
Highland Oaks Packages (Flight + Hotel)
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Where to stay in Highland Oaks

Pass-a-Grille
As you view this neighborhood’s iconic pink hotel it feels as if you’ve crossed into the past. Find beautiful beaches and serene enjoyment here.
Top hotels in Highland Oaks

Wyndham Grand Clearwater Beach
"Very clean hotel with very helpful staff! Great location, in walking distance to all sorts of restaurants. Loved our stay!"
Reviewed on 3 Jun 2026

Hilton Clearwater Beach Resort & Spa
"We have a gulf view. Outside our window you could mattress, trash and unsightly view of air coolers. Staff was nice enough to comp 1 day. Food at the hotel was awful, we had chips and salsa 1 day and chicken tenders the next day. Guacamole was warm, chicken was heavily breaded with cold fries."
Reviewed on 3 Jun 2026

The Westin Tampa Bay
"Very clean updated and modern room and decor. Staff was exceptionally friendly and helpful"
Reviewed on 1 Jun 2026
Frequently asked questions
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.

Jannus Live
Jannus Live is just one of the places to see in St. Petersburg, so why not enjoy the other things to explore during your travels? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Eckerd College
Walk around the campus at Eckerd College as part of your travels around St. Petersburg. Amble around this family-friendly area's beautiful beaches and enjoy its lively bars.
Things to do

Sunset Celebration Cruise on Tropics Boat Tours

St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key




