On Top of The World Vacations from $297

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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.
New Hotel Collection Harbourside

New Hotel Collection Harbourside

3 out of 5
Save 100% on your flight
Price was $514, price is now $297 per person
$297
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
7.8/10 Good! (507 reviews)
Great service and very nice place to stay!! Definitely will be coming back.

Reviewed on Aug 6, 2025

Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $788, price is now $427 per person
$427
per person
Oct 7 - Oct 14
found 23 hours ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
8.6/10 Excellent! (59 reviews)
Close to downtown safety harbor, oldsmar and Clearwater, the perfect retreat being close to everything but not in the heart of it all.

Reviewed on May 12, 2025

Clearwater Suites

Clearwater Suites

2.5 out of 5
Save 100% on your flight
Price was $794, price is now $462 per person
$462
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (18 reviews)
Super convenient, clean, and right across the street from the beach. Staff was very friendly

Reviewed on Aug 25, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $844, price is now $494 per person
$494
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (598 reviews)
I love it, all staff super nice Beautiful place, clean, awesome beach Thanks

Reviewed on Aug 24, 2025

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,325, price is now $815 per person
$815
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (2,549 reviews)
The staff were amazing and very friendly. The breakfast buffet was good and the gym was well equipped. Plenty of places within walking distance to eat and shop. We will definitely be back!

Reviewed on Aug 27, 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
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

RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
6000 Gulf Blvd, St. Pete Beach, FL
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $192 total per night from Aug 28 to Aug 29
$192 total
Aug 28 - Aug 29
Total with taxes and fees
8.2/10 Very Good! (1,378 reviews)
"Go every year. Always a joy to be there."

Reviewed on Aug 23, 2025

RumFish Beach at TradeWinds
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
$112 nightly
The price is $127 total per night from Sep 7 to Sep 8
$127 total
Sep 7 - Sep 8
Total with taxes and fees
8.4/10 Very Good! (1,012 reviews)
"Nice rooms"

Reviewed on Aug 25, 2025

Hilton Tampa Airport Westshore
Grand Hyatt Tampa Bay

Grand Hyatt Tampa Bay

4 out of 5
2900 Bayport Drive, Tampa, FL
Fully refundableReserve now, pay when you stay
$200 nightly
The price is $227 total per night from Aug 29 to Aug 30
$227 total
Aug 29 - Aug 30
Total with taxes and fees
8.8/10 Excellent! (1,030 reviews)
"Neat"

Reviewed on Aug 24, 2025

Grand Hyatt Tampa Bay
See all 15,217 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

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 lively bars.

John's Pass Village & Boardwalk
The sunset behind the lifeguard tower in combination with a bit of filtering made this image quite unique. #LifeAtExpedia

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 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
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.