Family-Friendly Vacation Rentals in Pleasant Hill Lakes, FL: Compare 10+ Sites & Save

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1123 Best Family Vacation Rentals in Pleasant Hill Lakes (Starting from $158)

Storey Lake Resort 32 - Hosted by Top Villas
Storey Lake Resort 32 - Hosted by Top Villas
Apartment
Kissimmee, FL, USA
1.2k from Pleasant Hill Lakes center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay, Family

1 Bedroom7 Guests
New to Booking
$292
Average price / night
Check Availability
Modern Oasis Golden Elegance Disney Lego Land Area 5 bedrooms big lot
Modern Oasis Golden Elegance Disney Lego Land Area 5 bedrooms big lot
House
Kissimmee, FL, 34746, United States
1.1k from Pleasant Hill Lakes center

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

5 Bedrooms16 Guests
10.0

Exceptional

5 reviews

$359
Average price / night
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Spacious Vacation Rental with Yard in Kissimmee!
Spacious Vacation Rental with Yard in Kissimmee!
House
Kissimmee, FL, USA
1.4k from Pleasant Hill Lakes center

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

4 Bedrooms8 Guests
New to Booking
$491
Average price / night
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Nature-Packed Family Escape Near Lake Tohopekaliga
Nature-Packed Family Escape Near Lake Tohopekaliga
House
Kissimmee, FL, 34746, United States
2.7k from Pleasant Hill Lakes center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$200
Average price / night
Check Availability
TRANQUILITY! PRIVATE Gated Estate! Boats, RVs OK! Has Separate Apt, Fishing, Hiking, LOW Rates!
TRANQUILITY! PRIVATE Gated Estate! Boats, RVs OK! Has Separate Apt, Fishing, Hiking, LOW Rates!
House
Kissimmee, FL, USA
1.8k from Pleasant Hill Lakes center

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

4 Bedrooms9 Guests
New to Booking
$176
Average price / night
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Luxury villa  close to city yet very serene/private/spacious and close to nature
Luxury villa close to city yet very serene/private/spacious and close to nature
Villa
Kissimmee, FL, 34758, United States
3.9k from Pleasant Hill Lakes center

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

4 Bedrooms8 Guests
8.8

Fabulous

6 reviews

$243
Average price / night
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Ultimate Escape! Indoor Pool, Game Room, Movie Room, and more!
Ultimate Escape! Indoor Pool, Game Room, Movie Room, and more!
House
Kissimmee, FL, USA
2.5k from Pleasant Hill Lakes center

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

2 Bedrooms13 Guests
New to Booking
$172
Average price / night
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Private Ranch Style Suite Enourmous Yard
Private Ranch Style Suite Enourmous Yard
House
Kissimmee, FL, 34746, United States
4.1k from Pleasant Hill Lakes center

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

1 Bedroom3 Guests
7.0

Good

2 reviews

$172
Average price / night
Check Availability
The Oaks Bay
The Oaks Bay
House
Kissimmee, FL, 34758, United States
4.2k from Pleasant Hill Lakes center

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

4 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$232
Average price / night
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Stars Manor-Disney-Universal-Pool-22people
Stars Manor-Disney-Universal-Pool-22people
Villa
Kissimmee, FL, USA
3.2k from Pleasant Hill Lakes center

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

7 Bedrooms22 Guests
9.5

Superb

2 reviews

$692
Average price / night
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NEW 3BD Themed Room | Near Disney | Amazing Resort
NEW 3BD Themed Room | Near Disney | Amazing Resort
Apartment
Kissimmee, FL, 34746, United States
4.3k from Pleasant Hill Lakes center

AC, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
New to Booking
$492
Average price / night
Check Availability
2668DR VILLA 5 BED/5 BA (SANITIZED)
2668DR VILLA 5 BED/5 BA (SANITIZED)
House
Kissimmee, FL, USA
4.3k from Pleasant Hill Lakes center

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

4 Bedrooms15 Guests
8.0

Good

1 reviews

$259
Average price / night
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Bright Pool Villa | Gated Resort • Disney Shuttle Nearby
Bright Pool Villa | Gated Resort • Disney Shuttle Nearby
Villa
Kissimmee, FL, 34746, United States
4.3k from Pleasant Hill Lakes center

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

5 Bedrooms12 Guests
New to Booking
$368
Average price / night
Check Availability
5BR Family Haven Near Disney with Private Pool
5BR Family Haven Near Disney with Private Pool
House
Kissimmee, FL, USA
4.3k from Pleasant Hill Lakes center

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

5 Bedrooms12 Guests
New to Booking
$327
Average price / night
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ALWAYS FREE POOL HEAT - 2 KINGS, Games room! 5 smart TV’s - S/Steel appliances
ALWAYS FREE POOL HEAT - 2 KINGS, Games room! 5 smart TV’s - S/Steel appliances
House
Kissimmee, FL, 34758, United States
4.3k from Pleasant Hill Lakes center

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

4 Bedrooms10 Guests
9.6

Exceptional

211 reviews

$227
Average price / night
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5 Star Mansion with Private Pool on Veranda Palms Orlando Mansion 5377
5 Star Mansion with Private Pool on Veranda Palms Orlando Mansion 5377
Villa
Kissimmee, FL, USA
4.3k from Pleasant Hill Lakes center

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

1 Bedroom30 Guests
New to Booking
$3459
Average price / night
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RS4964 Storey Lake Home 4BDRM 3BATH Private Pool Free Waterpark
RS4964 Storey Lake Home 4BDRM 3BATH Private Pool Free Waterpark
House
Kissimmee, FL, 34746, United States
4.3k from Pleasant Hill Lakes center

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

4 Bedrooms11 Guests
8.8

Fabulous

8 reviews

$290
Average price / night
Check Availability
Exclusive Mansion with Large Private Pool on Veranda Palms Orlando Mansion 5378
Exclusive Mansion with Large Private Pool on Veranda Palms Orlando Mansion 5378
Villa
Kissimmee, FL, USA
4.3k from Pleasant Hill Lakes center

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

14 Bedrooms30 Guests
New to Booking
$1350
Average price / night
Check Availability
Modern 3BR Condo at Royal Palm Bay | Sleeps 8
Modern 3BR Condo at Royal Palm Bay | Sleeps 8
Condo
Kissimmee, FL, 34746, United States
4.3k from Pleasant Hill Lakes center

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

3 Bedrooms8 Guests
7.2

Good

9 reviews

$158
Average price / night
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Perfect Mansion on Veranda Palms Orlando Mansion 5379
Perfect Mansion on Veranda Palms Orlando Mansion 5379
Villa
Kissimmee, FL, USA
4.3k from Pleasant Hill Lakes center

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

1 Bedroom30 Guests
New to Booking
$1350
Average price / night
Check Availability
New Listing! Royal Palm Bay Resort, 5mi to Disney & 10mi to Universal - IT9921
New Listing! Royal Palm Bay Resort, 5mi to Disney & 10mi to Universal - IT9921
Apartment
Kissimmee, FL, 34746, United States
4.3k from Pleasant Hill Lakes center

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

4 Bedrooms8 Guests
New to Booking
$207
Average price / night
Check Availability
Villa Magic- Lucaya Villa Resort
Villa Magic- Lucaya Villa Resort
House
Kissimmee, FL, USA
4.3k from Pleasant Hill Lakes center

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

3 Bedrooms6 Guests
New to Booking
$211
Average price / night
Check Availability
Cheerful 12 BR  11.5 BA Game Villa   Sleep 25 near Disney
Cheerful 12 BR 11.5 BA Game Villa Sleep 25 near Disney
House
Kissimmee, FL, 34746, United States
4.3k from Pleasant Hill Lakes center

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

12 Bedrooms25 Guests
10.0

Exceptional

5 reviews

$1289
Average price / night
Check Availability
DR2668 Storey Lake Home 5 bed 5 bath Free Waterpark
DR2668 Storey Lake Home 5 bed 5 bath Free Waterpark
House
Kissimmee, FL, 34746, United States
4.3k from Pleasant Hill Lakes center

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

5 Bedrooms15 Guests
10.0

Exceptional

7 reviews

$369
Average price / night
Check Availability
Modern Resort House | Pool • Wi-Fi • Minutes to Disney
Modern Resort House | Pool • Wi-Fi • Minutes to Disney
Villa
Kissimmee, FL, 34746, United States
4.3k from Pleasant Hill Lakes center

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

5 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$368
Average price / night
Check Availability
Beautiful Villa 25 mins to Disney
Beautiful Villa 25 mins to Disney
House
Kissimmee, FL, 34758, United States
4.3k from Pleasant Hill Lakes center

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

3 Bedrooms6 Guests
8.8

Fabulous

3 reviews

$181
Average price / night
Check Availability
Relax in our hot tub at our 4 Bedroom, 3 Bathroom villa in Doral Woods
Relax in our hot tub at our 4 Bedroom, 3 Bathroom villa in Doral Woods
Villa
Kissimmee, FL, 34758, United States
4.4k from Pleasant Hill Lakes center

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

4 Bedrooms10 Guests
9.8

Exceptional

39 reviews

$262
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 Pleasant Hill Lakes.

Stay Near Pleasant Hill Lakes's Top Attractions

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

Pleasant Hill Lakes Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 1123 verified family-friendly vacation rentals in Pleasant Hill Lakes. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Pleasant Hill Lakes vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $158 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Pleasant Hill Lakes 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 Pleasant Hill Lakes 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 Pleasant Hill Lakes often include amenities such as Child Friendly, Wellness Facilities, and Fireplace/Heating. 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.