Clearwater-St. Pete Beaches Adventure Holidays

Book a Adventure Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to £335 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Packages with flights are ATOL protected

Top flight + Adventure hotel deals in Clearwater-St. Pete Beaches

Price found within the past 48 hours. Click for updated prices.
RumFish Beach at TradeWinds
Wyndham Grand Clearwater Beach
The Don CeSar
DoubleTree Beach Resort by Hilton Tampa Bay - North Redingto
Clearwater Beach Marriott Resort on Sand Key
Don't see what you're looking for?
See all available trips from Chicago to Clearwater-St. Pete Beaches
View all trips

Top Adventure Clearwater-St. Pete Beaches Hotels

Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
5500 Gulf Blvd, St. Pete Beach, FL
  • 11 min drive from John's Pass Village & Boardwalk
Stay at this beach resort in St. Pete Beach. Enjoy free Wi-Fi, 5 outdoor pools and 2 restaurants. Our guests praise the helpful staff and the clean rooms in ...
7.2/10 Good! (1,003 reviews)
"Great"

Reviewed on 22 Aug 2025

Island Grand at TradeWinds
Pier House 60 Clearwater Beach Marina Hotel

Pier House 60 Clearwater Beach Marina Hotel

3 out of 5
101 Coronado Drive, Clearwater Beach, FL
  • 33 min drive from John's Pass Village & Boardwalk
Stay at this 3-star business-friendly hotel in Clearwater Beach. Enjoy a rooftop terrace, a fitness centre and a 24-hour front desk. Our guests praise the restaurant ...
8.8/10 Excellent! (1,761 reviews)
"Enjoyed my stay. Conveniently located enjoyed the bar on the roof. Would recommend to friends"

Reviewed on 20 Aug 2025

Pier House 60 Clearwater Beach Marina Hotel
Alden Suites - A Beachfront Resort

Alden Suites - A Beachfront Resort

2.5 out of 5
5900 Gulf Blvd, St. Pete Beach, FL
  • 11 min drive from John's Pass Village & Boardwalk
Stay at this beach hotel in St. Pete Beach. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions John's Pass Village & Boardwalk and Pass-a-Grille ...
8.6/10 Excellent! (1,000 reviews)
"Best experience ever will definitely be back great family trip"

Reviewed on 20 Feb 2023

Alden Suites - A Beachfront Resort
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.

More holidays you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.