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.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on February 25, 2025.
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1. Spacious abode with private boat slip (from USD 1176)
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.
Top guest reviews
Host:
property manager was very friendly and quick to respond as wellLocation:
on the plus side it's a great locationthe location and having a pool is awesomethis rental property is a great location on a canal leading to the bayit is a quiet neighborhood but close enough to walk to fishtales and other great locationsvery happy with the location and the kids loved the poolCleanliness:
it was clean and tidyRead more reviewsAmenities & Room:
it was so nice to come home and dip in the pool every nightgood thing we measured the beds before ordering the linensit has a slip for your boat a private pool to enjoy and space to sleep 12 people
2. Family-friendly haven with game room (from USD 1198)
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.
Top guest reviews
Read more reviewsLocation:
todd's place was great incredible neighborhood for downtown ocean city i highly recommend renting this place
3. Spacious ocean-inspired home with street views (from USD 200)
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.
Top guest reviews
Host:
the check in process was really easy and brittani is a great hostbrittani was so nice and accommodatingLocation:
great location easy to get togreat beach house with nice locationthe location was amazing and couldn’t have been much closer to the boardwalkbeautiful home in a great locationclose to beach and boardwalk with great living space and a nice little market near byRead more reviewsCleanliness:
the second floor space is especially room and everything was clean and neatthe house was comfortable cute and clean — especially the kitchen and bathroomsgreat place and clean too even better than the photosthe inside is very spacious nicely decorated and well furnished
Nearby vacation rentals with private pool
4. 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.
5. Remodeled cottage with an in-ground pool (from USD 689)
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.
Top guest reviews
Host:
fantastic hosts fast answers to questions and easy communicationmichael was very quick with responses and helpfulLocation:
great location away from the hustle & bustlewe loved being able to walk to restaurantssuch an excellent spot for our family we felt very comfortable location was great near the beach and parksit is close enough to the boardwalk and all of ocean city fun without the noiseRead more reviewsCleanliness:
as soon as we entered the house we were surprised by how clean and how spacious the house was
6. Unique beach house with views of the canal
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.
13.18 km (8.2 mi) from Assateague State ParkAccommodates: 7
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 14 days before check-in.
Top guest reviews
Host:
owners were super responsivethe owner was responsive and helpfulthe owners were very accommodating and went out of their way to make sure we enjoyed our staywe had a wonderful time the owners were great we would love to visit againginny was communicative and answered all my questions thanks for having usLocation:
a great place great locationgreat location- close to everything without the hassle or noiseCleanliness:
we were looking for a clean & comfortable home with a poolhouse and property were beautiful and sparkling clean the pictures don’t do it justiceRead more reviewsAmenities & Room:
the deck and pool overlooking the canal was simply divineopen rooms make the house seem larger and back deck is amazingthe house is beautiful the deck/pool was perfect and access for kayaking was idealwe felt comfortable with our family of 5 and the pool in the back was delightful
7. Waterfront farmhouse with pier (from USD 1113)
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.
Top guest reviews
Host:
the host evelyn and property manager mary were very responsivemary one of the property managers is very helpful and provides prompt servicethe hosts are very friendly and responsiveyou and your property manager we’re both so quick and helpful in your responseswe booked last minute and had great response from owner and property managerLocation:
beautiful spot that close to it allthis house is absolutely amazing the location is perfectlocated super close to assateague we went there several times too for beach walks and swimmingthe perfect place to get away with your familyabsolutely loved the place would recommend to anybody great location and lots of things to doCleanliness:
everything was clean comfortable and spacioushouse was comfortable and clean and a few minor issues at check in were quickly resolvedRead more reviewsAmenities & Room:
the bedrooms and bedding comfy living room couches kitchen amenities and bikes were all much appreciated as wellthe house was very nice beds were comfy and it had everything we needed for a weekend awaywe absolutely loved the place it was a very comfortable space with a lot of outdoor areas for relaxing
8. Huge vacation home with outdoor pool (from USD 734)
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.
Top guest reviews
Host:
the host was responsive and the house served its purpose perfectlyCleanliness:
property was clean and had enough towels lots of room space nice for large familythe main house was clean and well keptthe main house was clean and well keptclean bright house right by the beachclean bright house right by the beachRead more reviewsAmenities & Room:
both houses were perfect for our need with 6 adults we had room to spare
9. Beautiful A-frame rental with hot tub (from USD 368)
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.
Top guest reviews
Host:
the owner tim was great to communicate withowner was awesome to work with and responded very quickly to inquiriesthe host is the best i've ever come across very responsive and detailedLocation:
wonderful house great location everything we wanted and moreperfect location with little reason to leavethe house is in the perfect location easy drive to beachi loved the house location on a quiet cul de sac yet it so close to everythingvery comfortable and well furnished and in a great locationCleanliness:
the home was very clean and cozythe outdoor areas were spacious and made for easy relaxing even with 3 daughtersthe house was very clean and the owner was great to work withRead more reviewsAmenities & Room:
the beds were comfortable and there were plenty of extra pillow and blanketsthe bed up stairs was so comfortable to sleep inthe recovery room has it all and we had a fabulous staycationthe pool and hot tub was wonderful to relax by in the evening time
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.
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