Historic Uptown Vacation Packages

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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

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Top Holiday Package Deals in Historic Uptown

Price found within the past 48 hours. Click for updated prices.
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 14 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

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $2,513, price is now CA $1,524 per person
CA $1,524
per person
Sep 9 - Sep 16
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (526 reviews)
Beautiful facility. Perfect for families close to all the beaches and fun. Can't wait to return for our next visit!

Reviewed on Jun 18, 2026

CW Hotel

CW Hotel

4 out of 5
Price was CA $1,785, price is now CA $1,145 per person
CA $1,145
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
No reviews
The Don CeSar

The Don CeSar

4 out of 5
Price was CA $2,367, price is now CA $1,582 per person
CA $1,582
per person
Aug 29 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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

Driftwood at Anna Maria Island Inn

Driftwood at Anna Maria Island Inn

3 out of 5
Price was CA $2,300, price is now CA $1,614 per person
CA $1,614
per person
Jul 23 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.4/10 Very Good! (122 reviews)
Me gustó todo muy buena atención limpio , agradable todo súper

Reviewed on Jun 15, 2026

Where to stay in Historic Uptown

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

Pass-a-Grille

1 out of top 10 points of interest in this area

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

Historic Uptown 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 9 to Jul 10
CA $367
CA $471 total
Jul 9 - Jul 10
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 17,906 properties in Historic Uptown
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
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Frequently asked questions

How much does a Historic Uptown vacation package cost?
Our Historic Uptown packages, which start at just CA $1,051, are the perfect way to save big bucks. Pick and choose your preferred flights, hotels and rental cars to create your dream escape.
How do I get a cheap travel package to Historic Uptown?
Just imagine all the fun things you could do in Historic Uptown with extra cash in your wallet. Watch your savings stack up when you bundle your hotel and airfare bookings into a Historic Uptown vacation package. You have plenty of choice when you book with Expedia too. In fact, you can select from over 550 airlines and 1,000,000 hotels around the globe. Whether you're vacationing with the whole family or flying solo, exploring Historic Uptown is better with a package.
Where should I stay in Historic Uptown?
A journey to Historic Uptown isn't over until you've seen Salvador Dali Museum and Tropicana Field. Reserve a room close by for quick access to these popular attractions.
What are the top hotels in Historic Uptown?
Reserve a room at Stylish Centrally Located 3bedroom Close To The Beach. It's one of this neighborhood's most popular properties. Another reputable option in Historic Uptown is La Casa Azul Located Minutes From Dt St Petersburg.
How far in advance should I book my Historic Uptown vacation?
Smart travelers will likely want to reserve their seats early. You can usually compare international airfares on Expedia up to 12 months before your intended flight. If you're purchasing your ticket at the last minute, there's no need to worry. Bargain prices sometimes become available in the last weeks before departure.
What does an Expedia Historic Uptown travel package include?
With Expedia, you can choose a combination of car rentals, flights and hotels to create your ideal Historic Uptown package. Once you've made your booking, you can add on all the fun stuff like sightseeing tours and activities. Don't forget — the more you bundle, the more deals you'll score!
What should I know before booking a Historic Uptown travel package?
Whether it's relaxation or adventure you're chasing, a Historic Uptown vacation package lets you plan your escape your way. Plus, you'll score great discounts just for combining your hotel with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Historic Uptown Expedia vacation package?
With a vacation package, you're the one in charge. Whether you're eager to fly to Historic Uptown in coach or business class, simply choose from the available airline options. Expedia has access to over 550 partner airlines worldwide.
If I'm not able to travel, can I cancel my Historic Uptown vacation package?
If your vacation plans in Historic Uptown have been upended, it's good to know that it is possible to cancel or amend your booking. If you made your booking less than 24 hours ago, you may be eligible to receive a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose fees. To find out more, visit our Customer Service Portal.

Stay near popular Historic Uptown attractions

NOVA 535 Unique Event Space

You can get tickets for a performance at NOVA 535 Unique Event Space during your trip to St. Petersburg. Attend a baseball game or simply enjoy the top-notch restaurants while you're in the area.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.