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.
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 $1,425, price is now CA $663 per person
CA $663
per person
Apr 21 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
2/10 (2 reviews)
Family Home Tampa

Family Home Tampa

2 out of 5
Forest Hills
Price was CA $1,676, price is now CA $1,013 per person
CA $1,013
per person
Mar 23 - Mar 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
7.6/10 Good! (4 reviews)
The Don CeSar

The Don CeSar

4 out of 5
Price was CA $4,584, price is now CA $2,858 per person
CA $2,858
per person
Apr 24 - Apr 30
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9/10 Wonderful! (1,044 reviews)
Generally we lined the hotel. Room was nice, staff were terrific. The only issues were the room not entirely clean as toys were left behind in the floor and our second night there was a lot of noise from all the people partying - hard to sleep for an early flight.

Reviewed on Feb 6, 2026

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Price was CA $1,076, price is now CA $677 per person
CA $677
per person
May 3 - May 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (1,001 reviews)
The heat was not easy to get but the staff tried to help. Also the toilet was making a noise. And carpet between the beds was dirty.

Reviewed on Feb 10, 2026

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was CA $3,195, price is now CA $2,089 per person
CA $2,089
per person
Apr 5 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Tampa (TPA)
9.2/10 Wonderful! (1,097 reviews)
Rooms were clean, staff was good.

Reviewed on Feb 12, 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 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

Bay Pines 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 $456 per night from Feb 16 to Feb 17
CA $456
CA $569 total
Feb 16 - Feb 17
includes taxes & fees
9.2/10 Wonderful! (3,031 reviews)
We had an amazing stay at the Wyndham Grand Clearwater Beach. The hotel was super clean, the rooms were comfortable, and the location was perfect — literally right by the beach and close to everything. The staff was friendly and helpful the whole time, check-in was easy, and the atmosphere felt upscale ...

Reviewed on Feb 7, 2026

Wyndham Grand Clearwater Beach
Ramada by Wyndham Tampa Westshore Airport South

Ramada by Wyndham Tampa Westshore Airport South

3 out of 5
1200 N Westshore Blvd Tampa FL
The price is CA $100 per night from Mar 8 to Mar 9
CA $100
CA $114 total
Mar 8 - Mar 9
includes taxes & fees
6.2/10 (3,915 reviews)
Clean, comfortable room. Staff friendly and helpful.

Reviewed on Feb 7, 2026

Ramada by Wyndham Tampa Westshore Airport South
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 $334 per night from Feb 16 to Feb 17
CA $334
CA $461 total
Feb 16 - Feb 17
includes taxes & fees
8.2/10 Very Good! (1,625 reviews)
Amazing!

Reviewed on Feb 11, 2026

RumFish Beach at TradeWinds
See all 14,941 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 $663. 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

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
Fort De Soto Park which includes a sandy beach

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
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

Things to do

Stunning view of dolphins in St. Petersburg, Florida

Dolphin Racer Speedboat Adventure

CA $49
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
Aerial view of Calypso Breeze Cruise in Florida

Calypso Breeze Tropical Party Buffet Cruise

CA $98
per adult
88% of travellers recommend
Calypso Breeze Tropical Party Buffet Cruise
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.