Bay Pines Vacations from $364

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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.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Save 100% on your flight
Price was $713, price is now $364 per person
$364
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
No reviews
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $2,383, price is now $1,387 per person
$1,387
per person
Feb 21 - Feb 28
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,000 reviews)
This place was a great surprise ! So friendly so helpful ! Great location and rooms super clean . Tons of amenities too! Will definitely stay again

Reviewed on Dec 8, 2025

Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $634, price is now $370 per person
$370
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (60 reviews)
room was very good clean and comfortable

Reviewed on Dec 7, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,843, price is now $1,097 per person
$1,097
per person
Mar 9 - Mar 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (481 reviews)
Is excellent hotel. I recommend

Reviewed on Dec 9, 2025

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
$255 nightly
The price is $288 total per night from Jan 4 to Jan 5
$288 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.4/10 Exceptional! (2,874 reviews)
Yes

Reviewed on Dec 8, 2025

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
$174 nightly
The price is $196 total per night from Dec 21 to Dec 22
$196 total
Dec 21 - Dec 22
Total with taxes and fees
8/10 Very Good! (2,351 reviews)
All good

Reviewed on Dec 11, 2025

Hilton Clearwater Beach Resort & Spa
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
5303 W Kennedy Blvd Tampa FL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $157 total per night from Dec 21 to Dec 22
$157 total
Dec 21 - Dec 22
Total with taxes and fees
8.6/10 Excellent! (2,424 reviews)
Excellent customer service. Great shuttle bus service.

Reviewed on Dec 8, 2025

Hotel Alba, Tapestry Collection by Hilton
See all 14,863 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

4.5/5(17 reviews)

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

4.5/5(1,625 reviews)

You can do some window-shopping at John's Pass Village & Boardwalk during your stay in Madeira Beach. Stroll along the marina 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

5/5(5 reviews)

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

View of the StarLite Sapphire Yacht on St. Pete Beach

StarLite Sapphire Evening Yacht St. Pete Beach

$32
per adult
90% of travellers recommend
StarLite Sapphire Evening Yacht St. Pete Beach
Stunning view of dolphins in St. Petersburg, Florida

Dolphin Racer Speedboat Adventure

$28
per adult
94% of travellers recommend
Dolphin Racer Speedboat Adventure
Dolphin Shelling Snorkeling Cruise, Shell-Sanddollar key III

Dolphin Shelling Snorkeling Cruise, Shell-Sanddollar key

$52
per traveler
94% of travellers recommend
Dolphin Shelling Snorkeling Cruise, Shell-Sanddollar 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.