Highland Oaks Travel Guide
St. Petersburg - Clearwater
Visit Highland Oaks
Popular places to visit
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 visit its lively bars.
St. Petersburg - Clearwater Beaches
Nothing says holiday like spending a care-free day in St. Petersburg - Clearwater Beaches, a popular beach in St. Petersburg - Clearwater.
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.
Fort De Soto Park
Admire the vestiges of the fortress, bring your kids to the pirate ship playground and relax on the beaches of this archipelago.
Salvador Dali Museum
Browse the surrealistic masterpieces of a world-famous Spanish painter in a remarkable building that perfectly suits the style of the art exhibits.
Vinoy Park
While area beaches are abundant, it’s convenient to have this lovely spot right in the city. Lounge under a palm tree and enjoy the frequent entertainment.
Things to do
Sunset Celebration Cruise on Tropics Boat Tours
StarLite Majesty Evening Yacht Cruise Clearwater
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key
2 Hour Sunset Cruise in Clearwater, Florida
Mega Bite Dolphin Tour Boat in Clearwater Beach
Pirate Adventure Cruise - John's Pass
Top hotels in Highland Oaks
Wyndham Grand Clearwater Beach
"Little excessive on added fees"
Reviewed on 4 Jun 2026
Hilton Clearwater Beach Resort & Spa
"Pool and beach area were great. Close to shops and restaurants."
Reviewed on 4 Jun 2026
The Westin Tampa Bay
"Excellent amenities."
Reviewed on 5 Jun 2026
Compass Hotel by Margaritaville Anna Maria Sound
"Everything was awesome"
Reviewed on 4 Jun 2026
Opal Sands Resort
"We enjoyed the pool. There were plenty of chairs around the pool. The pool had a walk inside for my six-year-old. The pool was large. The staff around the pool was very helpful and gave us ice cream. The kids enjoyed that. There was also a connect for and cornhole next to the pool on a field. The ..."
Reviewed on 4 Jun 2026
Grand Hyatt Tampa Bay
"Good"
Reviewed on 4 Jun 2026
Where to stay in Highland Oaks
Pass-a-Grille
Pass-a-Grille is popular for its beaches, and if you're looking for more to see and do, you might think about a trip to St. Petersburg - Clearwater Beaches or Merry Pier.
Downtown St. Petersburg
Downtown St. Petersburg is beloved for its fantastic nightlife. Take some time to explore sights in the area like Tampa Bay and Palladium Theater.
Sand Key
If you're spending some time in Sand Key, St. Petersburg - Clearwater Beaches and Belleair Beach are top sights worth seeing.
Sunset Beach
Sunset Beach is noteworthy for its beaches, and you can make a stop at top attractions like St. Petersburg - Clearwater Beaches and Sunset Beach.
Don Cesar
Don Cesar might not have many top sights, but Gulf Beaches Historical Museum and Splash Island Water Park are two attractions nearby that you can check out.
