Vacation Rentals with Pool in Ocean Pines, MD: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Maryland

  5.  Ocean City
  6.  Ocean Pines

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2285 Best Vacation Rentals with Pool in Ocean Pines (Starting from $92)

Pet-Friendly Ocean Pines Cottage Family-Friendly Retreat with Amenities
Pet-Friendly Ocean Pines Cottage Family-Friendly Retreat with Amenities
House
Berlin, MD, USA
0.5k from Ocean Pines center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$440
Average price / night
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Canal-front dog-friendly home, shared pools, sports courts, views
Canal-front dog-friendly home, shared pools, sports courts, views
House
Ocean Pines, MD, 21811, United States
0.5k from Ocean Pines center

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

3 Bedrooms11 Guests
9.0

Fabulous

24 reviews

$280
Average price / night
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Turtle Shores
Turtle Shores
House
Ocean Pines, MD, USA
0.5k from Ocean Pines center

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

3 Bedrooms10 Guests
New to Booking
$222
Average price / night
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Serene Ocean Pines home w/private deck all-season room & fully stocked kitchen
Serene Ocean Pines home w/private deck all-season room & fully stocked kitchen
House
Ocean Pines, MD, 21811-1835, United States
0.7k from Ocean Pines center

AC, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
2.0

Review score

1 reviews

$216
Average price / night
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Admirals' Cottage
Admirals' Cottage
House
Ocean Pines, MD, USA
0.7k from Ocean Pines center

Sports/Activities, Wellness Facilities, Child Friendly, Entertainment, Oceanfront, Ocean View, Internet

1 Bedroom2 Guests
New to Booking
$100
Average price / night
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Lovely Ocean Pines home w/picnic area, firepit, fully stocked kitchen, AC & WiFi
Lovely Ocean Pines home w/picnic area, firepit, fully stocked kitchen, AC & WiFi
House
Ocean Pines, MD, 21811, United States
0.7k from Ocean Pines center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms10 Guests
6.8

Good

5 reviews

$328
Average price / night
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22 Harpoon rd
22 Harpoon rd
House
Ocean Pines, MD, USA
0.7k from Ocean Pines center

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

3 Bedrooms6 Guests
New to Booking
$365
Average price / night
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Newly Renovated Home With Impressive Views Of The 7Th Green!
Newly Renovated Home With Impressive Views Of The 7Th Green!
House
Ocean Pines, MD, 21811, United States
0.7k from Ocean Pines center

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

3 Bedrooms8 Guests
10.0

Exceptional

109 reviews

$425
Average price / night
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838 Ocean Parkway
838 Ocean Parkway
House
Ocean Pines, MD, USA
0.7k from Ocean Pines center

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

3 Bedrooms10 Guests
6.5

Good

2 reviews

$399
Average price / night
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Ocean Pines, 3 bedroom, sleeps 6, dog friendly
Ocean Pines, 3 bedroom, sleeps 6, dog friendly
House
Ocean Pines, MD, 21811, United States
0.8k from Ocean Pines center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Microwave, No Smoking

3 Bedrooms6 Guests
8.0

Good

1 reviews

$407
Average price / night
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Windjammer 156
Windjammer 156
House
Ocean Pines, MD, USA
0.7k from Ocean Pines center

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

3 Bedrooms9 Guests
9.5

Superb

4 reviews

$92
Average price / night
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Updated 3 Bedroom 2 Bathroom Home - Ocean Pines
Updated 3 Bedroom 2 Bathroom Home - Ocean Pines
House
Ocean Pines, MD, 21811, United States
0.8k from Ocean Pines center

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

3 Bedrooms6 Guests
10.0

Exceptional

40 reviews

$362
Average price / night
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The Boho Bungalow
The Boho Bungalow
House
Ocean Pines, Berlin, Maryland, USA
0.7k from Ocean Pines center

Pool, Balcony/Terrace, Laundry, Pet Friendly, Internet, Private Pool, Parking

3 Bedrooms6 Guests
New to Booking
$357
Average price / night
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Cozy home featuring a screened-in porch and access to a refreshing pool. Your oasis awaits!!
Cozy home featuring a screened-in porch and access to a refreshing pool. Your oasis awaits!!
House
Ocean Pines, MD, 21811, United States
0.9k from Ocean Pines center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

3 Bedrooms7 Guests
New to Booking
$345
Average price / night
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Seafarer 7
Seafarer 7
House
Ocean Pines, MD, USA
0.8k from Ocean Pines center

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

3 Bedrooms9 Guests
6.8

Good

8 reviews

$102
Average price / night
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Home on canal with views, pool/tennis access, spacious deck & lovely interior
Home on canal with views, pool/tennis access, spacious deck & lovely interior
House
Ocean Pines, MD, 21811, United States
0.9k from Ocean Pines center

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

5 Bedrooms10 Guests
8.0

Good

25 reviews

$487
Average price / night
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8 Mi to Beach Ocean Pines Home Near Marina and Golf
8 Mi to Beach Ocean Pines Home Near Marina and Golf
House
Ocean Pines, MD, USA
0.9k from Ocean Pines center

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

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$325
Average price / night
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This is it!! Rancher central to beaches, pools, golf, casino! Fenced yard, Deck.
This is it!! Rancher central to beaches, pools, golf, casino! Fenced yard, Deck.
House
Ocean Pines, MD, 21811, United States
1.0k from Ocean Pines center

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

5 Bedrooms10 Guests
10.0

Exceptional

14 reviews

$367
Average price / night
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Battersea on the Canal
Battersea on the Canal
House
Ocean Pines, Berlin, Maryland, USA
0.9k from Ocean Pines center

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

5 Bedrooms10 Guests
New to Booking
$327
Average price / night
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Fantastic gem near the beach with fast WiFi, shared pool, grill, central AC & WD
Fantastic gem near the beach with fast WiFi, shared pool, grill, central AC & WD
House
Ocean Pines, MD, 21811, United States
1.0k from Ocean Pines center

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

3 Bedrooms7 Guests
9.0

Fabulous

4 reviews

$341
Average price / night
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Cozy, dog-friendly home with pool & athletic court access, central AC, & W/D
Cozy, dog-friendly home with pool & athletic court access, central AC, & W/D
House
Ocean Pines, MD, 21811, United States
1.1k from Ocean Pines center

AC, Crib, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry, Living Area

3 Bedrooms7 Guests
7.4

Good

3 reviews

$448
Average price / night
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Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in
Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in
House
Ocean Pines, MD, 21811, United States
1.1k from Ocean Pines center

AC, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

23 reviews

$347
Average price / night
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Rabbit Run-Located in the heart of Ocean Pines! Minutes away from OC!
Rabbit Run-Located in the heart of Ocean Pines! Minutes away from OC!
House
Ocean Pines, MD, 21811, United States
1.2k from Ocean Pines center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$378
Average price / night
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Spacious - Ocean Pines home w/screened porch, full kitchen, washer/dryer & WiFi
Spacious - Ocean Pines home w/screened porch, full kitchen, washer/dryer & WiFi
House
Ocean Pines, MD, 21811, United States
1.3k from Ocean Pines center

AC, Arcade, Dryer, Free Parking, Heater, Kitchen, Living Area, Microwave, No Smoking

4 Bedrooms8 Guests
New to Booking
$312
Average price / night
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Recovery Room offers a Private Pool and Hot Tub !!   Now Available Monthly !!
Recovery Room offers a Private Pool and Hot Tub !! Now Available Monthly !!
House
Berlin, MD, 21811, United States
1.3k from Ocean Pines center

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

2 Bedrooms6 Guests
9.8

Exceptional

152 reviews

$416
Average price / night
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Ocean Pines-3 bdrm 2 bath home 8 minutes from Ocean City
Ocean Pines-3 bdrm 2 bath home 8 minutes from Ocean City
House
Berlin, MD, 21811, United States
1.4k from Ocean Pines center

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

3 Bedrooms6 Guests
8.8

Fabulous

41 reviews

$289
Average price / night
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FAIRWAY TO HEAVEN:  GOLF course views and BEACH parking pass
FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass
Condo
Ocean Pines, MD, 21811, United States
1.4k from Ocean Pines center

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

3 Bedrooms7 Guests
10.0

Exceptional

67 reviews

$287
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 Pool in Ocean Pines.

Stay Near Ocean Pines's Top Attractions

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Ocean Pines Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 2285 verified vacation rentals with a pool in Ocean Pines. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Ocean Pines vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $92 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Ocean Pines offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Ocean Pines welcome pets. Currently, 38 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Ocean Pines often include additional outdoor features such as Pool, Fireplace/Heating, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Ocean Pines offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.