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
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.
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
Little Toot Dolphin Adventure at Clearwater Beach
Our pick of the best Highland Oaks Hotel Deals
Wyndham Grand Clearwater Beach
"Great place to stay but just be aware they charge $40 to park a car on premise."
Reviewed on 8 June 2026
The Westin Tampa Bay
"Well located very helfpul and friendly staff. However not having a swimming pool that is open is an issue."
Reviewed on 8 June 2026
Hilton Clearwater Beach Resort & Spa
"Ok la limpieza es todos los dias eso si lo q pasa q para el precio deberían de darle ya mantenimiento al hotel tiene cosas como la puerta. Del balcón casi ni habría muy recia y para el precio mínimo el desayuno debería de incluirlo pero por todo lo demás bien una experiencia"
Reviewed on 8 June 2026
RumFish Beach at TradeWinds
"Front desk check out was very rude , when ask the question about the bill he said don’t worry about it you had a good time ! Very rude"
Reviewed on 8 June 2026
Compass Hotel by Margaritaville Anna Maria Sound
"It was great my staying"
Reviewed on 8 June 2026
Opal Sands Resort
"We loved everything about it! The location cannot be beat with views of the water only 20 feet from the pool! The staff were incredible everywhere you went ready to wait on you with a smile. We felt pampered the entire time and the entire place was very clean, well maintained and welcoming. We will ..."
Reviewed on 7 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.
