Harbor Hills Vacations from $343
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The Latest Harbor Hills Vacation Packages
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- ChartHouse Clearwater Beach Marina Hotel
Sep 25 - Sep 27ChartHouse Clearwater Beach Marina Hotel + Flight
Clearwater Beach2 nights2.0 star property9.6/10 - Exceptional (1,253 reviews)"Room was beautiful and clean."Reviewed July 16, 2026Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • 1 stop TPA - BOS • 1 stop - Cedar Cove Resort and Cottages
Oct 8 - Oct 12Cedar Cove Resort and Cottages + Flight
Holmes Beach4 nights3.0 star property9.2/10 - Wonderful (556 reviews)"Is definitely my new favorite place people staff and everyone was amazing"Reviewed July 16, 2026Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • 1 stop TPA - BOS • 1 stop - CW Hotel
Sep 25 - Sep 27CW Hotel + Flight
Clearwater Beach2 nights4.0 star property10/10 - Exceptional (6 reviews)"We had such a great stay at the CW Resort in Clearwater! The pool area was beautiful and relaxing, the views were amazing, and the entire property was very clean and well maintained. It was the perfect place to unwind and enjoy a Florida getaway. We would definitely stay here again!"Reviewed July 8, 2026Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • 1 stop TPA - BOS • 1 stop - Ocean Club Treasure Island Hotel
Sep 15 - Sep 20Ocean Club Treasure Island Hotel + Flight
Sunshine Beach5 nights4.0 star property9.6/10 - Exceptional (1,088 reviews)"We will definitely be back!! Staying here was so much nicer than a hotel. It was very roomy, clean and quiet. The staff was friendly and accommodating. It was nice being right on the beach. The pool area had a donation bin of beach chairs, boogie boards, umbrellas, pool tubes and sand toys. You can grab what you want and bring it to the beach."Reviewed July 12, 2026Roundtrip • New York (JFK) - Tampa (TPA)JFK - TPA • Nonstop TPA - JFK • Nonstop - Wyndham Grand Clearwater Beach
Sep 25 - Sep 27Wyndham Grand Clearwater Beach + Flight
Clearwater Beach2 nights4.0 star property9.4/10 - Exceptional (3,525 reviews)"Awesome"Reviewed July 16, 2026Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • 1 stop TPA - BOS • 1 stop
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.