Winston Park Vacations from ￥148,486

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The Latest Winston Park Vacation Packages

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

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was ￥234,059, price is now ￥148,486 per person
￥148,486
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Tampa (TPA)
No reviews
The resort is absolutely beautiful.We will definitely be staying here again.We actually decided to stay another night. What definitely recommended

Reviewed on Jan 1, 2026

The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
Rocky Point
Price was ￥270,639, price is now ￥217,230 per person
￥217,230
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Tampa (TPA)
8.4/10 Very Good! (1,047 reviews)
Staff was exceptional. Rooms were brand new and super clean. Pool is under construction, but other than that, the place was a gem!

Reviewed on Jan 7, 2026

The Don CeSar

The Don CeSar

4 out of 5
Price was ￥375,904, price is now ￥316,413 per person
￥316,413
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Tampa (TPA)
9/10 Wonderful! (1,044 reviews)
Nice clean, kids and family friendly!

Reviewed on Jan 4, 2026

Hilton Garden Inn Tampa Airport Westshore

Hilton Garden Inn Tampa Airport Westshore

3 out of 5
Westshore
Price was ￥238,622, price is now ￥201,494 per person
￥201,494
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Tampa (TPA)
9/10 Wonderful! (1,957 reviews)
Very kind maintenance guy

Reviewed on Jan 7, 2026

Homewood Suites by Hilton Tampa Airport - Westshore

Homewood Suites by Hilton Tampa Airport - Westshore

3 out of 5
Westshore
Price was ￥232,670, price is now ￥197,049 per person
￥197,049
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Tampa (TPA)
9/10 Wonderful! (1,006 reviews)
Staff was very helpful

Reviewed on Dec 13, 2025

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
Downtown St. Petersburg featuring outdoor art

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 hotels in Downtown St. Petersburg

Winston Park 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 ￥45,454 per night from Jan 11 to Jan 12
￥45,454
￥57,569 total
Jan 11 - Jan 12
includes taxes & fees
9.4/10 Exceptional! (2,972 reviews)
The hotel was really great. The service and staff were really helpful and courteous. The last day, housekeeping did not come to clean the room. The heated pool was a bit cold and would have preferred it to be warmer. Aside from that, it was a great resort. I would stay here again. It is family friendly ...

Reviewed on Jan 6, 2026

Wyndham Grand Clearwater Beach
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 ￥27,282 per night from Jan 11 to Jan 12
￥27,282
￥37,033 total
Jan 11 - Jan 12
includes taxes & fees
8/10 Very Good! (2,395 reviews)
Great place truly amazing

Reviewed on Jan 5, 2026

Hilton Clearwater Beach Resort & Spa
Ramada by Wyndham Tampa Westshore Airport South

Ramada by Wyndham Tampa Westshore Airport South

3 out of 5
1200 N Westshore Blvd Tampa FL
Fully refundableReserve now, pay when you stay
The price is ￥12,520 per night from Feb 8 to Feb 9
￥12,520
￥14,209 total
Feb 8 - Feb 9
includes taxes & fees
6.2/10 (3,782 reviews)
Affordable. Sometimes a bit noisy from the road. Room a tad “rough around the edges”

Reviewed on Jan 6, 2026

Ramada by Wyndham Tampa Westshore Airport South
See all 16,712 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 ￥148,486. 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

You can do some window-shopping at John's Pass Village & Boardwalk during your stay in Madeira Beach. Stroll along the seaside in this family-friendly area, or check out its top-notch restaurants.

John's Pass Village & Boardwalk
Vinoy Park

Vinoy Park

While area beaches are abundant, it’s convenient to have this lovely spot right in the city. Lounge under a palm tree and enjoy the frequent entertainment.

Vinoy Park
Salvador Dali Museum showing night scenes and modern architecture

Salvador Dali Museum

Browse the surrealistic masterpieces of a world-famous Spanish painter in a remarkable building that perfectly suits the style of the art exhibits.

Salvador Dali Museum

Things to do

The Pirate Ship at John's Pass

Pirate Adventure Cruise - John's Pass

￥7,036
per adult
100% of travellers recommend
Pirate Adventure Cruise - John's Pass
The Tropics Boat at Sunset

Sunset Celebration Cruise on Tropics Boat Tours

￥5,817
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
Dolphin Watching in Boca Ciega Bay

Dolphin Watching in Boca Ciega Bay

￥5,131
per adult
94% of travellers recommend
Dolphin Watching in Boca Ciega Bay
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.