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.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

CA $573
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.6/10 Exceptional! (1,341 reviews)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
CA $1,276
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,128 reviews)
location

Reviewed on Aug 19, 2026

Innisbrook Resort

Innisbrook Resort

CA $881
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.4/10 Very good! (1,001 reviews)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

CA $903
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.4/10 Exceptional! (3,672 reviews)
The Hotel Zamora

The Hotel Zamora

CA $709
per person
Oct 2 - Oct 5
found 6 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
8.8/10 Excellent! (388 reviews)

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

4 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.

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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.

Find hotels in Ybor City
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 Countryway Golf Club are top sights worth seeing.

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A calm lake with dense trees on both sides, a clear sky, and a distant house.

Temple Terrace

Rolling landscape, majestic trees, and Hillsborough River views define this Tree City USA, with attractions like Eureka Springs Park and Temple Terrace Golf and Country Club. The area is undergoing redevelopment for a pedestrian-oriented downtown.

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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 $86
CA $104 total
Sep 20 - Sep 21
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 $198
CA $224 total
Sep 3 - Sep 4
includes taxes & fees
8.6/10 Excellent! (1,520 reviews)
"Wonderful Stay at the Don CeSar We had a wonderful stay at the Don CeSar! The hotel is absolutely beautiful, the location is perfect, and the beach is spectacular. Everything about our experience was enjoyable, from the atmosphere and amenities to the friendly and welcoming staff. The iconic pink ..."

Reviewed on Aug 19, 2026

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 $142
CA $161 total
Sep 4 - Sep 5
includes taxes & fees
Four Points by Sheraton Suites Tampa Airport Westshore
See all 5,208 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

Clearwater Beach: Dolphin & Island Sandbar Cruise

Clearwater Beach: Dolphin & Island Sandbar Cruise

CA $39
per adult
92% of travellers recommend
Clearwater Beach: Dolphin & Island Sandbar Cruise
Starlite Infinity Evening Yacht Cruise Clearwater

Starlite Infinity Evening Yacht Cruise Clearwater

CA $52
per adult
90% of travellers recommend
Starlite Infinity Evening Yacht Cruise Clearwater
Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

CA $52
per adult
94% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
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.