A wooden bridge over a calm river, surrounded by dense trees and greenery.

Carrollwood Vacations from $588

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Your Carrollwood Vacation

Book a Carrollwood vacation package and get ready to experience all this city has to offer. Consider basing yourself in the neighborhood of Downtown Tampa, which is great for nightlife, shopping and families. Fill your itinerary with tours of Raymond James Stadium, ZooTampa at Lowry Park and Adventure Island, some of the top attractions you really should see during your trip to Carrollwood. Browse Expedia's wide range of travel options and start planning your dream vacation to Carrollwood now.

The Latest Carrollwood Vacation Packages

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

Jan 10 - Jan 15
ChartHouse Clearwater Beach Marina Hotel + Flight
Clearwater Beach
5 nights
2.0 star property
9.6/10 - Exceptional (1,560 reviews)
Roundtrip • Boston (BOS) - Tampa (TPA)
BOS - TPA • Nonstop TPA - BOS • Nonstop
Save 100% on your flight
~~$911~~
$588
per traveler
found 1 day ago
ChartHouse Clearwater Beach Marina Hotel
Jan 10 - Jan 15
The Avalon Club + Flight
Clearwater Beach
5 nights
4.0 star property
9.4/10 - Exceptional (620 reviews)
Roundtrip • Boston (BOS) - Tampa (TPA)
BOS - TPA • Nonstop TPA - BOS • Nonstop
Save 100% on your flight
~~$1,230~~
$777
per traveler
found 1 day ago
The Avalon Club
Jan 10 - Jan 15
CW Resort + Flight
Clearwater Beach
5 nights
4.0 star property
9.4/10 - Exceptional (297 reviews)
Roundtrip • Boston (BOS) - Tampa (TPA)
BOS - TPA • Nonstop TPA - BOS • Nonstop
Save 100% on your flight
~~$1,089~~
$694
per traveler
found 1 day ago
CW Resort
Jan 12 - Jan 18
Saddlebrook Resort + Flight
Wesley Chapel South
6 nights
4.0 star property
8.2/10 - Very good (194 reviews)
"N/A I won't book again. I have been to better resorts. For the money they charge I had torn curtains in my room and sugar ants and s stopped up tub that I had to call the maintenance"
Reviewed November 3, 2026
Roundtrip • Boston (BOS) - Tampa (TPA)
BOS - TPA • Nonstop TPA - BOS • 1 stop
~~$1,937~~
$1,312
per traveler
found 13 hours ago
Saddlebrook Resort
Dec 6 - Dec 11
The Knickerbocker by Delphius + Flight
Hyde Park
5 nights
3.0 star property
Roundtrip • Boston (BOS) - Tampa (TPA)
BOS - TPA • Nonstop TPA - BOS • Nonstop
~~$1,833~~
$1,243
per traveler
found 15 hours ago
The Knickerbocker by Delphius

Where to stay in Carrollwood

Find the best Carrollwood areas and neighborhoods for the activities you enjoy most. Learn more about Carrollwood

A cityscape with tall buildings, palm trees, and a fountain.

Downtown Tampa

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.

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

Hyde Park

You'll enjoy the restaurants and shopping in Hyde Park. You might want to make time for a stop at Hyde Park Village or Oxford Exchange.

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A city skyline at dusk with illuminated buildings and palm trees in the foreground.

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 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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