Bay Pines Vacations from $523

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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.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $844, price is now $523 per person
$523
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (4,624 reviews)
Room was clean and the staff was friendly.

Reviewed on Feb 24, 2026

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $914, price is now $558 per person
$558
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (2,193 reviews)
Great place to stay. Like a mini condo. Casey is the best - super friendly & helpful. Very convenient location & easy to get around. We’re definitely staying here again.

Reviewed on Feb 19, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,368, price is now $860 per person
$860
per person
Apr 30 - May 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (712 reviews)
The room was positively spotless and beds and bathrooms so clean. Very well stocked with dishes and cookware too!

Reviewed on Feb 23, 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 $984, price is now $636 per person
$636
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop 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

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,167, price is now $758 per person
$758
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,131 reviews)
Clean rooms great staff smells great

Reviewed on Feb 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
$423 nightly
The price is $478 total per night from Mar 22 to Mar 23
$478 total
Mar 22 - Mar 23
Total with taxes and fees
9.4/10 Exceptional! (3,039 reviews)
The room was spotless, comfortable, and had plenty of room. Staff were cordial and went out of their way to make our stay pleasant!

Reviewed on Feb 24, 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
$292 nightly
The price is $330 total per night from Feb 25 to Feb 26
$330 total
Feb 25 - Feb 26
Total with taxes and fees
8.2/10 Very Good! (1,655 reviews)
Very clean room, a surprise upgrade, wonderful stafg

Reviewed on Feb 23, 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
$203 nightly
The price is $231 total per night from Mar 8 to Mar 9
$231 total
Mar 8 - Mar 9
Total with taxes and fees
8.4/10 Very Good! (1,140 reviews)
Clean rooms very helpful stafff. Will stay again

Reviewed on Feb 22, 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.