Bay Pines Vacations
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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 Westin Sarasota
Aug 14 - Aug 21The Westin Sarasota + Flight
Central Sarasota7 nights9.0/10 - Wonderful (1,180 reviews)"My room is always very clean at the Westin (which should be the standard everywhere but unfortunately isn't, so of course it's always a relief to walk into a clean hotel room). However, the first day I was there, the pool was pretty murky/dirty and I did not want to use it. I did bring this to their attention. The next morning it looked like it had been properly shocked and cleaned. The QR code to order room service online was glitchy, but I called the front desk and they were very accomodating..."Reviewed June 2, 2026Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • Nonstop TPA - BOS • Nonstop$1,054$668found 1 day agoper traveler - The Marker
Aug 8 - Aug 15The Marker + Flight
Clearwater Beach7 nights6.0/10 - (3 reviews)Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • Nonstop TPA - BOS • Nonstop$2,453$1,513found 1 day agoper traveler - The Hotel Zamora
Aug 16 - Aug 22The Hotel Zamora + Flight
St. Pete Beach6 nights8.6/10 - Excellent (342 reviews)"Hotel is perfectly located. Aesthetically curated as soon as you walk into the lobby you can tell. The staff was great, everyone was very attentive and we even got a complimentary upgrade to a beautiful room that we very much enjoyed. The pool is great with a shaded area in case you do not want sun with the bar comfortably located upstairs in their restaurant that’s located inside the hotel. Didn’t get a chance to check out the rooftop. Only negative observation I have was finding some hairs on..."Reviewed June 5, 2026Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • Nonstop TPA - BOS • Nonstop - Ocean Club Treasure Island Hotel
Aug 14 - Aug 21Ocean Club Treasure Island Hotel + Flight
Sunshine Beach7 nights9.6/10 - Exceptional (996 reviews)"This property is very well maintained. We had a great stay!!"Reviewed June 4, 2026Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • Nonstop TPA - BOS • Nonstop$1,737$1,109found 1 day agoper traveler
Where to stay in Bay Pines
Pass-a-Grille
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.
Bay Pines Hotel Deals
Wyndham Grand Clearwater Beach
"Clean room"
Reviewed on Jun 5, 2026
Hilton Clearwater Beach Resort & Spa
"The room was okay, elevators were down with only 1 working causing lots of delays. We were on the 7th floor. The beaches were awesome and staff was friendly. However, they over charged me nearly $700. When I called to dispute they claimed it wasn’t them but it clearly was, so now my Credit Card company ..."
Reviewed on Jun 5, 2026
The Westin Tampa Bay
"I love staying at the Westin when I visit Tampa. On my next visit, their pool will be completed.Which will make my stay even better. Staff is great, Restaurant food is Phenomenal."
Reviewed on Jun 5, 2026
Discover the most popular places to visit in Bay Pines
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.
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 lively bars.
St. Petersburg - Clearwater Beaches
Nothing says vacation like spending a carefree day at St. Petersburg - Clearwater Beaches, a popular beach in St. Petersburg - Clearwater.
Things to do
Dolphin Racer Speedboat Adventure
