Historic Uptown Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Historic Uptown

Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was CA $1,620, price is now CA $1,057 per person
CA $1,057
per person
Jun 27 - Jul 3
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (906 reviews)
Cool, family friendly hotel close to almost everything at Clearwater Beach

Reviewed on Apr 19, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $3,201, price is now CA $1,953 per person
CA $1,953
per person
May 30 - Jun 6
found 1 hour ago
Roundtrip non-stop flight included
Halifax (YHZ) to Tampa (TPA)
9.6/10 Exceptional! (889 reviews)
Our room was clean and beautiful! We loved the beach view. The staff was helpful, friendly and incredibly accommodating. We will definitely be back!

Reviewed on Apr 18, 2026

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Price was CA $2,259, price is now CA $1,501 per person
CA $1,501
per person
Jun 22 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,005 reviews)
Second time here! Room was clean, replacement items were quick to receive. Room was able to hold temperature well. All amenities were utilized and nice. We spent a large majority of our time on the beach and found literally dozens of sand dollars. We went swimming in the pool and utilized the fishing poles to catch some fish -- caught 2 fish and saw a manatee!

Reviewed on Apr 18, 2026

Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
Price was CA $2,269, price is now CA $1,537 per person
CA $1,537
per person
Jun 22 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
7.6/10 Good! (1,074 reviews)
Lots of activities for kids.

Reviewed on Apr 19, 2026

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Price was CA $2,752, price is now CA $1,873 per person
CA $1,873
per person
Jun 22 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (3,155 reviews)
Pool always a fun place to meet and visit with new people!

Reviewed on Apr 19, 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
Downtown St. Petersburg

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

Historic Uptown 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 CA $310 per night from Apr 22 to Apr 23
CA $310
CA $404 total
Apr 22 - Apr 23
includes taxes & fees
9.4/10 Exceptional! (3,175 reviews)
Pool always a fun place to meet and visit with new people!

Reviewed on Apr 19, 2026

Wyndham Grand Clearwater Beach
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
200 N Ashley Dr Tampa FL
Fully refundableReserve now, pay when you stay
The price is CA $196 per night from May 3 to May 4
CA $196
CA $225 total
May 3 - May 4
includes taxes & fees
7/10 Good! (1,845 reviews)
No useful comments are merited. The staff was helpful but the facility was not worth the price

Reviewed on Apr 17, 2026

Hotel Tampa Riverwalk
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 $273 per night from May 3 to May 4
CA $273
CA $363 total
May 3 - May 4
includes taxes & fees
Hilton Clearwater Beach Resort & Spa
See all 17,842 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
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Historic Uptown vacation package cost?
Our Historic Uptown packages, which start at just CA $1,057, 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.

Discover the most popular places to visit in Historic Uptown

Aerial view of the pink-tinged waters reflecting the vibrant sunset hues next to the John's Pass Village & Boardwalk, Treasure Island, Florida, United States.

John's Pass Village & Boardwalk

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
White sand and palm trees in Clearwater beach

Clearwater Beach

Why not spend a lazy afternoon at Clearwater Beach during your trip to Clearwater Beach? Wander the clear-water beaches or discover the area's beautiful sunsets.

Clearwater Beach
Fort De Soto Park

Fort De Soto Park

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

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
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
The Pirate Ship at John's Pass

Pirate Adventure Cruise - John's Pass

CA $62
per adult
100% of travellers recommend
Pirate Adventure Cruise - John's Pass
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.