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
Price was CA $1,252, price is now CA $801 per person
CA $801
per person
May 10 - May 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (1,001 reviews)
The ladies at the front desk were super! Tiffany & Julie ❣️ Housekeeping was wonderful. The hotel was nice, bed was comfortable, location was convenient. Shuttle a plus although I wish they had offered initially to pick us up from the airport we Ubered not knowing. The keys kept getting deactivated multiple times which was a bit annoying. Probably 4x and we were here less than a week. Beach items were very poorly kept, chairs rusty, broken, umbrellas the same. Wish they had a better selection and beach wagons would be amazing to put it all in. Wish there was more staff at the restaurant/bar area. Overall great stay!

Reviewed on Feb 19, 2026

Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was CA $1,295, price is now CA $809 per person
CA $809
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (60 reviews)
Older property but very well maintained. It was clean and had everything we needed for our stay. Great communication with the host.

Reviewed on Feb 10, 2026

The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Central Sarasota
Price was CA $1,304, price is now CA $835 per person
CA $835
per person
May 10 - May 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.2/10 Very Good! (515 reviews)
All of those and the wonderful, helpful staff

Reviewed on Feb 19, 2026

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

3 out of 5
Town 'n' Country
Price was CA $1,855, price is now CA $1,189 per person
CA $1,189
per person
Apr 14 - Apr 21
found 16 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Tampa (TPA)
2/10 (4 reviews)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Price was CA $1,641, price is now CA $1,062 per person
CA $1,062
per person
May 10 - May 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,131 reviews)
Clean rooms great staff smells great

Reviewed on Feb 8, 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 featuring outdoor art

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
9.2/10 Wonderful! (3,028 reviews)
The hotel, staff, room was amazing!

Reviewed on Feb 18, 2026

Get rates
Wyndham Grand Clearwater Beach
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
6000 Gulf Blvd St. Pete Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $315 per night from Feb 24 to Feb 25
CA $315
CA $441 total
Feb 24 - Feb 25
includes taxes & fees
8.2/10 Very Good! (1,637 reviews)
The staff was friendly and helpful. The room was worn and dated - cracked bathroom floor, leaky bathroom sink faucet, low sh. ower pressure, dusty couch with very worn arms. Food/drinks are very expensive. Many amenities worn and broken.

Reviewed on Feb 17, 2026

RumFish Beach at TradeWinds
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
The price is CA $278 per night from Mar 8 to Mar 9
CA $278
CA $315 total
Mar 8 - Mar 9
includes taxes & fees
8.4/10 Very Good! (1,134 reviews)
Amazing experience!! Thank you!

Reviewed on Feb 16, 2026

The Westin Tampa Bay
See all 17,605 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 $801, 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

Florida. Madeira Beach Florida. Gulf of Mexico or ocean beach, Hotels and Resorts. John's Pass Village and Boardwalk. Turquoise color of salt water. American shore. Summer or Autumn vacation.

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 marina in this family-friendly area, or check out its top-notch restaurants.

John's Pass Village & Boardwalk
White sand and palm trees in Clearwater beach

Clearwater Beach

4.5/5(5 reviews)

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
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

The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

CA $50
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
The Tropics Boat at Sunset

Sunset Celebration Cruise on Tropics Boat Tours

CA $51
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
Picture 4 for Activity Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

CA $75
per adult
100% of travellers recommend
Bradenton: Anna Maria Island Guided Kayaking Manatee Tour
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.