Vacation Rentals with Private Pool in St. Michaels, MD: Compare 10+ Sites & Save

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45 Best Vacation Rentals with Private Pool in St. Michaels (Starting from $273)

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
0.6k from St. Michaels 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 St. Michaels | Pool | Hot Tub | Pickle Ball Court
Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court
House
Saint Michaels, MD, 21663, United States
1.2k from St. Michaels center

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

3 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$677
Average price / night
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Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C
Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C
House
Saint Michaels, MD, 21663, United States
1.3k from St. Michaels center

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

5 Bedrooms10 Guests
10.0

Exceptional

8 reviews

$1402
Average price / night
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Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur
Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur
House
Saint Michaels, MD, 21663, United States
1.9k from St. Michaels center

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

6 Bedrooms12 Guests
New to Booking
$1506
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
2.1k from St. Michaels 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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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
2.5k from St. Michaels 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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Minutes from Downtown St. Michaels | Pool | Dock
Minutes from Downtown St. Michaels | Pool | Dock
House
St Michaels, MD, 21663, United States
2.7k from St. Michaels center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$1004
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
2.7k from St. Michaels center

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

5 Bedrooms10 Guests
New to Booking
$1891
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
2.7k from St. Michaels 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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Minutes from Downtown St. Michaels | Pool | Cabana | Kayaks | Private Dock
Minutes from Downtown St. Michaels | Pool | Cabana | Kayaks | Private Dock
House
St. Michaels, MD, 21663, United States
3.2k from St. Michaels center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$1085
Average price / night
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Baydream Believer
Baydream Believer
House
Talbot County, MD, 21663, United States
3.4k from St. Michaels center

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

5 Bedrooms8 Guests
10.0

Exceptional

87 reviews

$1392
Average price / night
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St. Michaels Escape | Pool, Hot Tub & Fire Pit
St. Michaels Escape | Pool, Hot Tub & Fire Pit
House
Saint Michaels, MD, 21663, United States
3.5k from St. Michaels center

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

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$709
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
3.6k from St. Michaels 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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Minutes from Downtown St. Michaels | Pool | Hot Tub
Minutes from Downtown St. Michaels | Pool | Hot Tub
House
Bozman, MD, 21612, United States
4.1k from St. Michaels center

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

2 Bedrooms4 Guests
9.8

Exceptional

10 reviews

$680
Average price / night
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Brand-New Pool! Waterfront Bozman Village Home
Brand-New Pool! Waterfront Bozman Village Home
House
Bozman, MD, 21612, United States
4.1k from St. Michaels center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$549
Average price / night
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Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours
House
Easton, MD, 21601, United States
4.1k from St. Michaels center

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

6 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$2110
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
4.6k from St. Michaels 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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Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres
Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres
House
Wittman, MD, 21676, United States
4.7k from St. Michaels center

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

4 Bedrooms8 Guests
10.0

Exceptional

67 reviews

$1091
Average price / night
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Saint Michaels Summer Retreat with Pool & Hot Tub
Saint Michaels Summer Retreat with Pool & Hot Tub
House
Saint Michaels, MD, 21663-2402, United States
4.9k from St. Michaels center

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

3 Bedrooms6 Guests
9.8

Exceptional

9 reviews

$788
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
5.0k from St. Michaels 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 | Guest House | Pool | Private Dock
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock
House
St. Michaels, MD, 21663, United States
5.2k from St. Michaels 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 | Kayaks | Privat
Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Kayaks | Privat
House
Easton, MD, 21601, United States
5.2k from St. Michaels 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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Relaxing Waterfront Cottage Near St Michaels, Maryland
Relaxing Waterfront Cottage Near St Michaels, Maryland
Cottage
Wittman, MD, 21676, United States
5.4k from St. Michaels center

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

2 Bedrooms4 Guests
9.8

Exceptional

241 reviews

$273
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
6.0k from St. Michaels center

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

5 Bedrooms10 Guests
8.6

Fabulous

4 reviews

$948
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
6.1k from St. Michaels 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
6.2k from St. Michaels 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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Sunset Shores | an ESVR property
Sunset Shores | an ESVR property
House
Royal Oak, MD, 21662, United States
6.5k from St. Michaels center

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

4 Bedrooms8 Guests
New to Booking
$833
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 St. Michaels.

Stay Near St. Michaels's Top Attractions

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St. Michaels Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 45 verified vacation rentals with a private pool in St. Michaels. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in St. Michaels vary depending on the property size, location, and travel season. Rates typically start from around $273 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 St. Michaels also welcome pets. Currently, 23 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 St. Michaels 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 St. Michaels 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.