Bay Pines Vacations from $398

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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.
Hampton Inn Sarasota - I-75 Bee Ridge

Hampton Inn Sarasota - I-75 Bee Ridge

2.5 out of 5
Save 100% on your flight
Price was $766, price is now $398 per person
$398
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (317 reviews)
Inside room very frayed carpeting in room going from entryway to bedroom. Other than that everything is good.

Reviewed on Nov 28, 2025

Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $835, price is now $440 per person
$440
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.2/10 Very Good! (1,002 reviews)
Staff was very friendly and happy to help. The room was clean. The front area was organized, and plenty of snack items were available to purchase.

Reviewed on Nov 24, 2025

Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
Price was $1,612, price is now $863 per person
$863
per person
Jan 20 - Jan 27
found 17 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
9.4/10 Exceptional! (40 reviews)
Room was a little outdated but very clean, and comfy!

Reviewed on Nov 27, 2025

Holiday Inn Express Lake Wales N-Winter Haven by IHG

Holiday Inn Express Lake Wales N-Winter Haven by IHG

2.5 out of 5
Price was $904, price is now $486 per person
$486
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,002 reviews)
The hotel was very clean. We were rather pleased.. The breakfast choices left something to be desired. The lady's servicingThe breakfast cafe was wonderful.

Reviewed on Nov 28, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,224, price is now $674 per person
$674
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (481 reviews)
Room was great. Reception awesome. Location awesome. However, the washer stopped working middle of night - resulting in our laundry being stuck (door locked, would not release as water error). We couldn't get fixed. By time maintenance got fixed, we had to check out. TO credit, they mailed our laundry to us, but we needed it the for the next 3 days of our vacaction, and didn't have it available.

Reviewed on Nov 26, 2025

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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

DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront

4 out of 5
3050 N Rocky Point Dr W Tampa FL
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $139 total per night from Dec 18 to Dec 19
$139 total
Dec 18 - Dec 19
Total with taxes and fees
8.2/10 Very Good! (1,012 reviews)
Staff was great and friendly facilities where nice and relaxing rooms where clean the only thing I did or know is they charge for parking. Other than that great

Reviewed on Nov 24, 2025

DoubleTree by Hilton Tampa Rocky Point Waterfront
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundable
$151 nightly
The price is $172 total per night from Dec 21 to Dec 22
$172 total
Dec 21 - Dec 22
Total with taxes and fees
8.2/10 Very Good! (1,049 reviews)
Everything as a whole was really good- the only things were us not getting the room we reserved, and parking was a bit of a hassle and cost daily which was unexpected- other than those two things we were super happy with staff and amenities

Reviewed on Nov 22, 2025

The Westin Tampa Bay
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
$206 nightly
The price is $233 total per night from Dec 2 to Dec 3
$233 total
Dec 2 - Dec 3
Total with taxes and fees
9.4/10 Exceptional! (2,823 reviews)
Clean room.

Reviewed on Nov 24, 2025

Wyndham Grand Clearwater Beach
See all 14,822 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 beautiful beaches 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

Stunning view of dolphins in St. Petersburg, Florida

Dolphin Racer Speedboat Adventure

$28
per adult
92% of travellers recommend
Dolphin Racer Speedboat Adventure
View of the StarLite Sapphire Yacht on St. Pete Beach

StarLite Sapphire Evening Yacht St. Pete Beach

$32
per adult
86% of travellers recommend
StarLite Sapphire Evening Yacht St. Pete Beach
Madeira Beach: Pirate Adventure Cruise with Beer and Wine

Madeira Beach: Pirate Adventure Cruise

$45
per adult
100% of travellers recommend
Madeira Beach: Pirate Adventure 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.