
On Top of The World Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in On Top of The World
Price found within the past 48 hours. Click for updated prices.

Pelican Pointe Clearwater Beach Hotel
Price was CA $1,260, price is now CA $844 per person
CA $844
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,155 reviews)
We loved the location and the furnishings that reminded us of the beach hotels growing up.
Reviewed on Nov 4, 2026



Saddlebrook Resort
Wesley Chapel South
Price was CA $2,506, price is now CA $1,631 per person
CA $1,631
per person
Jan 19 - Jan 26
found 11 hours ago
Roundtrip flight included
Toronto (YTO) 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

ChartHouse Clearwater Beach Marina Hotel
Price was CA $1,696, price is now CA $1,125 per person
CA $1,125
per person
Jan 25 - Feb 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,532 reviews)
Need to use fabric softener because towels like sand paper
Reviewed on Nov 2, 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
The price is CA $331 per night from Nov 9 to Nov 10
CA $331
CA $430 total
Nov 9 - Nov 10
includes taxes & fees

Hyatt Regency Clearwater Beach Resort and Suites
301 S Gulfview Blvd Clearwater Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $314 per night from Nov 11 to Nov 12
CA $314
CA $410 total
Nov 11 - Nov 12
includes taxes & 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
The price is CA $206 per night from Nov 22 to Nov 23
CA $206
CA $233 total
Nov 22 - Nov 23
includes taxes & 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.
Frequently asked questions
Things to do

Starlite Infinity Evening Yacht Cruise Clearwater
CA $52
per adult
90% of travellers recommend

Dolphin Racer Speedboat Adventure
CA $51
per adult
94% of travellers recommend

Clearwater Beach: Dolphin & Island Sandbar Cruise
CA $40
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.










