On Top of The World Vacations from $706
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Your On Top of The World Vacation
Whatever your travel style, you can experience it all with a tailor-made On Top of The World vacation package. Spend your next break uncovering this neighborhood's golfing and its other appeals. Wondering what to see and do during your trip to On Top of The World? Nearby attractions such as Ruth Eckerd Hall, Eddie C. Moore Softball Complex and Westfield Countryside Mall are good places to start. Expedia is here to help put your travel plans into action. Book your ideal On Top of The World vacation today.
The Latest On Top of The World Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel
Sunshine Beach
Price was $2,693, price is now $1,542 per person
$1,542
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (1,282 reviews)
The room and location were amazing! The pool being closed at sunset, along with the bathroom, was not optimal. We wanted to use the pool/hot tub in the evening after a day out and found it closed. Then we went to the bar and met people from another resort who left due to the bathroom being closed because the pool was closed(?). Jake(Bartender) and Katherine(Front desk) were awesome!!
Reviewed on Nov 3, 2026
Saddlebrook Resort
Wesley Chapel South
Save 100% on your flight
Price was $1,412, price is now $985 per person
$985
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.2/10 Very Good! (184 reviews)
N/A
I won't book again. I have been to better resorts. For the money they charge I had torn curtains in my room and sugar ants and s stopped up tub that I had to call the maintenance
Reviewed on Nov 3, 2026
Where to stay in On Top of The World
Find the best On Top of The World areas and neighborhoods for the activities you enjoy most. Learn more about On Top of The World
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.
On Top of The World Hotel Deals
Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$263 nightly
The price is $298 total per night from Nov 10 to Nov 11
$298 total
Nov 10 - Nov 11
Total with taxes and fees
Hyatt Regency Clearwater Beach Resort and Suites
301 S Gulfview Blvd Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$259 nightly
The price is $293 total per night from Nov 11 to Nov 12
$293 total
Nov 11 - Nov 12
Total with taxes and fees
9.4/10 Exceptional! (2,490 reviews)
"The only complaint I have a the air conditioning only went down to 65 degrees and I felt super hot sleeping at night."
Reviewed on Nov 3, 2026
The Westin Tampa Bay
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $167 total per night from Nov 22 to Nov 23
$167 total
Nov 22 - Nov 23
Total with taxes and fees
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.
Things to do
Starlite Infinity Evening Yacht Cruise Clearwater
$37
per adult
90% of travellers recommend
Starlite Horizon Evening Yacht St. Pete Beach
$41
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.