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

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Orlando
  6.  Osceola Heritage Park

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3074 Best Vacation Rentals with Pool in Osceola Heritage Park (Starting from $80)

Walk to Silver Spurs Rodeo and Heritage Park home
Walk to Silver Spurs Rodeo and Heritage Park home
House
Kissimmee, FL, USA
0.7k from Osceola Heritage Park center

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

4 Bedrooms8 Guests
New to Booking
$265
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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Beautiful, home in a gated community
Beautiful, home in a gated community
House
Kissimmee, FL, USA
0.9k from Osceola Heritage Park center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs

4 Bedrooms9 Guests
8.6

Fabulous

37 reviews

$109
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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Magical Way
Magical Way
House
Kissimmee, FL, USA
0.9k from Osceola Heritage Park center

Internet, Ocean View, View, Air Conditioner, Hot Tub, Wellness Facilities, Security/Safety

3 Bedrooms8 Guests
New to Booking
$211
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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Heritage Park Inn
Heritage Park Inn
Apartment
Kissimmee, FL, USA
0.9k from Osceola Heritage Park center

Apartments, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Vacation rentals, Places to stay

19 Bedrooms6 Guests
6.2

Good

207 reviews

$80
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 Relax Villa
Family Friendly Relax Villa
House
Kissimmee, FL, USA
1.1k from Osceola Heritage Park center

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

4 Bedrooms10 Guests
New to Booking
$196
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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Modern Townhouse with Pool Close to Disney & Silver Spurs Arena
Modern Townhouse with Pool Close to Disney & Silver Spurs Arena
House
Kissimmee, FL, USA
1.1k from Osceola Heritage Park center

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

3 Bedrooms10 Guests
9.6

Exceptional

6 reviews

$158
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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Smart home near Disney world, Silver Spurs Arena
Smart home near Disney world, Silver Spurs Arena
House
Kissimmee, FL, USA
1.2k from Osceola Heritage Park center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$198
Average price / night
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Cloud Nine • 1BR 15 MIN from Kissimmee Main Street
Cloud Nine • 1BR 15 MIN from Kissimmee Main Street
Apartment
Kissimmee, FL, 34744, United States
0.9k from Osceola Heritage Park center

AC, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

5 reviews

$199
Average price / night
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Villas at Fortune Place
Villas at Fortune Place
Resort
Osceola Heritage Park, Kissimmee, Florida, USA
1.9k from Osceola Heritage Park center

Accommodations, Pools, Resorts, Parking, 3-star, Lodgings, Hot tubs, Places to stay, Family

75 Bedrooms22 Guests
8.8

Fabulous

213 reviews

$240
Average price / night
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3-bedroom house with a pool and jacuzzi in Kissimmee
3-bedroom house with a pool and jacuzzi in Kissimmee
House
Kissimmee, FL, 34744, United States
0.9k from Osceola Heritage Park center

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

3 Bedrooms9 Guests
7.6

Good

4 reviews

$256
Average price / night
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Lakeside Community, Pools, And More!
Lakeside Community, Pools, And More!
House
Kissimmee, FL, USA
2.1k from Osceola Heritage Park center

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

6 Bedrooms16 Guests
7.3

Good

3 reviews

$300
Average price / night
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The Tuxedo 2BD Stay in Kissimmee with fitness room, Free WIFI, Free Parking
The Tuxedo 2BD Stay in Kissimmee with fitness room, Free WIFI, Free Parking
Apartment
Kissimmee, FL, 34744, United States
1.0k from Osceola Heritage Park center

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

2 Bedrooms4 Guests
New to Booking
$276
Average price / night
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Island 1
Island 1
House
Kissimmee, FL, USA
2.5k from Osceola Heritage Park center

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

3 Bedrooms6 Guests
8.4

Very Good

13 reviews

$136
Average price / night
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Think Pink in Kissimmee - Gorgeous 2BD with free WIFI, free parking and more!!
Think Pink in Kissimmee - Gorgeous 2BD with free WIFI, free parking and more!!
Apartment
Kissimmee, FL, 34744, United States
1.1k from Osceola Heritage Park center

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

2 Bedrooms4 Guests
9.4

Superb

8 reviews

$246
Average price / night
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Cozy Home Near Disney!
Cozy Home Near Disney!
House
Kissimmee, FL, USA
2.7k from Osceola Heritage Park center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs

4 Bedrooms6 Guests
9.0

Fabulous

1 reviews

$190
Average price / night
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New & Updated  Peaceful family townhouse in Kissimmee, FL
New & Updated Peaceful family townhouse in Kissimmee, FL
House
Kissimmee, FL, 34744, United States
1.1k from Osceola Heritage Park center

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

3 Bedrooms8 Guests
9.6

Exceptional

11 reviews

$179
Average price / night
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Blue Haven • Cozy 1BR Boho • 15 MIN from Kissimmee Main Street • 25 Min Old Town
Blue Haven • Cozy 1BR Boho • 15 MIN from Kissimmee Main Street • 25 Min Old Town
Apartment
Kissimmee, FL, 34744, United States
1.2k from Osceola Heritage Park center

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

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$204
Average price / night
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4-bedroom home in Kissimmee, 8 mins to Silver Spurs Arena, Mecum Car Auction
4-bedroom home in Kissimmee, 8 mins to Silver Spurs Arena, Mecum Car Auction
House
Kissimmee, FL, 34744, United States
1.2k from Osceola Heritage Park center

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

4 Bedrooms10 Guests
New to Booking
$341
Average price / night
Check Availability
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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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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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
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 Vacation Rentals with Pool in Osceola Heritage Park.

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

Osceola Heritage Park Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 3074 verified vacation rentals with a pool in Osceola Heritage Park. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Osceola Heritage Park vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $80 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Osceola Heritage Park offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Osceola Heritage Park welcome pets. Currently, 33 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Osceola Heritage Park often include additional outdoor features such as Pool, Wellness Facilities, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Osceola Heritage Park offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.