A street sign reading "Welcome to Kissimmee, Florida" with a mural of horses on a building.

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

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Check availability on Historic Downtown Kissimmee Romantic Hotels

Our top choices for Historic Downtown Kissimmee romantic hotels

A two-story house with a porch, surrounded by lush greenery and hanging moss.

1. Kapp and Kappy B&B

Kapp and Kappy B&B
3.5 star property
Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (148 reviews)
"I stayed in the Steel Room, wonderful. Enjoyed visiting with the owner, learning about the house, as well as the plants surrounding it. What a comfortable and pleasant stay."
United States
john
The price is €164
includes taxes & fees
15 Nov - 16 Nov
Kapp and Kappy B&B
A swimming pool with lounge chairs, a hot tub, and inflatable toys.

2. Beautiful home near Disney Private PoolBBQ Downtown

Beautiful home near Disney Private PoolBBQ Downtown
Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (61 reviews)
"Very nice property, lots of amenities and very closed to restaurants, bars, etc."
United States
Sixto S.
The price is €411
includes taxes & fees
16 Nov - 17 Nov
Beautiful home near Disney Private PoolBBQ Downtown
A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.

3. Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort

Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort
2.0 star property
7.2 km from Historic Downtown Kissimmee
9.0 out of 10, Wonderful, (4,112 reviews)
"great stay"
United States
Viridiana
The price is €47
includes taxes & fees
16 Nov - 17 Nov
Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort
A resort pool area with a winding pool design, lounge chairs, and palm trees.

4. Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
18.3 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (6,482 reviews)
"Always a great stay"
United States
ivan
The price is €63
includes taxes & fees
17 Nov - 18 Nov
Kompose Boutique Resort at Theme Parks
A modern living room with a large flat-screen TV, a white sofa, and a coffee table.

5. Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
3.0 star property
9.5 km from Historic Downtown Kissimmee
8.6 out of 10, Excellent, (3,228 reviews)
"Beautiful place"
United States
Alfredo I
The price is €53
includes taxes & fees
18 Nov - 19 Nov
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
A hotel pool area with a water slide, palm trees, and a bridge.

6. Radisson Hotel Orlando Lake Buena Vista South

Radisson Hotel Orlando Lake Buena Vista South
3.5 star property
9.2 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (3,765 reviews)
"clean room, helpful staff, and great breakfast."
United States
Wilfredo
The price is €64
includes taxes & fees
19 Nov - 20 Nov
Radisson Hotel Orlando Lake Buena Vista South
A modern interior with a white spiral staircase, a large Christmas tree, and a dining area with white furniture.

7. Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
8.5 km from Historic Downtown Kissimmee
8.4 out of 10, Very good, (5,381 reviews)
"Great stay"
United States
Juan
The price is €52
includes taxes & fees
29 Nov - 30 Nov
Palazzo Lakeside Hotel
A large indoor swimming pool surrounded by lounge chairs and umbrellas, with a hotel building in the background.

8. Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
14.9 km from Historic Downtown Kissimmee
9.6 out of 10, Exceptional, (4,992 reviews)
"Great staff, location, resort was amazing"
United States
Dominic
The price is €108
includes taxes & fees
24 Nov - 25 Nov
Rosen Shingle Creek
A hotel breakfast area with self-serve stations for fruit & yogurt, bakery, and coffee.

9. Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South
4.0 star property
8.7 km from Historic Downtown Kissimmee
9.6 out of 10, Exceptional, (1,692 reviews)
"Great stay"
United States
Peterjohn
The price is €120
includes taxes & fees
24 Nov - 25 Nov
Embassy Suites by Hilton Orlando Lake Buena Vista South
A hotel with multiple floors, a rooftop pool, and a view of the city skyline at dusk.

10. Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG
3.0 star property
11.4 km from Historic Downtown Kissimmee
8.4 out of 10, Very good, (3,062 reviews)
"Excellent location"
United States
Edna
The price is €97
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn & Suites Orlando SW - Celebration Area by IHG
A hotel with a pool area, lounge chairs, and a restaurant.

11. Meliá Orlando Celebration

Meliá Orlando Celebration
4.0 star property
13.6 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (1,643 reviews)
"Nice to stay there"
United States
Yong Pin
The price is €100
includes taxes & fees
23 Nov - 24 Nov
Meliá Orlando Celebration
A water slide in a rocky enclosure with a view of the sea.

12. Delta Hotels by Marriott Orlando Celebration

Delta Hotels by Marriott Orlando Celebration
3.5 star property
13.5 km from Historic Downtown Kissimmee
8.2 out of 10, Very good, (3,076 reviews)
"Beautiful hotel with amazing, friendly staff."
United States
Amber
The price is €94
includes taxes & fees
17 Nov - 18 Nov
Delta Hotels by Marriott Orlando Celebration
A hotel with multiple swimming pools, a landscaped garden, and a large building with balconies.

13. Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
13.2 km from Historic Downtown Kissimmee
8.6 out of 10, Excellent, (5,311 reviews)
"Great stay"
United States
Jonatan
The price is €84
includes taxes & fees
29 Nov - 30 Nov
Vacation Village Orlando, Celebration
A modern reception area with a counter, a wall-mounted lamp, and a mural.

14. Wyndham Garden Orlando Airport

Wyndham Garden Orlando Airport
3.0 star property
18.4 km from Historic Downtown Kissimmee
9.0 out of 10, Wonderful, (4,285 reviews)
"Great place to stay"
United States
Roselle
The price is €89
includes taxes & fees
16 Nov - 17 Nov
Wyndham Garden Orlando Airport
A hotel with a swimming pool, multiple floors, and a parking lot.

15. Comfort Suites Maingate East

Comfort Suites Maingate East
3.0 star property
11.3 km from Historic Downtown Kissimmee
8.4 out of 10, Very good, (2,605 reviews)
"We loved our stay at the Kenmore, the hotel is beautiful and so close to the beach"
Canada
Maria
The price is €80
includes taxes & fees
13 Dec - 14 Dec
Comfort Suites Maingate East
A modern hotel lobby with a stone wall, a flat-screen TV, a yellow sofa, teal armchairs, a reception desk, and a digital information kiosk.

16. Best Western Plus Orlando Lake Buena Vista South Inn & Suites

Best Western Plus Orlando Lake Buena Vista South Inn & Suites
3.0 star property
10 km from Historic Downtown Kissimmee
8.2 out of 10, Very good, (1,533 reviews)
"Very nice hotel"
United States
ANASTASIA
The price is €75
includes taxes & fees
24 Nov - 25 Nov
Best Western Plus Orlando Lake Buena Vista South Inn & Suites
A high-rise hotel with multiple floors, a rooftop pool, and a well-lit outdoor area with a pond.

17. DoubleTree by Hilton Orlando Theme Park Resort

DoubleTree by Hilton Orlando Theme Park Resort
4.0 star property
14.8 km from Historic Downtown Kissimmee
7.6 out of 10, Good, (6,536 reviews)
"Great stay and great location. Would recommend to anyone."
United States
Richard Randy
The price is €64
includes taxes & fees
25 Nov - 26 Nov
DoubleTree by Hilton Orlando Theme Park Resort
A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.

18. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
3.0 star property
23 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (5,750 reviews)
"Always amazing stay!"
United States
kenyetta
The price is €80
includes taxes & fees
8 Dec - 9 Dec
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
An aerial view of a hotel complex with multiple buildings, a central courtyard, and a swimming pool.

19. Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Fairfield Inn & Suites Lake Buena Vista in Marriott Village
3.0 star property
13.2 km from Historic Downtown Kissimmee
8.4 out of 10, Very good, (1,941 reviews)
"Great breakfast, friendly staff!"
United States
Kara
The price is €80
includes taxes & fees
17 Nov - 18 Nov
Fairfield Inn & Suites Lake Buena Vista in Marriott Village
A spacious lobby with a large chandelier, a reception desk, and a view of the outside through large windows.

20. Star Island Resort and Club

Star Island Resort and Club
3.5 star property
8.6 km from Historic Downtown Kissimmee
8.4 out of 10, Very good, (1,506 reviews)
"Really nice hotel"
United Kingdom
Michelle
The price is €105
includes taxes & fees
30 Nov - 1 Dec
Star Island Resort and Club
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 Historic Downtown Kissimmee Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Room was very clean, property’s a bit confusing since it’s so big, it’s very easy to get lost in there lol."
Jason 2-night trip
Posted 1 hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/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.

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