Browse for Kissimmee Romantic Hotels from $55

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Featured Kissimmee Romantic Hotels

Star Island Resort and Club
3.5 out of 5
5000 Avenue Of The Stars, Kissimmee, FL
Free CancellationReserve now, pay when you stay
$83
per night
Jan 5 - Jan 6
4.1/5Very Good! (1,609 reviews)

"One of the best and convenient is the market place . and the activities are amazing"…"

Reviewed on Dec 5, 2019

Star Island Resort and Club
Reunion Resort & Golf Club
5 out of 5
7593 Gathering Drive, Kissimmee, FL
$161
per night
Dec 15 - Dec 16
4.4/5Wonderful! (1,943 reviews)

"Loved the peacefulness of the property and that our townhome faced one of the golf courses."…"

Reviewed on Nov 30, 2019

Reunion Resort & Golf Club
Mystic Dunes Resort & Golf Club by Diamond Resorts
3.5 out of 5
7600 Mystic Dunes Lane, Kissimmee, FL
Free CancellationReserve now, pay when you stay
$55
per night
Dec 12 - Dec 13
4.2/5Excellent! (8,099 reviews)

"Privacy and safety and convenience to the Disney parks"…"

Reviewed on Dec 5, 2019

Mystic Dunes Resort & Golf Club by Diamond Resorts
Red Lion Hotel Orlando Kissimmee Maingate
3 out of 5
7300 W Irlo Bronson Hwy, Kissimmee, FL
Get Rates
3.8/5Good! (7,317 reviews)

"Simple check in, VIP status is recognized and there's always a cheap rate, with being just a few miles shy of Disney, and everything else."…"

Reviewed on Dec 4, 2019

Red Lion Hotel Orlando Kissimmee Maingate
"the Lion Kings!" 2 King MBR Suites! 5 Min's Disney, Sleeps 8, Spectacular!!
5/5Exceptional! (1 review)
Great condo- highly recommend

"We enjoyed staying at the property. The condo was very clean and the mattresses were good quality. The condo was stocked with regular size bars of soap, dishwashing liquid and laundry detergent. Felt safe in the gated community. Very close to Disney. Excellent value for what you get. Owner very responsive. ..."…"

Reviewed on Oct 15, 2017

"the Lion Kings!" 2 King MBR Suites! 5 Min's Disney, Sleeps 8, Spectacular!!
1-103 Poolside Bamboo Themed Condo Just ten Minutes From Disney With Heated Pool
4.7/5Exceptional! (3 reviews)
Great

"The property was beautiful and very secure. The condo was very clean."…"

Reviewed on Dec 29, 2018

1-103 Poolside Bamboo Themed Condo Just ten Minutes From Disney With Heated Pool
1-107 1BR Poolside Condo Just Minutes From Disney World, Livingroom, Kitchen
4.5/5Wonderful! (2 reviews)
Great getaway spot

"Location was perfect and the place was in perfect condition as advertised."…"

Reviewed on Sep 15, 2018

1-107 1BR Poolside Condo Just Minutes From Disney World, Livingroom, Kitchen
14-105 Convenient, Quiet Location to Escape the Chaos at Disney World, Pool, GYM
4.3/5Excellent! (3 reviews)
Cute place

"The place it's self was nice. There were just a couple of problems in the master bedroom. They definitely need a new TV in there you can't turn the volume up or down with the remote nor can you turn off the TV (which is exactly why you have a remote other than turning the channel), not to mention ..."…"

Reviewed on Jul 8, 2016

14-105 Convenient, Quiet Location to Escape the Chaos at Disney World, Pool, GYM
16-201 Under Water Theme in a Gated Resort With Security, Swimming Pool, gym
16-306 Legacy Dunes, Tropical Swimming Pool, Playground, Room for the Family
4/5Very Good! (1 review)
Nice place to stay, everything was great

"I would recommend this to any one who rents it ."…"

Reviewed on Mar 31, 2017

16-306 Legacy Dunes, Tropical Swimming Pool, Playground, Room for the Family
19-202 Quiet, Secluded Resort, Perfect for a Family, Separate Bedrooms, Kitchen
4/5Very Good! (2 reviews)

"okay for the price you are paying. Bathrooms and appliances are dated. Traffic noise in the bedrooms"…"

Reviewed on Aug 28, 2018

19-202 Quiet, Secluded Resort, Perfect for a Family, Separate Bedrooms, Kitchen
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Romantic Hotels and Accommodations in Kissimmee

If you and your partner need a romantic escape, we've got just the ticket. 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 Center for the Arts, or Capone's Dinner Show.

Whether you'd like to get a couple's massage or enjoy a candlelit dinner, you'll have your choice of 150 hotels and other lodging options in Kissimmee to make for the perfect getaway.

Expedia travelers love these hotels and other accommodations for their romantic atmosphere and amenities:

Legacy Dunes Resort, 4 Miles From Disney, Relax and Recharge, Heated Tropical po: This condo offers free WiFi, a fitness center, and a garden. Our guests appreciate its pool and walkable location.

Legacy Dunes Resort, Just Steps From our Beach Style Pool, Minutes From Disney!: With a stay at this condo, you'll have access to free WiFi, a fitness center, and a garden. Expedia travelers speak highly of its comfortable beds and beach locale.

1-103 Poolside Bamboo Themed Condo Just ten Minutes From Disney With Heated Pool: This condo offers free WiFi, a fitness center, and a garden. Our guests appreciate its prime location.

Legacy Dunes, A few Steps you Will be Swimming in our Tropical, Beach Style Pool: Condo featuring free WiFi, a fitness center, and a kitchen. Customers give positive reviews for its comfortable beds.

When is the Best Time to Visit Kissimmee?

Weather can be a major factor for your romantic getaway, so we've pulled together rainfall and temperature averages to help you plan your vacation:

  • Hottest months: July, August, June, and September, with an average temperature of 91°F
  • Coldest months: January, December, February, and March, with an average temperature of 48°F
  • Driest months: November, April, January, and December, with an average rainfall of 2.33 inches
  • Rainiest months: August, June, July, and September, with an average rainfall of 7.32 inches

Sightseeing in and Around Kissimmee

There's nothing better than experiencing a new destination with your sweetheart, so consider taking time to discover all there is to see and do in Kissimmee. 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 consider a visit to Monument of States, Kissimmee Lakefront Park, or Brinson Park.

Travelers also pick Kissimmee for its:
  • Entertainment
  • Sports
  • Restaurants

Getting Around Kissimmee

To get to Kissimmee, book a flight to Kissimmee, FL (ISM-Kissimmee Gateway), which is the closest major airport, located 1.9 mi (3 km) from the city center. To see more of the larger area, hop on a train at Kissimmee Station.

More trip options

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