Search Romantic Hotels in Historic Downtown Kissimmee

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Historic Downtown Kissimmee Romantic Hotels

Our top choices for Historic Downtown Kissimmee romantic hotels

Outdoor banquet area
Rosen Shingle Creek

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
Orlando
9.4 out of 10, Exceptional, (4343)
"Great resort "
United States
Camille
The price is 2.931.454 ₫
3.297.886 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Rosen Shingle Creek
Lobby lounge
Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista
3.0 star property
Orlando
8.8 out of 10, Excellent, (1906)
"Great rooms, staff, and property!"
United States
Cindy
The price is 1.951.380 ₫
2.195.303 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Aloft Orlando Lake Buena Vista
Lobby
DoubleTree by Hilton Hotel Orlando Downtown

DoubleTree by Hilton Hotel Orlando Downtown

DoubleTree by Hilton Hotel Orlando Downtown
4.0 star property
Ivanhoe Village
8.2 out of 10, Very good, (2821)
"clean hotel and breakfast "
United States
Petros
The price is 2.789.419 ₫
3.138.097 ₫ total
includes taxes & fees
18 Dec - 19 Dec
DoubleTree by Hilton Hotel Orlando Downtown
Free daily on-the-go breakfast
Tru By Hilton Orlando Convention Center Area, FL

Tru By Hilton Orlando Convention Center Area, FL

Tru By Hilton Orlando Convention Center Area, FL
3.5 star property
International Drive District
9.0 out of 10, Wonderful, (3656)
"Great location clean rooms "
United States
Erika
The price is 2.087.870 ₫
2.348.854 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Tru By Hilton Orlando Convention Center Area, FL
Property amenity
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, (2483)
"Comfortable, nice pool, clean, friendly staff"
United States
Tammy
The price is 1.590.111 ₫
2.553.157 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Delta Hotels by Marriott Orlando Celebration
Exterior
Caribe Royale Orlando

Caribe Royale Orlando

Caribe Royale Orlando
4.5 star property
Orlando
9.2 out of 10, Wonderful, (4503)
"Clean and very friendly staff"
United States
Nafeeza
The price is 4.192.830 ₫
5.844.384 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Caribe Royale Orlando
3 outdoor pools, open 7 AM to 10:00 PM, pool cabanas (surcharge)
Hyatt Regency Grand Cypress

Hyatt Regency Grand Cypress

Hyatt Regency Grand Cypress
4.0 star property
Orlando
9.2 out of 10, Wonderful, (2281)
"The staff was attentive and we really enjoyed the amenities! "
United States
Michelle
The price is 4.248.207 ₫
6.262.546 ₫ total
includes taxes & fees
13 Dec - 14 Dec
Hyatt Regency Grand Cypress
Water park
Ramada by Wyndham Hotel & Water Park

Ramada by Wyndham Hotel & Water Park

Ramada by Wyndham Hotel & Water Park
3.0 star property
Kissimmee
7.0 out of 10, Good, (1622)
"Great place to stay "
Mexico
Velma
The price is 949.032 ₫
1.825.306 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Ramada by Wyndham Hotel & Water Park
In-room safe, laptop workspace, blackout curtains, iron/ironing board
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
Kissimmee
8.2 out of 10, Very good, (5139)
"Overall good experience would stay again"
United States
Jacquelyn
The price is 771.299 ₫
1.773.061 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Palazzo Lakeside Hotel
Lobby
Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South
4.0 star property
Kissimmee
9.4 out of 10, Exceptional, (1242)
"Nice place very good"
United States
Hugo
The price is 2.255.690 ₫
2.560.208 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Embassy Suites by Hilton Orlando Lake Buena Vista South
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 Historic Downtown Kissimmee Hotel Reviews

Explore a world of travel with Expedia

Frequently asked questions

Searching for romantic hotels in Historic Downtown Kissimmee?
If you and your partner need some romantic time away, we've got just the thing. Our guests also love Historic Downtown Kissimmee for its major shopping area and sporting events. If you'd like to explore some of the area's notable sights, you might make a stop by Lake Tohopekaliga, Violet's Venom Brewery or Monument of States. If you'd like to stay close to a certain attraction, you can sort properties by neighbourhood and proximity to top sights, so you and your partner will get to see everything on your list.
What is there to do in Historic Downtown Kissimmee?
There's nothing better than seeing a new destination with your sweetheart, so consider checking out all there is to see and do in Historic Downtown Kissimmee. If you're hoping to see some of the area's cultural attractions, you'll enjoy Historic Downtown Kissimmee for its festivals, theme park and shopping. You might think about stopping by Lake Tohopekaliga, Violet's Venom Brewery or Monument of States while you're seeing the sights.