Find Romantic Hotels in Kissimmee, FL

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Pick from 150 Kissimmee Romantic Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Star Island Resort and Club
2 outdoor pools, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers
Star Island Resort and Club
3.5 star property
8.0 out of 10, Very Good, (1245)
"I love everything. I mean the Resorted was Wonderful the 3 Rooms was more then I expected everyone was So Happy especially my grandson he had his own little Hotel Room in of the hotel room the Drinks at the bar was delicious didnt try the food brought my own since it was a full size kitchen I would go back thinking about doing it for my Birthday eeven Christmas.The Young lady which name was Brianna was great she just took one look at me and said u on the third floor but I see that u...
The price is ₩150,225
₩193,975 total
includes taxes & fees
Nov 5 - Nov 6
Star Island Resort and Club
Reunion Resort & Golf Club
Waterslide
Reunion Resort & Golf Club
5.0 star property
8.6 out of 10, Excellent, (1175)
"EXCELLENT STAY! Will stay again"
The price is ₩318,642
₩426,986 total
includes taxes & fees
Nov 7 - Nov 8
Reunion Resort & Golf Club
Hilton Vacation Club Mystic Dunes Orlando
4 outdoor pools, cabanas (surcharge), pool umbrellas
Hilton Vacation Club Mystic Dunes Orlando
9.0 out of 10, Wonderful, (3409)
"The property is huge and so is the room. Room was very clean and spacious. No complaints here. "
The price is ₩135,202
₩200,382 total
includes taxes & fees
Nov 17 - Nov 18
Hilton Vacation Club Mystic Dunes Orlando
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.
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Frequently asked questions

Searching for romantic hotels in Kissimmee?
Are you and your partner in need of a romantic escape? Couples choose Kissimmee for its top-notch restaurants and renowned opera house. If you’re a pair that loves cultural attractions, you might check out Medieval Times, Capone’s Dinner Show, or Osceola Performing Arts Center. Whether you want to get a couple’s massage or enjoy a candlelit dinner, you can pick from 45 hotels and other accommodations in Kissimmee to make for the perfect weekend away.
How many romantic hotels can we expect to find in Kissimmee?
Expedia has 45 romantic Kissimmee hotels for you to get cozy in.
When is the best time of year for a romantic getaway to Kissimmee?
If you’re hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Kissimmee: The hottest months are usually July and August with an average temp of 81°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Kissimmee are August, July, September, and June, with each month seeing an average of 8 inches of rainfall.
What is there to do in Kissimmee?
There’s nothing better than experiencing a new place with your sweetheart, so consider taking time to discover all that Kissimmee has to offer. If you’re hoping to experience some of the local culture, you’ll love Kissimmee for its lively festivals, fun-filled attractions, and major shopping area. You might think about stopping by Disney’s Animal Kingdom® Theme Park, Walt Disney World® Resort, or Old Town while you’re seeing the sights.
What's the best way to get to Kissimmee and around town during my romantic getaway?
This information about transportation options in Kissimmee might help your romantic getaway go off without a hitch: Make your way to Kissimmee with a flight to Kissimmee, FL (ISM-Kissimmee Gateway), which is the closest major airport located 1.8 mi (2.9 km) from the city center. Nearby metro stations include Tupperware Station and Poinciana Station. To see more of the larger area, hop aboard a train at Kissimmee Station.