Family-Friendly Vacation Rentals in Historic Downtown Kissimmee, FL: Compare 10+ Sites & Save

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  6.  Historic Downtown Kissimmee

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4834 Best Family Vacation Rentals in Historic Downtown Kissimmee (Starting from $139)

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
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
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
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The Royal Palm, Rooftop Jacuzzi | Mini Golf | 2 story games and play room
The Royal Palm, Rooftop Jacuzzi | Mini Golf | 2 story games and play room
Villa
Kissimmee, FL, 34747, United States
0.3k from Historic Downtown Kissimmee center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking

10 Bedrooms26 Guests
New to Booking
$3329
Average price / night
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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
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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
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Luxury 4 Bedroom Villa on the gated Bellavida Resort close to the Theme parks
Luxury 4 Bedroom Villa on the gated Bellavida Resort close to the Theme parks
Villa
Kissimmee, FL, 34746, United States
0.3k from Historic Downtown Kissimmee center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms10 Guests
9.6

Exceptional

189 reviews

$229
Average price / night
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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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Single Storey 5 Bed 3 Bath Villa with Pool, HD-TV , private beach + WiFi
Single Storey 5 Bed 3 Bath Villa with Pool, HD-TV , private beach + WiFi
Villa
Kissimmee, FL, 34746, United States
0.3k from Historic Downtown Kissimmee center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
8.2

Very Good

74 reviews

$193
Average price / night
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Lively Home Near Disney With Private Pool, Game And Themed Rooms With Waterpark & Resort Access At Encore Resorts Reunion - 670La
Lively Home Near Disney With Private Pool, Game And Themed Rooms With Waterpark & Resort Access At Encore Resorts Reunion - 670La
House
Orlando, FL, USA
0.3k from Historic Downtown Kissimmee center

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

1 Bedroom14 Guests
New to Booking
$499
Average price / night
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(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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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
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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
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Modern Home With Themed Rooms, Foosball Table And Waterpark & Resort Access Near Disney At Encore Resorts Reunion - 253Sf
Modern Home With Themed Rooms, Foosball Table And Waterpark & Resort Access Near Disney At Encore Resorts Reunion - 253Sf
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
$474
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
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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
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
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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
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Cozy home near Disney!!!
Cozy home near Disney!!!
House
Kissimmee, FL, 34744, United States
2.4k from Historic Downtown Kissimmee center

AC, Arcade, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms6 Guests
2.0

Review score

1 reviews

$178
Average price / night
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New Listing! Solara Resort, 8mi to Disney & 15mi to Universal - GRH575768
New Listing! Solara Resort, 8mi to Disney & 15mi to Universal - GRH575768
House
Kissimmee, FL, 34747, United States
2.5k from Historic Downtown Kissimmee center

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

9 Bedrooms22 Guests
New to Booking
$912
Average price / night
Check Availability
Looking in Orlando / Kissimmee great Location 2/1
Looking in Orlando / Kissimmee great Location 2/1
House
Kissimmee, FL, 34741, United States
2.9k from Historic Downtown Kissimmee center

AC, Extra Bed, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, TV

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$169
Average price / night
Check Availability
The best new 2-1 in Kissimmee, Excellent Location
The best new 2-1 in Kissimmee, Excellent Location
House
Kissimmee, FL, 34741, United States
3.1k from Historic Downtown Kissimmee center

AC, Internet, Living Area, Microwave, No Smoking

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$139
Average price / night
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Theater Room | Themed Games Room | Themed Kids Bedrooms | Screened Pool
Theater Room | Themed Games Room | Themed Kids Bedrooms | Screened Pool
House
Kissimmee, FL, 34747, United States
3.2k from Historic Downtown Kissimmee center

AC, Arcade, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

8 Bedrooms16 Guests
8.2

Very Good

26 reviews

$418
Average price / night
Check Availability
3bd 2ba Luxe Villa Located 20 Minutes From Disney
3bd 2ba Luxe Villa Located 20 Minutes From Disney
Villa
Kissimmee, FL, 34741, United States
3.5k from Historic Downtown Kissimmee center

AC, Balcony, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
New to Booking
$232
Average price / night
Check Availability
Elegant 8BR Bella Vida Resort Villa w/ Private Pool, Spa & Free Amenities
Elegant 8BR Bella Vida Resort Villa w/ Private Pool, Spa & Free Amenities
House
Kissimmee, FL, 34746, United States
3.6k from Historic Downtown Kissimmee center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

8 Bedrooms16 Guests
New to Booking
$495
Average price / night
Check Availability
Fish & Boat Lake Toho: Family Gem Near Theme Parks
Fish & Boat Lake Toho: Family Gem Near Theme Parks
House
Kissimmee, FL, 34746, United States
3.6k from Historic Downtown Kissimmee center

AC, Barbecue, Dryer, Free Parking, Heater, Kitchen, Microwave, No Smoking, Patio

5 Bedrooms12 Guests
New to Booking
$369
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 Family Vacation Rentals in Historic Downtown Kissimmee.

Stay Near Historic Downtown Kissimmee's Top Attractions

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Historic Downtown Kissimmee Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 4834 verified family-friendly vacation rentals in Historic Downtown Kissimmee. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Historic Downtown Kissimmee vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $139 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Historic Downtown Kissimmee offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Historic Downtown Kissimmee are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Historic Downtown Kissimmee often include amenities such as Child Friendly, Fireplace/Heating, and Wellness Facilities. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.