Find Romantic Hotels in Kissimmee, FL

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Check availability on Kissimmee Romantic Hotels

Tonight
25 Apr - 26 Apr
Tomorrow
26 Apr - 27 Apr
This weekend
25 Apr - 27 Apr
Next weekend
2 May - 4 May

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, (1296)
"Everything was great the room was a little outdated but it was everything we needed and a great price "
The price is AED 400
AED 517 total
includes taxes & fees
5 May - 6 May
Star Island Resort and Club
Reunion Resort & Golf Club
Water park

Reunion Resort & Golf Club

5.0 star property
8.6 out of 10, Excellent, (1266)
"Very nice "
The price is AED 769
AED 1,047 total
includes taxes & fees
11 May - 12 May
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, (3877)
"Great service, location and rooms were great. "
The price is AED 390
AED 568 total
includes taxes & fees
8 May - 9 May
Hilton Vacation Club Mystic Dunes Orlando
1-101 Legacy Dunes, Just Steps to the Beach Style Pool, Minutes to Disney!
Property grounds

1-101 Legacy Dunes, Just Steps to the Beach Style Pool, Minutes to Disney!

10.0 out of 10, Exceptional, (40)
"Great location, and host was so easy and quick to contact!"
1-101 Legacy Dunes, Just Steps to the Beach Style Pool, Minutes to Disney!
1-103 Legacy Dunes, Steps to Pool, Minutes to Disney, King Bed
Property grounds

1-103 Legacy Dunes, Steps to Pool, Minutes to Disney, King Bed

8.8 out of 10, Excellent, (3)
"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 Legacy Dunes, Steps to Pool, Minutes to Disney, King Bed
1-105 Legacy Dunes, Tropical Beach Style Walk-in Pool, King Bed, 65" Tv, Patio
Outdoor pool, a heated pool

1-105 Legacy Dunes, Tropical Beach Style Walk-in Pool, King Bed, 65" Tv, Patio

8.6 out of 10, Excellent, (13)
"Great price, location and process"
1-105 Legacy Dunes, Tropical Beach Style Walk-in Pool, King Bed, 65" Tv, Patio
1-304 Legacy Dunes, Pool View, Screened Balcony, King Bed, 4 miles To Disney !
Outdoor pool, a heated pool

1-304 Legacy Dunes, Pool View, Screened Balcony, King Bed, 4 miles To Disney !

9.4 out of 10, Exceptional, (23)
"We enjoyed our stay. We were close to restaurants, shopping and attractions."
1-304 Legacy Dunes, Pool View, Screened Balcony, King Bed, 4 miles To Disney !
14-206 Legacy Dunes Resort, 4 miles from Disney, relax and recharge, heated pool
Outdoor pool, a heated pool

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
Outdoor pool, a heated pool

19-104 Two Master Suites, gated resort with heated pool, playground, lakes. gym

9.4 out of 10, Exceptional, (72)
"Really good location for Disney and other activities. Safe gated community. We will be back! Highly recommend!"
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
Outdoor pool, a heated pool

19-202 Legacy Dunes, minutes from Disney! Senior/Family/Kid Friendly! Relax

9.4 out of 10, Exceptional, (43)
"If you're looking for a place to stay that has easy access to the parks, shopping, restaurants & everything Orlando has to offer, while also wanting somewhere to relax, then this is definitely the place for you! It was perfectly sized for our family of 4, but you could honestly have a couple more guests and still have plently of room. The pool is beautiful and a nice place to just chill. Will definitely be booking again the next time we find ourselves in the Orlando area. "
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 35 hotels and other accommodations in Kissimmee to make for the perfect weekend away.
What's the best place to stay for couples in Kissimmee?
All Suite Resort near Old Town Amusement Park and Disney World is a favorite resort for couples, and features private pools and kitchens. Other good options for your romantic getaway include AMAZING STUDIO AT WESTGATE TOWN CENTER RESORT & SPA NEAR DISNEY and GREAT TWO BEDROOM RESORT CONDO MINUTES FROM DISNEY.
How many romantic hotels can we expect to find in Kissimmee?
Expedia has 35 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.