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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Our top choices for Historic Downtown Kissimmee romantic hotels

Coffee/tea maker, fridge, microwave, oven

1. Lovely remodeled 1 bed, 1 bath Condo, Just miles from Disney! Great location.

Lovely remodeled 1 bed, 1 bath Condo, Just miles from Disney! Great location.
Kissimmee
9.4 out of 10, Exceptional, (91 reviews)
"Having a washer and dryer on site was a plus."
United States
Dorenda W.
The price is €201
includes taxes & fees
19 Aug - 20 Aug
Lovely remodeled 1 bed, 1 bath Condo, Just miles from Disney! Great location.
Exterior

2. 3 Bedrooms / 2 Bathrooms / Lake Berkley (1076 LB)

3 Bedrooms / 2 Bathrooms / Lake Berkley (1076 LB)
Lake Berkley
8.6 out of 10, Excellent, (14 reviews)
"Great house in a nice area close to everything. Fabulous view of a lake while sitting around the pool. Very enjoyable stay."
Canada
Jeff S.
The price is €431
includes taxes & fees
17 Aug - 18 Aug
3 Bedrooms / 2 Bathrooms / Lake Berkley (1076 LB)
Pool

3. 4BD/3BA Luxury Townhome w/pool at Storey Lake

4BD/3BA Luxury Townhome w/pool at Storey Lake
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"This place was a whole vacation within itself. Perfect modern layout with heated pool. Water park on the premises. Like a retreat house. I will definitely visit again."
United States
Nathaniel m.
The price is €355
includes taxes & fees
13 Sept - 14 Sept
4BD/3BA Luxury Townhome w/pool at Storey Lake
Pool

4. 4 Bedrooms / 3 Bathrooms / Storey Lake (4853 RC)

4 Bedrooms / 3 Bathrooms / Storey Lake (4853 RC)
Kissimmee
9.6 out of 10, Exceptional, (7 reviews)
"It was a very nice place with a private pool. Very spacious"
United States
Virginia B.
The price is €431
includes taxes & fees
15 Aug - 16 Aug
4 Bedrooms / 3 Bathrooms / Storey Lake (4853 RC)
Smart TV, Netflix, DVD player, books

5. Remodeled 3/2 condo minutes to Parks, shopping and entertainment

Remodeled 3/2 condo minutes to Parks, shopping and entertainment
Royal Palm Bay
9.4 out of 10, Exceptional, (44 reviews)
"This property is in excellent condition. It's the perfect place to stay if you're going to the Parks."
United States
kathy m.
The price is €225
includes taxes & fees
16 Aug - 17 Aug
Remodeled 3/2 condo minutes to Parks, shopping and entertainment
TV, video game console, stereo

6. 5Bd Home, Storey Lake with Private Pool 14 Guests - Private Pool - 2773 BD

5Bd Home, Storey Lake with Private Pool 14 Guests - Private Pool - 2773 BD
Kissimmee
9.2 out of 10, Wonderful, (33 reviews)
"Worked great for our trip!"
United States
Jennifer
The price is €483
includes taxes & fees
31 Aug - 1 Sept
5Bd Home, Storey Lake with Private Pool 14 Guests - Private Pool - 2773 BD
A heated pool

7. Amazing Disney Delight: 4BR, Pool, Near Parks - 2929 SS

Amazing Disney Delight: 4BR, Pool, Near Parks - 2929 SS
Kissimmee
8.0 out of 10, Very good, (5 reviews)
"Great place to stay, and close to basically everything you’re going to need or do. Would definitely stay again. The only cons would be that the frying pan was warped and could be replaced, outdoor lounging chairs could also use some replacements and could use some hand towels in the bathrooms. Overall, our family had a great time staying at the property. "
Canada
Reilly T.
Amazing Disney Delight: 4BR, Pool, Near Parks - 2929 SS
Coffee/tea maker, fridge, microwave, oven

8. 5 Stars House With WiFi, Game Room, Private Heated Spa & Pool In a Gated Area

5 Stars House With WiFi, Game Room, Private Heated Spa & Pool In a Gated Area
Crystal Cove
10.0 out of 10, Exceptional, (192 reviews)
"The house and pool was great. We would definitely stay here again"
United States
Tracy H.
5 Stars House With WiFi, Game Room, Private Heated Spa & Pool In a Gated Area
Sports court

9. 7 BDRM, Private Pool/HotTub, Heat Included, Games

7 BDRM, Private Pool/HotTub, Heat Included, Games
Kissimmee
9.0 out of 10, Wonderful, (67 reviews)
"Host was very welcoming. The house was very spacious and comfortable and the neighborhood was great. The pool and hot tub were perfect. Host was very responsive to questions /concerns. "
United States
Michele P.
The price is €396
includes taxes & fees
16 Aug - 17 Aug
7 BDRM, Private Pool/HotTub, Heat Included, Games
Pool

10. 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.
2bd/2ba condo close to Disney, Storey Lake
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

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

8/10 Good
"The property was well maintained. Staff was great and extremely friendly/helpful. Cons- variety of food was limited. Rooms were nice but some of the details were not well painted. Light switches were old and dirty. Overall I would stay there again. They can improve on some of their character."
Jeff 1-night trip
Posted less than an hour ago
Westgate Lakes Resort & Spa Universal Studios Area

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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