Osceola County Vacations & Trips from $431
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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 destinations in Osceola County
Kissimmee
Four Corners
Celebration
St. Cloud
Saint Cloud
Poinciana
Intercession City
Kenansville
Yeehaw Junction
The Latest Osceola County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Ocean Landings Resort and Racquet
Jan 28 - Feb 1Ocean Landings Resort and Racquet + Flight
Cocoa Beach4 nights2.5 star property7.2/10 - Good (52 reviews)"This is an older property but very clean and well maintained. The two ocean front buildings are under a major renovation but there is still access to the beach. We would stay again."Reviewed October 30, 2026Roundtrip • Philadelphia (PHL) - Orlando (MCO)TTN - MCO • Nonstop SFB - TTN • Nonstop - Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Jan 10 - Jan 16Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight
Kissimmee6 nights4.0 star property9.2/10 - Wonderful (1,000 reviews)Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop$1,799$781found 1 day agoper traveler - Disney's Animal Kingdom Lodge
Dec 13 - Dec 19Disney's Animal Kingdom Lodge + Flight
Bay Lake6 nights4.5 star property9.0/10 - Wonderful (1,004 reviews)Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • 1 stop$3,741$1,880found 2 days agoper traveler - Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
Jan 10 - Jan 16Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive + Flight
International Drive District6 nights3.0 star property7.8/10 - Good (637 reviews)Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop$848$441found 1 day agoper traveler - Meliá Orlando Celebration
Jan 10 - Jan 16Meliá Orlando Celebration + Flight
Celebration6 nights4.0 star property8.8/10 - Excellent (1,643 reviews)Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop$834$440found 1 day agoper traveler
Discover the most popular places to visit in Osceola County
What to do in Osceola County
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
$27
per adult
92% of travelers recommend
Universal Orlando Resort Express Passes
$138
per traveler
80% of travelers recommend
Osceola County Hotel Deals
Kompose Boutique Resort at Theme Parks
Kompose Boutique Resort at Theme Parks3.0 star property
11.3 mi from Osceola County
9.4 out of 10, Exceptional, (6,402 reviews)
9.4/10
Exceptional
(6,402 reviews)
$61 nightly
The price is $70
$70 total
Nov 9 - Nov 10
Total with taxes and fees
9.6 out of 10, Exceptional, (858 reviews)
9.6/10
Exceptional
(858 reviews)
$110 nightly
The price is $124
$124 total
Nov 15 - Nov 16
Total with taxes and fees
Quality Inn & Suites Heritage Park
Quality Inn & Suites Heritage Park2.5 star property
2.8 mi from Osceola County
8.2 out of 10, Very good, (1,285 reviews)
8.2/10
Very good
(1,285 reviews)
"We requested for a end of the hall room and were told they don’t have one and they could not move us to one once it became available. Other guess kept slamming the doors until pass midnight. We were unable to rest and we had to ask for our room to be clean and when we did we were told they don’t do that on Saturday they won’t no even offered towels."
$59 nightly
The price is $67
$67 total
Nov 30 - Dec 1
Total with taxes and fees
8.6 out of 10, Excellent, (907 reviews)
8.6/10
Excellent
(907 reviews)
$98 nightly
The price is $111
$111 total
Nov 9 - Nov 10
Total with taxes and fees
9.0 out of 10, Wonderful, (1,003 reviews)
9.0/10
Wonderful
(1,003 reviews)
$54 nightly
The price is $66
$66 total
Nov 11 - Nov 12
Total with taxes and fees
SpringHill Suites by Marriott Orlando Lake Buena Vista South
SpringHill Suites by Marriott Orlando Lake Buena Vista South3.0 star property
5.6 mi from Osceola County
8.8 out of 10, Excellent, (1,411 reviews)
8.8/10
Excellent
(1,411 reviews)
"The moment we entered the lobby of this facility, it didnt gave an impression of Marriott. The entire furniture in lobby was outdated and dirty, we could not sit around. The room did not have a cabinet for the clothes. It was not at all worth the price paid for this facility."
$79 nightly
The price is $90
$90 total
Nov 11 - Nov 12
Total with taxes and fees
Margaritaville Resort Orlando with H2O Waterpark
Margaritaville Resort Orlando with H2O Waterpark4.0 star property
12.7 mi from Osceola County
8.8 out of 10, Excellent, (3,789 reviews)
8.8/10
Excellent
(3,789 reviews)
$164 nightly
The price is $186
$186 total
Nov 29 - Nov 30
Total with taxes and fees
Embassy Suites by Hilton Orlando Lake Buena Vista South
Embassy Suites by Hilton Orlando Lake Buena Vista South4.0 star property
5.4 mi from Osceola County
9.6 out of 10, Exceptional, (1,682 reviews)
9.6/10
Exceptional
(1,682 reviews)
$118 nightly
The price is $134
$134 total
Nov 15 - Nov 16
Total with taxes and fees
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.
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 package bookings compared to the price of the same components booked separately. Savings not available on all packages.