Cheap Vacations in Hillsborough County

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Hillsborough County vacations

Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $596, price is now $396 per person
$396
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $886, price is now $451 per person
$451
per person
Dec 3 - Dec 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Leisure Resort

Westgate Leisure Resort

3.5 out of 5
International Drive District
Save 100% on your flight
Price was $862, price is now $507 per person
$507
per person
Dec 3 - Dec 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Siena at Bella Collina

Siena at Bella Collina

3.5 out of 5
Save 100% on your flight
Price was $1,252, price is now $782 per person
$782
per person
Nov 19 - Nov 22
found 14 hours ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Meliá Orlando Celebration

Meliá Orlando Celebration

4 out of 5
Save 100% on your flight
Price was $1,131, price is now $711 per person
$711
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $1,262, price is now $815 per person
$815
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,062, price is now $1,359 per person
$1,359
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Siesta Key Inn

Siesta Key Inn

2 out of 5
South Village
Save 100% on your flight
Price was $833, price is now $553 per person
$553
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $927, price is now $619 per person
$619
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,047, price is now $710 per person
$710
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)

3-night Hillsborough County vacations

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

Westgate Towers Resort

3.5 out of 5
Price was $475, price is now $300 per person
$300
per person
Dec 10 - Dec 13
found 16 hours ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Siena at Bella Collina

Siena at Bella Collina

3.5 out of 5
Save 100% on your flight
Price was $1,252, price is now $782 per person
$782
per person
Nov 19 - Nov 22
found 14 hours ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $1,262, price is now $815 per person
$815
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was $669, price is now $440 per person
$440
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,062, price is now $1,359 per person
$1,359
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Siesta Key Inn

Siesta Key Inn

2 out of 5
Save 100% on your flight
Price was $833, price is now $553 per person
$553
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $596, price is now $396 per person
$396
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,047, price is now $710 per person
$710
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Westgate Leisure Resort

Westgate Leisure Resort

3.5 out of 5
Price was $482, price is now $337 per person
$337
per person
Dec 10 - Dec 13
found 16 hours ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Westwinds Waterfront Resort

Westwinds Waterfront Resort

3 out of 5
Price was $709, price is now $505 per person
$505
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Tropic Isle at Anna Maria Island Inn

Tropic Isle at Anna Maria Island Inn

4 out of 5
Save 100% on your flight
Price was $947, price is now $676 per person
$676
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront

3 out of 5
Save 100% on your flight
Price was $844, price is now $602 per person
$602
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)

4-night Hillsborough County vacations

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

Westgate Leisure Resort

3.5 out of 5
Save 100% on your flight
Price was $487, price is now $305 per person
$305
per person
Dec 12 - Dec 16
found 18 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Orlando (MCO)
Disney's Animal Kingdom Lodge

Disney's Animal Kingdom Lodge

4.5 out of 5
Price was $2,296, price is now $1,221 per person
$1,221
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Orlando (MCO)
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $564, price is now $331 per person
$331
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Save 100% on your flight
Price was $890, price is now $533 per person
$533
per person
Dec 3 - Dec 7
found 4 hours ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $598, price is now $361 per person
$361
per person
Dec 6 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Save 100% on your flight
Price was $663, price is now $419 per person
$419
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Save 100% on your flight
Price was $930, price is now $589 per person
$589
per person
Dec 5 - Dec 9
found 12 hours ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,359, price is now $861 per person
$861
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $1,278, price is now $833 per person
$833
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $643, price is now $422 per person
$422
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Siesta Key Inn

Siesta Key Inn

2 out of 5
Save 100% on your flight
Price was $894, price is now $590 per person
$590
per person
Dec 3 - Dec 7
found 13 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,165, price is now $1,444 per person
$1,444
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)

5-night Hillsborough County vacations

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

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $672, price is now $374 per person
$374
per person
Nov 18 - Nov 23
found 12 hours ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Save 100% on your flight
Price was $1,022, price is now $510 per person
$510
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $690, price is now $379 per person
$379
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $1,539, price is now $850 per person
$850
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $680, price is now $394 per person
$394
per person
Nov 19 - Nov 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $710, price is now $423 per person
$423
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Save 100% on your flight
Price was $773, price is now $486 per person
$486
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Meliá Orlando Celebration

Meliá Orlando Celebration

4 out of 5
Save 100% on your flight
Price was $1,131, price is now $711 per person
$711
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Save 100% on your flight
Price was $965, price is now $622 per person
$622
per person
Dec 3 - Dec 8
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,748, price is now $1,901 per person
$1,901
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $634, price is now $440 per person
$440
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)
Kapp and Kappy B&B

Kapp and Kappy B&B

3.5 out of 5
Price was $713, price is now $498 per person
$498
per person
Nov 18 - Nov 23
found 12 hours ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)

6-7 night Hillsborough County vacations

Price found within the past 48 hours. Click for updated prices.
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $809, price is now $435 per person
$435
per person
Dec 4 - Dec 10
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Save 100% on your flight
Price was $1,565, price is now $733 per person
$733
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $917, price is now $451 per person
$451
per person
Dec 3 - Dec 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $886, price is now $451 per person
$451
per person
Dec 3 - Dec 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $1,105, price is now $599 per person
$599
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $2,182, price is now $1,196 per person
$1,196
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Save 100% on your flight
Price was $1,131, price is now $639 per person
$639
per person
Nov 29 - Dec 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,607, price is now $937 per person
$937
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Westgate Leisure Resort

Westgate Leisure Resort

3.5 out of 5
Save 100% on your flight
Price was $862, price is now $507 per person
$507
per person
Dec 3 - Dec 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Save 100% on your flight
Price was $1,373, price is now $810 per person
$810
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Meliá Orlando Celebration

Meliá Orlando Celebration

4 out of 5
Save 100% on your flight
Price was $1,526, price is now $904 per person
$904
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Save 100% on your flight
Price was $877, price is now $522 per person
$522
per person
Dec 5 - Dec 11
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

Top places to visit in Hillsborough County

A city skyline with illuminated buildings, a bridge over a river, and a park with trees.
FlightsFlightsHotelsHotels

Tampa

Tampa

Flight deals to Hillsborough County

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Nov 13 - Mon, Nov 16
PHL
Philadelphia
PIE
St. Petersburg
$93 Roundtrip, found 1 day ago
$93
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Fri, Nov 13 from Philadelphia to St. Petersburg, returning Mon, Nov 16, priced at $93 found 1 day ago
Fri, Nov 13 - Sat, Nov 14
DTW
Detroit
TPA
Tampa
$104 Roundtrip, found 21 hours ago
$104
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Fri, Nov 13 from Detroit to Tampa, returning Sat, Nov 14, priced at $104 found 21 hours ago
Sun, Dec 6 - Sat, Dec 12
CLE
Cleveland
TPA
Tampa
$118 Roundtrip, just found
$118
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Dec 6 from Cleveland to Tampa, returning Sat, Dec 12, priced at $118 just found

Top rated hotels for your Hillsborough County vacation

Four Points by Sheraton Suites Tampa Airport Westshore

Four Points by Sheraton Suites Tampa Airport Westshore

3 out of 5
4400 W Cypress St Tampa FL
Free Cancellation
Reserve now, pay when you stay
3.65 mi from city center
$118 nightly
The price is $134 total per night
$134 total
Oct 25 - Oct 26
Total with taxes and fees
With a stay at Four Points by Sheraton Suites Tampa Airport Westshore in Tampa (Westshore), you'll be within a 5-minute drive of Westshore Plaza Mall and Cypress Point Park.
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
6.69 mi from city center
$155 nightly
The price is $176 total per night
$176 total
Oct 25 - Oct 26
Total with taxes and fees
With a stay at The Westin Tampa Bay in Tampa (Rocky Point), you'll be a 1-minute drive from Tampa Bay and 8 minutes from Raymond James Stadium.
OASIS BAY SUITES, Tampa, Busch Gardens, USF

OASIS BAY SUITES, Tampa, Busch Gardens, USF

3 out of 5
3001 University Center Dr Tampa FL
Free Cancellation
Reserve now, pay when you stay
6.96 mi from city center
$129 nightly
The price is $146 total per night
$146 total
Oct 21 - Oct 22
Total with taxes and fees
With a stay at OASIS BAY SUITES, Tampa, Busch Gardens, USF, you'll be centrally located in Tampa, within a 5-minute drive of University of South Florida and Busch Gardens Tampa Bay.
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.