Windsor Park Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Windsor Park

Price found within the past 48 hours. Click for updated prices.
Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
Wesley Chapel South
Save 100% on your flight
per person
Nov. 17 - Nov. 23
found 20 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
6.8/10 (1,001 reviews)
I'm sure this place was really nice back in the day. But its not great anymore. The grounds were all flooded from the rain. No ceiling fan, mini fridge or microwave in rooms. The hair dryer didnt work. And we only got 10 TV channels on the TV..

Reviewed on Sep. 8, 2024

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Nov. 4 - Nov. 11
found 5 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
9.6/10 Exceptional! (353 reviews)
Very clean, staff are very pleasant and attentive. The walk to the beach was great!! Highly recommend!! Again the staff were amazing!!!

Reviewed on Sep. 26, 2024

FUSION Resort Two Bedroom Suites

FUSION Resort Two Bedroom Suites

3.5 out of 5
Save 100% on your flight
per person
Nov. 4 - Nov. 11
found 5 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
9.2/10 Wonderful! (1,002 reviews)
The staff that work at the front desk are so friendly and accommodating. I will be coming back again. Thank you for an amazing vacation.

Reviewed on Sep. 18, 2024

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Downtown Tampa
Save 100% on your flight
per person
Nov. 17 - Nov. 23
found 20 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
8.2/10 Very Good! (201 reviews)
Amazing stay. Beautiful hotel. Wonderful staff.

Reviewed on Sep. 26, 2024

Barsala At The Wayland

Barsala At The Wayland

4 out of 5
per person
Nov. 15 - Nov. 22
just found
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
No reviews

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
Downtown St. Petersburg featuring outdoor art

Downtown St. Petersburg

1 out of top 10 points of interest in this area

A noteworthy feature of Downtown St. Petersburg is its fantastic nightlife. While you're in town, be sure to stop and check out St. Pete's Historic Coliseum and Jannus Live.

Find hotel + flight trips in Downtown St. Petersburg

Windsor Park Hotel Deals

The Westin Tampa Bay
The Westin Tampa Bay
4 out of 5
7627 W Courtney Campbell Cswy, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Oct. 11 to Oct. 12
CA $217
CA $246 total
includes taxes & fees
Oct 11 - Oct 12
8/10 Very Good! (1,005 reviews)
"I enjoyed my stay."

Reviewed on Sep. 25, 2024

The Westin Tampa Bay
RumFish Beach at TradeWinds
RumFish Beach at TradeWinds
4 out of 5
6000 Gulf Blvd, St. Pete Beach, FL
The price is CA $183 per night from Oct. 27 to Oct. 28
CA $183
CA $291 total
includes taxes & fees
Oct 27 - Oct 28
8.2/10 Very Good! (1,154 reviews)
"This resort has so much to offer for the whole family. Great amenities and convenient location. Would definitely recommend it."

Reviewed on Sep. 24, 2024

RumFish Beach at TradeWinds
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 $153 per night from Sep. 29 to Sep. 30
CA $153
CA $234 total
includes taxes & fees
Sep 29 - Sep 30
7.2/10 Good! (2,364 reviews)
"The AC in my room BARELY worked. I had a very hard time sleeping because it felt like I was outside. I was there for 3 nights, I may have gotten 10 hours of sleep total. They need to upgrade their AC units in the rooms. Overall, it’s a great place to stay for 2 nights, nothing more."

Reviewed on Sep. 26, 2024

Sirata Beach Resort
See all 15,055 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.

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 $586. 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 beautiful beaches 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 Vinoy Park

Vinoy Park

4.5/5(8 reviews)

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

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 Day Trip to Clearwater Beach with Sea Screamer Ride

Day Trip to Clearwater Beach with Sea Screamer Ride

CA $161
Per adult
90% of travellers recommend
Day Trip to Clearwater Beach with Sea Screamer Ride
Image for Deep-Sea Fishing Tour in the Gulf of Mexico with Lunch

Deep-Sea Fishing Tour in the Gulf of Mexico with Lunch

CA $243
Per adult
82% of travellers recommend
Deep-Sea Fishing Tour in the Gulf of Mexico with Lunch
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.