Paradise Key Holidays

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Where to stay in Paradise Key

Find the best Paradise Key areas and neighborhoods for the activities you enjoy most. Learn more about Paradise Key

A beach with people, a city skyline, and a distinctive pink building.

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.

A modern plaza with a large sculpture, palm trees, and a high-rise building in the background.

Downtown St. Petersburg

1 out of top 10 points of interest in this area

Downtown St. Petersburg is beloved for its fantastic nightlife. Take some time to explore sights in the area like Tampa Bay and The Coliseum.

Sand Key

1 out of top 10 points of interest in this area

If you're spending some time in Sand Key, St. Petersburg - Clearwater Beaches and Belleair Beach are top sights worth seeing.

A beach with people walking along the shore, waves crashing onto the sand, and a city skyline in the background.

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.

A sunset over the ocean with a person paddleboarding and a floating structure.

Sunshine Beach

While visiting Sunshine Beach, you might make a stop by sights like St. Petersburg - Clearwater Beaches and St. Petersburg Municipal Beach at Treasure Island.

Top hotels in Paradise Key

Island Grand at TradeWinds

5500 Gulf Blvd St. Pete Beach FL

Fully refundableReserve now, pay when you stay

4.217.062 ₫

6.396.719 ₫ total

7 Sept - 8 Sept

includes taxes & fees

7.8/10 Good! (1,309 reviews)

"Great place, lots to do! Our room wasn't ready when we got there but they did give us a late checkout and a credit to make up for it. Our Jr sweet courtyard view was nice and roomy. They did have coffee in the room but if you want to bring your own, you'll need filters."

Reviewed on 7 Aug 2026

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

Fully refundableReserve now, pay when you stay

4.440.188 ₫

5.758.975 ₫ total

13 Aug - 14 Aug

includes taxes & fees

RumFish Beach at TradeWinds

6000 Gulf Blvd St. Pete Beach FL

Fully refundableReserve now, pay when you stay

3.993.937 ₫

6.144.587 ₫ total

12 Aug - 13 Aug

includes taxes & fees

See all 17,274 properties in Paradise Key

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.