Historic Uptown Vacation Packages

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Top Holiday Package Deals in Historic Uptown

Price found within the past 48 hours. Click for updated prices.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.2/10 Wonderful! (1,008 reviews)
The location was great so close to everything

Reviewed on Jul. 15, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Aug 24 - Aug 31
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (518 reviews)
The suite was very clean, spacious, and stocked with all we needed. The property is well maintained. We enjoyed our suite and the views from the balcony and the roof top. The beach is so beautiful. Front desk staff very knowledgeable and polite.

Reviewed on Jul. 17, 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
per person
Aug 24 - Aug 31
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (1,040 reviews)
Wonderful reception

Reviewed on Jul. 14, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Oct 9 - Oct 13
found 16 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Tampa (TPA)
9.4/10 Exceptional! (430 reviews)
Beautiful property I would highly recommend this place to anyone looking for clean,friendly,convenience with a beautiful view.

Reviewed on Jul. 10, 2025

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9/10 Wonderful! (1,025 reviews)
The staff at the front desk and at the pool were very pleasant and attentive. Parking Was expensive in my opinion, but the guys and girls would run around and get your car when you needed. Valet only. No microwave to heat anything up even though it’s always hot in Florida.

Reviewed on Jul. 17, 2025

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
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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 hotels in Pass-a-Grille

Historic Uptown Hotel Deals

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 $255 per night from Aug 12 to Aug 13
CA $255
CA $342 total
Aug 12 - Aug 13
includes taxes & fees
8/10 Very Good! (2,019 reviews)
Great
"We had a great time here. The only negative was the rooms weren’t updated, laminate floor will be much better than the old carpets that were in the room. The bed was super comfortable though overall we had a great stay. The staff was great. The beach and the pool. Everything was wonderful."

Reviewed on Jul. 15, 2025

Hilton Clearwater Beach Resort & Spa
The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
4860 West Kennedy Boulevard, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Aug 18 to Aug 19
CA $191
CA $217 total
Aug 18 - Aug 19
includes taxes & fees
8.6/10 Excellent! (1,657 reviews)
"Nice overnight stay! Super comfortable"

Reviewed on Jul. 12, 2025

The Westshore Grand, A Tribute Portfolio Hotel, Tampa
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 $377 per night from Aug 17 to Aug 18
CA $377
CA $480 total
Aug 17 - Aug 18
includes taxes & fees
9.2/10 Wonderful! (2,384 reviews)
"Great hotel in a prime position with most things in walking distance. Room was large and clean. Guests were a mixture of families and couples. Daily service charge high, but same for most similar hotels and unfortunately valet only which is also a high daily rate. That said, we walked most places ..."

Reviewed on Jul. 17, 2025

Wyndham Grand Clearwater Beach
See all 16,779 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 $516, 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

John's Pass Village & Boardwalk

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

John's Pass Village & Boardwalk
Fort De Soto Park which includes a sandy beach

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
Tropicana Field

Tropicana Field

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

Tropicana Field

Things to do

The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

CA $44
per adult
88% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

CA $51
per adult
94% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
Sea Screamer boat in Orlando

Day Trip to Clearwater Beach with Sea Screamer Ride

CA $171
per adult
90% of travellers recommend
Day Trip to Clearwater Beach with Sea Screamer Ride
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.