Highland Oaks Travel Guide
St. Petersburg - Clearwater
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 top-notch restaurants.
St. Petersburg - Clearwater Beaches
Why not spend a lazy afternoon at St. Petersburg - Clearwater Beaches during your trip to 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.
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.
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.
Things to do
Sunset Celebration Cruise on Tropics Boat Tours
StarLite Majesty Evening Yacht Cruise Clearwater
Bradenton: Anna Maria Island Guided Kayaking Manatee Tour
Madeira Beach: Pirate Adventure Cruise
Little Toot Dolphin Adventure at Clearwater Beach
Calypso Breeze Tropical Party Buffet Cruise
Top hotels in Highland Oaks
Wyndham Grand Clearwater Beach
Great resort, beautiful pool and lobby. Perfect location right on the beach! Food was good, busy pool and hot tub, wait times on drinks and food. Best sunset views! Super comfy beds!
Reviewed on 20 Feb 2026
The Westin Tampa Bay
Clean room
Reviewed on 18 Feb 2026
Ramada by Wyndham Tampa Westshore Airport South
Staff were nice and helpful, shuttles were great but the breakfast was severally diminished in availability of food and seating
Reviewed on 21 Feb 2026
Quality Inn Airport - Cruise Port
Amazing helpful lady thst works in the breakfast area every morning
Reviewed on 16 Feb 2026
RumFish Beach at TradeWinds
The room was very big. The bed is very very cozy. Overall it was a great stay. I would highly recommend this hotel, on the beach great food. Staff was friendly. Can’t wait to go go back.
Reviewed on 21 Feb 2026
Hilton Clearwater Beach Resort & Spa
The room was clean, but lamp looked like it had black mold inside. Rooms were outdated for the price we paid. Staff was very friendly and accommodating along with all the staff I encountered.
Reviewed on 19 Feb 2026
Other neighbourhoods around Highland Oaks
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 St. Pete's Historic Coliseum.
Historic Old Northeast
While visiting Historic Old Northeast, you might make a stop by sights like Renaissance Vinoy Golf Club and Vinoy Park Beach.
Isla del Sol
Isla del Sol might not have many top sights, but Dolphin Landings Charter Boat Center and Gulfport Beach are two attractions nearby that you can check out.
South Pasadena
You'll enjoy the restaurants and seafood restaurants in South Pasadena. You might want to make time for a stop at Corey Ave or Pasadena Shopping Center.
Belle Vista
If you're spending some time in Belle Vista, Pass-a-Grille Beach and St. Petersburg - Clearwater Beaches are top sights worth seeing.
Don Cesar
Don Cesar might not have many top sights, but Splash Island Water Park and Pass-a-Grille Beach are two attractions nearby that you can check out.
