Greater Pinellas Point Vacation Packages

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    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 Greater Pinellas Point

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 24 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 17 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 Greater Pinellas Point

Find the best Greater Pinellas Point areas and neighborhoods for the activities you enjoy most. Learn more about Greater Pinellas Point
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

Greater Pinellas Point Hotel Deals

SkyBeach Resort

SkyBeach Resort

4 out of 5
6800 Sunshine Skyway Lane St. Petersburg FL
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Jun 30 to Jul 1
CA $186
CA $282 total
Jun 30 - Jul 1
includes taxes & fees
8.6/10 Excellent! (763 reviews)
"Good location, beachfront was good except for sea weed"

Reviewed on Jun 17, 2026

SkyBeach Resort
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
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Jun 30 to Jul 1
CA $217
CA $284 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (2,266 reviews)
"My complaint is they start cleaning at 830 am and, when you are trying to rest that is no good,you ask for coffee or other things oh we don't have any more, no microwave you can use and charge you 25 dollars for service fee per day but is not there when you do your reservation."

Reviewed on Jun 18, 2026

Compass Hotel by Margaritaville Anna Maria Sound
See all 18,694 properties in Greater Pinellas Point
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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Family Vacations

Frequently asked questions

How much does a Greater Pinellas Point vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Greater Pinellas Point from just CA $960. And the more you bundle, the more money you save. The vacation of your dreams has never been so affordable.
How do I get a cheap travel package to Greater Pinellas Point?
Combining your hotel and flight with Expedia won't just save you time — it'll save you dollars too. A Greater Pinellas Point vacation package makes it simple to create your perfect trip. With more than 550 airlines across the world to select from, finding convenient flights that fit your schedule won't be a hassle. On top of that, we have over 1,000,000 properties globally to take your pick of. Now that's what we call choice. No matter who you are, Expedia brings the world within your reach.
Where should I stay in Greater Pinellas Point?
Visitors come from near and far to see Salvador Dali Museum and Tropicana Field in Greater Pinellas Point. Book yourself a room near these awesome attractions and visit them whenever you want.
What are the top hotels in Greater Pinellas Point?
The Wave Unit 517 - 1 Bedroom Condo and Great Location With Heated Pool With Beautiful Outdoor Patio are among the most sought-after hotels in Greater Pinellas Point. Why not look up the amenities and rates at each and then make a decision?
How far in advance should I book my Greater Pinellas Point vacation?
Browse Expedia to compare airfares as early as possible. In most cases, you can purchase a ticket up to 12 months before departure. If you can't find your preferred air carrier, or you're booking late, fear not. Cheap tickets to Greater Pinellas Point sometimes occur a few weeks before departure.
What does an Expedia Greater Pinellas Point travel package include?
Hotels, rental cars and flights, or any combination of them — the choice is yours. Whether you're exploring Greater Pinellas Point with the kids or traveling with your friends, there's a package to suit every budget and style. Once you've made your booking, why not add on some tours as well?
What should I know before booking a Greater Pinellas Point travel package?
So many places to travel to, so many things to experience. With a travel package, you'll be able to afford more of them. Bundle your flights, hotels and rental cars and make big savings.
Can I choose my airline with a Greater Pinellas Point Expedia vacation package?
Yes, the choice is yours. We offer more than 550 airlines globally, so you can design your Greater Pinellas Point escape according to your budget and style.
If I'm not able to travel, can I cancel my Greater Pinellas Point vacation package?
It's impossible to predict what the future holds, so it's good to know that you can cancel or change your Greater Pinellas Point vacation package. If you booked in the last 24 hours, you may be eligible for a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

Discover the most popular places to visit in Greater Pinellas Point

A coastal cityscape with a prominent waterfront, a bridge, and a distinctive building with a red facade.

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
Aerial sunset view of Clearwater beach and Sand key in Western Florida on the Mexican Gulf coast with vacation homes, hotels and bridges connecting

Clearwater Beach

Nothing says vacation like spending a carefree day at Clearwater Beach, a popular beach in 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

Stunning view of dolphins in St. Petersburg, Florida

Dolphin Racer Speedboat Adventure

CA $50
per adult
94% of travellers recommend
Dolphin Racer Speedboat Adventure
View of the StarLite Sapphire Yacht on St. Pete Beach

StarLite Sapphire Evening Yacht St. Pete Beach

CA $56
per adult
90% of travellers recommend
StarLite Sapphire Evening Yacht St. Pete Beach
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
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.