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

This weekend
3 Jul - 5 Jul
Next weekend
10 Jul - 12 Jul

Our top choices for Historic Downtown Kissimmee romantic hotels

Exterior

Eastpark. Pet friendly! Lake Nona

Eastpark. Pet friendly! Lake Nona
East Park
9.2 out of 10, Wonderful, (100 reviews)
"Very nice accommodations. Great stay!!"
United States
John G.
The price is €252
includes taxes & fees
14 Jul - 15 Jul
Eastpark. Pet friendly! Lake Nona
Fridge, microwave, oven, stovetop

Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!

Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!
Buena Ventura Lakes
9.8 out of 10, Exceptional, (38 reviews)
"The house was absolutely perfect for my family to spend the week! Amazing views, extremely clean, and the pool was perfect size for us to all enjoy! Will definitely stay there again if we come back to the area! "
United States
John M.
The price is €303
includes taxes & fees
21 Jul - 22 Jul
Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!
Outdoor pool, a heated pool

Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
9.8 out of 10, Exceptional, (64 reviews)
"Great stay. "
United States
rick s.
The price is €356
includes taxes & fees
6 Jul - 7 Jul
Mills Cottage by the Little Lake
Exterior detail

Lake House Pets allowed

Lake House Pets allowed
Lake Weldona
9.8 out of 10, Exceptional, (56 reviews)
"Cozy dog friendly stay for 3 a dog"
United States
David S.
The price is €353
includes taxes & fees
1 Jul - 2 Jul
Lake House Pets allowed
Outdoor pool, a heated pool

Large, beautiful, very comfortable one bedroom on small lake

Large, beautiful, very comfortable one bedroom on small lake
Lake Weldona
10.0 out of 10, Exceptional, (67 reviews)
"This is one of the best places we have stayed. It is nestled in its own little world, surrounded by greenery, water, and wildlife. Plenty of lakes to walk around, leisurely or for an exercise workout. The hosts were helpful and responsive."
United States
Dorothy V.
The price is €306
includes taxes & fees
1 Jul - 2 Jul
Large, beautiful, very comfortable one bedroom on small lake
Exterior

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
Kissimmee
9.2 out of 10, Wonderful, (168 reviews)
"Not far from Disney properties. Great amenities!"
United States
DELMA T.
The price is €211
includes taxes & fees
6 Jul - 7 Jul
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
5 bedrooms, in-room safe, iron/ironing board, travel cot

MAGIC 5* LAKE VIEW VILLA HEATED POOL&HOT SPA, near DISNEY, 10 Guests

MAGIC 5* LAKE VIEW VILLA HEATED POOL&HOT SPA, near DISNEY, 10 Guests
Lake Berkley
8.8 out of 10, Excellent, (41 reviews)
"Beautiful home and perfect for our family! Pool was great, bedroom setups were nice and my daughter loved the princess dress up clothes!"
United States
Anonymous traveller
MAGIC 5* LAKE VIEW VILLA HEATED POOL&HOT SPA, near DISNEY, 10 Guests
Fridge, microwave, oven, stovetop

Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!

Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!
Orlando
9.8 out of 10, Exceptional, (272 reviews)
"Jim was just amazing to work with! The condo was perfect and in an ideal location to shops, restaurants and of course Universal and Disney. We just loved it!"
United States
Michelle A.
The price is €406
includes taxes & fees
2 Jul - 3 Jul
Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!
Pool

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

Crystal 3 BR TH Gated Resort Close to Disney

Crystal 3 BR TH Gated Resort Close to Disney
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Nice and clean house patio chairs were broken blinds were broken beds were not comfortable make noises, right beside highway too much traffic noise, saw a lizard and cockraches in the kitchen. Lot of parking"
Canada
Mohammad zaki A.
The price is €427
includes taxes & fees
1 Jul - 2 Jul
Crystal 3 BR TH Gated Resort Close to Disney
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

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

8/10 Good
"Location is excellent for when transiting through Orlando. But what I didn’t realise is that the windows don’t face outside but the arrivals hall of the airport, so no fresh air. There was a knocking noise in my room, I suspect pipes, which kept waking me up at night. The bed was comfortable and linen was very good."
Irina 1-night trip
Posted less than an hour ago
Hyatt Regency Orlando International Airport

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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