Cheap Vacations in Osceola County

Choose two or more items and save on your trip:

Osceola 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
Price was $739, price is now $484 per person
$484
per person
Jun 29 - Jul 2
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
International Drive District
Price was $1,618, price is now $671 per person
$671
per person
Jul 5 - Jul 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $1,115, price is now $585 per person
$585
per person
Jul 1 - Jul 8
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 $1,066, price is now $569 per person
$569
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Davis
Save 100% on your flight
Price was $879, price is now $514 per person
$514
per person
Jul 3 - Jul 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
International Drive District
Save 100% on your flight
Price was $817, price is now $495 per person
$495
per person
Jul 2 - Jul 7
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,993, price is now $1,208 per person
$1,208
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Reunion
Save 100% on your flight
Price was $1,435, price is now $948 per person
$948
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Hilton Daytona Beach Oceanfront Resort

Hilton Daytona Beach Oceanfront Resort

4 out of 5
Brush - Stewarts
Save 100% on your flight
Price was $793, price is now $525 per person
$525
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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 $962, price is now $639 per person
$639
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)

3-night Osceola County vacations

Price found within the past 48 hours. Click for updated prices.
Hilton Daytona Beach Oceanfront Resort

Hilton Daytona Beach Oceanfront Resort

4 out of 5
Price was $481, price is now $352 per person
$352
per person
Jul 24 - Jul 27
found 22 hours ago
Roundtrip flight included
New York (JFK) 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 $911, price is now $504 per person
$504
per person
Jul 6 - Jul 9
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $726, price is now $421 per person
$421
per person
Jul 7 - Jul 10
found 21 hours 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 $739, price is now $484 per person
$484
per person
Jun 29 - Jul 2
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 $755, price is now $498 per person
$498
per person
Jul 15 - Jul 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $627, price is now $420 per person
$420
per person
Jun 29 - Jul 2
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,173, price is now $791 per person
$791
per person
Jul 13 - Jul 16
found 19 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 $1,107, price is now $755 per person
$755
per person
Jul 7 - Jul 10
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Price was $784, price is now $539 per person
$539
per person
Jul 6 - Jul 9
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
Price was $581, price is now $419 per person
$419
per person
Jun 29 - Jul 2
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Price was $722, price is now $531 per person
$531
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $536, price is now $397 per person
$397
per person
Jun 29 - Jul 2
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)

4-night Osceola County vacations

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

Seasons Florida Resort

2 out of 5
Price was $669, price is now $454 per person
$454
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $1,338, price is now $478 per person
$478
per person
Jul 1 - Jul 5
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 $1,112, price is now $591 per person
$591
per person
Jul 16 - Jul 20
found 23 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $840, price is now $482 per person
$482
per person
Jul 2 - Jul 6
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 $1,360, price is now $788 per person
$788
per person
Jul 11 - Jul 15
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
Price was $975, price is now $626 per person
$626
per person
Jul 1 - Jul 5
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
Price was $989, price is now $681 per person
$681
per person
Jul 2 - Jul 6
found 22 hours ago
Roundtrip non-stop 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
Price was $794, price is now $553 per person
$553
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Parkway International Resort

Parkway International Resort

3 out of 5
Price was $690, price is now $487 per person
$487
per person
Jul 17 - Jul 21
found 1 hour ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
New Smyrna MOD Collection by Sonesta

New Smyrna MOD Collection by Sonesta

3 out of 5
Save 100% on your flight
Price was $860, price is now $625 per person
$625
per person
Jul 21 - Jul 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Price was $921, price is now $671 per person
$671
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Riviere Apartments King Bed Suite & Pool & Gym & Pet Friendly & Near Epic Universe

Riviere Apartments King Bed Suite & Pool & Gym & Pet Friendly & Near Epic Universe

4 out of 5
Save 100% on your flight
Price was $704, price is now $522 per person
$522
per person
Jul 18 - Jul 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)

5-night Osceola 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 $591, price is now $352 per person
$352
per person
Jul 8 - Jul 13
found 24 hours 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
Save 100% on your flight
Price was $1,083, price is now $624 per person
$624
per person
Jul 2 - Jul 7
found 2 hours 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 $1,643, price is now $960 per person
$960
per person
Jul 8 - Jul 13
found 24 hours ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Save 100% on your flight
Price was $879, price is now $514 per person
$514
per person
Jul 3 - Jul 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 $817, price is now $495 per person
$495
per person
Jul 2 - Jul 7
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,993, price is now $1,208 per person
$1,208
per person
Jul 22 - Jul 27
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 $1,080, price is now $697 per person
$697
per person
Jul 2 - Jul 7
found 18 hours ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $641, price is now $422 per person
$422
per person
Jul 2 - Jul 7
found 2 hours ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Hilton Daytona Beach Oceanfront Resort

Hilton Daytona Beach Oceanfront Resort

4 out of 5
Save 100% on your flight
Price was $793, price is now $525 per person
$525
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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 $962, price is now $639 per person
$639
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Save 100% on your flight
Price was $933, price is now $633 per person
$633
per person
Jul 2 - Jul 7
found 18 hours ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Costa d'Este Beach Resort and Spa

Costa d'Este Beach Resort and Spa

4 out of 5
Save 100% on your flight
Price was $1,296, price is now $890 per person
$890
per person
Jul 20 - Jul 25
found 21 hours ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)

6-7 night Osceola County vacations

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

Alhambra Villas

3 out of 5
Save 100% on your flight
Price was $624, price is now $393 per person
$393
per person
Jul 7 - Jul 14
found 15 hours ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Hawthorn Extended Stay by Wyndham Orlando

Hawthorn Extended Stay by Wyndham Orlando

3 out of 5
Save 100% on your flight
Price was $855, price is now $614 per person
$614
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Price was $1,618, price is now $671 per person
$671
per person
Jul 5 - Jul 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $1,184, price is now $607 per person
$607
per person
Jul 1 - Jul 8
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 $1,115, price is now $585 per person
$585
per person
Jul 1 - Jul 8
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 $1,066, price is now $569 per person
$569
per person
Jul 1 - Jul 8
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 $1,198, price is now $683 per person
$683
per person
Jul 5 - Jul 11
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 $2,223, price is now $1,311 per person
$1,311
per person
Jul 18 - Jul 25
found 17 hours ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $732, price is now $446 per person
$446
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Save 100% on your flight
Price was $649, price is now $399 per person
$399
per person
Jul 3 - Jul 9
found 13 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Orlando (MCO)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,415, price is now $906 per person
$906
per person
Jul 5 - Jul 11
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 $1,435, price is now $948 per person
$948
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

Top places to visit in Osceola County

Delonix regia tree in bloom
FlightsFlightsHotelsHotels

Poinciana

Poinciana

Flight deals to Osceola County

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

Tue, Sep 29 - Tue, Oct 13
ORD
Chicago
MCO
Orlando
$102 Roundtrip, found 18 hours ago
$102
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Tue, Sep 29 from Chicago to Orlando, returning Tue, Oct 13, priced at $102 found 18 hours ago
Tue, Aug 25 - Thu, Sep 3
SWF
Newburgh
MCO
Orlando
$137 Roundtrip, found 5 hours ago
$137
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Tue, Aug 25 from Newburgh to Orlando, returning Thu, Sep 3, priced at $137 found 5 hours ago
Sun, Aug 30 - Thu, Sep 3
PHL
Philadelphia
MCO
Orlando
$142 Roundtrip, found 5 days ago
$142
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Aug 30 from Philadelphia to Orlando, returning Thu, Sep 3, priced at $142 found 5 days ago

Top rated hotels for your Osceola County vacation

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3 out of 5
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
11.31 mi from city center
The price is $78 total per night
$78 total
per night
May 31 - Jun 1
With a stay at Kompose Boutique Resort at Theme Parks in Kissimmee, you'll be a 5-minute drive from Walt Disney World® Resort and 10 minutes from ESPN Wide World of Sports Complex.
Pool
Hot Tub
Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

3 out of 5
2975 Arabian Nights Blvd Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
8.13 mi from city center
The price is $106 total per night
$106 total
per night
May 31 - Jun 1
Located in Kissimmee, Vacation Village Orlando, Celebration is in the entertainment district, within a 5-minute drive of Old Town and Fun Spot America.
Pool
Hot Tub
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

4 out of 5
8000 Fins Up Circle Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
12.72 mi from city center
The price is $215 total per night
$215 total
per night
Jun 2 - Jun 3
Located in Kissimmee, Margaritaville Resort Orlando with H2O Waterpark is a 1-minute drive from Island H2O Live! and 8 minutes from Walt Disney World® Resort.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Osceola 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.