Vacation Rentals with Private Pool in Royal Oak, MD: Compare 10+ Sites & Save

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  5.  Royal Oak

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36 Best Vacation Rentals with Private Pool in Royal Oak (Starting from $426)

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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Waterfront Paradise | Pool, Views & Serenity
Waterfront Paradise | Pool, Views & Serenity
House
Royal Oak, MD, 21662, United States
2.2k from Royal Oak center

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

4 Bedrooms8 Guests
New to Booking
$930
Average price / night
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15% to 25% off on Early Bookings, Private Waterfront Estate  Pool, Hot Tub, Dock
15% to 25% off on Early Bookings, Private Waterfront Estate Pool, Hot Tub, Dock
House
Royal Oak, MD, 21662, United States
2.4k from Royal Oak center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub

5 Bedrooms10 Guests
9.6

Exceptional

23 reviews

$794
Average price / night
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Sunset Shores | an ESVR property
Sunset Shores | an ESVR property
House
Royal Oak, MD, 21662, United States
2.6k from Royal Oak center

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

4 Bedrooms8 Guests
New to Booking
$833
Average price / night
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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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Thorneton Point Estate
Thorneton Point Estate
House
Easton, MD, 21601, United States
3.1k from Royal Oak center

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

6 Bedrooms12 Guests
9.6

Exceptional

22 reviews

$1931
Average price / night
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Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.
House
Easton, MD, 21601, United States
3.4k from Royal Oak center

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

5 Bedrooms10 Guests
10.0

Exceptional

11 reviews

$1414
Average price / night
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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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Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock
House
St. Michaels, MD, 21663, United States
3.9k from Royal Oak center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

6 Bedrooms12 Guests
8.6

Fabulous

4 reviews

$1281
Average price / night
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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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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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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
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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
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Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels
Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels
House
St Michaels, MD, 21663, United States
6.8k from Royal Oak center

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

4 Bedrooms8 Guests
9.4

Superb

59 reviews

$1014
Average price / night
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Eastern Shore Waterside Cottage Near St. Michaels
Eastern Shore Waterside Cottage Near St. Michaels
Cottage
Neavitt, MD, 21652, United States
6.9k from Royal Oak center

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

3 Bedrooms6 Guests
10.0

Exceptional

24 reviews

$426
Average price / night
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Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
House
St. Michaels, MD, 21663, United States
7.1k from Royal Oak center

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

4 Bedrooms8 Guests
8.0

Good

2 reviews

$913
Average price / night
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Waterfront | Pet Friendly & Close to St. Michaels
Waterfront | Pet Friendly & Close to St. Michaels
House
Bozman, MD, 21612, United States
7.2k from Royal Oak center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$797
Average price / night
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Beautiful Tidewater home between Easton & ST Michaels!
Beautiful Tidewater home between Easton & ST Michaels!
House
Easton, MD, 21601, United States
7.4k from Royal Oak center

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

4 Bedrooms8 Guests
10.0

Exceptional

49 reviews

$1485
Average price / night
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Grandview- Main House
Grandview- Main House
House
Bozman, MD, 21612, United States
7.4k from Royal Oak center

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

4 Bedrooms9 Guests
9.8

Exceptional

45 reviews

$885
Average price / night
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Historic Waterfront Estate with Pool & Pet-Friendly  – Perfect for Fall Getaways
Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways
House
Oxford, MD, 21654, United States
7.4k from Royal Oak center

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

5 Bedrooms10 Guests
9.8

Exceptional

20 reviews

$951
Average price / night
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Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
House
Easton, MD, 21601, United States
7.4k from Royal Oak center

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

3 Bedrooms6 Guests
New to Booking
$673
Average price / night
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St. Michaels Waterfront | Pool and Sunset Views
St. Michaels Waterfront | Pool and Sunset Views
House
Saint Michaels, MD, 21663, United States
7.5k from Royal Oak center

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

5 Bedrooms10 Guests
New to Booking
$1891
Average price / night
Check Availability
St. Michael's Premier In-Town Rental with heated pool. Pool opens 4/3
St. Michael's Premier In-Town Rental with heated pool. Pool opens 4/3
Cottage
St. Michaels, MD, 21663, United States
7.9k from Royal Oak center

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

2 Bedrooms4 Guests
10.0

Exceptional

147 reviews

$824
Average price / night
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Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Kayaks | Privat
Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Kayaks | Privat
House
Easton, MD, 21601, United States
7.9k from Royal Oak center

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

5 Bedrooms10 Guests
10.0

Exceptional

14 reviews

$1038
Average price / night
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Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
House
Easton, MD, 21601, United States
8.0k from Royal Oak center

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

5 Bedrooms10 Guests
10.0

Exceptional

141 reviews

$961
Average price / night
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Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova
Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova
House
Bozman, MD, 20815, United States
8.3k from Royal Oak center

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

5 Bedrooms10 Guests
9.8

Exceptional

8 reviews

$1138
Average price / night
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GRATITUDE FARM - A Tranquil Waterfront Renovated Farmhouse - Bozman, MD
GRATITUDE FARM - A Tranquil Waterfront Renovated Farmhouse - Bozman, MD
House
Bozman, MD, 21612, United States
8.4k from Royal Oak center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$682
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 Private Pool in Royal Oak.

Stay Near Royal Oak's Top Attractions

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Royal Oak Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 36 verified vacation rentals with a private pool in Royal Oak. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Royal Oak vary depending on the property size, location, and travel season. Rates typically start from around $426 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Royal Oak also welcome pets. Currently, 19 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Royal Oak often include additional features such as Bedding/Linens, Kitchen, and Laundry. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Royal Oak include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.