Deals on vacations and trips to Osceola County

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Located south of Kissimmee FL, the area is being brought back to its natural state, there is a couple of walking trails and scientific studies are also done here.

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Vacations
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Osceola County flight + hotel vacation packages

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 $666, price is now $279 per person
$279
per person
Mar 4 - Mar 10
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free resort features a water park, a marina, and 2 restaurants. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and get free self parking.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $1,087, price is now $294 per person
$294
per person
Apr 11 - Apr 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel features an outdoor pool, a gym, and a restaurant. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $760, price is now $283 per person
$283
per person
Apr 4 - Apr 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free resort features a water park, a marina, and 2 restaurants. There's fun for all ages with a children's club and mini golf, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and perks like free self parking and free WiFi.
Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Price was $1,400, price is now $619 per person
$619
per person
Apr 4 - Apr 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Free water park access, 4 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. You'll appreciate the hot tub, poolside bar, and snack bar/deli.
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $2,427, price is now $1,077 per person
$1,077
per person
Mar 14 - Mar 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Free water park access and an outdoor pool are featured at this smoke-free condo resort. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's fun for all ages with a lazy river and a children's pool, and barbecue grills are available on site.

Top Osceola County hotels deals

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
$132 nightly
The price is $150 total per night
$150 total
Jan 31 - Feb 1
Total with taxes and fees
2 hot tubs, an outdoor pool, and a 24-hour gym are all featured at this smoke-free resort. Enjoy the sauna and free perks like buffet breakfast and WiFi in public areas. A bar/lounge, a 24-hour front desk, and a poolside bar are also provided.
Pool
Hot Tub
Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

3 out of 5
5711 W Irlo Bronson Memorial Hwy Kissimmee FL
Free Cancellation
$84 nightly
The price is $95 total per night
$95 total
Feb 2 - Feb 3
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Bring the family and enjoy the children's pool, free theme park shuttle, and playground. Enjoy the gym and perks like free self parking and free WiFi.
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
$121 nightly
The price is $137 total per night
$137 total
Feb 1 - Feb 2
Total with taxes and fees
7 outdoor pools, 7 hot tubs, and a gym are all featured at this smoke-free condo. Bring the family and enjoy the children's pool, playground, and arcade/game room. WiFi in public areas is free.
Pool
Hot Tub
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

4 out of 5
7600 Mystic Dunes Lane Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
$136 nightly
The price is $155 total per night
$155 total
Feb 25 - Feb 26
Total with taxes and fees
A golf course, 4 outdoor pools, and 2 outdoor tennis courts are all featured at this smoke-free hotel. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.
Pool
Parking included
Margaritaville Resort Orlando

Margaritaville Resort Orlando

4 out of 5
8000 Fins Up Circle Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
$191 nightly
The price is $217 total per night
$217 total
Feb 2 - Feb 3
Total with taxes and fees
This smoke-free resort features free water park access, a full-service spa, and 3 restaurants. Bring the family and enjoy the lazy river, waterslide, and arcade/game room. Enjoy the 3 outdoor pools and perks like free WiFi.
Pool
Hot Tub
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
4944 W. Irlo Bronson Memorial Highway Kissimmee FL
$100 nightly
The price is $114 total per night
$114 total
Feb 1 - Feb 2
Total with taxes and fees
This hotel features an outdoor pool, a gym, and a restaurant. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.
Pool
Breakfast included
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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.

Photos of local treasures

Browse Osceola County vacation photos for more inspiration

Old Timer Car.
Old Timer Car.
The boardwalk
This is part of the Everglades Eco System spanning over 23,000 acres, but only about 10 feet in depth at the deepest point. #boggycreek #kissimmeeflorida
Bank building

Frequently asked questions

How much are vacation packages to Osceola County?
Travelocity offers package deals to Osceola County, including flights and hotels, starting from an impressive $279. With the money you save, you could include some awesome tours or maybe even add on a few extra nights to your vacation.
Where can I get the best vacation package deals for Osceola County?
You'll find a fantastic range of Osceola County package deals on Travelocity. With 400 airlines and 1,000,000 properties around the globe, arranging a dream getaway will be simple.
Why should I book my Osceola County vacation package via Travelocity?
We offer 24/7 support, top-notch service and a Price Match Guarantee. Travel is all about the journey — and we have amazing destinations for you to journey to in every nook and cranny of the globe. Explore with us and make your hip pocket happy.
Can I save on my Osceola County car rental if I bundle it with a hotel or flight?
Combining your bookings into an Osceola County vacation package will certainly save you money. Book a flight and car; a hotel, car and flight; or a car and hotel. You won't find a better way to discover the greater Osceola County area than from the comfort of your own rental car. You can also add experiences and activities to your Travelocity package.
Which airport is best for Osceola County?
Orlando Intl. Airport (MCO) and Orlando Sanford Intl. Airport (SFB) are the top options for touching down in Osceola County.
What is there to do in Osceola County?
A diverse and inspiring destination, Osceola County is home to some fantastic sights and attractions. Lake Tohopekaliga and Disney Wilderness Preserve are just two of the top picks.

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