Osceola County Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Osceola County Vacation

Head off on your next thrilling adventure with an Osceola County vacation package, and leave knowing the finer details are taken care of. And with the ability to tailor your escape, you know it'll be one to remember. Get your trip to Osceola County off to a great start by exploring its top cities. Saint Cloud is one you shouldn't miss. If you're ready to stop dreaming and start doing, Expedia will help turn your Osceola County vacation into a reality.

Top vacation destinations in Osceola County

Delonix regia tree in bloom
FlightsFlightsHotelsHotels

Poinciana

Poinciana

Top Osceola County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was CA $1,418, price is now CA $814 per person
CA $814
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very Good! (1,944 reviews)
Its ok and good for family because of water park

Reviewed on May 23, 2026

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $2,613, price is now CA $1,276 per person
CA $1,276
per person
Jul 25 - Aug 1
found 13 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.8/10 Excellent! (1,250 reviews)
Our room was extremely clean and quiet. It was very close to Universal Studios. Highly recommend!

Reviewed on May 16, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $1,895, price is now CA $1,125 per person
CA $1,125
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.4/10 Very Good! (6,490 reviews)
Muy bueno lo recomiendo

Reviewed on May 23, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was CA $3,023, price is now CA $1,796 per person
CA $1,796
per person
Jul 25 - Aug 1
found 13 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
9.2/10 Wonderful! (1,004 reviews)
Loved the clean lesson the space. Loved how close o was to the pool and how friendly everyone was. Definitely 10/10

Reviewed on May 16, 2026

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was CA $2,447, price is now CA $1,485 per person
CA $1,485
per person
Jun 30 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (546 reviews)
Everuthing was perfect

Reviewed on May 17, 2026

Osceola County Hotel Deals

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

3 out of 5
2975 Arabian Nights Blvd Kissimmee FL
Fully refundableReserve now, pay when you stay
The price is CA $90 per night from May 27 to May 28
CA $90
CA $136 total
May 27 - May 28
includes taxes & fees
8.6/10 Excellent! (4,189 reviews)
"This vacation rental stay was nothing short of amazing!!! Why you see is what you get!!! It was everything! Couldn’t ask for a better stay! Effortless, welcoming and amazing staff, loved the entry security measures!! I definitely would book whenever I’m in Kissimmee. It met expectations! Loved the ..."

Reviewed on May 23, 2026

Vacation Village Orlando, Celebration
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3 out of 5
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
Fully refundableReserve now, pay when you stay
The price is CA $69 per night from May 26 to May 27
CA $69
CA $139 total
May 26 - May 27
includes taxes & fees
9.4/10 Exceptional! (4,131 reviews)
"Super clean. Ridiculous value! Terrific buffet breakfast included with room... Eggs, bacon AND sausage, potatos, waffles, etc. great pool areas (main pool and lazy river) with good shaded seating areas if that's your preference. If back in the area, will definitely look too stay here again. Cuban ..."

Reviewed on May 22, 2026

Kompose Boutique Resort at Theme Parks
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

4 out of 5
8000 Fins Up Circle Kissimmee FL
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from May 25 to May 26
CA $180
CA $280 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (3,599 reviews)
"This is my second time staying here and each time I couldn't wait to go back ! The place is clean and the staff is wonderful . There's a rental car in the lobby and even that gentleman was very helpful . Each time I have traveled there , there was a big event going on so it gets a big congested at ..."

Reviewed on May 23, 2026

Margaritaville Resort Orlando with H2O Waterpark
See all 32,349 properties in Osceola County
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an Osceola County vacation package cost?
Browse and book everything in one place with our Osceola County vacation packages, which start from only CA $814. Pick the flights and hotels that match your travel style. Then, add on a few enriching experiences to cap off your unique escape.
How do I get a cheap travel package to Osceola County?
Book everything all in one place with our Osceola County vacation packages. You'll find deals on hotels, flights, tours and more that'll keep your bank account happy and your spirit of adventure alive. And, with more than 550 airlines and 1,000,000 properties throughout the world to pick from, you'll have endless opportunities to mix and match all you want.
What are the top hotels in Osceola County?
For properties in Poinciana with cozy beds and friendly service, you can't top Magic Moment Resort and Kids Club and Delta Hotels Orlando Celebration. If you're visiting St. Cloud as well, you can look forward to a solid night's sleep at Red Lion Hotel Orlando Lake Buena Vista South or Palazzo Lakeside Hotel.
How far in advance should I book my Osceola County vacation?
While prices change from time to time, we generally advise booking your vacation as soon as possible. Most international fares become available on Expedia up to 12 months in advance. If you're booking late, you may still get lucky. Discount prices to Osceola County sometimes occur only weeks before departure.
What does an Expedia Osceola County travel package include?
It's up to you! You can select from a variety of Osceola County bundles, such as a rental car, flight and hotel. You can also book a flight with a hotel, or a rental car with a flight. Once you've made your booking, you can add on the fun stuff like experiences and tours. Whatever your Osceola County trip looks like, you're sure to save!
What should I know before booking an Osceola County travel package?
Our prices are already low. However, you'll enjoy an even better deal when you book your flights, hotels and car rentals together. With an Expedia travel package, you'll always get transparent pricing and a great range of choice.
Can I choose my airline with an Osceola County Expedia vacation package?
With a vacation package, you're in charge. Whether you're hoping to fly to Osceola County in economy or business class, simply pick from the available airline options. Expedia has access to over 550 airline partners globally.
If I'm not able to travel, can I cancel my Osceola County vacation package?
Because we know life is full of surprises, the answer is yes. To learn more, head to our Customer Service Portal. But generally speaking, if you've booked your Osceola County vacation package in the last 24 hours, you may be able to change or cancel it for free. Your airline, hotel or car rental company may charge a fee if you made your booking a while ago.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.