Historic Downtown Kissimmee Hotel Guide - Romantic Hotels in Historic Downtown Kissimmee, Orlando

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

Tonight
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Historic Downtown Kissimmee romantic hotels

4 outdoor pools, open 5:30 AM to midnight, pool cabanas (surcharge)
Rosen Shingle Creek

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
Orlando
9.4 out of 10, Exceptional, (4405)
"Great place to stay. Definitely will stay here again.."
United States
Donnell
The price is €114
includes taxes & fees
23 Jan - 24 Jan 2026
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, (1926)
"Good place to stay "
United States
victor
The price is €75
includes taxes & fees
4 Jan - 5 Jan 2026
Aloft Orlando Lake Buena Vista
2 outdoor pools, pool 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, (2527)
"Loved our stay! Great hotel and staff. "
Canada
isabella
The price is €89
includes taxes & fees
4 Jan - 5 Jan 2026
Delta Hotels by Marriott Orlando Celebration
View from room
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista
3.5 star property
Orlando
8.6 out of 10, Excellent, (5657)
"Great property to stay"
United States
Deepankar
The price is €78
includes taxes & fees
23 Jan - 24 Jan 2026
Rosen Inn Lake Buena Vista
Outdoor pool, pool umbrellas, pool loungers
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center
3.5 star property
International Drive District
7.4 out of 10, Good, (3962)
"Great location "
United States
Mark
The price is €77
includes taxes & fees
5 Jan - 6 Jan 2026
Wyndham I-Drive Avanti Resort & Conference Center
Outdoor pool, pool cabanas (surcharge), pool umbrellas
Hyatt Regency Orlando

Hyatt Regency Orlando

Hyatt Regency Orlando
4.5 star property
International Drive District
9.2 out of 10, Wonderful, (1903)
"Great service good rooms."
United States
Omran
The price is €175
includes taxes & fees
2 Jan - 3 Jan 2026
Hyatt Regency Orlando
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, (5164)
"Beautiful place to stay."
United States
Mohammad
The price is €55
includes taxes & fees
4 Jan - 5 Jan 2026
Palazzo Lakeside Hotel
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, (3913)
"Phenomenal hotel for the price point as well as the children. "
United States
Destiny
The price is €66
includes taxes & fees
20 Jan - 21 Jan 2026
Ramada by Wyndham Kissimmee Gateway
Exterior
DoubleTree by Hilton Hotel Orlando at SeaWorld

DoubleTree by Hilton Hotel Orlando at SeaWorld

DoubleTree by Hilton Hotel Orlando at SeaWorld
4.0 star property
International Drive District
7.6 out of 10, Good, (6369)
"Clean room, the breakfast buffet was great, and the pool area was beautiful "
United States
Brandon
The price is €94
includes taxes & fees
5 Jan - 6 Jan 2026
DoubleTree by Hilton Hotel Orlando at SeaWorld
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, (1117)
"Great hotel"
United States
Steven
The price is €85
includes taxes & fees
12 Jan - 13 Jan 2026
Holiday Inn Resort Kissimmee by the Parks by IHG
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

Hyatt Regency Orlando

Hyatt Regency Orlando

10/10 Excellent
"Neat and clean place "
Paramesh 3-night trip
Posted 2 days ago
Hyatt Regency Orlando

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.

Explore a world of travel with Expedia