Bay Pines Holidays

Book a Hotel + Flight or Car together to unlock savings

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
Pass-a-Grille

Pass-a-Grille

1 out of top 10 points of interest in this area
5/5(3 area reviews)

Pass-a-Grille is popular for its beaches, and if you're looking for more to see and do, you might think about a trip to Pass-a-Grille Beach or St. Petersburg - Clearwater Beaches.

Find hotels in Pass-a-Grille

Top hotels in Bay Pines

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 4.479.073 ₫ per night from 16 Apr to 17 Apr
4.479.073 ₫
6.697.887 ₫ total
16 Apr - 17 Apr
includes taxes & fees
8.2/10 Very Good! (1,776 reviews)
Clean, excellent service , safe and kid friendly!

Reviewed on 8 Apr 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 9.378.142 ₫ per night from 10 May to 11 May
9.378.142 ₫
11.638.731 ₫ total
10 May - 11 May
includes taxes & fees
9.4/10 Exceptional! (3,128 reviews)
Very clean room

Reviewed on 8 Apr 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 6.793.393 ₫ per night from 7 May to 8 May
6.793.393 ₫
8.717.999 ₫ total
7 May - 8 May
includes taxes & fees
8.2/10 Very Good! (2,528 reviews)
Our bathroom wasnt clean.

Reviewed on 8 Apr 2026

Hilton Clearwater Beach Resort & Spa
See all 15,120 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.

Frequently asked questions

How much does a Bay Pines holiday package cost?
Handcraft your Bay Pines package from as little as . 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 holiday 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 1null000null000 hotels in all corners of the globe, so that everyone has an opportunity to travel and fulfil those holiday dreams.
Where should I stay in Bay Pines?
A holiday in Bay Pines isn't complete without paying a visit to Johns Pass Village & Boardwalk, Bay Pines VA Medical Centre 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 holiday?
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 travelling 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 holiday is just clicks away.
Can I choose my airline with a Bay Pines Expedia holiday 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 holiday package?
Yes, you can. We realise things don't always go to plan, so we're here to help if you need to make changes to your Bay Pines holiday 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.

Popular places to visit

Bay Pines VA Medical Center

Bay Pines VA Medical Center

If Bay Pines VA Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Madeira Beach.

Bay Pines VA Medical Center
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(34 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 visit its lively bars.

John's Pass Village & Boardwalk
Vinoy Park

Vinoy Park

After visiting Vinoy Park, make a plan to see the other sights and activities in St. Petersburg. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Vinoy Park