On Top of The World Vacations from $487

Book a Hotel + Flight or Car together to unlock savings

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.
Hampton Inn Sarasota - I-75 Bee Ridge

Hampton Inn Sarasota - I-75 Bee Ridge

2.5 out of 5
Save 100% on your flight
Price was $915, price is now $487 per person
$487
per person
Feb 21 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (317 reviews)
Friendly staff, restaurants next door. Small, but decent gym.

Reviewed on Nov 29, 2025

Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Price was $1,542, price is now $723 per person
$723
per person
Feb 21 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.2/10 Very Good! (1,002 reviews)
Staff was very friendly and happy to help. The room was clean. The front area was organized, and plenty of snack items were available to purchase.

Reviewed on Nov 24, 2025

The Avalon Club

The Avalon Club

4 out of 5
Price was $3,062, price is now $1,567 per person
$1,567
per person
Feb 6 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (481 reviews)
Room was great. Reception awesome. Location awesome. However, the washer stopped working middle of night - resulting in our laundry being stuck (door locked, would not release as water error). We couldn't get fixed. By time maintenance got fixed, we had to check out. TO credit, they mailed our laundry to us, but we needed it the for the next 3 days of our vacaction, and didn't have it available.

Reviewed on Nov 26, 2025

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,268, price is now $670 per person
$670
per person
Feb 21 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (4,624 reviews)
Super clean, comfortable beds, good rooms, and polite staff. The hotel is really good!

Reviewed on Nov 29, 2025

Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
Price was $1,612, price is now $863 per person
$863
per person
Jan 20 - Jan 27
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
9.4/10 Exceptional! (40 reviews)
Room was a little outdated but very clean, and comfy!

Reviewed on Nov 27, 2025

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

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 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

On Top of The World Hotel Deals

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
$206 nightly
The price is $233 total per night from Dec 2 to Dec 3
$233 total
Dec 2 - Dec 3
Total with taxes and fees
9.4/10 Exceptional! (2,823 reviews)
Clean room.

Reviewed on Nov 24, 2025

Wyndham Grand Clearwater Beach
DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront

4 out of 5
3050 N Rocky Point Dr W Tampa FL
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $139 total per night from Dec 18 to Dec 19
$139 total
Dec 18 - Dec 19
Total with taxes and fees
8.2/10 Very Good! (1,012 reviews)
Staff was great and friendly facilities where nice and relaxing rooms where clean the only thing I did or know is they charge for parking. Other than that great

Reviewed on Nov 24, 2025

DoubleTree by Hilton Tampa Rocky Point Waterfront
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
$174 nightly
The price is $196 total per night from Dec 7 to Dec 8
$196 total
Dec 7 - Dec 8
Total with taxes and fees
8/10 Very Good! (2,333 reviews)
Perfect

Reviewed on Nov 22, 2025

Hilton Clearwater Beach Resort & Spa
See all 15,736 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)

You can do some window-shopping at John's Pass Village & Boardwalk during your stay in Madeira Beach. Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.

John's Pass Village & Boardwalk
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
Clearwater Beach

Clearwater Beach

4.5/5(44 reviews)

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

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
90% 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
90% 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.