Family-Friendly Vacation Rentals in Royal Oak, MD: Compare 10+ Sites & Save

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63 Best Family Vacation Rentals in Royal Oak (Starting from $292)

Loon Cottage
Loon Cottage
House
Oxford, MD, USA
0.8k from Royal Oak center

Security/Safety, Parking, Pet Friendly, Internet, Child Friendly

1 Bedroom6 Guests
New to Booking
$407
Average price / night
Check Availability
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
House
Royal Oak, MD, 21662, United States
1.7k from Royal Oak center

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

6 Bedrooms12 Guests
10.0

Exceptional

31 reviews

$1337
Average price / night
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Ferry View
Ferry View
House
Oxford, MD, USA
2.6k from Royal Oak center

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

1 Bedroom8 Guests
New to Booking
$824
Average price / night
Check Availability
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien
House
Royal Oak, MD, 21662, United States
2.6k from Royal Oak center

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

5 Bedrooms8 Guests
9.6

Exceptional

5 reviews

$676
Average price / night
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Chesapeake Pines
Chesapeake Pines
House
Royal Oak, MD, USA
2.9k from Royal Oak center

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

1 Bedroom8 Guests
New to Booking
$663
Average price / night
Check Availability
Minutes from Downtown Easton and St. Michaels | Pool
Minutes from Downtown Easton and St. Michaels | Pool
House
Easton, MD, 21601, United States
3.1k from Royal Oak center

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

5 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$1267
Average price / night
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Blue Herons Villa
Blue Herons Villa
House
Royal Oak, MD, USA
3.1k from Royal Oak center

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

1 Bedroom10 Guests
New to Booking
$1336
Average price / night
Check Availability
Waterfront Farmhouse Retreat on 18 Acres, Pool
Waterfront Farmhouse Retreat on 18 Acres, Pool
House
Royal Oak, MD, 21662, United States
3.4k from Royal Oak center

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

8 Bedrooms16 Guests
10.0

Exceptional

1 reviews

$2682
Average price / night
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25 Bedrooms - Retreat Center Waterfront Renovated
25 Bedrooms - Retreat Center Waterfront Renovated
House
MD, USA
3.4k from Royal Oak center

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

25 Bedrooms40 Guests
New to Booking
$14533
Average price / night
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Moofy's Farmhouse: Main Lodge ; Private Waterfront Retreat Center, New Reno on 18 Acres
Moofy's Farmhouse: Main Lodge ; Private Waterfront Retreat Center, New Reno on 18 Acres
House
Royal Oak, MD, 21662, United States
3.4k from Royal Oak center

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

1 Bedroom50 Guests
New to Booking
$10158
Average price / night
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Bayside The Point
Bayside The Point
House
Royal Oak, MD, USA
3.9k from Royal Oak center

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

1 Bedroom12 Guests
New to Booking
$1407
Average price / night
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Waterfront Cottage, Private Hot Tub, Fire Pit, Pool - perfect Romantic Getaway
Waterfront Cottage, Private Hot Tub, Fire Pit, Pool - perfect Romantic Getaway
House
Easton, MD, 21601, United States
3.5k from Royal Oak center

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

2 Bedrooms4 Guests
10.0

Exceptional

107 reviews

$473
Average price / night
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Pride and Joy of Oxford
Pride and Joy of Oxford
House
Oxford, MD, USA
4.3k from Royal Oak center

Security/Safety, Parking, Pet Friendly, Internet, Child Friendly

1 Bedroom6 Guests
New to Booking
$604
Average price / night
Check Availability
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Luxury
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Luxury
House
Royal Oak, MD, 21662, United States
3.8k from Royal Oak center

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

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$2401
Average price / night
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Beach House
Beach House
House
Oxford, MD, USA
4.5k from Royal Oak center

Security/Safety, Parking, Pool, Internet, Child Friendly

1 Bedroom8 Guests
New to Booking
$1221
Average price / night
Check Availability
Stunning Chesapeake Waterfront Home
Stunning Chesapeake Waterfront Home
House
Oxford, MD, 21654, United States
4.4k from Royal Oak center

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

5 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$971
Average price / night
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Ships Ahoy
Ships Ahoy
House
Oxford, MD, USA
4.5k from Royal Oak center

Security/Safety, Parking, Pet Friendly, Internet, Child Friendly

1 Bedroom6 Guests
New to Booking
$292
Average price / night
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Downtown Oxford | Outdoor Dining | Character Filled
Downtown Oxford | Outdoor Dining | Character Filled
House
Oxford, MD, 21654, United States
4.7k from Royal Oak center

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

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$488
Average price / night
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Down By The Docks
Down By The Docks
House
Oxford, MD, USA
4.6k from Royal Oak center

Security/Safety, Parking, Pet Friendly, Internet, Child Friendly

1 Bedroom6 Guests
New to Booking
$462
Average price / night
Check Availability
Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Private Dock |
Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Private Dock |
House
Saint Michaels, MD, 21663, United States
4.7k from Royal Oak center

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

3 Bedrooms6 Guests
8.8

Fabulous

16 reviews

$803
Average price / night
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Tranquil  Beautiful Waterfront  Near Historic St. Michaels & Royal Oak
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
House
easton, MD, 21601, United States
4.7k from Royal Oak center

AC, Arcade, Barbecue, Breakfast Available, Dryer, Fireplace, Free Parking, Heater, Hot Tub

5 Bedrooms10 Guests
10.0

Exceptional

51 reviews

$1027
Average price / night
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Historic Oxford Waterfront Estate
Historic Oxford Waterfront Estate
House
Oxford, MD, 21654, United States
5.3k from Royal Oak center

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

6 Bedrooms12 Guests
10.0

Exceptional

90 reviews

$1007
Average price / night
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Waterfront Property, kayaks, private dock, near town
Waterfront Property, kayaks, private dock, near town
House
St. Michaels, MD, 21653, United States
5.4k from Royal Oak center

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

3 Bedrooms6 Guests
9.8

Exceptional

154 reviews

$711
Average price / night
Check Availability
Cozy, Family Friendly, Log Cabin-St. Michaels, MD
Cozy, Family Friendly, Log Cabin-St. Michaels, MD
House
Saint Michaels, MD, 21663, United States
5.5k from Royal Oak center

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

4 Bedrooms8 Guests
9.8

Exceptional

7 reviews

$603
Average price / night
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St. Michaels Waterfront Home
St. Michaels Waterfront Home
House
New comb, MD, 21663, United States
5.5k from Royal Oak center

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

2 Bedrooms4 Guests
9.8

Exceptional

32 reviews

$823
Average price / night
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Breathtaking Waterfront Estate
Breathtaking Waterfront Estate
Villa
Neavitt, MD, 21652, United States
5.7k from Royal Oak center

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

6 Bedrooms12 Guests
10.0

Exceptional

73 reviews

$1941
Average price / night
Check Availability
TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool
TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool
House
St Michaels, MD, 21663, United States
6.4k from Royal Oak center

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

5 Bedrooms8 Guests
10.0

Exceptional

68 reviews

$1593
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 Royal Oak.

Stay Near Royal Oak's Top Attractions

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

Royal Oak Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 63 verified family-friendly vacation rentals in Royal Oak. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Royal Oak vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $292 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Royal Oak 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 Royal Oak 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 Royal Oak 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.