Family-Friendly Vacation Rentals in South Blooming Grove, NY: Compare 10+ Sites & Save

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39 Best Family Vacation Rentals in South Blooming Grove (Starting from $236)

Secluded Sanctuary in Nature
Secluded Sanctuary in Nature
House
Monroe, NY, USA
2.1k from South Blooming Grove center

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

6 Bedrooms16 Guests
New to Booking
$839
Average price / night
Check Availability
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
Villa
Monroe, NY, 10950, United States
1.5k from South Blooming Grove center

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

7 Bedrooms19 Guests
6.8

Good

5 reviews

$1294
Average price / night
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Stunning, Private House in the Hills - Extra calm!
Stunning, Private House in the Hills - Extra calm!
Villa
Monroe, NY, USA
3.1k from South Blooming Grove center

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

5 Bedrooms14 Guests
New to Booking
$754
Average price / night
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Private 5-Bed Country Estate on 22 Acres
Private 5-Bed Country Estate on 22 Acres
House
Chester, NY, 10918, United States
3.7k from South Blooming Grove center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Laundry, Living Area, Microwave

5 Bedrooms12 Guests
New to Booking
$961
Average price / night
Check Availability
Very Private Large Home on 22 Acres
Very Private Large Home on 22 Acres
House
Chester, NY, USA
3.8k from South Blooming Grove center

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

5 Bedrooms14 Guests
New to Booking
$913
Average price / night
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Spacious 7BR Villa on 14 Acres w/ Indoor Pool
Spacious 7BR Villa on 14 Acres w/ Indoor Pool
House
Washingtonville, NY, 10992, United States
3.9k from South Blooming Grove center

AC, Crib, Fireplace, Free Parking, Heater, Internet, Laundry, Living Area, Microwave

6 Bedrooms16 Guests
New to Booking
$1188
Average price / night
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Spacious Smart Home Retreat on 14 Acres of Nature
Spacious Smart Home Retreat on 14 Acres of Nature
House
Monroe, NY, 10950, United States
4.1k from South Blooming Grove center

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

5 Bedrooms15 Guests
7.4

Good

3 reviews

$906
Average price / night
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Estate with pool on 11 beautiful acres
Estate with pool on 11 beautiful acres
House
Monroe, NY, USA
4.4k from South Blooming Grove center

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

9 Bedrooms24 Guests
New to Booking
$1758
Average price / night
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Charming 3-bedroom villa with WiFi, AC in fabulous Monroe
Charming 3-bedroom villa with WiFi, AC in fabulous Monroe
Villa
Monroe, NY, 10950, United States
4.6k from South Blooming Grove center

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

3 Bedrooms10 Guests
7.4

Good

3 reviews

$485
Average price / night
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Incredible Ranch in the Woods - Peace and Luxury!
Incredible Ranch in the Woods - Peace and Luxury!
House
South Blooming Grove, Monroe, New York, USA
4.4k from South Blooming Grove center

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

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$309
Average price / night
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Spacious 9-bedroom house in tranquil Monroe with AC
Spacious 9-bedroom house in tranquil Monroe with AC
House
Monroe, NY, 10950, United States
4.6k from South Blooming Grove center

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

9 Bedrooms32 Guests
New to Booking
$1915
Average price / night
Check Availability
Cozy Beautiful Pondside Luxurious Retreat
Cozy Beautiful Pondside Luxurious Retreat
House
Monroe, NY, USA
5.1k from South Blooming Grove center

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

4 Bedrooms11 Guests
9.5

Superb

2 reviews

$489
Average price / night
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Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
House
Monroe, NY, 10950, United States
4.7k from South Blooming Grove center

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

4 Bedrooms14 Guests
9.4

Superb

16 reviews

$546
Average price / night
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Cedar Mill Hideaway
Cedar Mill Hideaway
House
Woodbury, NY, USA
6.5k from South Blooming Grove center

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

3 Bedrooms10 Guests
New to Booking
$585
Average price / night
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A Premium Hudson Valley Retreat 60-75min from NYC
A Premium Hudson Valley Retreat 60-75min from NYC
House
Highland Mills, NY, 10930, United States
6.5k from South Blooming Grove center

AC, Arcade, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking

3 Bedrooms10 Guests
9.6

Exceptional

17 reviews

$377
Average price / night
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Malkita Terra -Earthly Elegance
Malkita Terra -Earthly Elegance
Villa
Woodbury, NY, USA
6.8k from South Blooming Grove center

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

6 Bedrooms15 Guests
New to Booking
$995
Average price / night
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Lake Views • Spacious 7BR Retreat • Sleeps 12 • Fireplace • King Beds
Lake Views • Spacious 7BR Retreat • Sleeps 12 • Fireplace • King Beds
House
Monroe, NY, 10950, United States
7.1k from South Blooming Grove center

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

7 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$1068
Average price / night
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Malkita Aria Mountainview Retreat
Malkita Aria Mountainview Retreat
Villa
South Blooming Grove, Monroe, New York, USA
6.8k from South Blooming Grove center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

4 Bedrooms8 Guests
8.2

Very Good

5 reviews

$1045
Average price / night
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11BR Retreat w Pool & Game Room
11BR Retreat w Pool & Game Room
Villa
Chester, NY, 10918, United States
7.2k from South Blooming Grove center

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

11 Bedrooms28 Guests
New to Booking
$2617
Average price / night
Check Availability
Secluded 9BR Getaway, Pool, Hot Tub & Huge Deck
Secluded 9BR Getaway, Pool, Hot Tub & Huge Deck
Villa
Chester, NY, USA
7.9k from South Blooming Grove center

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

9 Bedrooms28 Guests
New to Booking
$1991
Average price / night
Check Availability
The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC
The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC
House
Harriman, NY, 10926, United States
7.3k from South Blooming Grove center

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

3 Bedrooms10 Guests
10.0

Exceptional

13 reviews

$784
Average price / night
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Grand 10BR Retreat w/Pool & Hot Tub
Grand 10BR Retreat w/Pool & Hot Tub
Villa
Chester, NY, 10918, United States
7.7k from South Blooming Grove center

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

10 Bedrooms23 Guests
2.0

Review score

1 reviews

$2210
Average price / night
Check Availability
6 bedroom colonial house
6 bedroom colonial house
House
Chester, NY, 10918, United States
7.7k from South Blooming Grove center

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

5 Bedrooms16 Guests
8.6

Fabulous

4 reviews

$236
Average price / night
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Tranquil apartment with AC in charming Monroe
Tranquil apartment with AC in charming Monroe
Apartment
Monroe, NY, 10950, United States
7.8k from South Blooming Grove center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Laundry, Living Area, Microwave

7 Bedrooms14 Guests
New to Booking
$1013
Average price / night
Check Availability
Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
Villa
Chester, NY, 10918, United States
8.2k from South Blooming Grove center

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

7 Bedrooms16 Guests
9.6

Exceptional

13 reviews

$1676
Average price / night
Check Availability
Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC
Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC
Villa
Harriman, NY, 10926, United States
8.3k from South Blooming Grove center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

8 Bedrooms25 Guests
10.0

Exceptional

81 reviews

$2199
Average price / night
Check Availability
NEW – TWO Side-by-Side Lake Homes Sleep 17 - 2 Private Docks -1 hr NYC pets ok
NEW – TWO Side-by-Side Lake Homes Sleep 17 - 2 Private Docks -1 hr NYC pets ok
House
Monroe, NY, 10950, United States
8.3k from South Blooming Grove center

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

7 Bedrooms17 Guests
10.0

Exceptional

12 reviews

$2686
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 South Blooming Grove.

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South Blooming Grove Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 39 verified family-friendly vacation rentals in South Blooming Grove. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in South Blooming Grove vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $236 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in South Blooming Grove 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 South Blooming Grove 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 South Blooming Grove often include amenities such as Child Friendly, Internet, 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.