Paradise Key Holidays
Book a Hotel + Flight or Car together to unlock savings
Where to stay in Paradise Key
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.
Top hotels in Paradise Key
RumFish Beach at TradeWinds
"Our only issue was that our room wasn’t cleaned until the second to the last day we were do to leave. I had spoken to a housekeeper during the middle of the week, who was at the room next door. I asked if she was stopping at our room next. She appeared to have said yes but no one showed. Later that ..."
Reviewed on 9 Jun 2026
Compass Hotel by Margaritaville Anna Maria Sound
"Good location"
Reviewed on 10 Jun 2026
Island Grand at TradeWinds
"We loved this resort for our family vacation with our 5 year old son. The beach is huge & stunning & easy to walk in! He had a blast for hours on the slide. We also liked that we could have an umbrella and 2 beach chairs at no additional cost. We also ate way too many smores at nightly s’mores party! ..."
Reviewed on 9 Jun 2026
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.
Fort De Soto Park
Enjoy the beautiful sunsets and explore Fort De Soto Park, a lovely green space in Tierra Verde. Discover the top-notch restaurants and great live music in this family-friendly area.
Salvador Dali Museum
You can spend time browsing the exhibits at Salvador Dali Museum during your trip to St. Petersburg. Attend a sporting event or simply enjoy the lively bars while you're in the area.