11 Best Vacation Rentals With Private Pool In Ocean City, Maryland - Updated 2023


Ocean City, Maryland, is a year-round vacation spot less than three hours away from Baltimore. It is a beautiful place to enjoy the sun and sand. The vibrant resort community feels intimate with its coastal setting yet is filled with endless possibilities. Aside from boasting 10 miles (16 kilometers) of sparkling sand, it offers great destinations like Jolly Roger Amusement Park and museums like Ocean City Life-Saving Museum that are worth visiting. While you are here, you can also enjoy water sports, recreational parks, and fishing. If you want to enjoy your Ocean City vacation to the fullest, consider booking an oceanfront Vrbo or a pet-friendly vacation rental so your furry friends don’t miss out on all the fun. Another great option are vacation rentals with private pool in Ocean City, Maryland. Keep reading below.

1. Spacious abode with private boat slip (from USD 463)

With a heated pool and a private boat slip, this property is indeed one of the rare finds in Ocean City. It offers 4 bedrooms and 3 full bathrooms, making it an ideal place to stay for a total of 12 guests. This rental also has a remodeled kitchen complete with cooking basics and appliances. Other amenities include air conditioning, Wi-Fi, a TV, and a parking spot for 2 vehicles in the driveway.

This vacation rental is also strategically located close to the beach and the iconic Ocean City Boardwalk. Guests can also enjoy easy access to several restaurants, bars, water sports rentals, and amusement parks.

Marlin Drive House with private pool and a boat dock
7 reviews  Wifi Available
House 12 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 12
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
it was so nice to come home and dip in the pool every night
good thing we measured the beds before ordering the linens
it has a slip for your boat a private pool to enjoy and space to sleep 12 people
it was clean and tidy
property manager was very friendly and quick to respond as well
on the plus side it's a great location
the location and having a pool is awesome
this rental property is a great location on a canal leading to the bay
it is a quiet neighborhood but close enough to walk to fishtales and other great locations
very happy with the location and the kids loved the pool
Read more reviews

2. Family-friendly haven with game room (from USD 799)

Located in an elite neighborhood in downtown Ocean City, Teal Time is a wonderful retreat ideal for up to 13 guests. It features a private pool beside the outdoor lounge. Due to special regulations, only families can be accommodated in this rental.

The rental offers 5 bedrooms, 5 bathrooms, and a fully equipped kitchen. Other amenities include air conditioning, Wi-Fi, gas fireplaces, smart TVs, and video gaming areas for the children. The property also has a garage with ample parking space for 2 vehicles. When they’re not swimming in the pool, families can also head to the sandy public beach located just a 7-minute walk away.

Teal Time - Private pool / 5 BR / Sleeps 13
3 reviews  Wifi Available
House 13 Guests 5 Bedrooms 5 Bathrooms

Accommodates: 13
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
todd's place was great incredible neighborhood for downtown ocean city i highly recommend renting this place
Read more reviews

3. Spacious ocean-inspired home with street views

If you’re looking for a vacation home with plenty of space for rest and relaxation, this ocean-inspired accommodation is for you. Spend the weekend in a charming two-story vacation property with street-view balconies. The living room is laid-back yet tastefully decorated in shades of khaki and white. The space opens up all the way to the dining area and the fully equipped kitchen. There is a second living room upstairs for guests who want more privacy. The community swimming pool is just a few steps away if you wish to enjoy some refreshing laps.

3 Bed/2 Bath Downtown Ocean City Home w/ a Pool
Ocean City, Maryland, United States
56 reviews Superhost  Wifi Available
ENTIRE HOME 6 Beds 14 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 14

Top guest reviews
the second floor space is especially room and everything was clean and neat
the house was comfortable cute and clean — especially the kitchen and bathrooms
great place and clean too even better than the photos
the inside is very spacious nicely decorated and well furnished
the check in process was really easy and brittani is a great host
brittani was so nice and accommodating
great location easy to get to
great beach house with nice location
the location was amazing and couldn’t have been much closer to the boardwalk
beautiful home in a great location
close to beach and boardwalk with great living space and a nice little market near by
Read more reviews

4. Cheerful home with a poolside bar (from USD 237)

This bright and intimate vacation rental comes with three bedrooms and two bathrooms. The living spaces are vibrant, with furnishings in varying shades of ocean blue and sea green. In the open-plan kitchen and dining area, there is a colorful art mural of the beach. The color-themed bedrooms in sky blue, teal, and salmon pink are just as cheery. After a fun day outdoors, you can unwind in the backyard with a private swimming pool, deck chairs, bar, and barbecue grill.

Vacation Dream at this 3BR 2BA House w/ Amazing Backyard Patio & Private Pool
19 reviews
House 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
pool and tiki bar are perfect additions and rare finds in the town
the other two beds were more comfortable
the king bed was very comfortable
reviewer comments:we loved this charming 3 bed 2 bath home for the week
there is ample room to cook relax sleep and celebrate in the pool
this property was incredibly clean when we checked in
very clean and efficient check in/out process
this property is spacious clean and comfortable in a quiet residential neighborhood
reviewer comments:this house is spacious clean cute and perfect for a small group/family stay
rating details:the property manager was very helpful
rating details:the property manager was very helpful
rating details:the property manager was very helpful
had a few minor issues but property manager was very responsive and easy to work with
the location was great
plenty of delicious food close by too we cannot wait to go back next year
great location- close to restaurants the beach mini golf
i was very happy with the location
i was very happy with the location
Read more reviews

5. Bayfront home with backyard pool

You can’t go wrong with Casa Marlin, a two-story bayfront property within walking distance of the beach. The rental has five bedrooms and four bathrooms, perfect for a group of up to twelve guests. Casa Marlin’s interiors are subtle and elegant, with cream-colored walls and small touches of beach decor. The master bedroom upstairs is fitted with an opulent four-poster bed and a bathtub for a relaxing soak. Highlights include a private swimming pool in the backyard, where you can enjoy a refreshing swim, and a wooden pier for boats, water sports, and relaxing views.

November-April Special: Stay 3 nights get one Free
79 reviews
House 12 Guests 5 Bedrooms 4 Bathrooms
Top guest reviews
everything was clean and just as advertised online
beautiful and clean and peaceful
cleaning guy could have left some tp and the front door needs better instructions
house was great and owner/manager was quick to answer questions before our stay
the owner was awesome and checked in on us via text during our stay
the owner is very nice and helpful and you virtually have no issues to deal with
the property manger was very attentive and very easy to work with
homeowner was very attentive and made sure our stay was great
perfect location in a quiet neighborhood minutes from the ocean boardwalk and many other attractions
Read more reviews

Nearby vacation rentals with private pool

6. Pet-friendly house with a seasonal pool (from USD 321)

This three-bedroom house proudly features amazing outdoor spaces that are sure to make your stay worthwhile. Perfect for couples and families, this rental promises a serene secluded getaway complemented by excellent amenities. Amenities include a Smart TV for indoor entertainment and an outdoor fire pit for gathering around and stargazing. A private swimming pool is also available on the property. The pool is open between the months of May and September for guests’ use. Please note that the pool is not heated.

For those who love to cook, a kitchen with an ice maker, stove, and oven is available inside the house. If you’re bringing a car, there is ample parking space available. Additionally, a maximum of two pets, each weighing less than 50 lbs (22.6 kg), are allowed on the property.

West OC Bayside Getaway W/ Pool
Ocean City, MD, US
7 Guests 3 Bedrooms 2 Bathrooms

7. Remodeled cottage with an in-ground pool (from USD 233)

Convenience and comfort are what this cute refurbished cottage offers its guests. With a front porch, a deck, and a patio area with a fire pit, guests are spoiled for choice when looking for a place to relax. The private in-ground pool is another relaxing spot for you to enjoy. The pool area comes with comfy seating and a barbecue grill for some poolside fun.

The cottage is close to a beloved local establishment called Harborside Bar and Grill. It’s also minutes away from several shopping outlets, Ocean City Harbor, Oceanic Fishing Pier, Baja Amusements, and Sunset Park.

Cute renovated cottage , close to park and ride restaurants and boat ramp
8 reviews  Wifi Available
House 8 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 3
Refund Policy :

Top guest reviews
as soon as we entered the house we were surprised by how clean and how spacious the house was
fantastic hosts fast answers to questions and easy communication
michael was very quick with responses and helpful
great location away from the hustle & bustle
we loved being able to walk to restaurants
such an excellent spot for our family we felt very comfortable location was great near the beach and parks
it is close enough to the boardwalk and all of ocean city fun without the noise
Read more reviews

8. Unique beach house with views of the canal (from USD 500)

This one-of-a-kind rental offers an amazing backyard swimming pool with a large patio and a stylish poolside bar. There is also a separate pool house with its own bedroom and bath. The interiors of this vacation home are just as lovely, featuring a modern living room and kitchen looking out onto a canal. The cozy bedrooms are adorned with charming beach-inspired decor and are equipped with comfortable beds for a restful sleep.

Peaceful and private one of a kind beach treasure with private pool and deck.
32 reviews  Wifi Available
House 7 Guests 3 Bedrooms 4 Bathrooms

Accommodates: 7
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
the deck and pool overlooking the canal was simply divine
open rooms make the house seem larger and back deck is amazing
the house is beautiful the deck/pool was perfect and access for kayaking was ideal
we felt comfortable with our family of 5 and the pool in the back was delightful
we were looking for a clean & comfortable home with a pool
house and property were beautiful and sparkling clean the pictures don’t do it justice
owners were super responsive
the owner was responsive and helpful
the owners were very accommodating and went out of their way to make sure we enjoyed our stay
we had a wonderful time the owners were great we would love to visit again
ginny was communicative and answered all my questions thanks for having us
a great place great location
great location- close to everything without the hassle or noise
Read more reviews

9. Waterfront farmhouse with pier

Golden Quarter Farm is a premier vacation rental tucked away in the historic town of Berlin, Maryland. The farmhouse property boasts a pier and nature trails you can explore. The heart of the estate is a four-bedroom, three-bathroom country house that can accommodate up to ten guests. The home features a stately living room, a fully equipped kitchen, a laid-back breakfast nook, and themed bedrooms.

Just steps away from the house is a private swimming pool with a basketball hoop and wooden lounge chairs. You can also enjoy access to an outdoor dining area, grill, and fire pit for chilly evenings. Laundry facilities, table tennis, kayaks, and bicycles are available for guests’ use.

Private pool, waterfront, kayaks, bikes, firepits!
Berlin, Maryland, United States
56 reviews  Wifi Available
ENTIRE HOME 6 Beds 10 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
the bedrooms and bedding comfy living room couches kitchen amenities and bikes were all much appreciated as well
the house was very nice beds were comfy and it had everything we needed for a weekend away
we absolutely loved the place it was a very comfortable space with a lot of outdoor areas for relaxing
everything was clean comfortable and spacious
house was comfortable and clean and a few minor issues at check in were quickly resolved
the host evelyn and property manager mary were very responsive
mary one of the property managers is very helpful and provides prompt service
the hosts are very friendly and responsive
you and your property manager we’re both so quick and helpful in your responses
we booked last minute and had great response from owner and property manager
beautiful spot that close to it all
this house is absolutely amazing the location is perfect
located super close to assateague we went there several times too for beach walks and swimming
the perfect place to get away with your family
absolutely loved the place would recommend to anybody great location and lots of things to do
Read more reviews

10. Huge vacation home with outdoor pool

Do you prefer a vacation rental with more legroom for your large group? If so, you may want to consider this bright and airy 6-bedroom, 4-bathroom house that accommodates up to 22. Ocean City Boardwalk and some family-friendly resorts are just a few steps away from this property. On the first floor, you can find a spacious living room, a kitchen, and a separate dining room.

On the second floor, there are three bedrooms that can ensure a good night’s rest. The large private swimming pool in the backyard completes the experience.

Large House near the Ocean w/Free WiFi, Private W/D, Outdoor Pool, & Central A/C
25 reviews
House 22 Guests 6 Bedrooms 4 Bathrooms

Accommodates: 22
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
both houses were perfect for our need with 6 adults we had room to spare
property was clean and had enough towels lots of room space nice for large family
the main house was clean and well kept
the main house was clean and well kept
clean bright house right by the beach
clean bright house right by the beach
the host was responsive and the house served its purpose perfectly
Read more reviews

11. Beautiful A-frame rental with hot tub (from USD 330)

Are you looking for a unique home base for your Ocean City vacation? This casual two-bedroom A-frame rental is ideal for a party of six. On the ground floor, you can find a warm and relaxing living room, a fully stocked kitchen, and a bedroom equipped with bunk beds. A spiral staircase leads to the upper bedroom loft.

The two balconies offer plenty of space for lounging with a cup of coffee. The centerpiece of this property is an elevated bean-shaped pool with a slide and a separate hot tub. It’s a great place to come home to after an exhausting trip to the city, visiting wonderful attractions and perhaps attending one of the city’s popular festivals.

Recovery Room offers a Private Pool and Hot Tub !! Rental License # 1993
120 reviews  Wifi Available
House 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6
Minimum Nights: 7
Refund Policy :

Top guest reviews
Amenities & Room:
the beds were comfortable and there were plenty of extra pillow and blankets
the bed up stairs was so comfortable to sleep in
the recovery room has it all and we had a fabulous staycation
the pool and hot tub was wonderful to relax by in the evening time
the home was very clean and cozy
the outdoor areas were spacious and made for easy relaxing even with 3 daughters
the house was very clean and the owner was great to work with
the owner tim was great to communicate with
owner was awesome to work with and responded very quickly to inquiries
the host is the best i've ever come across very responsive and detailed
wonderful house great location everything we wanted and more
perfect location with little reason to leave
the house is in the perfect location easy drive to beach
i loved the house location on a quiet cul de sac yet it so close to everything
very comfortable and well furnished and in a great location
Read more reviews

Enjoy a relaxing stay in Ocean City

Offering plenty of attractions, this resort town is a wonderful place to visit, whether you are traveling alone or with your loved ones. Dine in a kid-friendly restaurant or a local breakfast place, or head to Ocean City Boardwalk where you can also find some culinary delights. For a relaxing stay, consider booking any of these best vacation rentals in Ocean City, Maryland.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Carla is a freelance travel writer who enjoys planning itineraries, visiting art museums, and reading ebooks. Before jumping into freelancing at the height of the COVID-19 pandemic, she was a...Read more

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