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
Pool
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 AED 380
AED 482 total
includes taxes & fees
24 Nov - 25 Nov
Star Island Resort and Club
Reunion Resort & Golf Club
Pool waterfall
Reunion Resort & Golf Club
5.0 star property
8.6 out of 10, Excellent, (1182)
"Nice!!"
The price is AED 640
AED 879 total
includes taxes & fees
23 Nov - 24 Nov
Reunion Resort & Golf Club
Hilton Vacation Club Mystic Dunes Orlando
Pool
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 AED 294
AED 450 total
includes taxes & fees
24 Nov - 25 Nov
Hilton Vacation Club Mystic Dunes Orlando
1-101 Legacy Dunes, Just steps from our beach style pool, minutes from Disney!
Pool
1-101 Legacy Dunes, Just steps from our beach style pool, minutes from Disney!
10.0 out of 10, Exceptional, (35)
"Great central location for many activities. In our stay we went to SeaWorld (30 minutes), discovery cove (30 minutes), Universal (40 minutes with traffic), Kennedy space center (1 hour 5”6 minutes), and cocoa beach which was about 20 minutes from Kennedy and an hour and 30 minutes return to the rental from cocoa beach with traffic. We had flown into and out of Orlando international airport which was about 30 minutes drive. The condo was clean and as described. There was construction during...
1-101 Legacy Dunes, Just steps from our beach style pool, minutes from Disney!
1-103 Minutes from Disney with a heated beach style swimming pool, free cabanas
Pool
1-103 Minutes from Disney with a heated beach style swimming pool, free cabanas
9.0 out of 10, Wonderful, (2)
"Location relative to the Pool is excellent. Cleanliness of the Condo was good. It had a skunk smell when we arrived. We cleared it quickly. The grounds and pool area was not cleaned daily. There were crews working on cleaning so maybe we were there at a bad time. This complex has many owners using their properties. The owners were very friendly with the renting guests. We will return to Legacy again"
1-103 Minutes from Disney with a heated beach style swimming pool, free cabanas
1-105 Legacy Dunes, tropical, beach style walk-in swimming pool, gated, security
Pool
1-105 Legacy Dunes, tropical, beach style walk-in swimming pool, gated, security
8.6 out of 10, Excellent, (13)
"Great price, location and process"
1-105 Legacy Dunes, tropical, beach style walk-in swimming pool, gated, security
1-304 Legacy Dunes, pool view from our balcony, just 4 miles from Disney
Pool
1-304 Legacy Dunes, pool view from our balcony, just 4 miles from Disney
9.4 out of 10, Exceptional, (22)
"Fantastic"
1-304 Legacy Dunes, pool view from our balcony, just 4 miles from Disney
14-206 Legacy Dunes Resort, 4 miles from Disney, relax and recharge, heated pool
Exterior
14-206 Legacy Dunes Resort, 4 miles from Disney, relax and recharge, heated pool
9.2 out of 10, Wonderful, (30)
"The condo was beautiful and perfect for our trip to WDW! It was as described, and the private patio was a plus. My two boys and I enjoyed our stay here very much, it had everything needed for a relaxing stay. Shops, restaurants, and activities were conveniently located within a short driving distance. We highly recommend this property!"
14-206 Legacy Dunes Resort, 4 miles from Disney, relax and recharge, heated pool
19-104 Two Master Suites, gated resort with heated pool, playground, lakes. gym
Pool
19-104 Two Master Suites, gated resort with heated pool, playground, lakes. gym
9.4 out of 10, Exceptional, (64)
"Great location! Close to everything! Very clean and comfortable!"
19-104 Two Master Suites, gated resort with heated pool, playground, lakes. gym
19-202 Legacy Dunes, minutes from Disney! Senior/Family/Kid Friendly! Relax
Living area
19-202 Legacy Dunes, minutes from Disney! Senior/Family/Kid Friendly! Relax
9.2 out of 10, Wonderful, (35)
"Nice quiet location (despite nearby road). Great pool area. Near restaurants and shops and not too far from attractions."
19-202 Legacy Dunes, minutes from Disney! Senior/Family/Kid Friendly! Relax
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.
What's the best place to stay for couples in Kissimmee?
AMAZING STUDIO AT WESTGATE TOWN CENTER RESORT & SPA NEAR DISNEY is a favorite resort for couples, and features a fitness center and a garden. Other good options for your romantic getaway include All Suite Resort near Old Town Amusement Park and Disney World and GREAT TWO BEDROOM RESORT CONDO MINUTES FROM DISNEY.
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.