Winston Park Vacations from ￥250,932

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The Latest Winston Park Vacation Packages

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

Bilmar Beach Resort

4 out of 5
per person
Oct 2 - Oct 7
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Tampa (TPA)
8.6/10 Excellent! (1,007 reviews)
The staff at fromt desk could have ben a little more pleasant , the lady with the glasses is not so welcoming , i asked her if she can hold my balloons to set up the room for our 50th birthday celebration and she's like I don't have anywhere to put them but then all the sudden she said she could put them in the office that just wasn't very nice when I called previously ahead of time and they said they were set up them in the room for me... also asked for a later check out and they said no, i also asked for early check in and they said no .wasnt ready ....i loved thenarea ,but need a friendlier staff at front desk ....our room was nice .i woukd of prefereed a room not all the way in tje corner next to a wall blocking the view ...

Reviewed on Jul 21, 2025

Fun Family-friendly Largo Home Heated Pool

Fun Family-friendly Largo Home Heated Pool

2 out of 5
Save 100% on your flight
per person
Oct 2 - Oct 7
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Tampa (TPA)
No reviews
Beach House Cottage Pool Spa on Beach Access

Beach House Cottage Pool Spa on Beach Access

2 out of 5
per person
Oct 2 - Oct 7
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Tampa (TPA)
No reviews
Seminole Hard Rock Hotel & Casino Tampa

Seminole Hard Rock Hotel & Casino Tampa

4 out of 5
per person
Oct 2 - Oct 7
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Tampa (TPA)
8.8/10 Excellent! (1,354 reviews)
The property is nice. The front desk gentleman was cold in demeanor. I booked a view of the pool and was told when I checked in that it would cost me an additional fifty per a night which should have been included in my booking.

Reviewed on Jul 21, 2025

Four Bed Home With Pool Game Room Bar Near Beach

Four Bed Home With Pool Game Room Bar Near Beach

2 out of 5
Central Park District
per person
Oct 2 - Oct 7
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Tampa (TPA)
No reviews

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

5/5(26 area reviews)

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 hotels in Pass-a-Grille

Winston Park Hotel Deals

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 ￥27,439 per night from Jul 29 to Jul 30
￥27,439
￥36,835 total
Jul 29 - Jul 30
includes taxes & fees
8/10 Very Good! (2,040 reviews)
Nice place but not so nice view.
"We chose to forgo our usual condo rental in Treasure Island to stay in the heart of Clearwater. We chose Hilton due to its closeness to the beach, stores, and restaurants. We were not disappointed with the location. This hotel is considered a resort and you pay resort prices for your stay. If you ..."

Reviewed on Jul 21, 2025

Hilton Clearwater Beach Resort & Spa
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
5303 W Kennedy Blvd, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is ￥18,668 per night from Aug 10 to Aug 11
￥18,668
￥21,189 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (2,004 reviews)
"No elevador servicio tiene que arrreglar lo más pronto posible"

Reviewed on Jul 20, 2025

Hotel Alba, Tapestry Collection by Hilton
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 ￥40,934 per night from Aug 12 to Aug 13
￥40,934
￥52,140 total
Aug 12 - Aug 13
includes taxes & fees
9.2/10 Wonderful! (2,399 reviews)
"Hotel could use a refresh and deep cleaning. Lobby is a bit run down. Room was great. Thank you"

Reviewed on Jul 19, 2025

Wyndham Grand Clearwater Beach
See all 16,062 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 vacation package cost?
We make it easy to explore the world, with Winston Park packages starting from just ￥250,932. 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 for more information.

Discover the most popular places to visit in Winston Park

John's Pass Village & Boardwalk

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 seaside in this family-friendly area, or check out its lively bars.

John's Pass Village & Boardwalk
Fort De Soto Park which includes a sandy beach

Fort De Soto Park

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

Fort De Soto Park
Tropicana Field

Tropicana Field

Catch an event at Tropicana Field during your trip to St. Petersburg. Attend a baseball game or simply enjoy the lively bars while you're in the area.

Tropicana Field

Things to do

The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

￥4,698
per adult
88% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

￥5,424
per adult
94% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
Sea Screamer boat in Orlando

Day Trip to Clearwater Beach with Sea Screamer Ride

￥18,324
per adult
90% of travellers recommend
Day Trip to Clearwater Beach with Sea Screamer Ride
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.