On Top of The World Vacations from $294

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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.
EVEN Hotel Sarasota-Lakewood Ranch by IHG

EVEN Hotel Sarasota-Lakewood Ranch by IHG

3.5 out of 5
Save 100% on your flight
per person
Sep 10 - Sep 15
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
8.4/10 Very Good! (994 reviews)
I love this hotel! Comfortable and clean! I really recommend!

Reviewed on Jul 8, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
per person
Sep 7 - Sep 12
found 8 hours ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
9.6/10 Exceptional! (499 reviews)
We enjoyed our stay here and definitely will come again in the future Clean, well maintained, staffs are nice. Easy access to beach.

Reviewed on Jul 6, 2025

Coral Reef Beach Resort

Coral Reef Beach Resort

3.5 out of 5
Save 100% on your flight
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
8.8/10 Excellent! (251 reviews)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Sep 5 - Sep 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
9.6/10 Exceptional! (421 reviews)
Clean nice I am use to big hotels Very nice staff and helpful pool is little small besides that good

Reviewed on Jul 6, 2025

Barsala At The Wayland Condos

Barsala At The Wayland Condos

4 out of 5
Save 100% on your flight
per person
Sep 5 - Sep 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
7.8/10 Good! (9 reviews)
My little getaway was amazing!!! The studio was beautiful, had everything we needed I wasn't expecting a full kitchen with baking utensils as well. We had a blast the view was incredible. I loved the outside setup near the pool as well. Will definitely be booking another getaway real soon!!

Reviewed on Jun 10, 2025

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
Pass-a-Grille

Pass-a-Grille

5/5(26 area reviews)

Discover a quaint beach neighborhood featuring the Pass-a-Grille Historic District and Gulf Beaches Historical Museum. Enjoy walkable attractions like boutiques, an ice cream shop, outdoor art market, and fishing piers around 8th Street.

Find hotels in Pass-a-Grille

On Top of The World Hotel Deals

Hilton Clearwater Beach Resort & Spa
Hilton Clearwater Beach Resort & Spa
4 out of 5
400 Mandalay Ave, Clearwater Beach, FL
$227 nightly
The price is $257 total per night from Jul 14 to Jul 15
$257 total
Jul 14 - Jul 15
Total includes taxes and fees
8/10 Very Good! (1,979 reviews)
"Had a great stay. Easy to get around to restaurants and stores in foot."

Reviewed on Jul 5, 2025

Hilton Clearwater Beach Resort & Spa
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
4 out of 5
4860 West Kennedy Boulevard, Tampa, FL
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $172 total per night from Aug 3 to Aug 4
$172 total
Aug 3 - Aug 4
Total includes taxes and fees
8.6/10 Excellent! (1,638 reviews)
"Very beautiful"

Reviewed on Jul 5, 2025

The Westshore Grand, A Tribute Portfolio Hotel, Tampa
Wyndham Grand Clearwater Beach
Wyndham Grand Clearwater Beach
4 out of 5
100 Coronado Drive, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
$290 nightly
The price is $328 total per night from Aug 3 to Aug 4
$328 total
Aug 3 - Aug 4
Total includes taxes and fees
9.4/10 Exceptional! (2,352 reviews)
"Great stay!! Straight from the start til we had to leave. The cleanliness, atmosphere and layout was top notch! Dining options were excellent. We didn't get everyone's name but special shoutouts to Audra at the front desk, Marty(my boy) at the luggage desk, Nathan at Docks and John at Ocean Hai. ..."

Reviewed on Jul 6, 2025

Wyndham Grand Clearwater Beach
See all 15,139 properties in On Top of The World
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 On Top of The World

John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

4.5/5(1,625 reviews)

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

John's Pass Village & Boardwalk
Tropicana Field

Tropicana Field

4.5/5(591 reviews)

Catch an event at Tropicana Field during your trip to St. Petersburg. Attend a baseball game or simply enjoy the lively bars while you're in the area.

Tropicana Field
Beach Walk featuring a sandy beach

St. Petersburg - Clearwater Beaches

5/5(5 reviews)

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 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
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

$37
per adult
96% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
Sea Screamer boat in Orlando

Day Trip to Clearwater Beach with Sea Screamer Ride

$125
per adult
90% of travellers recommend
Day Trip to Clearwater Beach with Sea Screamer Ride
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.