Bay Pines Vacation Packages

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Your Bay Pines Vacation

Unforgettable adventures await when you book a Bay Pines vacation package. Whether you're a foodie, history enthusiast or just a traveler who appreciates new places, there's something for everyone in this awesome city. Johns Pass Village & Boardwalk, St. Petersburg - Clearwater Beaches and Upham Beach are just some of the many attractions worth exploring during your trip to Bay Pines. Expedia will help you escape your daily routine. Tailor your vacation to Bay Pines to suit your travel style, whatever that may look like.

Top Holiday Package Deals in Bay Pines

Price found within the past 48 hours. Click for updated prices.
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Downtown Tampa
Price was CA $1,675, price is now CA $1,065 per person
CA $1,065
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (2,549 reviews)
Had no complaints on anything

Reviewed on Apr 16, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $2,939, price is now CA $1,759 per person
CA $1,759
per person
Jun 22 - Jun 29
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (889 reviews)
Beach was a walk but phenomenal spot

Reviewed on Apr 15, 2026

Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Downtown Tampa
Price was CA $1,985, price is now CA $1,292 per person
CA $1,292
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
7/10 Good! (1,839 reviews)
The property is being renovated so there are very limited amenities. The staff are super helpful, friendly and professional. We stayed in a building adjacent to the building where the reception is. The building was old and obviously in need of an upgrade but room and bathroom were clean. Location on the River Walk is super.

Reviewed on Apr 16, 2026

Delray House With Hot tub & Game Room

Delray House With Hot tub & Game Room

3.5 out of 5
Palm River-Clair Mel
Price was CA $1,931, price is now CA $1,267 per person
CA $1,267
per person
Jun 22 - Jun 29
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
2/10 (3 reviews)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Price was CA $2,229, price is now CA $1,470 per person
CA $1,470
per person
Jun 22 - Jun 29
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,005 reviews)
Beautiful beach friendly staff, rooms were perfect for a family

Reviewed on Apr 9, 2026

Where to stay in Bay Pines

Find the best Bay Pines areas and neighborhoods for the activities you enjoy most. Learn more about Bay Pines
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

Bay Pines Hotel Deals

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 $208 per night from May 11 to May 12
CA $208
CA $321 total
May 11 - May 12
includes taxes & fees
8.2/10 Very Good! (1,812 reviews)
Had a two night stay with friends… the beach is perfect and enjoyed umbrellas and chairs provided by the resort. Bars were on point and attended to me quickly. Room was spacious and well done and clean. The only negative thing I can say is we had thunder feet above us on the 2nd floor.

Reviewed on Apr 16, 2026

RumFish Beach at TradeWinds
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 $444 per night from Apr 20 to Apr 21
CA $444
CA $555 total
Apr 20 - Apr 21
includes taxes & fees
9.4/10 Exceptional! (3,163 reviews)
What a beautiful hotel right across the street from the beach and within walking distance to everything!! Our room was clean and modern and the hotel staff were very nice.

Reviewed on Apr 16, 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 $364 per night from May 10 to May 11
CA $364
CA $466 total
May 10 - May 11
includes taxes & fees
8.2/10 Very Good! (2,546 reviews)
This property needs TLC the furniture in room was old and falling apart. The beds were neat and clean. You have to pay to use the beach chairs and umbrellas on the beach… The pool was nice.

Reviewed on Apr 16, 2026

Hilton Clearwater Beach Resort & Spa
See all 15,187 properties in Bay Pines
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 Bay Pines vacation package cost?
Handcraft your Bay Pines package from as little as CA $1,065. Choose from any combination of rental cars, flights and hotels to create the getaway you've long been dreaming about. Remember to add on a few activities!
How do I get a cheap travel package to Bay Pines?
It's easy. Just bundle everything together. Hotels, flights and rental cars — combine whatever you need into a Bay Pines vacation package to save tons of cash. Score even bigger bargains when you add extras such as experiences or tours to your booking. But that's not the only good part. You have the flexibility to put together your trip your own way. We offer over 550 air carriers and 1,000,000 hotels in all corners of the globe, so that everyone has an opportunity to travel and fulfill those vacation dreams.
Where should I stay in Bay Pines?
A vacation in Bay Pines isn't complete without paying a visit to Johns Pass Village & Boardwalk, Bay Pines VA Medical Center and St. Petersburg Municipal Beach. Stay close to these popular sights and make sightseeing easy.
How far in advance should I book my Bay Pines vacation?
To score discount prices, book early. Airlines typically release flight tickets, along with some of the lowest fares, up to a year prior to departure. Hotels, experiences and car rental should also be booked early to avoid disappointment. If you've decided on a last-minute getaway to Bay Pines, there are always plenty of great deals to be had on Expedia. Book your escape today!
What does an Expedia Bay Pines travel package include?
Flights, rental cars and hotels, or any combination of the three — you decide! Whether you're venturing to Bay Pines with the kids or traveling with your friends, there's a bundle to suit every style and budget. Once you've made your booking, why not add on a couple of tours as well?
What should I know before booking a Bay Pines travel package?
Tailor deals to suit your budget with an Expedia package. Hotels, flights, rental cars — we have everything you need to plan your escape. You'll save a packet just for bundling your bookings. Whether you're taking off on a ski adventure or drinking cocktails on a beach, your dream vacation is just clicks away.
Can I choose my airline with a Bay Pines Expedia vacation package?
Most definitely. Expedia has over 550 partner airlines to choose from worldwide. With such a big range of choice, finding the ideal carrier to bring you to Bay Pines will be a cinch.
If I'm not able to travel, can I cancel my Bay Pines vacation package?
Yes, you can. We realize things don't always go to plan, so we're here to help if you need to make changes to your Bay Pines vacation package. It may be possible to change or cancel your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for more information. Also, check your itinerary for the nitty-gritty on change fees.

Discover the most popular places to visit in Bay Pines

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

4.5/5(141 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 lively bars.

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
Fort De Soto Park

Fort De Soto Park

4.5/5(28 reviews)

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
Shell Key Island bird's eye view

Shell Key Island Excursion

CA $88
per adult
84% of travellers recommend
Shell Key Island Excursion
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.