Pinellas County Holidays

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  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

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

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Top hotels in Pinellas County

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 S$362 per night from 29 Oct to 30 Oct
S$362
29 Oct - 30 Oct
includes taxes & fees
9.4/10 Exceptional! (4,022 reviews)
"Beach cabanas and poolside bar were awesome!"

Reviewed on 26 Oct, 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 S$404 per night from 29 Oct to 30 Oct
S$404
29 Oct - 30 Oct
includes taxes & fees
9.4/10 Exceptional! (2,473 reviews)
"We really enjoyed the proximity to the beach as well as restaurants and stores. The pool on the 8th floor was also very unique and a great place to relax and also enjoy poolside food and drinks. Our room was also very large and had much more than we had anticipated."

Reviewed on 26 Oct, 2026

Hyatt Regency Clearwater Beach Resort and Suites
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 S$286 per night from 8 Nov to 9 Nov
S$286
8 Nov - 9 Nov
includes taxes & fees
8.2/10 Very good! (3,094 reviews)
"Customer service is horrible"

Reviewed on 27 Oct, 2026

Hilton Clearwater Beach Resort & Spa
See all 14,147 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 holiday package cost?
Much less than you might think — from as low as , 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 holiday 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 cosy 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 holiday?
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 holiday package is the most convenient way to organise 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 holiday 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 holiday package?
We get it — life sometimes gets in the way of your plans. If you've booked a Pinellas County holiday 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 enjoy retail therapy at John's Pass Village & Boardwalk during your trip to Madeira Beach. Stroll along the beautiful beaches in this family-friendly area or visit its top-notch restaurants.
See properties

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.