Find Romantic Hotels in Kissimmee, FL

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Compare Kissimmee Romantic Hotels 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, (1285)
"Great place"
The price is ₩200,848
₩252,569 total
includes taxes & fees
Jan 4 - Jan 5, 2025
Star Island Resort and Club
Reunion Resort & Golf Club
11 outdoor pools, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers

Reunion Resort & Golf Club

5.0 star property
8.6 out of 10, Excellent, (1193)
"Great stay!"
The price is ₩465,491
₩596,823 total
includes taxes & fees
Dec 26 - Dec 27
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, (3427)
"Beautiful well maintained property. "
The price is ₩124,410
₩190,406 total
includes taxes & fees
Jan 21 - Jan 22, 2025
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, Osceola Performing Arts Center, or Capone’s Dinner Show. Whether you want to get a couple’s massage or enjoy a candlelit dinner, you can pick from 49 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 49 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.