed on May 8, 2026

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Price was CA $1,459, price is now CA $1,099 per person
CA $1,099
per person
Jul 12 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9/10 Wonderful! (1,001 reviews)
Exterior really smelled of cigarette smoke. Room itself was ok as smoking inside wasn’t permitted, but smoking was permitted on the property and ashtrays were abundantly available outside at all tables and outside each room.

Reviewed on May 11, 2026

The Capri at Siesta

The Capri at Siesta

3 out of 5
South Village
Price was CA $1,452, price is now CA $1,108 per person
CA $1,108
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (765 reviews)
Great relaxing vacation steps from white sandy beaches.

Reviewed on May 12, 2026

Pinellas County 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 $470 per night from May 25 to May 26
CA $470
CA $585 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (3,237 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 ...

Reviewed on May 12, 2026

Wyndham Grand Clearwater Beach
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
5500 Gulf Blvd St. Pete Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from May 20 to May 21
CA $208
CA $320 total
May 20 - May 21
includes taxes & fees
7.6/10 Good! (1,151 reviews)
The hotel with very good condition

Reviewed on May 11, 2026

Island Grand at TradeWinds
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
The price is CA $276 per night from May 26 to May 27
CA $276
CA $365 total
May 26 - May 27
includes taxes & fees
8.2/10 Very Good! (2,619 reviews)
Room and property appeared run down. Broken patio door, leaking shower head, broken toilet seat. Bathroom faucet was loose. Room overlooked equipment area so even though it was a “gulf view” it was dirty and noisy and they did a poor job trying to cover the equipment. This was very subpar from what ...

Reviewed on May 11, 2026

Hilton Clearwater Beach Resort & Spa
See all 13,881 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.
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Frequently asked questions

How much does a Pinellas County vacation package cost?
Much less than you might think — from as low as CA $962, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.