Old Clearwater Bay Vacations from $655

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Your Old Clearwater Bay Vacation

Our Old Clearwater Bay vacation packages are an easy and handy way to arrange and book your next exciting adventure. Discover the true character of this unique neighborhood without the bother of organizing everything yourself. When it's time to head out and explore, you'll find a lot of top attractions nearby including Coachman Park, Church of Scientology and Jack Russell Stadium. Visit one, two or all during your trip to Old Clearwater Bay. Expedia will help turn your dream Old Clearwater Bay vacation into reality, whatever your travel plans or budget.

The Latest Old Clearwater Bay Vacation Packages

Price found within the past 48 hours. Click for updated prices.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,060, price is now $655 per person
$655
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,003 reviews)
It was nice to have a gym available and it was always empty. Shower was my favorite park, really big and open, bed was super comfy. The elevators were outnof order though and the coffee machine in the room didnt work, but over all it was a pretty nice hotel. One of the nicest ive been too.

Reviewed on Oct 4, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $2,296, price is now $1,310 per person
$1,310
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (635 reviews)
The place is great, excellent location, close to many outdoor activities, amazing ocean view, staff is very good and attentive to our needs, hotel is clean, parking very convenient, rooms are very nice, clean and confortable. We’ll definitely come back and recommend Ocean Club.

Reviewed on Oct 13, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,638, price is now $1,634 per person
$1,634
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (456 reviews)
Resort and room were very clean. On the beach a huge bonus. Staff extremely friendly. Downsides: The phrase "Total includes taxes and fees" is not correct. Was hit with a resort and parking fee after booking. Unacceptable. Include them in final price or show "additional fees" prior to booking. Rooftop bar closes too early. Fitness center closes too early. Photo on website shows beautiful Adirondack chairs but resort gave out used/dirty beach chairs. Free towels were also quite harsh. Glad we brought our own. Bottom line - would stay here again but only when "added fees" are removed.

Reviewed on Oct 13, 2025

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $1,079, price is now $709 per person
$709
per person
Jan 6 - Jan 12
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (2,173 reviews)
Clean, centrally located, excellent customer service.

Reviewed on Oct 5, 2025

Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Save 100% on your flight
Price was $2,137, price is now $1,418 per person
$1,418
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.4/10 Very Good! (1,003 reviews)
Staff are wonderful. Rooms and the buildings are a little outdated but still clean. Overall a wonderful experience.

Reviewed on Oct 8, 2025

Where to stay in Old Clearwater Bay

Find the best Old Clearwater Bay areas and neighborhoods for the activities you enjoy most. Learn more about Old Clearwater Bay
Downtown St. Petersburg featuring outdoor art

Downtown St. Petersburg

1 out of top 10 points of interest in this area

Come here for the beaches and sunshine and discover much more in this Florida city with something for all ages and tastes.

Find hotels in Downtown St. Petersburg

Old Clearwater Bay Hotel Deals

Hilton Tampa Airport Westshore

Hilton Tampa Airport Westshore

4 out of 5
2225 N Lois Ave, Tampa, FL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $144 total per night from Nov 2 to Nov 3
$144 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (1,039 reviews)
"Great place to stay for an event at the stadium."

Reviewed on Oct 13, 2025

Hilton Tampa Airport Westshore
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
$215 nightly
The price is $242 total per night from Oct 21 to Oct 22
$242 total
Oct 21 - Oct 22
Total with taxes and fees
8/10 Very Good! (2,246 reviews)
"Right on the beach with excellent amenities"

Reviewed on Oct 11, 2025

Hilton Clearwater Beach Resort & Spa
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
5303 W Kennedy Blvd, Tampa, FL
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $167 total per night from Oct 26 to Oct 27
$167 total
Oct 26 - Oct 27
Total with taxes and fees
8.6/10 Excellent! (2,262 reviews)
"Rooms were clean. Staff was friendly and hotel is just a great place to stay."

Reviewed on Oct 12, 2025

Hotel Alba, Tapestry Collection by Hilton
See all 13,757 properties in Old Clearwater Bay
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Old Clearwater Bay

John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.

John's Pass Village & Boardwalk
Clearwater Beach

Clearwater Beach

Why not spend a lazy afternoon at Clearwater Beach during your trip to Clearwater Beach? Wander the clear-water beaches or discover the area's beautiful sunsets.

Clearwater Beach
Beach Walk featuring a sandy beach

St. Petersburg - Clearwater Beaches

Why not spend a lazy afternoon at St. Petersburg - Clearwater Beaches during your trip to St. Petersburg - Clearwater?

St. Petersburg - Clearwater Beaches

Things to do

The Tropics Boat at Sunset

Sunset Celebration Cruise on Tropics Boat Tours

$37
per adult
88% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

$32
per adult
88% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

$35
per adult
88% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
See all activities in St. Petersburg - Clearwater
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.