Windsor Park Vacation Packages

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Top Holiday Package Deals in Windsor Park

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

The Don CeSar

4 out of 5
Save 100% on your flight
per person
Aug. 8 - Aug. 11
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (1,003 reviews)
Absolute pleasure to be there. The room was very nice and the view of the ocean is amazing. The pool and service in the pool area was excellent. A true resort. We plan to make it an annual event. : )

Reviewed on Jun. 24, 2024

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Sep. 9 - Sep. 14
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (314 reviews)
Lack of information for the employer in the desk where you do check in

Reviewed on Jun. 21, 2024

Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Belle Vista
Save 100% on your flight
per person
Jul. 27 - Aug. 2
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.4/10 Very Good! (499 reviews)
Patking lot was very small. Did not know this property was more like a Motel. It was very small but clean and the deck over the pier was great. We stayed just 1 night.

Reviewed on Jun. 24, 2024

TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
Sep. 15 - Sep. 22
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
7.6/10 Good! (1,008 reviews)
We had a lot of fun. Great activities for my daughter (zip linning, huge blow up slide, activities at the pool for everyone, duck feeding and petting zoo, paddle boats). The rooms were very clean. My one recommendation would be that this resort needs a major renovation. Some sliding doors in the walk way area would not slide open or were broken and water was dripping from the ceiling, just very outdated overall and would be a beautiful resort once updated.

Reviewed on Jun. 24, 2024

FUSION Resort Two Bedroom Suites

FUSION Resort Two Bedroom Suites

3.5 out of 5
per person
Sep. 15 - Sep. 22
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (958 reviews)
Everyone was amazing, Place was clean, updated and quiet.

Reviewed on Jun. 20, 2024

Where to stay in Windsor Park

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

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

Windsor Park Hotel Deals

Sirata Beach Resort
Sirata Beach Resort
3 out of 5
5300 Gulf Blvd, St. Pete Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $213 per night from Jul. 16 to Jul. 17
CA $213
CA $302 total
includes taxes & fees
Jul 16 - Jul 17
7.2/10 Good! (2,297 reviews)
Quick staycay
"2 nights in deluxe dbl queen room. Requested accessible bathroom & was told there were none but fortunately there was a shower with handle inside. Other than that they delivered microwave quickly, room was clean & stocked & most importantly, the ac was cold! Queen beds were comfy. Wish the had a ..."

Reviewed on Jun. 23, 2024

Sirata Beach Resort
RumFish Beach Resort by TradeWinds
RumFish Beach Resort by TradeWinds
4 out of 5
6000 Gulf Blvd, St. Pete Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $301 per night from Jul. 1 to Jul. 2
CA $301
CA $426 total
includes taxes & fees
Jul 1 - Jul 2
8.2/10 Very Good! (1,034 reviews)
"Absolutely gorgeous beach! The property is kept clean and organized and all amenities were available."

Reviewed on Jun. 24, 2024

RumFish Beach Resort by TradeWinds
TradeWinds Island Grand
TradeWinds Island Grand
4 out of 5
5500 Gulf Blvd, St. Pete Beach, FL
The price is CA $356 per night from Jun. 30 to Jul. 1
CA $356
CA $488 total
includes taxes & fees
Jun 30 - Jul 1
7.6/10 Good! (1,008 reviews)
Great Family Vacation Destination
"This was my family‘s first time staying at Island grand. Last year we stayed at RumFish. Overall we had an excellent time however I would like to make note of the things that were a bother to us during our trip. First inside of our room, our phone was not working. Our microwave broke, we were not ..."

Reviewed on Jun. 22, 2024

TradeWinds Island Grand
See all 15,209 properties in Windsor 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Windsor Park vacation package cost?
Custom build your Windsor Park package from as little as CA $1,093. Choose from any combination of flights, hotels and rental cars to create the getaway you’ve long been dreaming about. Don’t forget to add on a few experiences or tours!
How do I get a cheap travel package to Windsor Park?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Hotels, flights, rental cars and activities — we’ve got it all. Choose the combination that suits you and see your savings pile up. We know a package deal is never a one-size-fits-all. That’s why we offer over 550 airlines and 1,000,000 hotel options globally, which lets you customize your Windsor Park adventure.
Where should I stay in Windsor Park?
With fascinating attractions like Church of Scientology and Westfield Countryside Mall in this area, look for a hotel positioned near either one. Bright House Field is another sight that lures the crowds.
How far in advance should I book my Windsor Park vacation?
While prices change frequently, we generally recommend reserving your seat as soon as possible. Many international fares are found on Expedia up to 12 months in advance. If circumstances have left you booking last minute, you might still be in luck. Cheaper tickets to Windsor Park sometimes appear in the weeks prior to departure.
What does an Expedia Windsor Park travel package include?
That depends on what sort of escape you want to have. Windsor Park vacation deals can include hotels, flights and car rentals. You can mix and match to find the travel package that works for you! You can also add on activities and experiences after you’ve booked to get even bigger discounts.
What should I know before booking a Windsor Park travel package?
An Expedia travel package can be customized for your circumstances and is a terrific way to make your budget go further. How little or much you include is your call. Rental cars, hotels and flights — mix and match whatever combination works with your plans.
If I'm not able to travel, can I cancel my Windsor Park vacation package?
We totally get that life sometimes gets in the way of your plans. If you’ve locked in a Windsor Park vacation package and have to change or cancel it, we’re here to help. We recommend looking up our Customer Service Portal first for information. But generally speaking, if you’ve taken out your package in the last 24 hours, you may be able to cancel and rebook for free. If it’s more than 24 hours, your airline, hotel or car rental company may impose a charge.

Discover the most popular places to visit in Windsor Park

Image for John's Pass Village & Boardwalk

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

John's Pass Village & Boardwalk
Image for Tropicana Field

Tropicana Field

4/5(26 reviews)

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

Tropicana Field
Image for Fort De Soto Park

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.

Fort De Soto Park

Things to do

Image for StarLite Majesty Evening Yacht Cruise Clearwater

StarLite Majesty Evening Yacht Cruise Clearwater

CA $43
Per adult
88% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Image for 2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

CA $47
Per adult
88% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
Image for Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar

Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar

CA $81
Per adult
100% of travellers recommend
Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar
See all activities in St. Petersburg - Clearwater

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