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 $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 Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Save 100% on your flight
Price was $876, price is now $449 per person
$449
per person
Oct 15 - Oct 19
found 13 hours ago
Roundtrip flight included
Detroit (DTW) 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 $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)
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 River Ranch Resort & Rodeo

Westgate River Ranch Resort & Rodeo

3.5 out of 5
Save 100% on your flight
Price was $1,054, price is now $631 per person
$631
per person
Oct 16 - Oct 22
found 12 hours ago
Roundtrip flight included
Detroit (DTW) 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 10 hours 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 $1,198, price is now $805 per person
$805
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
Magic Village Views Trademark Collection by Wyndham

Magic Village Views Trademark Collection by Wyndham

3.5 out of 5
Save 100% on your flight
Price was $1,484, price is now $996 per person
$996
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $496, price is now $349 per person
$349
per person
Oct 7 - Oct 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Hilton Garden Inn Orlando I-4 Millenia Blvd Mall

Hilton Garden Inn Orlando I-4 Millenia Blvd Mall

3 out of 5
Florida Center
Price was $520, price is now $370 per person
$370
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

3-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 $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)
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 7 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)
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 10 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)
Magic Village Views Trademark Collection by Wyndham

Magic Village Views Trademark Collection by Wyndham

3.5 out of 5
Save 100% on your flight
Price was $648, price is now $445 per person
$445
per person
Oct 29 - Nov 1
found 14 hours ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool

Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool

4 out of 5
Save 100% on your flight
Price was $655, price is now $453 per person
$453
per person
Oct 29 - Nov 1
found 14 hours ago
Roundtrip flight included
Detroit (DTW) 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)
ette hotel

ette hotel

5 out of 5
Save 100% on your flight
Price was $888, price is now $634 per person
$634
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 Osceola County vacations

Price found within the past 48 hours. Click for updated prices.
The Irlo

The Irlo

3 out of 5
Save 100% on your flight
Price was $341, price is now $229 per person
$229
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 $876, price is now $449 per person
$449
per person
Oct 15 - Oct 19
found 13 hours ago
Roundtrip flight included
Detroit (DTW) 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)
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)
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 Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $679, price is now $427 per person
$427
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
New York (JFK) 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 5 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)
Summer Bay Orlando MOD Collection by Sonesta

Summer Bay Orlando MOD Collection by Sonesta

3.5 out of 5
Save 100% on your flight
Price was $422, price is now $280 per person
$280
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,198, price is now $805 per person
$805
per person
Oct 16 - Oct 20
found 1 day 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
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)

5-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 $1,218, price is now $355 per person
$355
per person
Oct 6 - Oct 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
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)
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 $846, price is now $466 per person
$466
per person
Oct 14 - Oct 19
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $673, price is now $372 per person
$372
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip flight included
New York (LGA) 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)
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)
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)
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 $766, price is now $515 per person
$515
per person
Oct 21 - Oct 26
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)

6-7 night Osceola County vacations

Price found within the past 48 hours. Click for updated prices.
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Save 100% on your flight
Price was $596, price is now $382 per person
$382
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip non-stop 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
just found
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 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)
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)
Westgate River Ranch Resort & Rodeo

Westgate River Ranch Resort & Rodeo

3.5 out of 5
Save 100% on your flight
Price was $1,054, price is now $631 per person
$631
per person
Oct 16 - Oct 22
found 12 hours ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
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)
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 $1,186, price is now $754 per person
$754
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ

4 out of 5
Save 100% on your flight
Price was $850, price is now $547 per person
$547
per person
Oct 25 - Nov 1
found 11 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 $622, price is now $400 per person
$400
per person
Oct 11 - Oct 17
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 $1,323, price is now $854 per person
$854
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Villas At Regal Palms

Villas At Regal Palms

4 out of 5
Save 100% on your flight
Price was $811, price is now $528 per person
$528
per person
Oct 25 - Nov 1
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.

Wed, Oct 14 - Mon, Oct 19
DTW
Detroit
MCO
Orlando
$98 Roundtrip, found 4 hours ago
$98
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Oct 14 from Detroit to Orlando, returning Mon, Oct 19, priced at $98 found 4 hours ago
Mon, Oct 5 - Fri, Oct 9
PHL
Philadelphia
MCO
Orlando
$100 Roundtrip, found 1 hour ago
$100
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Oct 5 from Philadelphia to Orlando, returning Fri, Oct 9, priced at $100 found 1 hour ago
Fri, Oct 16 - Tue, Oct 20
SJU
San Juan
MCO
Orlando
$120 Roundtrip, just found
$120
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Oct 16 from San Juan to Orlando, returning Tue, Oct 20, priced at $120 just found

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
$67 nightly
The price is $76 total per night
$76 total
Sep 30 - Oct 1
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.
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
12.72 mi from city center
$187 nightly
The price is $212 total per night
$212 total
Sep 7 - Sep 8
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
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

3 out of 5
5200 West Irlo Bronson Memorial Highway Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
5.87 mi from city center
$56 nightly
The price is $64 total per night
$64 total
Sep 3 - Sep 4
Total with taxes and fees
Located in Kissimmee, Magic Moment Resort & Kids Club, Dazzler Select by Wyndham is within a 10-minute drive of Orlando Vineland Premium Outlets and Disney Springs™.
Pool
Breakfast included
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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.