Bay Pines Vacations from $287

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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
per person
Oct 30 - Nov 3
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (4,221 reviews)
Nice place in a great location. The rooms are very comfortable.

Reviewed on Aug 17, 2025

Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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
per person
Oct 30 - Nov 3
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,007 reviews)
The staff was very nice and helpful. The shuttle would take you anywhere within 3 miles. Pool was nice and the hotel was quiet.

Reviewed on Aug 12, 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
per person
Oct 2 - Oct 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,049 reviews)
Rooms are 2 bedroom suites. Full size kitchen makes an extended stay more affordable. Extremely pet friendly environment.

Reviewed on Aug 8, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Sep 18 - Sep 24
found 2 days ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (574 reviews)
This property was very clean and staff very polite an amazing experience thank you

Reviewed on Aug 17, 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
Pass-a-Grille

Pass-a-Grille

5/5(26 area reviews)

Discover a quaint beach neighborhood featuring the Pass-a-Grille Historic District and Gulf Beaches Historical Museum. Enjoy walkable attractions like boutiques, an ice cream shop, outdoor art market, and fishing piers around 8th Street.

Find hotels in Pass-a-Grille

Bay Pines Hotel Deals

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
$190 nightly
The price is $215 total per night from Aug 24 to Aug 25
$215 total
Aug 24 - Aug 25
Total includes taxes and fees
8.2/10 Very Good! (1,353 reviews)
"Cleaning staff did not do their job, nor did maintenance around the property."

Reviewed on Aug 15, 2025

RumFish Beach at TradeWinds
Hilton Tampa Airport Westshore

Hilton Tampa Airport Westshore

4 out of 5
2225 N Lois Ave, Tampa, FL
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $108 total per night from Aug 31 to Sep 1
$108 total
Aug 31 - Sep 1
Total includes taxes and fees
8.4/10 Very Good! (1,007 reviews)
"Really close to the Raymond James stadium and shuttle access."

Reviewed on Aug 14, 2025

Hilton Tampa Airport Westshore
Grand Hyatt Tampa Bay

Grand Hyatt Tampa Bay

4 out of 5
2900 Bayport Drive, Tampa, FL
Fully refundableReserve now, pay when you stay
$200 nightly
The price is $227 total per night from Aug 24 to Aug 25
$227 total
Aug 24 - Aug 25
Total includes taxes and fees
8.8/10 Excellent! (1,023 reviews)
"We enjoyed our stay at the hotel. Katy during our breakfast was definitely a highlight."

Reviewed on Aug 16, 2025

Grand Hyatt Tampa Bay
See all 14,380 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
John's Pass Village & Boardwalk

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 beautiful beaches in this family-friendly area, or check out its lively bars.

John's Pass Village & Boardwalk
The sunset behind the lifeguard tower in combination with a bit of filtering made this image quite unique. #LifeAtExpedia

Clearwater Beach

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

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
One Hour Guided JetSki Tour

One Hour Guided JetSki Tour

$99
per adult
86% of travellers recommend
One Hour Guided JetSki Tour
Dolphin and Shelling Tours Snorkeling Tours Private Charters

Dolphin /Shelling/Snorkeling tours Private Charters

$55
per adult
100% of travellers recommend
Dolphin /Shelling/Snorkeling tours Private Charters
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.