Short-Term Rentals in Historic Downtown Kissimmee, FL: Compare 10+ Sites & Save

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6511 Best Short-Term Rentals in Historic Downtown Kissimmee (Starting from $97)

Spacious Lakefront Condo in Kissimmee
Spacious Lakefront Condo in Kissimmee
Apartment
Kissimmee, FL, USA
0.1k from Historic Downtown Kissimmee center

Apartments, Accommodations, Lodgings, Places to stay, Condos

2 Bedrooms5 Guests
New to Booking
$450
Average price / night
Check Availability
Tuscan Dream - Premium Resort Condo
Tuscan Dream - Premium Resort Condo
Condo
Kissimmee, FL, 33896, United States
0.3k from Historic Downtown Kissimmee center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
7.2

Good

5 reviews

$160
Average price / night
Check Availability
Delightful Home Near Disney With Private Pool, Themed & Game Room With Waterpark & Resort Access At Encore Resorts Reunion - 451No
Delightful Home Near Disney With Private Pool, Themed & Game Room With Waterpark & Resort Access At Encore Resorts Reunion - 451No
House
Orlando, FL, USA
0.3k from Historic Downtown Kissimmee center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings

1 Bedroom12 Guests
New to Booking
$224
Average price / night
Check Availability
Beautiful home near Disney Private PoolBBQ Downtown
Beautiful home near Disney Private PoolBBQ Downtown
House
Kissimmee, FL, 34741, United States
0.3k from Historic Downtown Kissimmee center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

4 Bedrooms12 Guests
9.8

Exceptional

43 reviews

$508
Average price / night
Check Availability
Cheerful Home Near Disney With Themed Rooms, Pool Table & Waterpark And Resort Access At Encore Resorts Reunion - 200Mn
Cheerful Home Near Disney With Themed Rooms, Pool Table & Waterpark And Resort Access At Encore Resorts Reunion - 200Mn
House
Orlando, FL, USA
0.3k from Historic Downtown Kissimmee center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings

6 Bedrooms14 Guests
New to Booking
$532
Average price / night
Check Availability
Elegant Solara Escape: 7BR Oasis w/Pool & Spa
Elegant Solara Escape: 7BR Oasis w/Pool & Spa
House
Kissimmee, FL, 34747, United States
0.3k from Historic Downtown Kissimmee center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Laundry, Microwave

7 Bedrooms14 Guests
New to Booking
$453
Average price / night
Check Availability
Elegant Home With Private Pool, Waterpark & Resort Access Near Disney At Encore Resort - 7610Wi
Elegant Home With Private Pool, Waterpark & Resort Access Near Disney At Encore Resort - 7610Wi
House
Orlando, FL, USA
0.3k from Historic Downtown Kissimmee center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings

1 Bedroom18 Guests
New to Booking
$608
Average price / night
Check Availability
4BR 3BA, House overlooking the water
4BR 3BA, House overlooking the water
Condo
Kissimmee, FL, 34741, United States
0.3k from Historic Downtown Kissimmee center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Laundry

4 Bedrooms10 Guests
New to Booking
$165
Average price / night
Check Availability
Luxury Pet Friendly Homes
Luxury Pet Friendly Homes
House
Historic Downtown Kissimmee, Kissimmee, Florida, USA
0.3k from Historic Downtown Kissimmee center

Internet, Pool, Air Conditioner, Pet Friendly, Parking, Child Friendly

44 Bedrooms88 Guests
9.0

Fabulous

2 reviews

$600
Average price / night
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4 bedroom 2 storey pool home with stunning lake views on gated community
4 bedroom 2 storey pool home with stunning lake views on gated community
House
Kissimmee, FL, 34744, United States
0.3k from Historic Downtown Kissimmee center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

4 Bedrooms8 Guests
8.4

Very Good

38 reviews

$215
Average price / night
Check Availability
Modern Home With Private Pool, Ping Pong Table Near Disney With Waterpark & Resort Access At Encore Resort - 7758Wl
Modern Home With Private Pool, Ping Pong Table Near Disney With Waterpark & Resort Access At Encore Resort - 7758Wl
Apartment
Kissimmee, FL, USA
0.3k from Historic Downtown Kissimmee center

Apartments, Accommodations, Pools, Parking, Spa, Pet-friendly, Lodgings, Hot tubs, Places to stay

5 Bedrooms12 Guests
7.0

Good

1 reviews

$474
Average price / night
Check Availability
Superb Value Resort Townhome Near Shopping
Superb Value Resort Townhome Near Shopping
House
Kissimmee, FL, 34741, United States
0.3k from Historic Downtown Kissimmee center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
9.2

Superb

37 reviews

$140
Average price / night
Check Availability
Stylish Home With Themed Rooms, Game Room And Waterpark & Resort Access Near Disney At Encore Resorts Reunion - 267Sf
Stylish Home With Themed Rooms, Game Room And Waterpark & Resort Access Near Disney At Encore Resorts Reunion - 267Sf
House
Orlando, FL, USA
0.3k from Historic Downtown Kissimmee center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings

5 Bedrooms12 Guests
New to Booking
$448
Average price / night
Check Availability
(DR206) Storey Lake Condo 2/2, Free Waterpark
(DR206) Storey Lake Condo 2/2, Free Waterpark
Apartment
Kissimmee, FL, 34746, United States
0.3k from Historic Downtown Kissimmee center

AC, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms7 Guests
9.2

Superb

16 reviews

$200
Average price / night
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Gorgeous Home With Private Pool, Game Room Near Disney With Waterpark & Resort Access At Encore Resort - 781La
Gorgeous Home With Private Pool, Game Room Near Disney With Waterpark & Resort Access At Encore Resort - 781La
House
Orlando, FL, USA
0.3k from Historic Downtown Kissimmee center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

6 Bedrooms14 Guests
New to Booking
$843
Average price / night
Check Availability
Hakuna Matata - 4BR Townhouse, Lucaya Village Resort.
Hakuna Matata - 4BR Townhouse, Lucaya Village Resort.
House
Kissimmee, FL, 34746, United States
0.3k from Historic Downtown Kissimmee center

AC, Arcade, Barbecue, Breakfast Available, Dryer, Fireplace, Free Parking, Heater, Internet

4 Bedrooms10 Guests
New to Booking
$251
Average price / night
Check Availability
Charming Home With Themed Rooms, Game Room And Waterpark & Resort Access Near Disney At Encore Resorts Reunion - 300Pn
Charming Home With Themed Rooms, Game Room And Waterpark & Resort Access Near Disney At Encore Resorts Reunion - 300Pn
House
Orlando, FL, USA
0.3k from Historic Downtown Kissimmee center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings

6 Bedrooms14 Guests
New to Booking
$532
Average price / night
Check Availability
Solara Resort Gem - Pool, Game Room, Near Disney
Solara Resort Gem - Pool, Game Room, Near Disney
House
Kissimmee, FL, 34747, United States
0.3k from Historic Downtown Kissimmee center

AC, Arcade, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

9 Bedrooms22 Guests
8.0

Good

3 reviews

$938
Average price / night
Check Availability
Astounding Home Near Disney With Themed & Media Room, Pool Table With Waterpark & Resort Access At Encore Resorts Reunion - 240Cl
Astounding Home Near Disney With Themed & Media Room, Pool Table With Waterpark & Resort Access At Encore Resorts Reunion - 240Cl
House
Orlando, FL, USA
0.3k from Historic Downtown Kissimmee center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings

1 Bedroom24 Guests
New to Booking
$642
Average price / night
Check Availability
Charming cottage near the lakefront in Kissimmee. walking to downtown amenities.
Charming cottage near the lakefront in Kissimmee. walking to downtown amenities.
House
Kissimmee, FL, 34744, United States
0.5k from Historic Downtown Kissimmee center

AC, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
New to Booking
$147
Average price / night
Check Availability
Super Boho - At Lake Toho's Water
Super Boho - At Lake Toho's Water
House
319 East Monument Ave, Kissimmee, FL, 34741, United States
0.5k from Historic Downtown Kissimmee center

Internet

8.0

Good

1 reviews

$229
Average price / night
Check Availability
Modern Home at Solara Resort
Modern Home at Solara Resort
House
Kissimmee, FL, 34747, United States
1.0k from Historic Downtown Kissimmee center

AC, Arcade, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub

5 Bedrooms12 Guests
10.0

Exceptional

3 reviews

$404
Average price / night
Check Availability
Elite Home near Disney with Theater Room, Game Room and Private Pool with Water.
Elite Home near Disney with Theater Room, Game Room and Private Pool with Water.
House
Kissimmee, FL, 34747, United States
1.0k from Historic Downtown Kissimmee center

Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, No Smoking, Pool

9 Bedrooms20 Guests
7.6

Good

4 reviews

$843
Average price / night
Check Availability
1 BR Apt close to Disney/Universal/Shopping/Dining
1 BR Apt close to Disney/Universal/Shopping/Dining
Apartment
Kissimmee, FL, 34741, United States
1.1k from Historic Downtown Kissimmee center

AC, Extra Bed, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, TV

1 Bedroom4 Guests
8.6

Fabulous

23 reviews

$97
Average price / night
Check Availability
Charming 2-bedroom house in Kissimmee near Disney
Charming 2-bedroom house in Kissimmee near Disney
House
Kissimmee, FL, 34744, United States
1.2k from Historic Downtown Kissimmee center

AC, Barbecue, Dryer, Heater, Internet, Laundry, Microwave, No Smoking, TV

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$169
Average price / night
Check Availability
Cozy 2-beds Family Friendly Apt w/ Pool, Full Kitchen in Downtown Kissimmee
Cozy 2-beds Family Friendly Apt w/ Pool, Full Kitchen in Downtown Kissimmee
Apartment
Kissimmee, FL, 34741, United States
1.3k from Historic Downtown Kissimmee center

AC, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Patio, Pool

2 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$141
Average price / night
Check Availability
Magic & Comfort in the Palms!Near Disney-Universal.
Magic & Comfort in the Palms!Near Disney-Universal.
House
Kissimmee, FL, 34741, United States
1.3k from Historic Downtown Kissimmee center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms11 Guests
New to Booking
$462
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Historic Downtown Kissimmee.

Stay Near Historic Downtown Kissimmee's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Historic Downtown Kissimmee Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 6511 verified short-term rentals in Historic Downtown Kissimmee, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Historic Downtown Kissimmee vary depending on location, property size, and travel dates. Rates typically start from around $97 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Historic Downtown Kissimmee include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Historic Downtown Kissimmee, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Historic Downtown Kissimmee often include amenities such as Fireplace/Heating, Wellness Facilities, and Internet, providing a comfortable and convenient stay.

Short-term rentals in Historic Downtown Kissimmee are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.