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16 Ideas For The Ultimate Romantic Orlando Getaway

Added: Feb 01, 2019
Category: Travel Guides

16 Ideas For The Ultimate Romantic Orlando Getaway


As we move full steam ahead into the New Year, many people are making good on their New Year’s Resolutions to travel more, spend more time with their families and try new things. February and March are popular times for newlyweds to get away for their first romantic getaway of the new year, and with its warm temperatures, winter and spring themed events and plenty to do, Orlando is a great spot for a romantic getaway.


We’ve put together 16 of our favorite spots for a romantic date night, unforgettable proposal or quality time with your sweetheart. We’ve found a unique combination of classic Orlando venues and some lesser-known (but just as great) local places that Orlando residents like to keep to themselves.


For Music Loving Couples

Orlando is a hot spot for everything music, from vintage record stores and live music on a patio cafe to sold-out arena concerts and performing arts. If music is a foundation in your relationship, you’ll have to check out some of these incredible venues during your romantic Orlando getaway:


Amway Center

The Amway is where top recording artists put on their shows for music-loving Orlando residents. In February and March, the Amway will host greats like Andrew Bocelli, Michael Buble, Travis Scott, and Lionel Richie. If you want to attend a big concert while you’re here, the newly renovated Amway Center is the place to do it.


CityWalk’s Rising Star

CityWalk’s Rising Star bar redefines karaoke night. Sign up to sing your favorite song, get up on a real stage and sing your heart out with a real band and backup singers to help. Drinks are pricey, but it is a unique and fun party atmosphere that brings people together over good music and strong drinks.


House of Blues

In our opinion, there is nothing like a concert at House of Blues. This iconic music venue is small enough that no matter where you are, you’ve got incredible views of the stage. Artists like Lyfe Jennings, Dylan Scott and the band 311 will put on memorable shows during February. House of Blues offers impressive happy hour deals during the week and a gospel brunch on Sundays that you can’t miss!


RNR Record Shop

If you’d prefer to thumb through vintage records instead of attending a high-energy concert, RNR Record Shop is the place for you. This chill, no-frills vinyl record shop is a perfect place to spend a rainy afternoon with your love and browse the extensive selection of records, CD’s, and other collectibles.


Country Thunder 2019

Put on your boots and cowboy hats and bring your sweetie down yonder to the Osceola Heritage Park. This annual music festival features top country recording artists like Toby Keith, Luke Bryan, Mitchell Tenpenny, and Luke Combs. The festival takes place March 22-24 and offers both camping and glamping options for those who want to get the full experience


Our vacation rental recommendations for couples that love music: Hollywood Dreams and Goofy’s Grotto



For Couples Who Appreciate A Good Brew

Kissimmee has no shortage of unique breweries, wine bars and other places to enjoy a good cocktail. If you prefer to skip the traditional bar experience and want something a little more local and authentic, you’ll have to add these 21+ hangouts to your romantic Orlando getaway:


Crooked Can

Crooked Can is about 30 minutes from Kissimmee, but it is worth the trip. Tucked away under Oak Trees in Downtown Winter Garden, this local brewery offers inside and outside seating, an impressive selection of handcrafted brews, and live music on the weekends. It is located in an adorable market that features a dozen other vendors, ranging from a pizza place and smoothie shop to sushi and a gourmet mac and cheese stop.


Dead Lizard Brewery Company

Craft beer lovers appreciate the industrial feel of the taproom, and order flights of craft beer to enjoy with friends. The large open space is surrounded by metal and concrete and offers plenty of seating, an extensive beer list and a friendly staff that can help you find the perfect brew for you. Dead Lizard Brewing Company is located about 25 minutes from most of Loyalty’s vacation rentals.


Hidden Speakeasies

If you like a little mystery with your brew, you’ll love discovering some of these hidden speakeasies, some of which require a password to get in! Three Sister Speakeasy is a modern hangout with an eclectic menu, offers a pet-friendly patio and is located in Downtown Kissimmee. You’ll need a password to get into the 1920’s inspired speakeasies like Hanson’s Shoe Repair or Park Social. The Pharmacy is another fun, hidden hangout in Orlando, and if you can find the door, you’re in! If you’d like to learn more about how to get into these underground spots, contact us!


Wine Tastings

If you prefer grapes over wheat, you’ll have no issue enjoying a glass (or bottle) of wine in some of the area’s coolest and most romantic wine bars and wine-themed events. Vintage Vino offers wine flights, comfy armchairs and cheese plates to complete your romantic evening. Wine Bar George in Celebration is a great spot to sip wine and people watch, and Imperium Food and Wine consistently gets rave reviews for their small plates and appetizers.


Our vacation rental recommendations for couples that love a good brew: Disney’s Beach House and Audez Tropical Haven


For “Foodie” Couples

One of the best parts of being on vacation is trying all of the new food and stumbling upon local restaurants that you can’t find back home. If you and your sweetie enjoy sharing a meal together and trying out new places, you’ll find an abundance of options in Orlando. But, we have to be honest, you will have to search a little bit to find the hidden gems. Orlando and Kissimmee especially is a haven for chain restaurants, but if you know where to look, you can find some excellent local hangouts.


Big John’s Rockin’ BBQ

While it may not be the most romantic place to eat in Kissimmee, it’s a must-try when you are in the area. The little house-converted-to-BBQ-heaven in downtown Kissimmee offers mouth-watering brisket, homemade styles, sweet, sweet tea, and friendly staff. Portions are big, prices are fair, and it feels intimate and homey.


Woodsby’s Cafe

If you’re after a hearty, All-American Breakfast (that doesn’t feel like Denny’s Or IHop), you’ll love Woodsby’s Cafe. Don’t let the unassuming exterior fool you, the food that comes out of this kitchen feels like it was made by a loving grandma on Saturday morning. We recommend the Philly Cheesesteak Omelette or Brittany's Loaded Hash Browns. Monday through Friday they are open until 7:30 so you can satisfy your “breakfast for dinner” craving.


World Showcase At Epcot

If you are craving Mexican and your love is dying for Chinese, there is only one way to compromise: Epcot’s World Showcase. Walk hand and hand through the park and try samples of food (and drinks!) from around the world.


Better Than Sex Dessert

If it is ultimate romance you’re after, you have to swing into this dimly lit dessert place in downtown Orlando. Snuggle into a booth (pull a curtain for extra privacy) order delectable desserts with names that might make you blush. Designed to bring couples close through the beauty of sweet dessert, this sexy dessert spot is a must-try during a romantic Orlando getaway.


If you prefer to keep your dessert experience “rated G,” Kissimmee has old-fashioned ice cream stores, self-serve ice cream shops, bakeries, cafes and other delicious options to satisfy your sweet tooth.


Our vacation rental recommendations for couples that love to eat: Seven Dwarfs Escape and Sunny Oaks Poolside


As we move full steam ahead into the New Year, many people are making good on their New Year’s Resolutions to travel more, spend more time with their families and try new things. February and March are popular times for newlyweds to get away for their first romantic getaway of the new year, and with its warm temperatures, winter and spring themed events and plenty to do, Orlando is a great spot for a romantic getaway.


We’ve put together 16 of our favorite spots for a romantic date night, unforgettable proposal or quality time with your sweetheart. We’ve found a unique combination of classic Orlando venues and some lesser-known (but just as great) local places that Orlando residents like to keep to themselves.



For Adventurous Couples

If your idea of a romantic getaway is trying new things and stepping out of your comfort zone together, Orlando has plenty of ways to get your heart racing and try something that might scare you a little bit:


Swamp Tours

You can’t come to Florida and not pay a visit to the swamp! Book an airboat tour or swap tour and head out into the water to spot some of Florida’s most feared animals, gators! A trained tour guide will take you out into the trenches, and if you’re lucky, you’ll spot massive gators on the shore or creeping in the water below. Terrifying? Maybe. Safe? Absolutely. Doing scary/thrilling things together just gives you two another reason to huddle close together and hold hands through the adventure!


Kayak/Paddleboards

For a day out on the water that doesn’t involve gators, sign up or a paddleboarding tour or rent kayaks and glide down one of Orlando’s peaceful rivers. Pack a picnic lunch, lather on the sunscreen and take in the natural sights and sounds of the area. The Paddling Center at Shingle Creek is a great stop for all of your kayak, paddleboarding, and canoe rental needs.


Super Shot At Old Town

Adrenaline junkies should head straight to the Super Shot at Old Town for a high-speed thrill ride that you’ll never forget. Strap in, hold your sweetheart’s hand, and wait to be shot 300+ feet into the air like a slingshot at speeds of over 80 miles an hour! If you are a couple that likes to try new things, face fears and experience high-speed thrills, you’ll love the Super Shot.


Our vacation rental recommendations for couples that love adventure: Mickey’s Family Fun House and Minnie’s Movie House


Orlando is a hot-spot for families, but couples coming for a romantic getaway can find more than enough to do to reconnect, relax and recharge. If you want to spoil your sweetheart with something special, check out all of our fully furnished vacation homes that can add a level of privacy and to your romantic Orlando getaway!




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Loyalty Vacation Homes is one of the leading vacation rental Companies in Orlando. Founded in 1999 the Loyalty Story goes from strength to strength, ensuring our Owners and Guests have an amazing experience, EVERY time. Our offices are close to all of our homes so that we can manage very efficiently.

We have amazing owners who we work very closely with and who are very pro-active in ensuring their home is the best it can be for every guest’s enjoyment. Our guests have been loyal to us since the start, we have many guests who have been returning to us every year since our first year. We pride ourselves on having the best customer service experience for our guests and owners at all times. From our very dedicated team in the office, who will take care of our guests from the quotation stage, during their stay, to departure and beyond. We are not dependent on external contractors, we have our own in-house maintenance and housekeeping technicians who excel in what they do and who have also been part of the Loyalty family since the beginning. They CARE!!! We’re not just a booking company, we maintain, clean and upkeep the homes, so when you are here, WE are the ones you will call with any questions, help or advice and we will take care of you. Our Motto is “As long as the guest is happy, we’re happy” Call us today to make your next stay here the most MAGICAL one ever.

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