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A waterfront promenade with palm trees, a sign reading "Clearwater Beach," and a cityscape in the background.

Clearwater
St. Petersburg - Clearwater
Florida
United States of America
North America
Hotwire.com

Clearwater Flight + Hotel Packages

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

Ocean Club Treasure Island Hotel

4 out of 5

Save 100% on your flight

Price was $1,147, price is now $757 per person

$757

per person

Jan 7 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.

Nice hotel

Reviewed on Oct 25, 2026

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5

Price was $1,446, price is now $910 per person

$910

per person

Jan 15 - Jan 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this business-friendly aparthotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Very nice suite for multi night stays. Staff were always friendly and helpful, with clean easy to maintain rooms. The heating /cooling unit housed in the closet of the bedroom was quite noisy for those of us with good hearing. Very happy with our stay and plan to return in the spring.

Reviewed on Oct 25, 2026

CW Resort

4 out of 5

Price was $1,554, price is now $997 per person

$997

per person

Jan 4 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Stay at this hotel in Clearwater Beach. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.

La Tortuga Historic Downtown Pass A Grille

4 out of 5

Price was $1,607, price is now $1,043 per person

$1,043

per person

Jan 13 - Jan 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Stay at this aparthotel in St. Pete Beach. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Fort De Soto Park and Merry Pier are located nearby.

Such a beautiful place!!! My only recommendation is they need to lock the gates at the pool! We left at 3:30 am and there were 3 people swimming in the pool… they took off running away when they saw us, so definitely not guests!!! The property is so beautiful and well cared for that I’d hate to see someone destroy something!

Reviewed on Oct 18, 2026

The Avalon Club

4 out of 5

Price was $2,015, price is now $1,324 per person

$1,324

per person

Jan 4 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Stay at this aparthotel in Clearwater Beach. Enjoy a fitness center, parking (surcharge), and in-room massages. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.

Much more spacious than we expected. Very clean, entire staff were very friendly and knowledgeable. A nice scent was all over the hotel, a nice touch. Definitely would recommend this hotel.

Reviewed on Oct 23, 2026

Stylish Treasure Island Escape

3 out of 5

Price was $7,898, price is now $5,209 per person

$5,209

per person

Jan 13 - Jan 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Stay at this apartment in Treasure Island. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.

Captiva Beach Resort

3 out of 5

Price was $1,427, price is now $972 per person

$972

per person

Jan 15 - Jan 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Cedar Cove Resort and Cottages

3 out of 5

Save 100% on your flight

Price was $1,404, price is now $958 per person

$958

per person

Jan 15 - Jan 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Bradenton Beach and Coquina Beach are located nearby.

Everything was perfect. Clean rooms Great Beach

Reviewed on Oct 25, 2026

Clearwater Vacation Packages 3-4 Night Stays

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

CW Resort

4 out of 5

Price was $827, price is now $574 per person

$574

per person

Nov 27 - Nov 30

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Tampa (TPA)