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
Pool

Star Island Resort and Club

3.5 star property
8.0 out of 10, Very Good, (1285)
"Great place"
The price is AED 511
AED 642 total
includes taxes & fees
4 Jan - 5 January 2025
Star Island Resort and Club
Reunion Resort & Golf Club
Room

Reunion Resort & Golf Club

5.0 star property
8.6 out of 10, Excellent, (1193)
"Great stay!"
The price is AED 1,183
AED 1,517 total
includes taxes & fees
26 Dec - 27 Dec
Reunion Resort & Golf Club
Hilton Vacation Club Mystic Dunes Orlando
Pool

Hilton Vacation Club Mystic Dunes Orlando

9.0 out of 10, Wonderful, (3427)
"Beautiful well maintained property. "
The price is AED 316
AED 484 total
includes taxes & fees
12 Jan - 13 January 2025
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, (36)
"First, great location not too far from WDW and Disney Springs, local shops, and restaurants. Second, overall stay was just what we needed: space for our toddler and 1.5 YO, clean, easy enough access with easy instructions, and great amenities! Third, host was very responsive and always replied timely. We look forward to returning and booking here again!"
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, (66)
"Really nice place everything was as described in add "
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, (37)
"Often when we rent a condo there are lots of things in need of repair. However, this unit was great. Everything was in working order and was well cared for. Plenty of towels and other necessities were supplied. Manager was quick to respond to questions. Location was close to all WDW parks. I would recommend staying here."
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, 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.
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 Designer Renovated Condo in Gorgeous Tropical Setting.
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.