Romantic Hotels in Kissimmee, Orlando

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Check availability on Kissimmee Romantic Hotels

Tonight
Dec 31 - Jan 1
Tomorrow
Jan 1 - Jan 2
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Kissimmee romantic hotels

Exterior
Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway
3.0 star property
Kissimmee
8.0 out of 10, Very Good, (3919)
"Phenomenal hotel for the price point as well as the children. "
United States
Destiny
The price is P3,173
P4,803 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Ramada by Wyndham Kissimmee Gateway
Exterior
Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG
3.5 star property
Kissimmee
8.4 out of 10, Very Good, (1121)
"Very clean and comfortable rooms , friendly stuff!Great locations "
United States
Nermin
The price is P4,178
P5,911 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Holiday Inn Resort Kissimmee by the Parks by IHG
2 outdoor pools, sun loungers
Delta Hotels by Marriott Orlando Celebration

Delta Hotels by Marriott Orlando Celebration

Delta Hotels by Marriott Orlando Celebration
3.5 star property
Kissimmee
8.2 out of 10, Very Good, (2530)
"Loved our stay! Great hotel and staff. "
Canada
isabella
The price is P3,941
P6,143 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Delta Hotels by Marriott Orlando Celebration
Lobby
Margaritaville Resort Orlando

Margaritaville Resort Orlando

Margaritaville Resort Orlando
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (3629)
"Great , great hotel great location "
United States
Adrian
The price is P9,134
P13,574 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Margaritaville Resort Orlando
In-room safe, laptop workspace, blackout drapes, iron/ironing board
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
Kissimmee
8.2 out of 10, Very Good, (5145)
"Clean Room good breakfast great place "
United States
Prasad
The price is P2,022
P4,298 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Palazzo Lakeside Hotel
Daily buffet breakfast (USD 17 per person)
Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG
3.0 star property
Kissimmee
8.4 out of 10, Very Good, (2131)
"Excellent attention, great hotel for short trips"
United States
Yanet
The price is P3,471
P5,608 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Holiday Inn & Suites Orlando SW - Celebration Area by IHG
4 outdoor pools, cabanas (surcharge), pool umbrellas
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando
4.0 star property
Kissimmee
9.0 out of 10, Wonderful, (4536)
"Clean room, staff was great at check in. "
United States
Amanda Lee
The price is P5,902
P8,703 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Hilton Vacation Club Mystic Dunes Orlando
7 outdoor pools, cabanas (surcharge), pool umbrellas
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG
4.0 star property
Orange Lake
8.8 out of 10, Excellent, (2540)
"The staff and the rooms are always amazing "
United States
Jorge Alexander
The price is P7,474
P10,997 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Aerial view
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort
4.0 star property
Kissimmee
8.0 out of 10, Very Good, (1724)
"We enjoyed our stay and the warmth of Florida!"
United States
MIgdalia
The price is P4,996
P7,673 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Westgate Vacation Villas Resort
Outdoor pool, sun loungers
Best Western Plus Orlando Lake Buena Vista South Inn & Suites

Best Western Plus Orlando Lake Buena Vista South Inn & Suites

Best Western Plus Orlando Lake Buena Vista South Inn & Suites
2.5 star property
Kissimmee
8.0 out of 10, Very Good, (1447)
" Great staff, quick check in and out, room big enough for 4 with 2 individual twins+ 1 king, location. "
United States
Amparo
The price is P4,204
P5,289 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Best Western Plus Orlando Lake Buena Vista South Inn & Suites
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.
View all properties

Top Kissimmee Hotel Reviews

Destiny Palms Hotel Maingate West

Destiny Palms Hotel Maingate West

10/10 Excellent
"Clean rooms, great location, staff was nice. Would stay there again. "
Karen 2-night trip
Posted 1 day ago
Destiny Palms Hotel Maingate West

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 36 hotels and other accommodations in Kissimmee to make for the perfect weekend away.
How many romantic hotels can we expect to find in Kissimmee?
Expedia has 36 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.