Bay Pines Vacations from $513

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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 $935, price is now $513 per person
$513
per person
Apr 30 - May 6
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (60 reviews)
Staff was very responsive although we did not meet in person. Very old but clean Florida Motel which is all we needed for the night and the price was good!

Reviewed on Feb 26, 2026

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,204, price is now $743 per person
$743
per person
Apr 30 - May 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,131 reviews)
Clean rooms great staff smells great

Reviewed on Feb 8, 2026

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $1,472, price is now $931 per person
$931
per person
Apr 30 - May 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,000 reviews)
The room was clean, and the staff were so nice and helpful!

Reviewed on Feb 20, 2026

The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,792, price is now $1,193 per person
$1,193
per person
Mar 31 - Apr 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.2/10 Very Good! (515 reviews)
All of those and the wonderful, helpful staff

Reviewed on Feb 19, 2026

Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Downtown Tampa
Save 100% on your flight
Price was $1,223, price is now $814 per person
$814
per person
Apr 29 - May 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
7/10 Good! (1,744 reviews)
Everything was very easy check-in check out communication with front desk

Reviewed on Feb 25, 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
$417 nightly
The price is $471 total per night from Mar 29 to Mar 30
$471 total
Mar 29 - Mar 30
Total with taxes and fees
9.4/10 Exceptional! (3,034 reviews)
Hotel restaurant employee was so rude, and room wasn’t cleaned for a few days!

Reviewed on Feb 26, 2026

Wyndham Grand Clearwater Beach
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
$352 nightly
The price is $397 total per night from Mar 1 to Mar 2
$397 total
Mar 1 - Mar 2
Total with taxes and fees
8.2/10 Very Good! (1,658 reviews)
Our refrigerator never worked. It leaked onto the floor. We did not have hot water one day. The beds were comfortable.

Reviewed on Feb 26, 2026

RumFish Beach at TradeWinds
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
$195 nightly
The price is $221 total per night from Mar 29 to Mar 30
$221 total
Mar 29 - Mar 30
Total with taxes and fees
8.4/10 Very Good! (1,141 reviews)
Very clean and updated

Reviewed on Feb 27, 2026

The Westin Tampa Bay
See all 14,966 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
Flag at half mast at the Veterans Memorial Island Sanctuary in Vero Beach, Florida.

War Veteran Memorial Park

After visiting War Veteran Memorial Park, make a plan to see the other sights and activities in Madeira Beach. Amble around this family-friendly area's beautiful beaches or experience its great live music.

War Veteran Memorial Park
Florida. Madeira Beach Florida. Gulf of Mexico or ocean beach, Hotels and Resorts. John's Pass Village and Boardwalk. Turquoise color of salt water. American shore. Summer or Autumn vacation.

John's Pass Village & Boardwalk

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 check out its top-notch restaurants.

John's Pass Village & Boardwalk

Things to do

Stunning view of dolphins in St. Petersburg, Florida

Dolphin Racer Speedboat Adventure

$36
per adult
94% of travellers recommend
Dolphin Racer Speedboat Adventure
Shell Key Island bird's eye view

Shell Key Island Excursion

$64
per adult
84% of travellers recommend
Shell Key Island Excursion
View of the StarLite Sapphire Yacht on St. Pete Beach

StarLite Sapphire Evening Yacht St. Pete Beach

$41
per adult
90% of travellers recommend
StarLite Sapphire Evening Yacht St. Pete Beach
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.