Family-Friendly Vacation Rentals in Charles Deering Estate, FL: Compare 10+ Sites & Save

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  2. Family Vacation Rentals
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  4.  Florida
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  6.  Charles Deering Estate

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149 Best Family Vacation Rentals in Charles Deering Estate (Starting from $75)

Miami Dream Home/Pool/Jacuzzi/Fire Pit
Miami Dream Home/Pool/Jacuzzi/Fire Pit
House
Miami, FL, USA
2.7k from Charles Deering Estate center

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

4 Bedrooms12 Guests
7.0

Good

2 reviews

$791
Average price / night
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FirePit / Beach / Basketball / LuxuryVilla
FirePit / Beach / Basketball / LuxuryVilla
Villa
Palmetto Bay, FL, 33157, United States
0.7k from Charles Deering Estate center

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

5 Bedrooms15 Guests
10.0

Exceptional

1 reviews

$2809
Average price / night
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Family 4BR Escape Pool Arcade Sleeps 12 L57
Family 4BR Escape Pool Arcade Sleeps 12 L57
House
Palmetto Bay, FL, USA
2.7k from Charles Deering Estate center

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

1 Bedroom9 Guests
New to Booking
$620
Average price / night
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Terraza Del sol
Terraza Del sol
House
Palmetto Bay, FL, 33157, United States
1.9k from Charles Deering Estate center

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

5 Bedrooms10 Guests
New to Booking
$1591
Average price / night
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Villa Oasis with Heated Pool,Sauna, BBQ and Pool Table
Villa Oasis with Heated Pool,Sauna, BBQ and Pool Table
Villa
Pinecrest, FL, USA
2.8k from Charles Deering Estate center

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

5 Bedrooms10 Guests
New to Booking
$2751
Average price / night
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Las Terrazas
Las Terrazas
House
Palmetto Bay, FL, 33157, United States
1.9k from Charles Deering Estate center

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

5 Bedrooms14 Guests
New to Booking
$1243
Average price / night
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Queen's Tropical Garden View Room
Queen's Tropical Garden View Room
House
Palmetto Bay, FL, USA
3.1k from Charles Deering Estate center

Internet, Kitchen, Pool, Air Conditioner, Parking, Balcony/Terrace, Breakfast

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$75
Average price / night
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Palmetto Bay Tropical Home w/Game Room, Pool & Fun
Palmetto Bay Tropical Home w/Game Room, Pool & Fun
House
Palmetto Bay, FL, 33157, United States
2.6k from Charles Deering Estate center

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

4 Bedrooms12 Guests
9.0

Fabulous

8 reviews

$523
Average price / night
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Peacock Villa Palmetto Bay
Peacock Villa Palmetto Bay
Villa
Palmetto Bay, FL, USA
3.2k from Charles Deering Estate center

Internet, Balcony/Terrace, Pool, Air Conditioner, Parking, Kitchen, Pet Friendly

4 Bedrooms10 Guests
New to Booking
$360
Average price / night
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Palmetto Bay #2 | 2BR • 4 Beds • by Miami SoFi Vacation Rentals
Palmetto Bay #2 | 2BR • 4 Beds • by Miami SoFi Vacation Rentals
Apartment
Palmetto Bay, FL, 33176, United States
3.0k from Charles Deering Estate center

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

2 Bedrooms5 Guests
New to Booking
$367
Average price / night
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Chic-ness Oasis
Chic-ness Oasis
House
Cutler Bay, FL, USA
3.4k from Charles Deering Estate center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$380
Average price / night
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Hamilton House Miami - Tropical Oasis / Heated Pool / Tiki / Brazilian BBQ
Hamilton House Miami - Tropical Oasis / Heated Pool / Tiki / Brazilian BBQ
House
Palmetto Bay, FL, 33157, United States
3.0k from Charles Deering Estate center

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

6 Bedrooms16 Guests
9.8

Exceptional

34 reviews

$1179
Average price / night
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Stylish Haven Heated Pool Pool Table L28
Stylish Haven Heated Pool Pool Table L28
House
Cutler Bay, FL, USA
3.6k from Charles Deering Estate center

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

7 Bedrooms12 Guests
New to Booking
$1296
Average price / night
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Pinecrest #4 | 2BR • 4 Beds • by Miami SoFi Vacation Rentals
Pinecrest #4 | 2BR • 4 Beds • by Miami SoFi Vacation Rentals
Apartment
Palmetto Bay, FL, 33176, United States
3.1k from Charles Deering Estate center

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

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$361
Average price / night
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7545 Southwest 124th Street
7545 Southwest 124th Street
House
Miami, FL, USA
3.7k from Charles Deering Estate center

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

3 Bedrooms8 Guests
8.2

Very Good

5 reviews

$228
Average price / night
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5BR Italian Villa Vizalli • Heated Pool&Jacuzzi • Office+Baby Rm-Tropical Escape
5BR Italian Villa Vizalli • Heated Pool&Jacuzzi • Office+Baby Rm-Tropical Escape
Villa
Palmetto Bay, FL, 33157, United States
3.1k from Charles Deering Estate center

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

5 Bedrooms8 Guests
9.2

Superb

7 reviews

$1735
Average price / night
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Stylish Retreat Heated Pool Basketball Game Room L41
Stylish Retreat Heated Pool Basketball Game Room L41
House
Cutler Bay, FL, USA
3.7k from Charles Deering Estate center

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

5 Bedrooms10 Guests
New to Booking
$576
Average price / night
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Private Villa • Pool & Waterfall
Private Villa • Pool & Waterfall
Villa
Cutler Bay, FL, 33157, United States
3.2k from Charles Deering Estate center

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

4 Bedrooms10 Guests
10.0

Exceptional

7 reviews

$1150
Average price / night
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My Garden in Miami Florida
My Garden in Miami Florida
Apartment
Palmetto Bay, FL, USA
3.8k from Charles Deering Estate center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Self-catering

1 Bedroom2 Guests
9.7

Exceptional

3 reviews

$127
Average price / night
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Palmetto Bay #3 | 2BR • 4 Beds • by Miami SoFi Vacation Rentals
Palmetto Bay #3 | 2BR • 4 Beds • by Miami SoFi Vacation Rentals
Apartment
Palmetto Bay, FL, 33176, United States
3.2k from Charles Deering Estate center

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

2 Bedrooms5 Guests
New to Booking
$387
Average price / night
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Elegant Retreat Near Thallata Estate - spacious and modern amenities
Elegant Retreat Near Thallata Estate - spacious and modern amenities
House
Palmetto Bay, FL, 33157, United States
3.3k from Charles Deering Estate center

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

4 Bedrooms9 Guests
7.0

Good

4 reviews

$541
Average price / night
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Pinecrest #1 | 2BR • 4 Beds • by Miami SoFi Vacation Rentals
Pinecrest #1 | 2BR • 4 Beds • by Miami SoFi Vacation Rentals
Apartment
Palmetto Bay, FL, 33176, United States
3.3k from Charles Deering Estate center

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

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$398
Average price / night
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Charming 3-bedroom house with HEATED pool, Near Stadium ⚽ FIFA World Cup 2026  •
Charming 3-bedroom house with HEATED pool, Near Stadium ⚽ FIFA World Cup 2026 •
House
Miami, FL, 33157, United States
3.4k from Charles Deering Estate center

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

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$930
Average price / night
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Palms, Pool and Waterfall-your perfect Miami vacation home
Palms, Pool and Waterfall-your perfect Miami vacation home
House
Palmetto Bay, FL, 33157, United States
3.4k from Charles Deering Estate center

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

4 Bedrooms8 Guests
8.0

Good

2 reviews

$430
Average price / night
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Quiet 4BR Villa w/ Hot Tub, Games & Fenced Yard
Quiet 4BR Villa w/ Hot Tub, Games & Fenced Yard
Villa
Cutler Bay, FL, 33157, United States
3.5k from Charles Deering Estate center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1637
Average price / night
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6BR | Heated Pool | Jacuzzi | Sauna | Beach area
6BR | Heated Pool | Jacuzzi | Sauna | Beach area
Villa
Cutler Bay, FL, 33157, United States
3.6k from Charles Deering Estate center

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

6 Bedrooms16 Guests
10.0

Exceptional

6 reviews

$1134
Average price / night
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Home w/ Pool in Upscale Pinecrest Village
Home w/ Pool in Upscale Pinecrest Village
House
Miami, FL, 33156, United States
3.8k from Charles Deering Estate center

AC, Dryer, Extra Bed, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms8 Guests
9.4

Superb

42 reviews

$674
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 Family Vacation Rentals in Charles Deering Estate.

Where to stay in Charles Deering Estate? Best neighborhoods & areas

Charles Deering Estate Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 149 verified family-friendly vacation rentals in Charles Deering Estate. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Charles Deering Estate vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $75 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Charles Deering Estate 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 Charles Deering Estate 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 Charles Deering Estate often include amenities such as Child Friendly, Balcony/Terrace, and Pool. 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.