Vacation Rentals with Private Pool in Osceola Heritage Park, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Orlando
  6.  Osceola Heritage Park

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1844 Best Vacation Rentals with Private Pool in Osceola Heritage Park (Starting from $103)

3 Bed 2.5 Bath Villa with Lakeside Pool
3 Bed 2.5 Bath Villa with Lakeside Pool
Villa
Kissimmee, FL, USA
6.7k from Osceola Heritage Park center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom6 Guests
8.3

Very Good

3 reviews

$123
Average price / night
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Magic Landings Near Heritage Park w/Pool
Magic Landings Near Heritage Park w/Pool
House
Kissimmee, FL, 34744, United States
0.5k from Osceola Heritage Park center

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

3 Bedrooms6 Guests
9.2

Superb

36 reviews

$274
Average price / night
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3-BR Condo BBQ Heated Pool Near DisneyMalls
3-BR Condo BBQ Heated Pool Near DisneyMalls
House
Kissimmee, FL, USA
7.4k from Osceola Heritage Park center

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

1 Bedroom9 Guests
New to Booking
$227
Average price / night
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Spacious 4BR Home with Private Pool & Game Room, 19 Miles to Disney
Spacious 4BR Home with Private Pool & Game Room, 19 Miles to Disney
House
Kissimmee, FL, 34744, United States
0.7k from Osceola Heritage Park center

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

4 Bedrooms8 Guests
9.6

Exceptional

63 reviews

$279
Average price / night
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Kissimmee Condo Community Perks, 10 Mi to Disney!
Kissimmee Condo Community Perks, 10 Mi to Disney!
Apartment
Kissimmee, FL, USA
7.4k from Osceola Heritage Park center

Apartments, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay, Condos

4 Bedrooms8 Guests
8.7

Fabulous

3 reviews

$135
Average price / night
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Walk to Silver Spurs Rodeo and Heritage Park
Walk to Silver Spurs Rodeo and Heritage Park
House
Kissimmee, FL, 34744, United States
0.7k from Osceola Heritage Park center

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

4 Bedrooms8 Guests
6.0

Review score

2 reviews

$186
Average price / night
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Upstay Luxury Resort Mansion w Pool Near Disney
Upstay Luxury Resort Mansion w Pool Near Disney
House
Kissimmee, FL, USA
7.9k from Osceola Heritage Park center

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

8 Bedrooms20 Guests
8.0

Good

8 reviews

$472
Average price / night
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Magical Family Friendly Pool and Lake House
Magical Family Friendly Pool and Lake House
House
Kissimmee, FL, 34744, United States
0.7k from Osceola Heritage Park center

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

4 Bedrooms10 Guests
10.0

Exceptional

33 reviews

$226
Average price / night
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Family-Friendly Mansion at Sonoma Luxury Resort
Family-Friendly Mansion at Sonoma Luxury Resort
House
Kissimmee, FL, USA
7.9k from Osceola Heritage Park center

Luxury, Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings

10 Bedrooms20 Guests
8.7

Fabulous

8 reviews

$655
Average price / night
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Luxury Themed Room Villa w/Private Pool & Playground! Gameroom.  🛏🥂pool table
Luxury Themed Room Villa w/Private Pool & Playground! Gameroom. 🛏🥂pool table
Villa
Kissimmee, FL, 34744, United States
0.8k from Osceola Heritage Park center

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

4 Bedrooms8 Guests
9.2

Superb

54 reviews

$245
Average price / night
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Beautiful and cozy home at Sonoma Resort
Beautiful and cozy home at Sonoma Resort
House
Kissimmee, FL, USA
7.9k from Osceola Heritage Park center

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

6 Bedrooms12 Guests
New to Booking
$213
Average price / night
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Disney Vacation Home With 2 Master Bedrooms
Disney Vacation Home With 2 Master Bedrooms
House
Kissimmee, FL, 34744, United States
0.8k from Osceola Heritage Park center

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

4 Bedrooms8 Guests
9.4

Superb

82 reviews

$236
Average price / night
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Mario Bros Game room 8BD Pool Movie Room 2622
Mario Bros Game room 8BD Pool Movie Room 2622
House
Kissimmee, FL, USA
7.9k from Osceola Heritage Park center

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

8 Bedrooms16 Guests
New to Booking
$434
Average price / night
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Cheerful three bedroom home with Heated Pool in Kissimmee, Florida
Cheerful three bedroom home with Heated Pool in Kissimmee, Florida
House
Kissimmee, FL, 34744, United States
1.7k from Osceola Heritage Park center

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

3 Bedrooms8 Guests
9.4

Superb

53 reviews

$219
Average price / night
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Magnificent Home- Private Pool Game Room SO2601
Magnificent Home- Private Pool Game Room SO2601
House
Kissimmee, FL, USA
7.9k from Osceola Heritage Park center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom23 Guests
8.0

Good

2 reviews

$552
Average price / night
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Villas at Fortune Place 2BR Suite Saturday Check-In
Villas at Fortune Place 2BR Suite Saturday Check-In
Condo
Kissimmee, FL, 34744, United States
1.9k from Osceola Heritage Park center

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

2 Bedrooms6 Guests
New to Booking
$103
Average price / night
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13-Bedroom Resort Home with Pool Hot Tub & BBQ
13-Bedroom Resort Home with Pool Hot Tub & BBQ
House
Kissimmee, FL, USA
8.0k from Osceola Heritage Park center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom26 Guests
8.3

Very Good

3 reviews

$843
Average price / night
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Disney Location with Secluded Pool and King Sized 4-Poster Bed
Disney Location with Secluded Pool and King Sized 4-Poster Bed
House
Kissimmee, FL, 34743, United States
2.0k from Osceola Heritage Park center

AC, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

4 Bedrooms9 Guests
9.4

Superb

135 reviews

$186
Average price / night
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Upstay-Mansion w Spa-Pool-Cinema-Games - Sleeps 36
Upstay-Mansion w Spa-Pool-Cinema-Games - Sleeps 36
House
Kissimmee, FL, USA
8.0k from Osceola Heritage Park center

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

15 Bedrooms36 Guests
9.3

Superb

3 reviews

$953
Average price / night
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South facing with lake view pool home, gated community Cumbrian Lakes
South facing with lake view pool home, gated community Cumbrian Lakes
House
Kissimmee, FL, 34746, United States
2.3k from Osceola Heritage Park center

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

4 Bedrooms8 Guests
8.6

Fabulous

10 reviews

$294
Average price / night
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2606YA Luxurious En-Suite Single Home Pool
2606YA Luxurious En-Suite Single Home Pool
House
Kissimmee, FL, USA
8.0k from Osceola Heritage Park center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals

1 Bedroom17 Guests
8.0

Good

1 reviews

$540
Average price / night
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Elegant 3 Bedrooms with private pool, close to Disney World,Downtown Kissimmee.
Elegant 3 Bedrooms with private pool, close to Disney World,Downtown Kissimmee.
House
Kissimmee, FL, 34744, United States
2.3k from Osceola Heritage Park center

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

3 Bedrooms6 Guests
8.6

Fabulous

4 reviews

$164
Average price / night
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Charming 3-bedroom house with Lake view, in fantastic Kissimmee
Charming 3-bedroom house with Lake view, in fantastic Kissimmee
House
Kissimmee, FL, 34743, United States
2.5k from Osceola Heritage Park center

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

3 Bedrooms6 Guests
9.6

Exceptional

12 reviews

$246
Average price / night
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Disney Orlando Lake 4 Bed Luxury Pool Villa
Disney Orlando Lake 4 Bed Luxury Pool Villa
Villa
Kissimmee, FL, 34743, United States
2.5k from Osceola Heritage Park center

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

4 Bedrooms8 Guests
9.8

Exceptional

53 reviews

$192
Average price / night
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Private house with pool Kissimmee/Orlando
Private house with pool Kissimmee/Orlando
House
Kissimmee, FL, 34743, United States
2.5k from Osceola Heritage Park center

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

3 Bedrooms9 Guests
9.8

Exceptional

55 reviews

$445
Average price / night
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Cozy home near Disney!!!
Cozy home near Disney!!!
House
Kissimmee, FL, 34744, United States
2.7k from Osceola Heritage Park 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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Beautiful Vacation Home With PRIVATE POOL In Orlando
Beautiful Vacation Home With PRIVATE POOL In Orlando
House
kissemmee, FL, 34744, United States
2.7k from Osceola Heritage Park center

AC, Arcade, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms7 Guests
10.0

Exceptional

25 reviews

$247
Average price / night
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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 Vacation Rentals with Private Pool in Osceola Heritage Park.

Where to stay in Osceola Heritage Park? Best neighborhoods & areas

Osceola Heritage Park Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 1844 verified vacation rentals with a private pool in Osceola Heritage Park. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Osceola Heritage Park vary depending on the property size, location, and travel season. Rates typically start from around $103 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Osceola Heritage Park also welcome pets. Currently, 17 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Osceola Heritage Park often include additional features such as Pool, Private Pool, and Fireplace/Heating. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Osceola Heritage Park include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.