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Vacation rentals with a pool in Ocean Pines

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Ocean Pines

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

An illuminated pool reflects a tranquil blue under the evening sky, surrounded by a well-maintained deck. The adjacent building features multiple balconies and yellow facades, providing a pleasant environment for guests. Safety fencing outlines the area, ensuring a secure setting.

Condo in Ocean City

4.91 out of 5 average rating, 281 reviews

Wight Bay Unit 245

2 bedroom, 2 bath, sleeps 6 *2nd bedroom will have twin bunk beds & 1 queen bed for 2025! Beautiful recently renovated condo! Bay-side 47th street on the canal with an amazing bay view. The building is in a prime location right next door to Seacrets! There is a pool, two piers, and it’s only a block from the beach. Perfect for getaways with friends or family! Bedroom 1: 1 Queen bed Bedroom 2: Twin bunk beds, 1 Queen Bed Living room: 1 Queen pull out couch 1 Parking Pass, Pool, Elevator

A light-filled living area features a soft, neutral-toned sectional sofa facing a wooden coffee table. Floor-to-ceiling windows showcase ocean views, with sunlight reflecting off the water. A flat-screen TV is mounted on a wooden entertainment unit, complementing the room's modern design.

Condo in Ocean City

4.91 out of 5 average rating, 322 reviews

Oceanfront Family Oasis: Pool, Beach & Parking!

CONSTRUCTION NOTICE NOV 24 to MAY 25, noise may be heard Wake up to the ocean sunrise in this modern 2 bedroom, completely renovated, condo. Prime location on 29th street, 2 blocks north of the famous OC Boardwalk, 2 blocks east of OC's premier amusement and water park along with two famous crab house and other restaurants within walking distance. One hassle free off street parking spot, free WIFI, full size washer & dryer, and a beautiful outdoor pool steps from the beach. Enjoy the bay sun

Top guest favorite

The spacious pool area is surrounded by shaded umbrellas and lounge chairs. A large group of individuals enjoys the water, with a vibrant blue sky above. Steps lead into the pool, providing easy access for guests. Lush greenery frames the scene, enhancing the sense of relaxation.

Condo in Ocean Pines

4.97 out of 5 average rating, 182 reviews

Ocean Pines Getaway

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

An outdoor community pool is depicted, featuring a spacious area of clear blue water surrounded by lounge chairs. Sun umbrellas provide shade, and a diving board is visible. Lush greenery and a distant building are present in the background, enhancing the inviting environment.

Condo in Ocean City

4.96 out of 5 average rating, 105 reviews

Gone Coastal *Pool* Bayside with view* Top Floor

Welcome to Gone Coastal! Relax in this beautiful 2BR/2BA getaway featuring: 🛏 1 King (Master) | 1 Twin-over-Full Bunk | 1 Sleeper Sofa 🏊‍♂️ Outdoor Community Pools – Lap & Family Pool (Directly Across!) 🔑 Keyless, Contactless Check-in 🌅 Spacious Deck – Outdoor Dining + Bay & Pool Views 📺 Smart TVs + YouTube TV 🛒 1-Minute to Grocery Store 🍽 Fully Equipped Kitchen 📍 Prime Location – 120th St, Heron Harbor 🚗 Ample Free Onsite Parking A perfect retreat for families & beach lovers! 🌊☀️

Top guest favorite

The exterior of a single-story house is visible, featuring a spacious front porch with white railings. Large windows allow natural light to enter, while a driveway provides parking for two vehicles. A wooded area surrounds the property, enhancing its peaceful setting.

Home in Ocean Pines

4.98 out of 5 average rating, 130 reviews

Camelot

HIGHEST RATED HOUSE IN OCEAN PINES! CHECK OUT OUR AMAZING GUEST REVIEWS :) Jumpstart your ultimate beach getaway at this impressive 3-bedroom, 2-bathroom retreat house! Complete with amenity-packed living spaces with vaulted ceilings and a serene location, you’ll never hunger for entertainment at this family friendly home. Grill out on the patio, roast marshmallows by the fire pit, tee off at a nearby golf course, or enjoy some retail therapy at Outlets Ocean City! A short drive to the beach!

A two-story blue house is framed by trees, with a well-maintained front yard. The home features black shutters and white steps leading to a central door. A porch flag and a welcoming bench are visible, enhancing the inviting exterior.

Home in Ocean Pines

4.96 out of 5 average rating, 137 reviews

Little house in Berlin, Md.

Our home is located in Ocean Pines, Maryland. Spend the day at the beach, golf, come back and relax on our spacious screened porch. The community has 5 pools, walking trails, Parks, and more. The house is a short drive to Ocean City, Md. (8 Miles) via Rt. 90 or Rt. 50. Assateague Island National Seashore is also just a short drive 12 miles. You can see wild horses, beautiful sunsets, ride bikes, or go to the beach. There are many golf courses within 15 miles of the house all very nice.

Top guest favorite

The exterior of a two-story house is framed by lush greenery and neatly arranged flower beds. A covered front porch with white railings invites guests, while the clean lawn extends towards the street. The sky above showcases a mix of clouds and blue.

5 out of 5 average rating, 114 reviews

Stay Salty OC Beach House

Welcome to your ultimate getaway near Assateague State Park & Ocean City! Our spacious retreat sleeps 14 guests and boasts resort-style amenities including pools, a gym, kayaks, and tennis courts. Located just moments from beaches, charming towns, and exciting attractions, you'll have everything you need for an unforgettable vacation. With a fully stocked kitchen, game rooms, cozy reading nooks, puzzles, and a balcony, there's something for everyone. Book now and let the relaxation begin!

An outdoor pool area features a clear blue swimming pool bordered by lounge chairs and umbrellas. The space is well-lit by lamps, and distant greenery is visible in the background, providing a relaxing atmosphere for guests.

Condo in Ocean City

4.81 out of 5 average rating, 102 reviews

Lovely beach-front condo with pool and views

Kick back and relax in this calm, stylish space. This one-bedroom condo is the perfect space for 1-2 couples, or a family. You have floor-to-ceiling beach views, plus amazing sunrises and sunsets from the two separate balconies. The kitchen is well equipped to cook every meal, or eat out at Ocean City's many restaurants. Your stay also comes with 4 pool passes for accessing the onsite seasonal outdoor pool (viewable from the unit) and access to the building’s tennis/pickleball courts!

Top guest favorite

A bright, open kitchen area is visible, featuring modern appliances and a spacious countertop. Large windows allow natural light to fill the room. A comfortable chair sits beside a decorative rug, while a sleek ceiling fan contributes to the airy atmosphere.

Guest suite in Ocean Pines

4.99 out of 5 average rating, 131 reviews

Newly built bright and airy guest suite!!!!

FREE oceanfront parking pass with bookings. 2nd floor private suite with parking, patio/firepit, and self check-in private entry. We are located just minutes from the Ocean City beaches, quaint small town of Berlin, Ocean Downs Casino, Assateague, Windmill Creek Winery, restaurants, and outlets. Enjoy neighborhood amenities such as a waterfront Yacht Club with restaurant and live music (seasonal), golf, farm market, playgrounds, 5 pools/fee, (no pool on property) racquet club.

Home in Ocean Pines

4.84 out of 5 average rating, 133 reviews

Peaceful Beach Cottage - Sanitized & WiFi!

Fully renovated clean, sanitized, quaint house in a quiet neighborhood minutes from the beach/ocean! Community offers many amenities such as pools, restaurants, playgrounds, etc. Have peace and quiet while only being minutes from the beach and main OC drag. Very close to the casino! Voted "#1 Safest Neighborhood in Maryland!" *June-August we only accept 7 day rentals with a Saturday check in* *Memorial & Labor Day weekends have 3 night minimum with Fri check in*

An indoor pool area is featured, with clear water and comfortable seating around the perimeter. The pool is surrounded by light-colored walls and large windows, allowing natural light to fill the space. Accessible steps lead into the water, contributing to ease of entry.

Condo in Ocean City

4.92 out of 5 average rating, 246 reviews

Sun, Sand & Sea | Your Cozy Oceanfront Hideaway

-Oceanfront -Indoor pool & Hot tub -Walk to local dining and shopping -Elevator accessible plus luggage carts -Full kitchen for cooking meals -Fast Wifi and Streaming TVs -Fully Stocked Home: Clean linens, towels, toilet paper, paper towels & more! **2025 guests: Our pool and hot tub are in the process of being renovated and will be closed during your stay. This does not impact our condo, but you will not be able to use these amenities.**

A blue water slide is displayed adjacent to a large indoor swimming pool. Brightly colored bunting decorations hang along the poolside. Nearby, lifeguard chairs and railings are positioned for safety, complementing the spacious and well-maintained aquatic environment.

Home in Ocean Pines

4.87 out of 5 average rating, 150 reviews

Tortuga Cottage: Your All- Season Getaway

This is an escape to reacquaint with family, nature, and your best self. Come home from the beach just a few miles away to enjoy the gas fire place, outdoor fire pit, and hot tub on chilly nights, fenced in back yard. Take advantage of the parks indoor outdoor pools golf yacht club, just moments from the cottage. Dogs are part of our family, and we are happy to consider canine guests on a case by case basis. Please see policies for breeds.

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Popular amenities for Ocean Pines rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

The front exterior of the house features a yellow facade with large windows and a welcoming doorway. A wooden deck is accessed by a set of stairs, and outdoor chairs are positioned for seating. Surrounding trees indicate a natural, wooded setting.

Home in Ocean Pines

4.96 out of 5 average rating, 28 reviews

Salty Serenity

Top guest favorite

Home in Ocean Pines

4.94 out of 5 average rating, 32 reviews

Sunshine at Ocean Pines

A light and airy deck features a rectangular dining table surrounded by aqua-colored chairs. A calm water view is visible beyond the railing, with flags gently waving in the breeze. Soft lighting is provided by string lights overhead, enhancing the inviting atmosphere.

Home in Ocean City

4.94 out of 5 average rating, 257 reviews

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

Top guest favorite

Home in Ocean City

4.87 out of 5 average rating, 182 reviews

Beach Paradise IV-Downtown Luxury Condo Bay View

A community pool is surrounded by concrete flooring and shaded by trees. In the background, a pavilion with picnic tables can be seen, along with mobile homes lining the area. Lifeguards are stationed under an umbrella, observing the calm waters.

4.93 out of 5 average rating, 57 reviews

Amazing 2 Bedroom home close to the beach!

A large swimming pool is surrounded by a concrete deck, with numerous white lounge chairs arranged along one side. The calm water reflects the clear blue sky, while the distant community homes are visible in the background, creating an inviting leisure space.

4.8 out of 5 average rating, 208 reviews

Reduced rates Bayside OCMD trip, fall is beautiful

A modern two-story home is situated on a tree-lined lot, featuring a welcoming front entrance. Brightly colored adirondack chairs provide seating in the gravel area by the driveway, which accommodates several vehicles. Natural light filters through the trees, creating a serene environment.

Home in Ocean Pines

4.95 out of 5 average rating, 39 reviews

Beautiful Spacious 4 Bedroom Home in Ocean Pines

The waterfront home is positioned along the canal, featuring a spacious deck with seating areas and landscaping. A stone pathway leads to the dock, which is equipped for boating. The exterior is complemented by greenery and a calm water view, providing a serene outdoor setting.

Home in Ocean Pines

4.79 out of 5 average rating, 24 reviews

Ocean Pines 3BR 2BA Canal Front Home with Sunroom

Condo rentals with a pool

Top guest favorite

Condo in Ocean City

5 out of 5 average rating, 6 reviews

2 Blocks to Boardwalk - Panoramic Assateague Views

An indoor pool is seen under a high, skylight ceiling, with clear blue water reflecting the light. Plants are arranged along the edges, and lounge chairs are positioned around the pool area. Large windows provide views of the surrounding scenery.

Condo in Ocean City

4.87 out of 5 average rating, 150 reviews

Gorgeous oceanfront Capri Beach and Bay Views!!!!

Top guest favorite

Condo in Ocean City

4.93 out of 5 average rating, 103 reviews

"Aren't You Fancy?!" Prime Coastal Getaway

An oceanfront pool is visible in the foreground, featuring a circular design with wooden decking surrounding it. The clear blue water reflects the sunlight, offering a serene view of the ocean and sandy beach in the distance.

Condo in Ocean City

4.98 out of 5 average rating, 236 reviews

Cozy oceanfront condo with stunning ocean views

A fenced outdoor swimming pool area features a rectangular pool surrounded by a concrete deck. Several white lounge chairs are positioned around the pool, and a few tables are also visible nearby. The serene environment is complemented by a light blue building in the background.

Condo in Ocean City

4.83 out of 5 average rating, 131 reviews

Ocean Block - Clean, cozy 1 Bedroom. Pool, Wifi

An indoor pool area is captured, featuring a circular pool with swimmers enjoying the water. Colorful banners hang from the ceiling, and large windows provide views of the outside. Lounge chairs surround the pool, adding to the inviting atmosphere.

Condo in Ocean City

4.86 out of 5 average rating, 106 reviews

Ocean View Condo W/ Indoor and Outdoor Pool

A sunlit indoor lounge area is surrounded by large windows, offering a view of the indoor pool. Rattan furniture with tropical-patterned cushions is arranged around a low table. Decorative plants enhance the green ambiance, contributing to a relaxing environment.

Condo in Ocean City

4.87 out of 5 average rating, 208 reviews

🌊Oceanfront studio w/ amazing views & amenities🏖

A welcoming kitchen and dining area is displayed, with modern appliances and a wooden dining table. Colorful letters spelling 'Welcome' are arranged on a sideboard, while a refrigerator and seating area are visible in the background, enhancing the cozy atmosphere.

Condo in Ocean City

4.9 out of 5 average rating, 48 reviews

BaysideGetaway | 2 Blk to Beach & Boardwalk | Pool

Other vacation rentals with a pool

A charming retreat is surrounded by tall trees, showcasing a welcoming front porch with steps leading up to the entrance. The light-colored exterior is complemented by large windows, offering a bright and airy feel. Lush greenery lines the pathway and soft earth tones create a serene atmosphere.

Home in Ocean Pines

5 out of 5 average rating, 7 reviews

Ocean Pines, 3 bedroom, sleeps 6, dog friendly

A private pool is surrounded by a paved patio and lush greenery, providing a serene setting for relaxation. Adirondack chairs are positioned near the pool, while colorful flowers add visual interest to the landscape. The clear water reflects the bright blue sky and scattered clouds.

4.96 out of 5 average rating, 76 reviews

Private pool, waterfront, kayaks, bikes, firepits!

A private pool is surrounded by a paved patio, providing spacious outdoor lounging areas. Two vibrant green chairs are positioned beside the water, with gently swaying plants creating a relaxing ambiance.

Home in Ocean City

4.94 out of 5 average rating, 48 reviews

West OC Bayside Getaway w/ pool

A spacious outdoor deck is surrounded by lush trees, offering a serene atmosphere. Comfortable seating is arranged alongside a glass-top table, while string lights add a soft glow. A fenced-in backyard features a firepit area with seating for relaxation and gatherings.

Home in Ocean Pines

4.96 out of 5 average rating, 83 reviews

*Catch Me By The Sea*

Top guest favorite

Home in Ocean Pines

5 out of 5 average rating, 56 reviews

Ocean Pines Fun – Arcade, Pools & Near O.C. Beach

A comfortable living room is highlighted by a large television set on a white cabinet. A soft blue couch and loveseat provide seating, complemented by a colorful coffee table featuring a coastal design. Two lamps illuminate the space, along with natural light from a nearby window.

Home in Ocean Pines

4.95 out of 5 average rating, 64 reviews

Close to OC, Family Friendly, Pool Access

A spacious living area features a large sectional sofa adorned with decorative pillows. A ceiling fan provides airflow, while hardwood-style flooring complements the stylish furnishings. The open kitchen and dining area are visible in the background, creating a welcoming flow between spaces.

Vacation home in Ocean Pines

4.93 out of 5 average rating, 89 reviews

Bayside Blue Getaway near Ocean City

A pair of teal Adirondack chairs sits on a wooden dock overlooking calm water. Decorative pillows add a touch of comfort. Boat slips are visible in the background, with a soft reflection on the water's surface as the sun sets behind scattered clouds.

Home in Ocean Pines

4.94 out of 5 average rating, 36 reviews

Cottage on the water

Quick stats about vacation rentals with a pool in Ocean Pines

Total rentals
160 properties
Nightly prices starting at
€ 43 before taxes and fees
Total number of reviews
3.8K reviews
Family-friendly rentals
160 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
90 properties have a dedicated workspace

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