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
"Very large resort, but not overwhelming. My kids loved how late the pool stayed open. The night swims were their favorite part of the stay. Also, housekeeping was great and always on top of things when we needed extra towels. Very busy resort. Seats at the pool fill up fast. Get there by 11am to ..."
Reviewed on 19 June 2026
Hilton Clearwater Beach Resort & Spa
"Moved our room twice! Hair in shower drain in first room! Second room had chocolate ice cream all over curtains, wall to balcony and on balcony railings! Dusty moldy vent in bathroom and ac broke last night!!"
Reviewed on 19 June 2026
RumFish Beach at TradeWinds
"Perfect location, good food, great nightlife, so many amenities. Great place to stay."
Reviewed on 18 June 2026
Compass Hotel by Margaritaville Anna Maria Sound
"My complaint is they start cleaning at 830 am and, when you are trying to rest that is no good,you ask for coffee or other things oh we don't have any more, no microwave you can use and charge you 25 dollars for service fee per day but is not there when you do your reservation."
Reviewed on 18 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.
