Pinellas Trail Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.

The Inn on Third

Downtown St. Petersburg

$525

per person

Nov 5 - Nov 9

found 17 hours ago

Roundtrip flight included

St. Louis (STL) to Tampa (TPA)

The staff was so amazing! It felt like home there. The room was great... clean.. and so comfortable. I love downtown st Pete and I've stayed at quite a few places.. but this has been one of my top favorite place

Reviewed on Sep 27, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,211

per person

Nov 5 - Nov 9

found 15 hours ago

Roundtrip flight included

St. Louis (STL) to Tampa (TPA)

Best place to stay on island!

Reviewed on Oct 1, 2026

Seaside at Anna Maria Island Inn

Save 100% on your flight

$2,157

per person

Nov 5 - Nov 9

found 15 hours ago

Roundtrip flight included

St. Louis (STL) to Tampa (TPA)

Wyndham Grand Clearwater Beach

Save 100% on your flight

$994

per person

Nov 4 - Nov 9

found 13 hours ago

Roundtrip non-stop flight included

St. Louis (STL) to Tampa (TPA)

Reviewed on Oct 1, 2026

Edge Hotel Clearwater Beach

Save 100% on your flight

$721

per person

Nov 4 - Nov 9

found 13 hours ago

Roundtrip non-stop flight included

St. Louis (STL) to Tampa (TPA)

VIinoy House

Historic Old Northeast

Save 100% on your flight

$939

per person

Nov 5 - Nov 9

found 17 hours ago

Roundtrip flight included

St. Louis (STL) to Tampa (TPA)

Shephard's Beach Resort

Save 100% on your flight

$767

per person

Nov 4 - Nov 9

found 13 hours ago

Roundtrip non-stop flight included

St. Louis (STL) to Tampa (TPA)

Waterfront

Reviewed on Sep 30, 2026

ChartHouse Clearwater Beach Marina Hotel

$721

per person

Nov 4 - Nov 9

found 13 hours ago

Roundtrip non-stop flight included

St. Louis (STL) to Tampa (TPA)

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Best Lodging Options Near Pinellas Trail

Home2 Suites by Hilton Largo

10145 Ulmerton Road Largo FL

3.2 km from Pinellas Trail

Book a stay at this business-friendly hotel in Largo. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...

Holiday Inn & Suites Clearwater Beach S-Harbourside by IHG

401 2nd St Indian Rocks Beach FL

4.14 km from Pinellas Trail

Book a stay at this family-friendly hotel in Indian Rocks Beach. Enjoy free WiFi, a marina, and 3 bars/lounges. Our guests praise the helpful staff in our reviews. ...

Harbourside Resort, a New Hotel Collection Property

399 2nd St Indian Rocks Beach FL

4.13 km from Pinellas Trail

Stay at this hotel in Indian Rocks Beach. Enjoy free WiFi, free parking, and water park access (surcharge). Our guests praise the helpful staff in our reviews. ...

Holiday Inn Express Hotel & Suites Largo-Clearwater by IHG

210 Seminole Blvd Largo FL

4.21 km from Pinellas Trail

Book a stay at this business-friendly hotel in Largo. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...

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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.