Cheap Vacations in Hillsborough County

Choose two or more items and save on your trip:

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 $439, price is now $263 per person
$263
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,674, price is now $916 per person
$916
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $1,331, price is now $729 per person
$729
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $2,196, price is now $1,348 per person
$1,348
per person
Aug 22 - Aug 29
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 $445, price is now $276 per person
$276
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,705, price is now $1,777 per person
$1,777
per person
Aug 19 - Aug 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was $579, price is now $383 per person
$383
per person
Aug 28 - Sep 1
found 24 hours ago
Roundtrip flight included
New York (NYC) 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
International Drive District
Price was $611, price is now $405 per person
$405
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $936, price is now $622 per person
$622
per person
Aug 27 - Aug 30
found 11 hours ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Coastal Waters Inn

Coastal Waters Inn

2 out of 5
Coronado Beach
Save 100% on your flight
Price was $768, price is now $513 per person
$513
per person
Aug 27 - Aug 31
found 10 hours ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)

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
Save 100% on your flight
Price was $439, price is now $263 per person
$263
per person
Aug 20 - Aug 23
found 1 day 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
Price was $744, price is now $441 per person
$441
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $456, price is now $278 per person
$278
per person
Aug 19 - Aug 22
found 11 hours ago
Roundtrip flight included
Philadelphia (PHL) 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 $445, price is now $276 per person
$276
per person
Sep 6 - Sep 9
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 $982, price is now $617 per person
$617
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,188, price is now $777 per person
$777
per person
Aug 27 - Aug 30
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Price was $611, price is now $405 per person
$405
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $936, price is now $622 per person
$622
per person
Aug 27 - Aug 30
found 11 hours ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
WorldQuest Orlando Resort

WorldQuest Orlando Resort

4 out of 5
Price was $558, price is now $391 per person
$391
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
New York (LGA) to Orlando (MCO)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Price was $728, price is now $515 per person
$515
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was $534, price is now $380 per person
$380
per person
Aug 27 - Aug 30
found 24 hours ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $502, price is now $358 per person
$358
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

4-night Hillsborough County vacations

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

Palazzo Lakeside Hotel

3 out of 5
Price was $847, price is now $240 per person
$240
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $938, price is now $487 per person
$487
per person
Sep 4 - Sep 8
found 24 hours ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
WorldQuest Orlando Resort

WorldQuest Orlando Resort

4 out of 5
Save 100% on your flight
Price was $683, price is now $440 per person
$440
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
New York (NYC) 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
Price was $721, price is now $466 per person
$466
per person
Aug 20 - Aug 24
found 5 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was $579, price is now $383 per person
$383
per person
Aug 28 - Sep 1
found 24 hours ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Coastal Waters Inn

Coastal Waters Inn

2 out of 5
Save 100% on your flight
Price was $768, price is now $513 per person
$513
per person
Aug 27 - Aug 31
found 10 hours ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,454, price is now $975 per person
$975
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was $1,175, price is now $794 per person
$794
per person
Sep 7 - Sep 11
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
CW Hotel

CW Hotel

4 out of 5
Save 100% on your flight
Price was $1,050, price is now $720 per person
$720
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $974, price is now $675 per person
$675
per person
Aug 28 - Sep 1
found 9 hours ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was $715, price is now $497 per person
$497
per person
Aug 22 - Aug 26
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
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 $745, price is now $523 per person
$523
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Orlando (MCO)

5-night Hillsborough County vacations

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

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $490, price is now $255 per person
$255
per person
Sep 6 - Sep 11
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Price was $954, price is now $395 per person
$395
per person
Sep 11 - Sep 16
found 1 hour 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 $1,548, price is now $799 per person
$799
per person
Aug 23 - Aug 28
found 1 day ago
Roundtrip non-stop 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 $748, price is now $422 per person
$422
per person
Aug 31 - Sep 5
found 22 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
WorldQuest Orlando Resort

WorldQuest Orlando Resort

4 out of 5
Save 100% on your flight
Price was $834, price is now $480 per person
$480
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip flight included
New York (NYC) 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 $859, price is now $501 per person
$501
per person
Sep 9 - Sep 14
found 20 hours ago
Roundtrip flight included
New York (JFK) 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 $835, price is now $515 per person
$515
per person
Sep 6 - Sep 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,168, price is now $738 per person
$738
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,705, price is now $1,777 per person
$1,777
per person
Aug 19 - Aug 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
CW Hotel

CW Hotel

4 out of 5
Save 100% on your flight
Price was $1,264, price is now $841 per person
$841
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $733, price is now $490 per person
$490
per person
Aug 24 - Aug 29
just found
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $1,108, price is now $745 per person
$745
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

6-7 night Hillsborough County vacations

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

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $540, price is now $284 per person
$284
per person
Sep 3 - Sep 9
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 $821, price is now $379 per person
$379
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 $1,234, price is now $571 per person
$571
per person
Aug 23 - Aug 29
found 2 hours ago
Roundtrip flight included
Philadelphia (PHL) 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
Price was $1,043, price is now $510 per person
$510
per person
Sep 7 - Sep 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Save 100% on your flight
Price was $847, price is now $453 per person
$453
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,674, price is now $916 per person
$916
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $1,331, price is now $729 per person
$729
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
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 $921, price is now $513 per person
$513
per person
Aug 20 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
CW Hotel

CW Hotel

4 out of 5
Save 100% on your flight
Price was $1,506, price is now $892 per person
$892
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $2,196, price is now $1,348 per person
$1,348
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,132, price is now $1,325 per person
$1,325
per person
Aug 31 - Sep 6
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
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 $1,215, price is now $768 per person
$768
per person
Aug 28 - Sep 4
found 6 hours ago
Roundtrip flight included
Islip (ISP) 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.

Mon, Oct 12 - Thu, Oct 15
TTN
Trenton
TPA
Tampa
$68 Roundtrip, found 4 days ago
$68
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Oct 12 from Trenton to Tampa, returning Thu, Oct 15, priced at $68 found 4 days ago
Mon, Oct 12 - Thu, Oct 15
PHL
Philadelphia
TPA
Tampa
$68 Roundtrip, found 4 days ago
$68
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Oct 12 from Philadelphia to Tampa, returning Thu, Oct 15, priced at $68 found 4 days ago
Thu, Oct 15 - Sun, Oct 18
TTN
Trenton
PIE
St. Petersburg
$78 Roundtrip, found 3 days ago
$78
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Thu, Oct 15 from Trenton to St. Petersburg, returning Sun, Oct 18, priced at $78 found 3 days ago

Top rated hotels for your Hillsborough County vacation

Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
5303 W Kennedy Blvd Tampa FL
Free Cancellation
Reserve now, pay when you stay
4.54 mi from city center
$115 nightly
The price is $130 total per night
$130 total
Aug 3 - Aug 4
Total with taxes and fees
Located in Tampa (Westshore), Hotel Alba, Tapestry Collection by Hilton is within a 5-minute drive of Westshore Plaza Mall and The Upper Tampa Bay Trail.
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
111 W Fortune St Tampa FL
Free Cancellation
Reserve now, pay when you stay
0.44 mi from city center
$136 nightly
The price is $154 total per night
$154 total
Aug 2 - Aug 3
Total with taxes and fees
With a stay at The Barrymore Hotel Tampa Riverwalk, you'll be centrally located in Tampa, within a 10-minute walk of Tampa Museum of Art and Tampa Theater.
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
$106 nightly
The price is $120 total per night
$120 total
Jul 26 - Jul 27
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.
Don't see what you're looking for?
See all available properties in Hillsborough County
View all properties
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.