Win a $1,000 Winter Park Village Date Night

Orlando Date Night Guide is a free guide to the best of Orlando! We're supported by our advertisers when they buy digital ads, listings, content, and through affiliate links, so some things you read might be paid for or if you buy something thru a link on our site we might get a commission.

Just in time for Valentine’s Day, this month’s Couple at Large Giveaway with Winter Park Village is going to be a ‘knock your socks off’ date night for one lucky couple.

Located on 17-92 between Lee Road and Fairbanks Avenue, Winter Park Village is a best bet for dining, nightlife, shopping and pampering. For this special giveaway, Winter Park Village will host one lucky couple for a spectacular date extravaganza.

The pampered pair will be spoiled beyond their wildest dreams for one special day and night of romance that includes brand new date night duds, dinner, drinks, movies and spa indulgences. The entire prize package is worth over $1,000.

This full-day couples experience includes:

The Couple at Large will have just one favor to return: they will be tasked with reporting back with a short, first-person blog about their experience, including original photos, due on or before February 8, 2017. (Read about our 2016 winner's experience here).

The experience can be scheduled any time between January 16 and February 5, 2017, based on availability. All components of the prize to be redeemed on the same day.

winter park village regal


WINNER: Lisa Ngai

Enter using the Rafflecopter widget below and cross your fingers. You and your sweetie can each enter… double your chances.

The winner will be chosen—completely at random—on Friday, January 13, 2017 using the Rafflecopter’s random winner generator. Watch your email that morning; that’s how we’ll be contacting the winner. We’ll also be announcing the winner on Twitter and Facebook.

Note: Please be sure you are viewing this page in a browser (not a reader) in order to see the entry widget.

a Rafflecopter giveaway

RULES & RESTRICTIONS: No purchase necessary. Must be 21+ to enter/win. This prize must be redeemed in its entirety by February 5, 2017. Tax is included but gratuity is not. Advance reservations required. The winner will be responsible for claiming this prize in their 2017 taxes. In the event that a prizewinner is disqualified for any reason, the prize will be awarded to an alternate winner at random. All prizes are non-transferable and no substitutions will be made. Read the entire Official Rules and Terms.

Orlando Date Night Guide is a free guide to the best of Orlando! We're supported by our advertisers when they buy digital ads, listings, content, and through affiliate links, so some things you read might be paid for or if you buy something thru a link on our site we might get a commission.

329 Responses to “Win a $1,000 Winter Park Village Date Night”

  1. Samantha Johnson

    Pick Me!!!!!!!!! Its my birthday too!!!!! 🙂

  2. Lauren

    My boyfriend and I haven’t been on a date in over a year! 🙁 Please pick me! 🙂

  3. Becky

    Pick me! We’re going to have our second child this year and would love an amazing date before we’re housebound for a while!

  4. Rachell

    Pick me! This is an amazing opportunity! Thank you!

  5. Danielle Hounshell

    New to the area. Would love to get out and explore!

  6. Heather Lane

    This would be an amazing 20th wedding anniversary treat 🙂

  7. Kristina

    PICK ME! This is amazing 🙂 thank you so much for the opportunity!

  8. Jessica Cabrera

    Please pick me! Pinky promise to post the blog and take pictures throughout the day! 🙂

  9. Amy T

    Please. Please…my husband and I need this oh so bad…. <3

  10. Nicole Calderon

    Pick Me!!! This would be AMAZING and very much needed!!! Plus a Birthday gift to me!!!

  11. Beatriz Torres

    PI know me, Please! We NEED this desperately.

  12. Beatriz Torres

    Pick me, Please! We NEED this desperately.

  13. Kate

    Please pick me! My husband and I need this so badly. Thank you for the opportunity.

  14. Amy Cummiskey

    Pick me please!!! Valentines Day 2013 is the date I knocked on my now-husbands door in Delaware. By July he’d sold his home in Delaware and moved to Orlando to begin our life together!! This would be an amazing surprise for my Fairy Tale Prince!!!

  15. Bethany Walti

    PICK ME!!!
    PICK ME!!!
    PICK ME!!!
    PICK ME!!!
    PICK ME!!!
    PICK ME!!!
    PICK ME!!!
    PICK ME!!!

  16. Sabrina D

    I would love to win this prize. I will be moving to Orlando to start my new job as a nurse in March. This would be an awesome gift before I take my NCLEX-RN.

  17. Regina S

    I want to go there! This will be my Belated Christmas gift before my baby twins born….Pick me please!!!

  18. Gayle Kuby

    Pick me! We need romance sooooo bad! Love Winter Park!

  19. Christina A.

    My New Year’s Resolution is hopefully winning this.
    Fingers crossed!

  20. Lynn

    Thank you… I look forward to more fun at the Winter Park Village!

  21. Abbey Sanders

    Pick Me!!! My fiance and I would love this!!!

  22. Felicia Nicole Vestal

    Ahhh i need this. Would be such a good date with my mom

  23. Rodney George

    Pick Me!!!!!!!!!!!!!!!! It’s my wife’s birthday

  24. Sheena

    I love Orlando Date Night guide and use it all the time for new date night and event ideas! I recommend it to everyone. Pick me!!

  25. Alison King

    Pick me! This sounds like an awesome date day.

  26. Autumn Sirmeyer

    Now that Benny is one year old i am ready for a date night out with my hubby! Plus: I had the flu on my birthday and need to make up for that. Pick me!!!

  27. Julie

    Pick me!! 🙂 It’s our 6 year anniversary too, so this would be lovely 🙂

  28. Cecilia V.

    Pick me!!!!
    Would love to win this, hubby and I sure need some time alone..

  29. Michelle

    Pick me!! Pick me!! February 5th is my 30 birthday!! I’m a mom of 3 under 4! Some pampering and alone time would be heaven!

  30. Crystal

    Pick me (us)! My girlfriend will be super surprised to have this experience. Her birthday is at the end of the month and mine is at beginning so not only would this be a fabulous date night but we could celebrate our birth month in style! And she’s totally good with shopping the mens department….plus she likes when I dress her! So a shopping date, dinner and massage sound incredible.

  31. Rafael Castillo

    Pick me! My wife and I have three kids, ages 5, 2, and 8 months. We love the family we’ve built, but it can be all-consuming, and we have very few real date nights throughout the year. I got us a subscription to the Orlando Date Night Club for Christmas to help with our nights out, and winning this raffle would be the BEST Valentine’s gift ever!! Fingers crossed!!

  32. Krystine Lopez

    Pick me 🙂 We’re saving up for our wedding, so date nights are few and far between!

  33. Dalia Perez

    Aww we had a baby recently so this would definitely be great. Pick me!

  34. Jennifer King

    Pick me! A poor college girl trying to take care of her and her man for valentine’s day 🙂

  35. Anna

    I just found Orlando Date Night Guide and am now a member of the Date Night Discovery Club. I love it!!!!

  36. Ryan Summers

    Thanks for the great contest and Happy New Year to all!

  37. Dana Summers

    What an amazing prize package. Thanks for the giveaway WPV!

  38. Cheyenne meyer

    Pick me 🙂 pick me 🙂 pick me 🙂 pick me:)

  39. Jennifer Belpre

    Please pick me! My husband and I never get a nice date night to ourselves! We would absolutely love this!

  40. Shana Coulthurst

    PICK ME!!! I’d love to win this and surprise my bf with it! <3

  41. Jasmine

    Pick me!! My husband and I just recently moved to Orlando and this would be a great celebration! 🙂

  42. Kris

    Absolutely love Winter Park Village, blogging and being able to share all of the amazing places that donated. Please PICK ME or pick us 🙂 Best of luck to all!

  43. Alma J. Coleman

    I just have to win this and do need to win!

  44. Wisangeles Walker

    Pick Me! I would love to have this date with my boyfriend! <3

  45. Jason Osorio

    I love Winter Park and I hope to win! Pick Me!

  46. Cliff

    Pick me. Wife deserves pampering for having to deal with me

  47. Janet Feliciano

    We love the Orlando Date Night Guide. So happy this exists!

  48. Jeff Adams

    Pick me!!!!! Trying t do something special before me and my girlfriend have to split up because of our jobs and this would be a great last way to tell her I love her!

  49. Abby N

    Pick Me!! (It’s our anniversary January 26th so a great way to celebrate!)

  50. Rachel Adelson

    PICK Me!! Husband and I haven’t been on a proper date since our son was born LAST January..


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