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Vacation rentals with a pool in Ocean Pines

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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

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, 174 reviews

Peaceful Getaway in Ocean Pines

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

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, 32 reviews

Cottage on the water

We are located right off of Route 90 and minutes to the beach. Ocean Pines is filled with amenities. We have a public access yacht club and golf course are close to the town of Berlin for dining and a visit to the famous Burley Oak Brewery. The family will enjoy Ocean City for fun at Jolly Rogers or the Boardwalk for the rides. West Ocean city has the famous Orange Crush at the Harborside restaurant and don't forget Assateague Island and the horses. We are also 2 miles from the local winery.

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, 126 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!

An aerial view of a marina with multiple boats docked along a well-maintained pathway. The surrounding residential community and parking area are visible, as sunlight reflects off the peaceful water, highlighting the scenic environment.

Townhouse in Ocean Pines

4.95 out of 5 average rating, 66 reviews

OceanPinesFamilyBeachRetreat~JettdTub~KingBed~Golf

Immediate removal of stress at the front door. Being nestled in a marina’s serene waterfront & nature park is good for the soul. Relax in a jetted tub after a sun filled day & an al fresco meal on a back porch with charming outdoor dining. An open concept main level features large windows & comfortable seating through the entire property. 2 full bathrooms upstairs & a king sized bed provide maximum comfort & outdoor living on 2 balconies. Additional fees for pools, pets, >3 guests may apply.

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, 134 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.

The bright living room features large windows overlooking the river, allowing natural light to fill the space. Comfortable seating arrangements are present, with patterned sofas and a wooden coffee table at the center. A television stands beside a cozy fireplace, enhancing the inviting ambiance.

Home in Ocean Pines

5 out of 5 average rating, 4 reviews

Riverside Retreat- 3 Story/Direct Waterfront

Welcome to your ideal vacation home! This spacious three-story residence features 4 bedrooms and 2.5 bathrooms, including a king bedroom with an en-suite bath & balcony. Enjoy an open kitchen, dining area, and a stunning living room with river views. The backyard offers a private "beach" with Adirondack chairs and a picnic table. Just 20 minutes from Ocean City’s shopping, dining, and beaches. Perfect for family fun and relaxation! A local manager is here to ensure everything goes smoothly

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, 127 reviews

Newly built bright and airy guest suite!!!!

Welcome to our new 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 breathtaking waterfront Yacht Club with restaurant and live music (seasonal), Robert Trent Jones Sr. golf, farm market, playgrounds, 5 pools/fee (4 seasonal), and racquet club.

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, 110 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 inviting beachfront pool area is presented, featuring bright blue water surrounded by a spacious deck. Yellow umbrellas and lounge chairs are arranged around the pool, offering a comfortable space to relax. A clear view of the ocean is visible in the background under a sunny sky.

Condo in Ocean City

4.96 out of 5 average rating, 283 reviews

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

Home in Ocean Pines

4.84 out of 5 average rating, 130 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*

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

4.88 out of 5 average rating, 147 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.

An outdoor patio area features a shaded pergola adorned with hanging plants. A lounge seating arrangement is positioned around a table, while a barbecue grill is nearby. In the background, a swimming pool is enclosed by a fence, surrounded by a manicured lawn.

Tiny home in Millsboro

4.82 out of 5 average rating, 142 reviews

Farm Cottage - POOL - 30 Min to BEACH

Enjoy this beautiful cottage/studio apartment. Perfect little getaway space for 2 (or 3). Our little cottage is surrounded by fields and the quiet sound of country sunrise. You'll wake up to chickens anxious to get out of their coop or Lucy, the turkey, peeking in your window. In the evenings, light the firepit or enjoy and a quiet nighttime swim with our duck. And our very friendly dog, Tanka (Cane Corso) will welcome you to our family.

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Popular amenities for Ocean Pines rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

An aerial view of a spacious waterfront property showcases a well-manicured yard with a private boat dock. The surrounding neighborhood is visible, featuring a variety of homes, some with outdoor amenities like pools and decks. The serene bay can be seen in the background.

Home in Ocean Pines

4.8 out of 5 average rating, 10 reviews

Waterfront Home with views of OC Skyline!

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, 81 reviews

*Catch Me By The Sea*

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.

4.94 out of 5 average rating, 54 reviews

Amazing 2 Bedroom home close to the beach!

A spacious living area is furnished with a large sectional sofa, complemented by decorative pillows. Two accent tables are placed beside the sofa, while a patterned area rug with nautical themes covers the floor. Natural light filters through the large windows adorned with light curtains.

Home in Ocean Pines

5 out of 5 average rating, 7 reviews

Royal Oaks Chalet

The exterior of the waterfront home is shown, with a spacious deck and screened porch overlooking the water. Lush landscaping and a pathway lead to the dock, while large windows create a welcoming atmosphere. A patio umbrella provides shade for outdoor seating.

Home in Ocean Pines

5 out of 5 average rating, 63 reviews

Ocean Pines, Waterfront Oasis

A single-story beach house features a light grey exterior with white shutters and a welcoming front porch. Lush greenery and a gravel path enhance the charming entrance, while tall trees create a natural backdrop, providing a serene setting.

Home in Ocean Pines

4.93 out of 5 average rating, 46 reviews

Charming Home in a Beach Town Community!

The exterior of a two-story house is shown at dusk, illuminated by soft lights from the large circular windows. A front porch is visible, welcoming guests into the home. Lush greenery surrounds the property, creating a tranquil atmosphere.

Home in Ocean Pines

4.84 out of 5 average rating, 58 reviews

Entire Home w King Bed in Peaceful OceanPines 🌊🌲

The exterior of a two-story home is shown, surrounded by lush greenery and mature trees. A wooden deck with railings is featured at the entrance, overlooking a pathway made of stones, while a large tree stands prominently beside the house.

Home in Ocean Pines

4.91 out of 5 average rating, 11 reviews

Cozy Corner Retreat

Condo rentals with a pool

Condo in Ocean City

4.95 out of 5 average rating, 158 reviews

Waterview, Steps from Beach, Linens Included!

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, 316 reviews

Oceanfront Family Oasis: Pool, Beach & Parking!

Top guest favorite

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

4.99 out of 5 average rating, 228 reviews

Cozy oceanfront condo with stunning ocean views

A spacious living area features a comfortable gray sectional sofa adorned with colorful cushions. An inviting lamp sits on a coffee table, while the light beige walls complement the tiled flooring. The open layout connects to the kitchen and dining space in the background.

Condo in Ocean City

4.82 out of 5 average rating, 290 reviews

🏖 *Ocean *Ocean *Ocean* 🏖 Beautiful Condo!!

Condo in Ocean City

4.93 out of 5 average rating, 123 reviews

Oceanfront 2 Bedroom-Sleeps 6-Indoor/Outdoor Pool

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, 100 reviews

Gone Coastal *Pool* Bayside with view* Top Floor

Top guest favorite

A cozy living area displays a light blue color scheme. A white sofa is positioned beside a coffee table on a patterned rug, while a dining table is set nearby. Floor-to-ceiling sliding doors open to a balcony, offering views of the ocean.

Condo in Ocean City

4.96 out of 5 average rating, 260 reviews

Caramar Couples Retreat

Condo in Ocean City

4.77 out of 5 average rating, 207 reviews

DirectOceanFront on Boardwalk/Newly Remodeled/Pool

Other vacation rentals with a pool

A spacious backyard features a pristine in-ground pool, surrounded by a patio area. Under a wooden pergola adorned with bistro lights, four hanging egg chairs invite relaxation, complemented by several polywood Adirondack chairs. Lush greenery serves as a backdrop, enhancing the outdoor ambiance.

5 out of 5 average rating, 13 reviews

Mins to Golf & Beach! Private Pool & Luxe Firepit

An aerial view captures a row of charming homes situated along a sandy beach, with the Indian River Bay visible in the background. Neatly manicured lawns and driveways are observed in front of each house, framed by tall trees and grassy areas.

Home in Dagsboro

4.9 out of 5 average rating, 20 reviews

Beauty On The Bay

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

4.93 out of 5 average rating, 46 reviews

West OC Bayside Getaway w/ pool

The A-frame cottage features large front windows, allowing natural light to fill the interior. Wooden siding blends harmoniously with the surrounding trees. A spacious deck is accessible, adorned with outdoor seating. Dappled sunlight casts shadows on the ground, creating a serene outdoor setting.

Home in Ocean Pines

4.88 out of 5 average rating, 34 reviews

Captivating A-Frame in beautiful, Ocean Pines

An open-concept living area is showcased, featuring a white sofa with colorful cushions and a light green accent chair. A large area rug anchors the space, while a dining table with six chairs is visible in the background. Natural light fills the room from tall windows.

Vacation home in Ocean Pines

4.63 out of 5 average rating, 51 reviews

Bright 3 bedroom vacation home near beach

Top guest favorite

A spacious sectional sofa occupies a corner of the living room, adorned with decorative pillows featuring ocean-themed designs. Soft, neutral-colored walls enhance the airy feel of the space, while sunlight filters through the nearby windows, creating a bright and inviting environment.

Home in Ocean Pines

4.88 out of 5 average rating, 41 reviews

Charming cul-de-sac House just minutes from OC.

The exterior of a charming house is surrounded by lush greenery. A covered front porch features white railings and a welcoming entry. An American flag hangs beside the door, with multiple windows adorned by green shutters, enhancing the inviting feel of the home.

Cottage in Ocean Pines

4.82 out of 5 average rating, 33 reviews

Ocean Pines Beach House in the Woods

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, 86 reviews

Bayside Blue Getaway near Ocean City

Quick stats about vacation rentals with a pool in Ocean Pines

Total rentals
160 properties
Nightly prices starting at
G$10,461 GYD 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

Destinations to explore