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Orlando Sweepstakes - Explore the Magic

Our exclusive Orlando sweepstakes offer you an opportunity to be part of this incredible journey. Don't miss out on being one of the lucky winners who will get to witness the city's evolution firsthand. Are you ready to embark on an extraordinary journey to the enchanting city of Orlando? Look no further! We are your ultimate destination for free Orlando sweepstakes, offering you a chance to experience the magic of this captivating city without spending a dime. Whether you dream of exploring world-famous theme parks, indulging in mouthwatering cuisine, or discovering hidden gems off the beaten path, our sweepstakes have got you covered! We understand your passion for adventure and the thrill of winning. That's why we curate an extensive list of Orlando sweepstakes that cater to your desires and aspirations. From family-friendly trips to romantic Orlando giveaways. Our sweepstakes cover a wide range of experiences, ensuring there's something for everyone. Imagine strolling down the iconic streets of Orlando in 2026, soaking up the vibrant atmosphere and creating memories that will last a lifetime. Our exclusive visit Orlando sweepstakes and contests offer you an opportunity to be part of this incredible journey. Don't miss out on being one of the lucky winners who will get to witness the city's evolution firsthand.

Orlando Giveaways



Found 12 total
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Enter to win the Ema Nikolovska and Sean Shibe Concert Ticket Giveaway.
One winner gets 2 tickets to see mezzo-soprano Ema Nikolovska and guitarist Sean Shibe perform Orlando at Telus Studio Theatre in Vancouver on November 8, 2026 (about CAD $146, US $106).
Open to legal residents of Canada, including Quebec. Ends November 3, 2026 at 11:59 PM PST.
To enter, fill out the Xtra gleam entry form for the Ema Nikolovska and Sean Shibe tickets. The winner is notified by email and has 72 hours to confirm.

Win $146 in value – Ema Nikolovska and Sean Shibe Concert Ticket Giveaway - Enter Now

Restrictions: Legal residents of Canada, including Quebec.
Limit: 1 Per Person
Added: 11-02-2026
Expires: 11-03-2026 11:59 PM PST
Hits: 4
Est. Value: $146.00
Category: Canada Only

Enter to win the Wesh-tv Live with Kelly and Mark St Pete-Clearwater Getaway Sweepstakes - 5 Winners.
Wesh-TV Live with Kelly and Mark St. Pete-Clearwater Getaway Sweepstakes offers five Grand Prize VIP Getaway Packages. - Five (5) Grand Prize VIP Getaway Packages awarded, each including two (2) VIP seats for the winner and one (1) guest at the Live with Kelly and Mark remote show taping at Sandpearl Resort (500 Mandalay Ave, Clearwater Beach, FL) on November 16, 2026. Admission for the winner ...
Open exclusively to legal residents of Florida who reside within the Orlando-Daytona Beach-Melbourne Designated Market Area (DMA) and are eighteen (18) years of age or older at the time of entry (18+).. Ends 11-11-2026 11:59 PM EST.
To enter, follow the on-post instructions on the X post (typically follow, like and comment/repost). Winner announced after the end date.

Win $5,000 in value – Wesh-tv Live with Kelly and Mark St Pete-Clearwater Getaway Sweepstakes - 5 Winners - Enter Now

Restrictions: Open exclusively to legal residents of Florida who reside within the Orlando-Daytona Beach-Melbourne Designated Market Area (DMA) and are eighteen (18) years of age or older at the time of entry (18+).
Limit: 1 Per Person
Added: 11-01-2026
Expires: 11-11-2026 11:59 PM EST
Hits: 3
Est. Value: $5,000.00
Category: Florida

Enter to win Christmas at Gaylord Palms ICE Featuring The Polar Express Sweepstakes.

Fifteen winners each get a four-pack of ICE! Featuring The Polar Express tickets (about $160 each; total about $2400). Tickets available for pickup at the sponsor location.

Open to US residents 18 and older in the Sponsor's Orlando DMA. Ends November 23, 2026 at 11:59 PM EST.

To enter, complete the sweepstakes entry form on clickorlando.com/Contests (unlimited entries per person/email/phone during the period).

Win $2,400 in value – Christmas at Gaylord Palms ICE Featuring The Polar Express Sweepstakes - 15 Winners - Enter Now

Restrictions: 18+ ClickOrlando / WKMG Orlando DMA
Limit: Unlimited
Added: 10-30-2026
Expires: 11-23-2026 11:59 PM EST
Hits: 11
Est. Value: $2,400.00
Category: Florida

Enter to win the Phoong Law Magic vs Kings Ticket Sweepstakes.

One winner gets two tickets to the Sacramento Kings vs Orlando Magic game on November 10, 2026.

Open to those 21 and older who live within driving distance of Sacramento and can attend. Ends November 6, 2026 at 12:00 PM PST.

To enter, submit the entry form; one entry per person. The winner is notified by email.

Win $1,400 in value – Phoong Law Magic vs Kings Ticket Sweepstakes - Enter Now

Restrictions: 21+; must live within driving distance of Sacramento and attend the game.
Limit: 1 Per Person
Added: 10-25-2026
Expires: 11-06-2026 12:00 PM PST
Hits: 1
Est. Value: $1,400.00
Category: California
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Visit Orlando Family Vacation Sweepstakes offers a single prize. - One 4‑day/3‑night Orlando family vacation for the winner and up to three guests (four people total). The prize includes four Frontier Airlines flight vouchers valued at $250 each ($1,000 total) toward flights to Orlando, FL from an airport served by Frontier Airlines. It also includes three consecutive nights of hotel accommodations in a standard quad‑occupancy room at a moderate Walt Disney World® Resort hotel. Additionally, the winner receives up to four 4‑day Theme Park Tickets with the Park Hopper® option at Walt Disney World® Resort. The Florida sweepstakes ends on Monday, January 18, 2027 at 11:59:59 PM ET.

Win $4,950 in value – Visit Orlando Family Vacation Sweepstakes - Enter Now

Restrictions: Open only to legal residents of the forty-eight (48) contiguous United States and Washington, D.C. who are at least twenty-one (21) years of age at the time of entry.
Limit: Daily Per Person
Added: 10-14-2026
Expires: 01-18-2027 11:59 PM EST
Hits: 2754
Est. Value: $4,950.00

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Enter to win the Disney Imagination Campus and The Muppet Studio 2027 Teachers Sweepstakes - 15 Winners.

Fifteen winners each receive a 4-day, 3-night Walt Disney World vacation for the winner and one guest (expected April 29 - May 2, 2027): round-trip coach airfare to Orlando, airport transfers, 3 nights at a Walt Disney World Resort hotel, two 3-day Park Hopper tickets, a $200 Disney gift card, access to the Disney Imagination Campus celebration event on April 30, 2027 and a $1,250 check toward taxes (ARV $5,000 each, $75,000 total).

To enter, complete the registration form on the Disney Imagination Campus Teachers Sweepstakes page. Limit one entry per person.

Open to full-time public or private elementary, middle or high school teachers 21+ in the 50 US states, DC and Puerto Rico. The Disney sweepstakes ends January 17, 2027 at 11:59 PM ET.

Win $75,000 in value – Disney Imagination Campus and The Muppet Studio 2027 Teachers Sweepstakes - 15 Winners - Enter Now

Restrictions: 21+ full-time K-12 teachers in US, DC, PR
Limit: 1 Per Person
Added: 10-05-2026
Expires: 01-17-2027 11:59 PM EST
Hits: 1153
Est. Value: $75,000.00

Enter to win the Main Street Collective Main Street Magic Orlando Giveaway.
One North Carolina winner and up to three guests receive a customized Orlando vacation worth up to $5,000, which may include Orlando-area resort accommodations, theme park experiences and personalized vacation planning (travel to/from Orlando not included).
To enter, complete the SweepWidget entry form (name, email, phone, address, NC residency) for one free entry, then earn bonus entries by following Main Street Collective on Instagram (+5) and Facebook (+5), referring friends (+3) and secret codes.
Open to legal residents of North Carolina, 18+. The giveaway ends November 30, 2026 at 11:59 PM EST.

Win $5,000 in value – Main Street Collective Main Street Magic Orlando Giveaway - Enter Now

Restrictions: 18+ North Carolina
Limit: Bonus Entries
Added: 10-04-2026
Expires: 11-30-2026 11:59 PM EST
Hits: 6
Est. Value: $5,000.00
Category: North Carolina

Star 102 Cleveland Visit Florida Contest offers four vacation packages for two people (winner and guest) to Orlando, Florida, one awarded each week. - Four vacation packages for two people (winner and guest) to Orlando, Florida, one awarded each week, each including three consecutive nights at Caribe Royale Orlando, round‑trip coach class airline tickets for two to Orlando International Airport, an intermediate‑size rental car for four consecutive days, two general admission tickets to Gatorland, and an ICON Park Orlando Experience that provides two tickets for The Orlando Eye, two admission tickets to SEA LIFE Orlando Aquarium, two admission tickets to Madame Tussauds Orlando, and two admission tickets to Museum of Illusions Orlando. The vacation packages are valid through December 15, 2027, and the winner must be at least 25 years old to book. The contest ends on November 6, 2026, at 4:00 PM ET.

Win $10,049 in value – Star 102 Cleveland Visit Florida Contest - 4 Winners - Enter Now

Restrictions: Open to legal residents within the Star 102 (WDOK) listening/viewing area; must be 25 years of age or older.
Limit: Bonus Daily Entry
Added: 10-03-2026
Expires: 11-06-2026 04:00 PM EST
Hits: 10
Est. Value: $10,049.00
Category: Ohio

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Enter the Visit Orlando Common Ground Orlando Sweepstakes for a chance to win an eight‑night Dream Vacation to Orlando, Florida valued at $15,000. The sweepstakes, presented by TripAdvisor, is open to legal residents of the United States, District of Columbia, Canada, Mexico and the United Kingdom who are 21 years or older. The draw will be held on January 7, 2027, so be sure to submit your entry before then. One winner will receive $8,000 in theme‑park funds plus round‑trip airfare, hotel accommodations and a travel planning session. No purchase necessary. This sweepstakes ends on January 7, 2027.

Win $15,000 in value – Visit Orlando Common Ground Orlando Sweepstakes - Enter Now

Restrictions: 21+ US, Canada, Mexico, UK
Limit: 1 Time Per Person
Added: 09-27-2026
Expires: 12-31-2026 11:59 PM EST
Hits: 4794
Est. Value: $15,000.00
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Enter the Choice Hotels Choice Privileges Sweepstakes for a chance to win exciting prizes. Choice Hotels International, Inc. is offering a grand prize deluxe vacation package to Hawaii, Las Vegas, or Orlando, including round-trip air transportation, 7-night accommodations, car rental, and 2,000,000 Choice Privileges Points, valued at $19,400. Alternatively, the grand prize winner can choose a $10,000 cash alternative. Additionally, 12 monthly prizes are available, each consisting of a 3-night stay at a Choice Hotels location, 100,000 Choice Privileges Points, a 5-day car rental, and a cruise, valued at $1,525. To enter, visit the website and follow the on-screen instructions, or use the alternate method of entry online without a mobile phone. Bonus entries are also available. The Choice Hotels sweepstakes is open to legal US residents 25 years or older, and winners must be Choice Privileges members. Enter now for a free chance to win, courtesy of Choice Hotels International, Inc. Giveaway begins on 5/1/26 at 12:00 AM ET and ends on 4/30/27 at 11:59 PM ET.

Win $37,700 in value – Choice Hotels Choice Privileges Sweepstakes - Enter Now

Restrictions: 25+ US
Limit: See Bonus Entries
Added: 05-08-2026
Expires: 04-30-2027 11:59 PM EST
Hits: 2282
Est. Value: $37,700.00