Bay Pines Vacations from $409

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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.

The Latest Bay Pines Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Zoo House Down Town Tampa

Zoo House Down Town Tampa

2.5 out of 5
Riverbend
Save 100% on your flight
Price was $776, price is now $409 per person
$409
per person
Mar 12 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
2/10 (1 review)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,469, price is now $867 per person
$867
per person
Mar 23 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (4,624 reviews)
Great place a liter expensive for that place

Reviewed on Jan 9, 2026

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $2,978, price is now $1,787 per person
$1,787
per person
Mar 19 - Mar 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,000 reviews)
We were pleasantly surprised with how clean the room was when we arrived and had everything we needed. The walk from our room to the beach was about 4 seconds... perfect.

Reviewed on Jan 10, 2026

The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Downtown Tampa
Save 100% on your flight
Price was $1,271, price is now $769 per person
$769
per person
Mar 28 - Apr 4
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.4/10 Very Good! (2,509 reviews)
I was not able to get breakfast, or even get a coffee. Many patrons walked out after waiting a long time, including myself. The restaurant was only about 75% full, and the wait staff was working exceptionally hard and moving fast but we’re unable to bring out any food and had exceptionally long walks to the back of the building or something. Even for people to get their check to cash out took a long time. I do not know if they’re just understaffed or the cooks were taking forever to get the food out or they had a long walk to even get the food. But I definitely do not recommend going to breakfast there. The rest of the place was OK.

Reviewed on Jan 9, 2026

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $2,380, price is now $1,447 per person
$1,447
per person
Mar 23 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,131 reviews)
Nice place! Will stay again! Had a great NYE!

Reviewed on Jan 8, 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
$322 nightly
The price is $364 total per night from Jan 26 to Jan 27
$364 total
Jan 26 - Jan 27
Total with taxes and fees
9.4/10 Exceptional! (2,978 reviews)
Great stay! Room was clean and bed was comfortable. Walkable to everything in the area. Did not eat at the hotel so can’t comment.

Reviewed on Jan 9, 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
$215 nightly
The price is $242 total per night from Jan 25 to Jan 26
$242 total
Jan 25 - Jan 26
Total with taxes and fees
8/10 Very Good! (2,394 reviews)
Rooms were clean, helpful staff, but the best part the beach!

Reviewed on Jan 9, 2026

Hilton Clearwater Beach Resort & Spa
Ramada by Wyndham Tampa Westshore Airport South

Ramada by Wyndham Tampa Westshore Airport South

3 out of 5
1200 N Westshore Blvd Tampa FL
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $91 total per night from Feb 8 to Feb 9
$91 total
Feb 8 - Feb 9
Total with taxes and fees
6.2/10 (3,782 reviews)
Affordable. Sometimes a bit noisy from the road. Room a tad “rough around the edges”

Reviewed on Jan 6, 2026

Ramada by Wyndham Tampa Westshore Airport South
See all 14,891 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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Bay Pines

Bay Pines VA Medical Center which includes signage

Bay Pines VA Medical Center

Though Bay Pines VA Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Madeira Beach while you are here.

Bay Pines VA Medical Center
John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

You can do some window-shopping at John's Pass Village & Boardwalk during your stay in Madeira Beach. Stroll along the seaside in this family-friendly area, or check out its top-notch restaurants.

John's Pass Village & Boardwalk
Beach Walk featuring a sandy beach

St. Petersburg - Clearwater Beaches

Why not spend a lazy afternoon at St. Petersburg - Clearwater Beaches during your trip to St. Petersburg - Clearwater?

St. Petersburg - Clearwater Beaches

Things to do

Dolphin Watching Nature Cruise and Eco Tour from Hubbard's Marina in John's Pass

Dolphin Watching Nature Cruise and Eco Tour from Hubbard's Marina in John's Pass

$29
per adult
100% of travellers recommend
Dolphin Watching Nature Cruise and Eco Tour from Hubbard's Marina in John's Pass
Madeira Beach: Pirate Adventure Cruise

Madeira Beach: Pirate Adventure Cruise

$45
per adult
100% of travellers recommend
Madeira Beach: Pirate Adventure Cruise
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key

St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key

$67
per adult
100% of travellers recommend
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key
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.