Winston Park Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ฿27,000 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

Where to stay in Winston Park

Find the best Winston Park areas and neighborhoods for the activities you enjoy most. Learn more about Winston Park
Pass-a-Grille

Pass-a-Grille

1 out of top 10 points of interest in this area
5/5(3 area reviews)

As you view this neighborhood’s iconic pink hotel it feels as if you’ve crossed into the past. Find beautiful beaches and serene enjoyment here.

Find hotels in Pass-a-Grille

Top hotels in Winston Park

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 ฿11,511 per night from 31 May to 1 Jun
฿11,511
฿14,286 total
31 May - 1 Jun
includes taxes & fees
9.4/10 Exceptional! (3,229 reviews)
Rooms took too long to clean. Our room still would not be cleaned after we were gone all day. Coming back sometimes at 3 or 4 pm

Reviewed on 14 May 2026

Wyndham Grand Clearwater Beach
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundable
The price is ฿5,471 per night from 24 May to 25 May
฿5,471
฿6,210 total
24 May - 25 May
includes taxes & fees
8.6/10 Excellent! (1,297 reviews)
Breakfast option available with room , staff at the restaurant was amazing specially Claudia . Breakfast menu outstanding! Pool was closed due to renovations ,one of the elevator was not working , there was not sign posted that elevator was out of service . Got stuck on 7 floor coming down to the ...

Reviewed on 14 May 2026

The Westin Tampa Bay
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 ฿6,937 per night from 26 May to 27 May
฿6,937
฿9,117 total
26 May - 27 May
includes taxes & fees
8.2/10 Very Good! (2,604 reviews)
Room had food and womens hair scrunchies on the floor. Needed a better cleaning and vacuuming. Limited view was air conditioning units!

Reviewed on 12 May 2026

Hilton Clearwater Beach Resort & Spa
See all 16,961 properties in Winston Park
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 Winston Park holiday package cost?
We make it easy to explore the world, with Winston Park packages starting from just . You'll have the flexibility to combine your favourite hotels, airlines and car rental. For the ultimate escape, why not add some activities and tours to your travel itinerary?
How do I get a cheap travel package to Winston Park?
Book everything in the one place with our Winston Park holiday packages. You'll find bargains on flights, hotels, tours and more that'll keep your travel budget happy and your sense of adventure alive. And, with more than 550 air carriers and 1,000,000 properties around the globe to select from, you'll have the flexibility to mix and match as you want.
Where should I stay in Winston Park?
Urban explorers come from all corners of the globe to see Salvador Dali Museum and Tropicana Field in Winston Park. Book a room close to these terrific attractions and visit them whenever you want.
How far in advance should I book my Winston Park holiday?
It can be tricky to know when the best time is to book your Winston Park trip. But generally the earlier you book, the better the prices. In some cases, you can lock in your flights and hotels up to a year before your departure date. If you're thinking of a last-minute getaway, no need to panic! There are fabulous bargains popping up on Expedia every single day.
What does an Expedia Winston Park travel package include?
You can choose from any combination of rental cars, flights and hotels. Once you've made your booking, you can add the fun stuff like experiences and activities. Want to pick your fare class? That's also easy to do. The choice is all yours when it comes to planning your ideal Winston Park getaway.
What should I know before booking a Winston Park travel package?
Our prices are already low. However, you'll pick up an even better deal when you book your flights, hotels and car rentals together. With an Expedia travel package, you'll get transparent pricing and tons of choice.
Can I choose my airline with a Winston Park Expedia holiday package?
You can, and with over 550 airlines to select from globally, you've got lots of choice. Look through the available options and see which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Winston Park holiday package?
Yes, it's possible to cancel your Winston Park booking if your travel plans have been upended. Whether you'll incur a fee or not depends on your hotel, airline or car rental company. It may be possible to cancel or change your booking free of charge if you booked in the last 24 hours. Head to our Customer Service Portal for more information.

Popular places to visit

Aerial view of the pink-tinged waters reflecting the vibrant sunset hues next to the John's Pass Village & Boardwalk, Treasure Island, Florida, United States.

John's Pass Village & Boardwalk

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the marina in this family-friendly area or visit its lively bars.

John's Pass Village & Boardwalk
Eckerd College

Eckerd College

Walk around the campus at Eckerd College as part of your travels around St. Petersburg. Amble around this family-friendly area's beautiful beaches and enjoy its lively bars.

Eckerd College
StPetersburg_JannusLive_553248621533125382_02

Jannus Live

Jannus Live is just one of the places to see in St. Petersburg, so why not enjoy the other things to explore during your travels? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Jannus Live

Things to do

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

฿1,186
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key

St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key

฿2,129
per adult
100% of travellers recommend
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

฿1,276
per adult
90% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
See all activities in St. Petersburg - Clearwater
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.