Osceola County Vacations & Trips 2026 from CA $803

Name: Holiday Inn & Suites Orlando SW - Celebration Area by IHG
Price range: CA $75
Rating: 8.4

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

A dense cluster of red flowers with green foliage.

Top Osceola County Vacation Deals

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

Seasons Florida Resort

CA $803

per person

Aug 10 - Aug 17

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Orlando (MCO)

9/10 Wonderful! (3,664 reviews)

Rooms got cleaned every other day. There was no continental breakfast! A/c was very noisy. Bathroom door would nut shut! If you want amenities, there aren’t many, then again the price was quite reasonable!

Reviewed on Jul 8, 2026

Westgate Town Center Resort

CA $1,159

per person

Sep 14 - Sep 25

found 1 day ago

Roundtrip flight included

St. John's (YYT) to Orlando (MCO)

8.2/10 Very good! (1,806 reviews)

As a solo traveler I truly enjoyed my time here. The resort had everything you need within close proximity and the room was an unbeatable price.

Reviewed on Jul 8, 2026

Westgate Vacation Villas Resort

CA $1,128

per person

Sep 14 - Sep 25

found 1 day ago

Roundtrip flight included

St. John's (YYT) to Orlando (MCO)

8.2/10 Very good! (1,979 reviews)

Clean room, not flexible if you want to stay extra nights but great place to stay for vacay!

Reviewed on Jul 7, 2026

Westgate Palace Hotel / Universal / I-Drive

International Drive District

CA $896

per person

Sep 2 - Sep 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Orlando (MCO)

9/10 Wonderful! (1,275 reviews)

Super clean and easy access

Reviewed on Jul 6, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

CA $1,264

per person

Sep 30 - Oct 4

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Orlando (MCO)

9.2/10 Wonderful! (1,003 reviews)

Excellent location

Reviewed on Jul 2, 2026

Osceola County Hotel Deals

Kompose Boutique Resort at Theme Parks

7491 W Irlo Bronson Memorial Hwy Kissimmee FL

Fully refundableReserve now, pay when you stay

CA $60

CA $131 total

Jul 13 - Jul 14

includes taxes & fees

9.4/10 Exceptional! (4,759 reviews)

"Environment is good and people are good with good motive and good work. But the design of the elevator and access is little inconvenience based on design and also single door shower in bathroom which makes more complicated in bathroom. These are the things need to be taken care by owner. Other than ..."

Reviewed on Jul 8, 2026

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

5711 W Irlo Bronson Memorial Hwy Kissimmee FL

Fully refundable

CA $75

CA $126 total

Jul 22 - Jul 23

includes taxes & fees

8.4/10 Very good! (2,805 reviews)

"Our stay was excellent from start to finish. Upon checking in, Carlos and Rafael at the front desk were both very professional and welcoming. The room was spotlessly clean, and the staff in the breakfast area were equally friendly. We were impressed with the breakfast selection, which offered plenty ..."

Reviewed on Jul 8, 2026

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL

CA $203

CA $308 total

Aug 4 - Aug 5

includes taxes & fees

8.8/10 Excellent! (3,658 reviews)

"Excellent resort."

Reviewed on Jul 8, 2026

See all 31,620 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.

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 $803. 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.

Stay near popular Osceola County attractions

A sign with 'Disney's Wide World of Sports' and 'All-Star Games' logos.

ESPN Wide World of Sports Complex

8.6/10 (1,630 reviews)

Catch an event at ESPN Wide World of Sports Complex, and enjoy other activities in Lake Buena Vista such as golfing. Experience the acclaimed theater scene and entertainment choices in this family-friendly area.

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