Title: Winston Park Vacation Packages & Trips 2025 from CA $465 | Expedia.ca

  

[Hotels in Winston Park](https://expedia.ca/Winston-Park-St-Petersburg-Clearwater-Hotels.0-n553248635976481259-0.Travel-Guide-Filter-Hotels)[Flights to St. Petersburg - Clearwater](https://expedia.ca/Cheap-Flights-To-St-Petersburg-Clearwater.d178310.Travel-Guide-Flights)[Things to do in St. Petersburg - Clearwater](https://expedia.ca/Things-To-Do-In-St-Petersburg-Clearwater.d178310.Travel-Guide-Activities)[Winston Park Car Rentals](https://expedia.ca/Car-Rentals-In-Winston-Park.d553248635976481259.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Winston Park Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

-   ## 
    
    Plan, book, travel with confidence
    
-   ### 
    
    Better together
    
    Save up to CA $1,096 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
    

## Top Holiday Package Deals in Winston Park

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

![Innisbrook Resort](https://images.trvl-media.com/lodging/1000000/20000/16700/16668/363b5cc9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Innisbrook Resort

CA $936

per person

Feb 1 - Feb 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

8.4/10 Very Good! (1,009 reviews)

Property was very clean and quiet. Loved the lap pool. We will be back!

Reviewed on Oct 23, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-02-01/2026-02-08/?FromAirport=YYZ&Destination=TPA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=16668&paandie=true&dealMarker=IR_dXAD83ur0hTEKtsihuwRBCtBo7_5kabhgYQdDq1l8p2r709mmRnGTvWyza3Zr)

![Crystal Palms Beach Resort](https://images.trvl-media.com/lodging/3000000/2310000/2301500/2301415/3379c3cf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Crystal Palms Beach Resort

Sunshine Beach

CA $1,435

per person

Feb 1 - Feb 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

9/10 Wonderful! (2,349 reviews)

Very quiet and enjoyable

Reviewed on Oct 5, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-02-01/2026-02-08/?FromAirport=YYZ&Destination=TPA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2301415&paandie=true&dealMarker=IR_dXAD83ur0hTEKtsihu_4KR9RVSIo-YvHr8-ywrMmV_TnnB1UlfoBrwjIQE-JD)

![The Avalon Club](https://images.trvl-media.com/lodging/68000000/67580000/67572800/67572769/a97427b8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Avalon Club

CA $1,789

per person

Dec 29 - Jan 1

found 5 hours ago

Roundtrip flight included

Detroit (DTW) to Tampa (TPA)

9.4/10 Exceptional! (466 reviews)

Overall the property was clean; however, it was a great disappointment to see the street light with wires as an ocean view literally right outside your balcony. I also didn’t appreciate upon greeting the staff stressed about the fees instead of stressing what is already included, such as the beach chairs, umbrella etc…

Reviewed on Oct 15, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-01/?FromAirport=DTW&Destination=TPA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=67572769&paandie=true&dealMarker=zC80xzzhXU-zQ333H1tYO8FGKYDiIXaWgtNONe0X_t4WtNDVAAPOjT2kM6Fsyr3U)

![Provident Oceana Beachfront Suites](https://images.trvl-media.com/lodging/34000000/33560000/33551400/33551358/162f1150_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Provident Oceana Beachfront Suites

CA $1,711

per person

Feb 1 - Feb 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

9.4/10 Exceptional! (600 reviews)

I love this condo building. It’s convenient to the beach and the view from the terrace to the bay is gorgeous. It’s my happy place. My only disappointment is the living room furniture is so uncomfortable. I always feel like crippled when standing up from the sofa.

Reviewed on Nov 7, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-02-01/2026-02-08/?FromAirport=YYZ&Destination=TPA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=33551358&paandie=true&dealMarker=aUccWOo31tf0nTjgJ6s1jyAAqGWAmrTekucJVzHruNI_VgLpxkNPyRtSx3hFNCeo)

![Plaza Beach Hotel Beachfront Resort](https://images.trvl-media.com/lodging/1000000/900000/894000/893981/196da8d7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Plaza Beach Hotel Beachfront Resort

CA $1,190

per person

Feb 1 - Feb 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

9/10 Wonderful! (1,018 reviews)

This is a small place but the location is great. Beautiful beach with direct access and views from Some Rooms. Conveniently located to stores and restaurants or public transportation. Rooms are clean, beds could’ve been more comfortable. Staff helpful and pleasant. Pool was very nice and clean with a small bar. Overall great place to stay.

Reviewed on Oct 26, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-02-01/2026-02-08/?FromAirport=YYZ&Destination=TPA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=893981&paandie=true&dealMarker=aUccWOo31tf0nTjgJ6s1j1r3VqqL9W6vY3NBgY5I8uwDY1KBr6BYK0kd0ZPzMRc4)

## 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](https://expedia.ca/St-Petersburg-Clearwater-Winston-Park.dx553248635976481259)

![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/496000/496143-st-petersburg.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Downtown St. Petersburg

1 out of top 10 points of interest in this area

Come here for the beaches and sunshine and discover much more in this Florida city with something for all ages and tastes.

[Find hotel + flight trips in Downtown St. Petersburg](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20St.%20Petersburg&DestID=6162954&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/340000/340037-Pass-A-Grille.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Pass-a-Grille

Discover a quaint beach neighborhood featuring the Pass-a-Grille Historic District and Gulf Beaches Historical Museum. Enjoy walkable attractions like boutiques, an ice cream shop, outdoor art market, and fishing piers around 8th Street.

[Find hotel + flight trips in Pass-a-Grille](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Pass-a-Grille&DestID=6005248&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/496000/496092-st-petersburg.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Sand Key

1 out of top 10 points of interest in this area

4.5/5(4 area reviews)

While visiting Sand Key, you might make a stop by sights like Belleair Beach and Sand Key Park.

[Find hotel + flight trips in Sand Key](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Sand%20Key&DestID=553248635976482162&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/496000/496285-sunset-beach-st-pete.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Sunset Beach

Sunset Beach is noteworthy for its beaches, and you can make a stop at top attractions like Sunset Beach and St. Petersburg Municipal Beach.

[Find hotel + flight trips in Sunset Beach](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Sunset%20Beach&DestID=6159959&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Clearwater featuring café scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/175000/175109-Clearwater.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Downtown Clearwater

While visiting Downtown Clearwater, you might make a stop by sights like Coachman Park and Nancy and David Bilheimer Capitol Theatre.

[Find hotel + flight trips in Downtown Clearwater](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Clearwater&DestID=939284294524882944&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Winston Park Hotel Deals

![The Westin Tampa Bay](https://images.trvl-media.com/lodging/1000000/10000/1600/1557/5e6ee943_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Westin Tampa Bay

7627 W Courtney Campbell Cswy, Tampa, FL

Fully refundable

CA $190

CA $216 total

Nov 23 - Nov 24

includes taxes & fees

8.2/10 Very Good! (1,038 reviews)

Excellent!

Reviewed on Nov 9, 2025

[](https://expedia.ca/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%2F2025&selected=1557&PinnedHotelID=1557&HadPinnedHotel=true&regionId=553248635976481259)

![Hotel South Tampa & Suites](https://images.trvl-media.com/lodging/1000000/30000/21700/21685/ebc5e46f_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hotel South Tampa & Suites

3314 S Dale Mabry Hwy, Tampa, FL

Fully refundableReserve now, pay when you stay

CA $113

CA $128 total

Nov 30 - Dec 1

includes taxes & fees

8.6/10 Excellent! (1,564 reviews)

Very good expreience

Reviewed on Nov 2, 2025

[](https://expedia.ca/Hotel-Search?startDate=30%2F11%2F2025&endDate=01%2F12%2F2025&selected=21685&PinnedHotelID=21685&HadPinnedHotel=true&regionId=553248635976481259)

![Quality Inn Airport - Cruise Port](https://images.trvl-media.com/lodging/1000000/10000/4500/4462/dbf70823_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Quality Inn Airport - Cruise Port

1020 S Dale Mabry Hwy, Tampa, FL

Fully refundableReserve now, pay when you stay

CA $104

CA $119 total

Dec 1 - Dec 2

includes taxes & fees

8.2/10 Very Good! (1,223 reviews)

Stayed quite e few times. Clean. Good value. Good breakfast. Helpful staff

Reviewed on Nov 7, 2025

[](https://expedia.ca/Hotel-Search?startDate=01%2F12%2F2025&endDate=02%2F12%2F2025&selected=4462&PinnedHotelID=4462&HadPinnedHotel=true&regionId=553248635976481259)

[See all 16,570 properties in Winston Park](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F11%2F2025&endDate=12%2F11%2F2025&regionId=553248635976481259)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does a Winston Park vacation package cost?

> We make it easy to explore the world, with Winston Park packages starting from just CA $936. You'll have the flexibility to combine your favorite 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 vacation 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 vacation?

> 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 vacation 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 vacation 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](https://www.expedia.ca/service/?langid=4105) for more information.

### Discover the most popular places to visit in Winston Park

![John's Pass Village & Boardwalk](https://mediaim.expedia.com/destination/1/d1d6f75bd85f60488d8bc159921cdcf2.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### John's Pass Village & Boardwalk

4.5/5(136 reviews)

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.

[](https://expedia.ca/Johns-Pass-Village-Boardwalk-St-Petersburg-Clearwater.d6162658.Vacation-Attraction)

![Clearwater Beach](https://mediaim.expedia.com/destination/9/702d482af2dd0623a2db6014863695f9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Clearwater Beach

4.5/5(5 reviews)

Why not spend a lazy afternoon at Clearwater Beach during your trip to Clearwater Beach? Wander the clear-water beaches or discover the area's beautiful sunsets.

[](https://expedia.ca/Clearwater-Beach-St-Petersburg-Clearwater.d553248635983990696.Vacation-Attraction)

![Fort De Soto Park which includes a sandy beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/174000/174956-St-Petersburg.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Fort De Soto Park

4.5/5(28 reviews)

Admire the vestiges of the fortress, bring your kids to the pirate ship playground and relax on the beaches of this archipelago.

[](https://expedia.ca/Fort-De-Soto-Park-St-Petersburg-Clearwater.d6047182.Vacation-Attraction)

### Things to do

![The StarLite Majesty Cruise Ship in Clearwater, Florida](https://mediaim.expedia.com/localexpert/614700/aa2c41b1-9599-4a2b-b690-98569abc7309.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### StarLite Majesty Evening Yacht Cruise Clearwater

CA $45

per adult

**90%** of travellers recommend

[](https://expedia.ca/things-to-do/starlite-majesty-evening-yacht-cruise-clearwater.a614700.activity-details)

![2 Hour Sunset Cruise in Clearwater, Florida](https://mediaim.expedia.com/localexpert/3907132/0d48bc87-4fcc-4c61-a95c-c67678f2ab32.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 2 Hour Sunset Cruise in Clearwater, Florida

CA $49

per adult

**88%** of travellers recommend

[](https://expedia.ca/things-to-do/2-hour-sunset-cruise-in-clearwater.a3907132.activity-details)

![Stunning view of dolphins in St. Petersburg, Florida  ](https://mediaim.expedia.com/localexpert/338288/367304c2-f6f9-4cca-9e9e-46b8251f0aad.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Dolphin Racer Speedboat Adventure

CA $39

per adult

**92%** of travellers recommend

[](https://expedia.ca/things-to-do/dolphin-racer-speedboat-adventure.a338288.activity-details)

[See all activities in St. Petersburg - Clearwater](https://expedia.ca/things-to-do/search?rid=553248635976481259)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.