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 $454, price is now $271 per person
$271
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)
Westgate River Ranch Resort & Rodeo

Westgate River Ranch Resort & Rodeo

3.5 out of 5
Save 100% on your flight
Price was $637, price is now $287 per person
$287
per person
Oct 2 - Oct 4
found 4 hours ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
Price was $1,419, price is now $782 per person
$782
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,460, price is now $825 per person
$825
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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
International Drive District
Save 100% on your flight
Price was $886, price is now $510 per person
$510
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,383, price is now $816 per person
$816
per person
Oct 20 - Oct 27
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,059, price is now $625 per person
$625
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,076, price is now $664 per person
$664
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,118, price is now $693 per person
$693
per person
Oct 20 - Oct 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Ocean Landings Resort and Racquet

Ocean Landings Resort and Racquet

2.5 out of 5
Save 100% on your flight
Price was $536, price is now $336 per person
$336
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)

3-night Hillsborough County vacations

Price found within the past 48 hours. Click for updated prices.
Motel 301

Motel 301

2 out of 5
Price was $304, price is now $225 per person
$225
per person
Oct 26 - Oct 29
found 24 hours ago
Roundtrip flight included
Cleveland (CLE) 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
Save 100% on your flight
Price was $612, price is now $361 per person
$361
per person
Oct 24 - Oct 27
found 9 hours ago
Roundtrip flight included
Boston (BOS) 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 $1,059, price is now $625 per person
$625
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $454, price is now $271 per person
$271
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Save 100% on your flight
Price was $854, price is now $536 per person
$536
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $391, price is now $248 per person
$248
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $591, price is now $392 per person
$392
per person
Oct 22 - Oct 25
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was $794, price is now $541 per person
$541
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $376, price is now $260 per person
$260
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Century Millenia

Century Millenia

3 out of 5
Save 100% on your flight
Price was $454, price is now $319 per person
$319
per person
Oct 9 - Oct 12
found 7 hours ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Save 100% on your flight
Price was $634, price is now $455 per person
$455
per person
Oct 22 - Oct 25
found 17 hours ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)
Ocean Landings Resort and Racquet

Ocean Landings Resort and Racquet

2.5 out of 5
Price was $540, price is now $389 per person
$389
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip 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.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $459, price is now $263 per person
$263
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Price was $804, price is now $354 per person
$354
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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 $1,256, price is now $663 per person
$663
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $886, price is now $510 per person
$510
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Leisure Resort

Westgate Leisure Resort

3.5 out of 5
Save 100% on your flight
Price was $480, price is now $283 per person
$283
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,076, price is now $664 per person
$664
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)
Ocean Landings Resort and Racquet

Ocean Landings Resort and Racquet

2.5 out of 5
Save 100% on your flight
Price was $536, price is now $336 per person
$336
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)
Royal Floridian South by Spinnaker

Royal Floridian South by Spinnaker

4.5 out of 5
Save 100% on your flight
Price was $860, price is now $558 per person
$558
per person
Oct 10 - Oct 14
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $407, price is now $269 per person
$269
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was $989, price is now $666 per person
$666
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Oceanique Resort

Oceanique Resort

3.5 out of 5
Save 100% on your flight
Price was $604, price is now $412 per person
$412
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,696, price is now $1,172 per person
$1,172
per person
Oct 16 - Oct 20
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

5-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
Save 100% on your flight
Price was $435, price is now $278 per person
$278
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 $1,053, price is now $493 per person
$493
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip flight included
New York (LGA) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $586, price is now $285 per person
$285
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,136, price is now $663 per person
$663
per person
Oct 21 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,554, price is now $908 per person
$908
per person
Oct 21 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $774, price is now $459 per person
$459
per person
Oct 15 - Oct 20
found 8 hours ago
Roundtrip flight included
Cincinnati (CVG) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $638, price is now $397 per person
$397
per person
Oct 21 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Magic Village Yards, Trademark Collection by Wyndham

Magic Village Yards, Trademark Collection by Wyndham

4 out of 5
Save 100% on your flight
Price was $1,200, price is now $772 per person
$772
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Quality Inn & Suites By the Parks

Quality Inn & Suites By the Parks

2.5 out of 5
Save 100% on your flight
Price was $779, price is now $502 per person
$502
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
New York (LGA) to Orlando (MCO)
Coco Key Hotel & Water Park Resort

Coco Key Hotel & Water Park Resort

3.5 out of 5
Save 100% on your flight
Price was $528, price is now $343 per person
$343
per person
Oct 20 - Oct 25
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Leisure Resort

Westgate Leisure Resort

3.5 out of 5
Save 100% on your flight
Price was $658, price is now $429 per person
$429
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip flight included
New York (LGA) to Orlando (MCO)
ette hotel

ette hotel

5 out of 5
Save 100% on your flight
Price was $1,866, price is now $1,225 per person
$1,225
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

6-7 night Hillsborough County vacations

Price found within the past 48 hours. Click for updated prices.
Quality Inn & Suites By the Parks

Quality Inn & Suites By the Parks

2.5 out of 5
Save 100% on your flight
Price was $817, price is now $465 per person
$465
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $973, price is now $508 per person
$508
per person
Oct 17 - Oct 24
found 2 hours ago
Roundtrip flight included
Boston (BOS) 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 $2,233, price is now $1,167 per person
$1,167
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
Price was $1,419, price is now $782 per person
$782
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,460, price is now $825 per person
$825
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,242, price is now $707 per person
$707
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,383, price is now $816 per person
$816
per person
Oct 20 - Oct 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,608, price is now $1,548 per person
$1,548
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $793, price is now $482 per person
$482
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,118, price is now $693 per person
$693
per person
Oct 20 - Oct 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
Save 100% on your flight
Price was $1,466, price is now $912 per person
$912
per person
Oct 20 - Oct 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Inn at Celebration, Autograph Collection

The Inn at Celebration, Autograph Collection

4 out of 5
Save 100% on your flight
Price was $1,307, price is now $819 per person
$819
per person
Oct 7 - Oct 14
found 1 day 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, Oct 2 - Mon, Oct 5
PHL
Philadelphia
PIE
St. Petersburg
$78 Roundtrip, found 3 days ago
$78
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Fri, Oct 2 from Philadelphia to St. Petersburg, returning Mon, Oct 5, priced at $78 found 3 days ago
Fri, Oct 2 - Mon, Oct 5
PHL
Philadelphia
TPA
Tampa
$80 Roundtrip, found 3 days ago
$80
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Oct 2 from Philadelphia to Tampa, returning Mon, Oct 5, priced at $80 found 3 days ago
Tue, Oct 6 - Tue, Oct 13
DTW
Detroit
TPA
Tampa
$101 Roundtrip, found 3 days ago
$101
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Oct 6 from Detroit to Tampa, returning Tue, Oct 13, priced at $101 found 3 days ago

Top rated hotels for your Hillsborough County vacation

The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Free Cancellation
Reserve now, pay when you stay
6.69 mi from city center
$147 nightly
The price is $167 total per night
$167 total
Sep 6 - Sep 7
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.
Hilton Tampa Airport Westshore

Hilton Tampa Airport Westshore

4 out of 5
2225 N Lois Ave Tampa FL
Free Cancellation
Reserve now, pay when you stay
3.51 mi from city center
$98 nightly
The price is $111 total per night
$111 total
Sep 10 - Sep 11
Total with taxes and fees
With a stay at Hilton Tampa Airport Westshore in Tampa (Westshore), you'll be within a 5-minute drive of International Plaza and Bay Street and Raymond James Stadium.
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
Sep 6 - Sep 7
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.