Cheap Vacations in Osceola County

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Osceola 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)
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 $794, price is now $473 per person
$473
per person
Aug 20 - Aug 25
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 $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 $1,340, price is now $881 per person
$881
per person
Sep 3 - Sep 7
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
Price was $579, price is now $383 per person
$383
per person
Aug 28 - Sep 1
found 21 hours ago
Roundtrip flight included
New York (NYC) 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 7 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 $1,058, price is now $712 per person
$712
per person
Sep 5 - Sep 12
found 4 hours ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,410, price is now $972 per person
$972
per person
Aug 19 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Budget Inn

Budget Inn

2 out of 5
Price was $467, price is now $327 per person
$327
per person
Sep 4 - Sep 9
found 11 hours ago
Roundtrip non-stop flight included
Islip (ISP) to Orlando (MCO)
Dune House Hotel & Spa

Dune House Hotel & Spa

4.5 out of 5
Save 100% on your flight
Price was $857, price is now $603 per person
$603
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

3-night Osceola 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 8 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 24 hours 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
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 9 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)
Dune House Hotel & Spa

Dune House Hotel & Spa

4.5 out of 5
Save 100% on your flight
Price was $857, price is now $603 per person
$603
per person
Aug 21 - Aug 24
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
Price was $534, price is now $380 per person
$380
per person
Aug 27 - Aug 30
found 21 hours ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Price was $664, price is now $475 per person
$475
per person
Aug 30 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Orlando (MCO)
Ocean Court Beachfront Hotel

Ocean Court Beachfront Hotel

2 out of 5
Price was $654, price is now $469 per person
$469
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)

4-night Osceola 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 22 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 2 hours ago
Roundtrip non-stop 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 $1,340, price is now $881 per person
$881
per person
Sep 3 - Sep 7
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
Price was $579, price is now $383 per person
$383
per person
Aug 28 - Sep 1
found 21 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 7 hours ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Save 100% on your flight
Price was $771, price is now $515 per person
$515
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $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)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $558, price is now $392 per person
$392
per person
Aug 19 - Aug 23
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 $811, price is now $575 per person
$575
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Orlando (MCO)
Oceanique Resort

Oceanique Resort

3.5 out of 5
Save 100% on your flight
Price was $715, price is now $512 per person
$512
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 $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
just found
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 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 $646, price is now $359 per person
$359
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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 20 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 $794, price is now $473 per person
$473
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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)
Vista Cay Resort by Millenium at Universal Blvd

Vista Cay Resort by Millenium at Universal Blvd

3.5 out of 5
Save 100% on your flight
Price was $771, price is now $518 per person
$518
per person
Aug 30 - Sep 4
found 10 hours ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,410, price is now $972 per person
$972
per person
Aug 19 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Budget Inn

Budget Inn

2 out of 5
Price was $467, price is now $327 per person
$327
per person
Sep 4 - Sep 9
found 11 hours ago
Roundtrip non-stop flight included
Islip (ISP) to Orlando (MCO)
Hilton Daytona Beach Oceanfront Resort

Hilton Daytona Beach Oceanfront Resort

4 out of 5
Save 100% on your flight
Price was $936, price is now $661 per person
$661
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)

6-7 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 $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)
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 23 hours 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)
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)
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)
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 4 hours ago
Roundtrip flight included
Islip (ISP) to Orlando (MCO)
Vero Beach Inn & Suites I-95

Vero Beach Inn & Suites I-95

3 out of 5
Save 100% on your flight
Price was $646, price is now $420 per person
$420
per person
Aug 24 - Aug 31
found 12 hours ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Pestana Orlando Suites - Lake Buena Vista

Pestana Orlando Suites - Lake Buena Vista

4 out of 5
Save 100% on your flight
Price was $593, price is now $391 per person
$391
per person
Sep 2 - Sep 8
found 13 hours ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Dune House Hotel & Spa

Dune House Hotel & Spa

4.5 out of 5
Save 100% on your flight
Price was $1,481, price is now $982 per person
$982
per person
Aug 18 - Aug 24
found 1 hour ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Coco Key Hotel & Water Park Resort

Coco Key Hotel & Water Park Resort

3.5 out of 5
Price was $577, price is now $386 per person
$386
per person
Sep 7 - Sep 14
found 23 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 $1,058, price is now $712 per person
$712
per person
Sep 5 - Sep 12
found 4 hours ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)

Top places to visit in Osceola County

A tree-lined pathway leading to a body of water.
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St. Cloud

St. Cloud

Flight deals to Osceola County

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

Mon, Oct 26 - Fri, Oct 30
TTN
Trenton
MCO
Orlando
$76 Roundtrip, found 1 day ago
$76
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Oct 26 from Trenton to Orlando, returning Fri, Oct 30, priced at $76 found 1 day ago
Mon, Oct 26 - Fri, Oct 30
TTN
Trenton
SFB
Orlando
$78 Roundtrip, found 1 day ago
$78
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Mon, Oct 26 from Trenton to Orlando, returning Fri, Oct 30, priced at $78 found 1 day ago
Fri, Sep 25 - Mon, Sep 28
SWF
Newburgh
SFB
Orlando
$94 Roundtrip, found 6 hours ago
$94
Roundtrip
found 6 hours ago
Select Allegiant Air flight, departing Fri, Sep 25 from Newburgh to Orlando, returning Mon, Sep 28, priced at $94 found 6 hours 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
$95 nightly
The price is $108 total per night
$108 total
Jul 21 - Jul 22
Total with taxes and fees
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 7 minutes from Old Town.
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
$96 nightly
The price is $109 total per night
$109 total
Aug 2 - Aug 3
Total with taxes and fees
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
$183 nightly
The price is $208 total per night
$208 total
Aug 19 - Aug 20
Total with taxes and fees
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
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See all available properties in Osceola County
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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.