Highland Oaks Travel Guide
Tourist Guide
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 seaside 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
Nothing says holiday like spending a care-free day in Clearwater Beach, a popular beach in 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.
Pass-a-Grille Beach
Why not spend a lazy afternoon at Pass-a-Grille Beach during your trip to St. Pete Beach? Wander the beautiful beaches in this romantic area.
Activities
Sunset Celebration Cruise on Tropics Boat Tours
Dolphin Racer Speedboat Adventure
Pirate Adventure Cruise - John's Pass
StarLite Majesty Evening Yacht Cruise Clearwater
2 Hour Sunset Cruise in Clearwater, Florida
Suncoast Sailing's Sunset Sailing Experience!
Our pick of the best Highland Oaks Hotel Deals
The Westin Tampa Bay
"Swimming pool was closed for our stay."
Reviewed on 15 June 2026
Wyndham Grand Clearwater Beach
"Great!"
Reviewed on 19 June 2026
Hilton Clearwater Beach Resort & Spa
"Coffee machine was infected with mold inside the water tank, also blood stains all over the bed sheets, AC was berly working, super small beds, safe box is not working"
Reviewed on 19 June 2026
RumFish Beach at TradeWinds
"This place was great! Really enjoyed rumfish overall but definitely need to come back. The kids night out was perfect for date night with my wife kid free Resort pools were always clean and areas around them well maintained. The beach area was breathtaking and included the loungers with our stay. ..."
Reviewed on 19 June 2026
Compass Hotel by Margaritaville Anna Maria Sound
"We loved the hotel ! We had a beautiful view and was in a great location !"
Reviewed on 20 June 2026
Opal Sands Resort
"Fantastic place! Probably the best place on Clearwater beach. Right on the ocean, great food, and staff was amazing and very helpful. If we come back to Clearwater this would be the only place we’d stay at. We walked in and out of other hotels to see for future trips but this one by far has best ..."
Reviewed on 19 June 2026
Our guide on 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 Gulf Beaches Historical Museum.
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.
