Bay Pines Vacations from $519

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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.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $937, price is now $519 per person
$519
per person
Nov 9 - Nov 16
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (59 reviews)
Close to downtown safety harbor, oldsmar and Clearwater, the perfect retreat being close to everything but not in the heart of it all.

Reviewed on May 12, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,027, price is now $550 per person
$550
per person
Dec 10 - Dec 14
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,003 reviews)
It was nice to have a gym available and it was always empty. Shower was my favorite park, really big and open, bed was super comfy. The elevators were outnof order though and the coffee machine in the room didnt work, but over all it was a pretty nice hotel. One of the nicest ive been too.

Reviewed on Oct 4, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $3,030, price is now $1,628 per person
$1,628
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (635 reviews)
The room was great, and the amenities better.

Reviewed on Oct 6, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $4,030, price is now $2,232 per person
$2,232
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (456 reviews)
Clean, quite, nice staff

Reviewed on Oct 6, 2025

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,638, price is now $1,027 per person
$1,027
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,080 reviews)
Roof top bar and pool was a good view cooler then being on street level

Reviewed on Oct 6, 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

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 Oct 14 to Oct 15
$242 total
Oct 14 - Oct 15
Total with taxes and fees
8/10 Very Good! (2,226 reviews)
"All Great!"

Reviewed on Oct 5, 2025

Hilton Clearwater Beach Resort & Spa
Hilton St. Petersburg Bayfront

Hilton St. Petersburg Bayfront

4 out of 5
333 1st St S, St. Petersburg, FL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $120 total per night from Oct 12 to Oct 13
$120 total
Oct 12 - Oct 13
Total with taxes and fees
7.6/10 Good! (1,000 reviews)
"This Hilton is conveniently located, the pool was lovely and the staff was nice. The room needed some renovation and the double beds were not of usual Hilton comfort. There were 2 beds of different height and the dresser drawers seemed to be painted over in white. Also, there was no complimentary ..."

Reviewed on Sep 30, 2025

Hilton St. Petersburg Bayfront
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
$287 nightly
The price is $324 total per night from Oct 31 to Nov 1
$324 total
Oct 31 - Nov 1
Total with taxes and fees
9.4/10 Exceptional! (2,704 reviews)
"We enjoyed the property and closeness to the beach. Restaurants were walkable. Pool bar food could be upgraded but found the remainder of the dinning options suitable. We had a great time and would recommend."

Reviewed on Oct 7, 2025

Wyndham Grand Clearwater Beach
See all 14,670 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)

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.

John's Pass Village & Boardwalk
Clearwater Beach

Clearwater Beach

4.5/5(44 reviews)

Why not spend a lazy afternoon at Clearwater Beach during your trip to Clearwater Beach? Wander the clear-water beaches or discover the area's beautiful sunsets.

Clearwater Beach

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

$42
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.