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Check availability on Kissimmee Romantic Hotels

Our top choices for Kissimmee romantic hotels

Exterior

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
Kissimmee
9.2 out of 10, Wonderful, (164 reviews)
"Excellent accommodations."
United States
Raychelle
The price is ￥10,244
￥32,667 total
includes taxes & fees
May 20 - May 21
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
Smart TV, DVD player, foosball, books

*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works

*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works
Kissimmee
9.6 out of 10, Exceptional, (144 reviews)
"The host was great, the pool and spa were warm and great. The house was clean and had good amenities! Will definitely keep in mind for future visits "
United States
Sarah H.
The price is ￥22,400
￥66,867 total
includes taxes & fees
May 20 - May 21
*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works
Fridge, microwave, oven, stovetop

Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!

Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!
Buena Ventura Lakes
10.0 out of 10, Exceptional, (35 reviews)
"Clean spacious very cozy & relaxing"
United States
Nicky B.
The price is ￥19,716
￥48,550 total
includes taxes & fees
May 21 - May 22
Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!
A heated pool

BreathTaking! Fantasy World Newly Renovated Near Disney 2+2 5 STAR UNIT!

BreathTaking! Fantasy World Newly Renovated Near Disney 2+2 5 STAR UNIT!
Kissimmee
9.0 out of 10, Wonderful, (121 reviews)
"Great little place very close to parks. Beautiful screened in patio."
United States
Erika H.
BreathTaking! Fantasy World Newly Renovated Near Disney 2+2 5 STAR UNIT!
Exterior

3 Bedrooms/ 2 Bathrooms/ Storey Lake (4751-308 CT)

3 Bedrooms/ 2 Bathrooms/ Storey Lake (4751-308 CT)
Kissimmee
9.6 out of 10, Exceptional, (4 reviews)
"This property was a great size for our family and we thoroughly enjoyed our stay. My boys loved the Minion themed room. Everything was clean and the kitchen was well stocked with dishes. Excellent stay! "
United States
Luke W.
The price is ￥16,737
￥69,935 total
includes taxes & fees
May 14 - May 15
3 Bedrooms/ 2 Bathrooms/ Storey Lake (4751-308 CT)
Pool

Crystal 3 BR TH Gated Resort Close to Disney

Crystal 3 BR TH Gated Resort Close to Disney
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Nice and clean house patio chairs were broken blinds were broken beds were not comfortable make noises, right beside highway too much traffic noise, saw a lizard and cockraches in the kitchen. Lot of parking"
Canada
Mohammad zaki A.
The price is ￥8,195
￥76,998 total
includes taxes & fees
Jun 2 - Jun 3
Crystal 3 BR TH Gated Resort Close to Disney
Pool

"Pequod Lakeview" - 4BD/3BA Townhome near Disney

"Pequod Lakeview" - 4BD/3BA Townhome near Disney
Kissimmee
9.4 out of 10, Exceptional, (20 reviews)
"We loved the pool and the location to the amenities was just a short walk down the path behind the house. We would definitely stay here again!"
United States
David C.
The price is ￥12,621
￥63,102 total
includes taxes & fees
Jun 7 - Jun 8
"Pequod Lakeview" - 4BD/3BA Townhome near Disney
Fridge, microwave, oven, stovetop

Lovely 1 bed/1 bath Condo, Just 7 miles from Disney!

Lovely 1 bed/1 bath Condo, Just 7 miles from Disney!
Kissimmee
9.4 out of 10, Exceptional, (89 reviews)
"Condo was perfect. Would stay again "
United States
Lori S.
The price is ￥11,035
￥34,401 total
includes taxes & fees
May 16 - May 17
Lovely 1 bed/1 bath Condo, Just 7 miles from Disney!
Pool

2bd/2ba condo close to Disney, Storey Lake

2bd/2ba condo close to Disney, Storey Lake
Kissimmee
10.0 out of 10, Exceptional, (5 reviews)
"It was an nice smooth experience renting out the property the pictures the were posted up on vrbo about the condo is exactly how the room is 10/10 experience"
United States
Luis C.
The price is ￥11,327
￥47,044 total
includes taxes & fees
May 31 - Jun 1
2bd/2ba condo close to Disney, Storey Lake
Pool

5BD/4BA Grand Townhome w/pool close to Disney

5BD/4BA Grand Townhome w/pool close to Disney
Kissimmee
9.8 out of 10, Exceptional, (13 reviews)
"This property was amazing. The place was clean and perfect for my family"
United States
April S.
The price is ￥18,773
￥75,714 total
includes taxes & fees
May 26 - May 27
5BD/4BA Grand Townhome w/pool close to Disney
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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Top Kissimmee Hotel Reviews

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8/10 Good
"The resort was huge, with lots to do. They do try to pitch the timeshare aspect of it but once you decline they leave you alone. It was about 20-30mins from SeaWorld (without using toll roads). The Publix store was about 3mins away for groceries and about 4mins from more shopping like Target. The rooms were nice and big! Prefect for our large family. We loved the washer and dryer as it made our life so much easier. We will definitely go back!"
Victoria 11-night trip
Posted 4 hours ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

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 Center for the Arts. Whether you want to get a couple's massage or enjoy a candlelit dinner, you can pick from 27 hotels and other accommodations in Kissimmee to make for the perfect weekend away.
What's the best place to stay for couples in Kissimmee?
NEAR DISNEY! 1 BR Condo - SLEEPS 4, Tennis, Baby Pool, Tennis, Shuffleboard, etc is a favorite resort for couples, and features a fitness center and a garden.
How many romantic hotels can we expect to find in Kissimmee?
Expedia has 27 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.