Bay Pines Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 Westin Sarasota
Central Sarasota
CA $1,177
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Tampa (TPA)
9/10 Wonderful! (1,151 reviews)
My only gripe was the lack of an ocean view, had a view of the harbor/bay, which wasn’t bad, but was hoping for more
Reviewed on Aug 14, 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
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.
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.
Sand Key
1 out of top 10 points of interest in this area
While visiting Sand Key, you might make a stop by sights like St. Petersburg - Clearwater Beaches and Sand Key Park.
Sunset Beach
Sunset Beach is noteworthy for its beaches, and you can make a stop at top attractions like St. Petersburg - Clearwater Beaches and Sunset Beach.
Don Cesar
Don Cesar might not have many top sights, but Splash Island Water Park and Pass-a-Grille Beach are two attractions nearby that you can check out.
Bay Pines Hotel Deals
Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
CA $290
CA $383 total
Aug 23 - Aug 24
includes taxes & fees
The Westin Tampa Bay
7627 W Courtney Campbell Cswy Tampa FL
CA $199
CA $226 total
Aug 31 - Sep 1
includes taxes & fees
Hilton Clearwater Beach Resort & Spa
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
CA $226
CA $311 total
Aug 23 - Aug 24
includes taxes & fees
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.
Frequently asked questions
How much does a Bay Pines vacation package cost?
Handcraft your Bay Pines package from as little as CA $858. 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.
Stay near popular Bay Pines attractions
War Veteran Memorial Park
8.0/10 (50 reviews)
After visiting War Veteran Memorial Park, make a plan to see the other sights and activities in Madeira Beach. Amble around this family-friendly area's beautiful beaches or experience its great live music.
Things to do
Dolphin Racer Speedboat Adventure
CA $51
per adult
94% of travellers recommend
Starlite Horizon Evening Yacht St. Pete Beach
CA $57
per adult
88% of travellers recommend
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key
CA $109
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.