South Westshore Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    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 South Westshore

Price found within the past 48 hours. Click for updated prices.
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Price was CA $1,394, price is now CA $960 per person
CA $960
per person
Jul 23 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,015 reviews)
Thank you to all the staff at the restaurant.

Reviewed on Jun 5, 2026

CW Hotel

CW Hotel

4 out of 5
Price was CA $2,872, price is now CA $1,808 per person
CA $1,808
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Tampa (TPA)
No reviews
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was CA $1,589, price is now CA $1,051 per person
CA $1,051
per person
Sep 9 - Sep 16
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (2,333 reviews)
Super bueno y muy cerca de todo

Reviewed on Jun 15, 2026

The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Central Sarasota
Price was CA $3,776, price is now CA $2,551 per person
CA $2,551
per person
Aug 3 - Aug 10
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Tampa (TPA)
8.2/10 Very Good! (556 reviews)
Excelente ubicación y 100% recomendado.

Reviewed on May 30, 2026

The Don CeSar

The Don CeSar

4 out of 5
Price was CA $2,041, price is now CA $1,412 per person
CA $1,412
per person
Aug 21 - Aug 26
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (1,165 reviews)
I have one word, WOW!!! You need to go and experience this amazing place for yourself!!!!!!

Reviewed on Jun 19, 2026

Where to stay in South Westshore

Find the best South Westshore areas and neighborhoods for the activities you enjoy most. Learn more about South Westshore
Downtown Tampa

Downtown Tampa

4 out of top 10 points of interest in this area
4.5/5(56 area reviews)

Explore top attractions like the Florida Aquarium, Glazer Children's Museum, and Tampa Riverwalk, or indulge in the vibrant nightlife and dining scene in the River Arts District. Easily navigate the area with TECO Streetcar and HART public transportation.

Find hotels in Downtown Tampa

South Westshore 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 $253 per night from Jun 21 to Jun 22
CA $253
CA $287 total
Jun 21 - Jun 22
includes taxes & fees
8.6/10 Excellent! (1,372 reviews)
"Swimming pool was closed for our stay."

Reviewed on Jun 15, 2026

The Westin Tampa Bay
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 CA $367 per night from Jul 8 to Jul 9
CA $367
CA $471 total
Jul 8 - Jul 9
includes taxes & fees
9.4/10 Exceptional! (3,380 reviews)
"Very welcoming place. Staff is pleasant and attentive. Located within walking distance to local attractions."

Reviewed on Jun 18, 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 CA $278 per night from Jun 30 to Jul 1
CA $278
CA $370 total
Jun 30 - Jul 1
includes taxes & fees
8.2/10 Very Good! (2,695 reviews)
"Overall the hotel was very nice, the amenities were great, the staff were friendly. Check in was a little rough, but check out was a breeze. Cons: the air conditioner did not work very well, there was mold all over the corner of our room, and everything was incredibly expensive, especially for a ..."

Reviewed on Jun 19, 2026

Hilton Clearwater Beach Resort & Spa
See all 14,241 properties in South Westshore
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 South Westshore vacation package cost?
The most affordable South Westshore package is CA $960, so the trip of your dreams can become a reality — without breaking the bank. Bundle flights, hotels and car rentals to tailor make a package that suits you.
How do I get a cheap travel package to South Westshore?
Just think of all the thrilling things you could do in South Westshore with extra cash in your wallet. Watch your savings stack up when you bundle your flights, hotels and extras into a South Westshore vacation package. You have plenty of choice when you book your trip with Expedia too. In fact, you can take your pick of over 550 air carriers and 1,000,000 hotel options globally. Whether you're vacationing with the family or embarking on a solo adventure, exploring South Westshore is better with a package.
Where should I stay in South Westshore?
A trip to South Westshore wouldn't be complete without paying a visit to Memorial Hospital of Tampa, Fresenius Medical Care at Memorial Hospital and Hester Park. Stay near these popular sights and make sightseeing easy.
What are the top hotels in South Westshore?
Calm Oasis In South Tampa - 4 Bedroom Private Pool Home and Entire House Near Tampa Airport And Downtown Close To Beaches are among the most popular hotels in South Westshore. Why not look up the amenities and rates at each and then decide?
How far in advance should I book my South Westshore vacation?
The earlier, the better. Air carriers typically release flight tickets up to a year prior to departure, and this is your chance to pick up some rock-bottom prices. Just been told you should take your vacation time in a few weeks? No problem! Expedia are never short on fantastic bargains to help you have the getaway of your dreams, at a price you can afford.
What does an Expedia South Westshore travel package include?
That's up to you. You can pick from a range of South Westshore bundles, such as a flight, rental car and hotel. You can also book a flight and a hotel, or a flight and a rental car. Once you've made your booking, you can add on the fun stuff like experiences and activities. Whatever your perfect South Westshore trip looks like, you're sure to save!
What should I know before booking a South Westshore travel package?
You'll pick up big savings when you bundle your hotels, flights and rental cars into a travel package. Plus, booking everything in one place just makes things easier. So why waste your money or time? Whether you're putting together a fancy romantic getaway or an affordable family break, browse our package deals today.
Can I choose my airline with a South Westshore Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my South Westshore vacation package?
Because we know life can be unpredictable, the answer is yes. To learn more, check out our Customer Service Portal. But generally speaking, if you've booked your South Westshore vacation package in the last 24 hours, you may be able to change or cancel it for free. Your hotel, airline or car rental company may impose a fee if you made your booking a while ago.

Discover the most popular places to visit in South Westshore

Busch Gardens Tampa Bay

Busch Gardens Tampa Bay

Exotic animals and thrill rides all on the one site at this theme park and zoo designed for the whole family.

Busch Gardens Tampa Bay
Tampa_RaymondJamesStadium_503050_03

Raymond James Stadium

Catch an event at Raymond James Stadium during your trip to Tampa. Attend a football game or simply enjoy the top-notch restaurants while you're in the area.

Raymond James Stadium
Tampa Riverwalk

Tampa Riverwalk

Walk, bike or rollerblade along Tampa’s waterside neighborhood, with public art, museums, restaurants and more attractions right on the waterfront.

Tampa Riverwalk

Things to do

The Pirate Ship at John's Pass

Pirate Adventure Cruise - John's Pass

CA $62
per adult
94% of travellers recommend
Pirate Adventure Cruise - John's Pass
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

CA $51
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

CA $51
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
See all activities in Tampa
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.