Highland Pines Vacation Packages

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Top Holiday Package Deals in Highland Pines

Price found within the past 48 hours. Click for updated prices.
CW Resort

CW Resort

Save 100% on your flight
CA $1,461
per person
Nov 26 - Dec 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (204 reviews)
The room Was clean. Very nice layout . If you order from the restaurant make sure all of your condiments and utensils are in the bag. They forgot it every time we order from them, but besides the minor inconveniences we Would definitely stay again.

Reviewed on Oct 5, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
Save 100% on your flight
CA $1,696
per person
Nov 26 - Dec 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,252 reviews)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

Save 100% on your flight
CA $2,313
per person
Nov 7 - Nov 14
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (603 reviews)
So clean and anything at all that we needed the staff was more than willing to do great experience

Reviewed on Oct 4, 2026

Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

Save 100% on your flight
CA $3,752
per person
Nov 7 - Nov 14
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.4/10 Exceptional! (132 reviews)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

Save 100% on your flight
CA $1,470
per person
Nov 26 - Dec 3
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,005 reviews)
Great place to stay great staff

Reviewed on Oct 4, 2026

Where to stay in Highland Pines

Find the best Highland Pines areas and neighborhoods for the activities you enjoy most. Learn more about Highland Pines
A cityscape with tall buildings, palm trees, and a fountain.

Downtown Tampa

3 out of top 10 points of interest in this area

Explore top attractions like the Florida Aquarium, Glazer Children's Museum, and Tampa Riverwalk, or indulge in the vibrant nightlife and dining scene in the River Arts District. Easily navigate the area with TECO Streetcar and HART public transportation.

Find hotels in Downtown Tampa
A street lined with palm trees, vintage buildings, and parked cars.

Ybor City

Designated as a National Historic Landmark District, this Tampa neighborhood boasts the Ybor City Museum State Park and a variety of attractions like the Cigar Museum. Enjoy Florida's oldest restaurant, Columbia, and vibrant nightlife along 7th Avenue, easily accessible via TECO Line Streetcar.

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A large, two-story house with a porch, surrounded by well-maintained lawns and trees.

Hyde Park

Historic homes and fine dining abound next to Downtown Tampa. Here it’s easy to develop a taste for the finer things in life.

Find hotels in Hyde Park
A coastal cityscape with a marina, beach, and high-rise buildings during sunset.

Town 'n' Country

If you're spending some time in Town 'n' Country, Tampa Bay and Rocky Point Golf Course are top sights worth seeing.

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A city skyline with modern skyscrapers, a bridge, and a waterfront.

Tampa Heights

While visiting Tampa Heights, you might make a stop by sights like Armature Works and Tampa Waterworks Park.

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Highland Pines Hotel Deals

Quality Inn & Suites Tampa near Fairgrounds and Casino

Quality Inn & Suites Tampa near Fairgrounds and Casino

4955 E 18th Avenue Tampa FL
Fully refundable
CA $94
CA $114 total
Nov 2 - Nov 3
includes taxes & fees
Quality Inn & Suites Tampa near Fairgrounds and Casino
The Westin Tampa Bay

The Westin Tampa Bay

7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
CA $233
CA $264 total
Oct 25 - Oct 26
includes taxes & fees
The Westin Tampa Bay
Four Points by Sheraton Suites Tampa Airport Westshore

Four Points by Sheraton Suites Tampa Airport Westshore

4400 W Cypress St Tampa FL
Fully refundableReserve now, pay when you stay
CA $133
CA $151 total
Oct 12 - Oct 13
includes taxes & fees
Four Points by Sheraton Suites Tampa Airport Westshore
See all 5,193 properties in Highland Pines
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
Family Vacations
Family Vacations
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations

Stay near popular Highland Pines attractions

Skatepark of Tampa

6.8/10 (18 reviews)
Enjoy an outing to Skatepark of Tampa during your stay in Tampa. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
See properties

Things to do

Starlite Infinity Evening Yacht Cruise Clearwater

Starlite Infinity Evening Yacht Cruise Clearwater

CA $51
per adult
90% of travellers recommend
Starlite Infinity Evening Yacht Cruise Clearwater
Clearwater Beach: Dolphin & Island Sandbar Cruise

Clearwater Beach: Dolphin & Island Sandbar Cruise

CA $39
per adult
94% of travellers recommend
Clearwater Beach: Dolphin & Island Sandbar Cruise
Tarpon Springs: Evening Dolphin Cruise

Tarpon Springs: Evening Dolphin Cruise

CA $40
per adult
100% of travellers recommend
Tarpon Springs: Evening Dolphin Cruise
See all activities in Tampa
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.