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, (1258)
"The amenities were fantastic. Enjoyed playing pickleball plus mini golf in the shade. The musicians were fantastic. Spent one night dancing. Loved the two pools and one was great for morning lengths. The walk along the lake was very serene. "
The price is ₩144,874
₩188,257 total
includes taxes & fees
Nov 24 - Nov 25
Star Island Resort and Club
Reunion Resort & Golf Club
Waterslide
Reunion Resort & Golf Club
5.0 star property
8.6 out of 10, Excellent, (1182)
"Nice!!"
The price is ₩243,854
₩343,088 total
includes taxes & fees
Nov 23 - Nov 24
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, (3380)
"This property has a super friendly and helpful staff. The amenities include mini golf, pickle ball courts, tennis courts, basketball courts, shuffle board, walking paths, and multiple pools all included with the price. There is a professional golf course on site for an additional nominal fee. The resort is close to Disney with shuttle service provided"
The price is ₩111,336
₩173,772 total
includes taxes & fees
Nov 26 - Nov 27
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.