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Vacation rentals with a pool in Ocean Pines

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Quick stats about vacation rentals with a pool in Ocean Pines

  • Total vacation rentals

    Explore 190 vacation rentals in Ocean Pines

  • Nightly prices starting at

    Ocean Pines vacation rentals start at €79 per night before taxes and fees

  • Verified guest reviews

    Over 4,540 verified reviews to help you choose

  • Family-friendly vacation rentals

    190 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wi-Fi availability

    190 of Ocean Pines vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Ocean Pines rentals

  • 4.8 Average rating

    Ocean Pines stays are highly rated by guests—averaging 4.8 out of 5!

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
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

Newly built bright and airy guest suite!!!!

FREE oceanfront parking pass with bookings. 2 PERSON MAX. 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.

4.99 out of 5 average rating, 149 reviews
Top guest favorite
The living area is spacious, featuring a light blue wall color and a large sectional sofa. Natural light floods through windows, illuminating the decorative rug. The outdoor porch includes dining furniture and offers views of the canal and neighboring buildings.
Condo in Ocean City

Beautiful waterview 2B condo w/Dock&Close to Beach

Welcome to the Canal Bungalow! A stylish 1000 sq. foot retreat to enjoy all the fun & relaxation of the coastal lifestyle in North Oc. Bring your boat with you and dock alongside your back porch, enjoy pool access in a private gated community, or bring your sports gear for Northside Park. We are tucked away on the quiet bayside of OC & only a few minutes walk to the beach. Unwind on our beautiful balcony while watching the boats go by & finally understand the true meaning of a coastal lifestyle!

5.0 out of 5 average rating, 123 reviews
Top guest favorite
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

Little house in Berlin, Md.

Our home is located in Ocean Pines, Maryland. The house is a short drive to Ocean City, Md. (8 Miles). Spend the day at the beach, golfing, fishing come back and relax on our spacious screened porch. The community has 5 pools, walking trails, Parks, and more. Assateague Island National Seashore is also just a short drive 12 miles. You can see wild horses, beautiful sunsets, ride bikes, drive on the beach. There are many golf courses within 15 miles of the house and a casino 2 miles away.

4.95 out of 5 average rating, 150 reviews
Top guest favorite
Home in Ocean Pines

OC Gateway: Modern 4BR/2.5BA home (dog friendly)

Have fun with the whole family at our stylish Ocean City-convenient home! This wooded beach house boasts many modern upgrades including a beautiful kitchen with gas range, large flat panel televisions in almost every room, a washer and dryer, and even a Wii video game system in the living room! Queens in 3 bedrooms and a bunk bed with trundle in the 4th! Finally, enjoy all the amenities of Ocean Pines including access to 5 pools, a private OC beach club (w/pool!), and much more! Lic. No. 4586.

5.0 out of 5 average rating, 93 reviews
Top guest favorite
A serene waterfront scene is captured at sunset, with vibrant colors reflected in the calm water. A charming building with large windows is illuminated, surrounded by lush trees, and boats are docked along the waterfront, creating a peaceful atmosphere.
Condo in Ocean Pines

Water view at Ocean Pines Yacht Club Condo

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

4.97 out of 5 average rating, 229 reviews
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

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!

4.97 out of 5 average rating, 154 reviews
Superhost
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

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 may apply.

4.87 out of 5 average rating, 110 reviews
Guest favorite
A charming house with a light blue exterior is surrounded by lush greenery. A spacious deck features potted plants and outdoor seating. Colorful Adirondack chairs in red and blue are placed around a small fire pit on a patterned stone patio, inviting relaxation.
Home in Ocean Pines

Cozy beach home away from home!

Welcome! Come enjoy a cozy experience at this centrally located home in the desired Ocean Pines Community! This home is near the playground and allows access to the on-site golf course, five pools (including indoor pool!) tennis courts, and marina for a small fee. Fun in the sun awaits 15 minutes away in downtown Ocean City, where you can stroll the boardwalk, lounge on the sand, or hit the amusement park. Plenty of restaurants, grocery stores and shopping within 15 minutes.

4.95 out of 5 average rating, 22 reviews
Guest favorite
Home in Ocean Pines

Dockside Oasis in Ocean Pines

Escape to this canal-front Ocean Pines retreat featuring a private boat dock, ample parking, and peaceful waterfront views. Bring your boat, kayak, or paddleboard and enjoy easy access to the bay. Just minutes from Ocean City beaches, Assateague Island, golf, restaurants, shopping, and all Ocean Pines amenities, this home is perfect for boating, fishing, crabbing, and relaxing. Book your waterfront vacation today and experience the best of Maryland's Eastern Shore.

5.0 out of 5 average rating, 5 reviews
Guest favorite
A modern kitchen features light grey cabinetry and stainless steel appliances. A round table is set for dining, accompanied by stylish metal chairs. Natural light filters through the window, enhancing the warm, inviting layout that connects seamlessly to adjacent living spaces.
Home in Ocean Pines

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*

4.84 out of 5 average rating, 148 reviews
Top guest favorite
Home in Ocean Pines

Nautical at 82 Newport l private dock & waterfront

Experience this spacious waterfront home featuring 6 bedrooms and 3.5 bathrooms, including 2 master suites. Enjoy a game room, hot tub, and two expansive outdoor areas perfect for sunset views. Recently updated and meticulously maintained, this home offers a clean, inviting atmosphere for your getaway. Ideal for families or groups seeking relaxation and fun by the water! A local manager is here to ensure everything goes smoothly. Driveway parking for 4 vehicles.

5.0 out of 5 average rating, 39 reviews
Guest favorite
Home in Ocean Pines

Private Oasis | Backyard Pool

Welcome to Private Oasis! Enjoy a freshly updated getaway featuring a new upstairs bath with walk-in shower, new carpets, and renovated kitchen and baths. Relax in your private backyard pool, grill on the patio, or unwind in spacious living areas with plenty of sleeping options. Includes an Ocean Pines Beach Club parking pass and access to community amenities. The perfect spot for fun, sun, and family memories. NEW RENOVATED PHOTOS COMING SOON.

5.0 out of 5 average rating, 7 reviews

Popular amenities for Ocean Pines rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favorite
The two-story waterfront home features a spacious exterior with a sloped roof and light-colored siding. A deck is visible at the back, accompanied by outdoor seating. The calm water reflects the bright blue sky, enhancing the serene riverside setting.
Home in Ocean Pines

Waterfront 3BR | Private Dock + Views

4.96 out of 5 average rating, 26 reviews
Top guest favorite
Home in Ocean Pines

Cabin in the Pines I Luxury Touches + EV Charging

5.0 out of 5 average rating, 22 reviews
Top guest favorite
A welcoming approach to a spacious home is depicted, framed by tall trees reaching towards a bright blue sky. A neatly paved driveway guides the eye towards the house, with manicured lawns and colorful foliage adding to the inviting landscape.
Home in Ocean Pines

Coastal Oasis in Ocean Pines

4.97 out of 5 average rating, 79 reviews
Top guest favorite
Home in Ocean Pines

Whimsical Willow l Beach Club Pass and No Pet Fee

4.97 out of 5 average rating, 38 reviews
Top guest favorite
A welcoming living area features two dark sofas and a light armchair arranged around a white coffee table. A large television is mounted on the wall. Natural light enters through sliding doors that lead to a deck, adorned with a blue umbrella.
Home in Ocean Pines

Beach Retreat is a 3 bedrooms2 baths beach house.

4.96 out of 5 average rating, 54 reviews
Top guest favorite
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

Salty Serenity

4.96 out of 5 average rating, 48 reviews
Guest favorite
A spacious living area features a large gray sectional sofa, providing ample seating. A flat-screen TV is mounted on the wooden wall with a light-colored media console beneath. Natural light enters through sliding glass doors, complemented by curtains that frame the space against warm wooden ceilings.
Home in Ocean Pines

Pines & Sea A-Frame • Coastal & Cozy Stay

5.0 out of 5 average rating, 15 reviews
Guest favorite
Home in Ocean Pines

Cozy Stay by the Bay

4.92 out of 5 average rating, 50 reviews

Condo rentals with a pool

Guest favorite
The living area features soft blue furnishings and a light wood coffee table. Floor-to-ceiling windows offer direct views of the ocean, while two lamps provide warm lighting. A coastal-themed artwork adorns the wall, enhancing the serene atmosphere of the space.
Condo in Ocean City

Direct Oceanfront with a View and Amenities Galore

4.94 out of 5 average rating, 339 reviews
Top guest favorite
A panoramic view of the ocean is visible, with gentle waves lapping at the sandy beach. Below, an outdoor pool is surrounded by lounge chairs and clear pathways, providing a peaceful atmosphere. Skies are blue, enhancing the serene coastal setting.
Condo in Ocean City

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

4.88 out of 5 average rating, 147 reviews
Guest favorite
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

Oceanfront Family Oasis: Pool, Beach & Parking!

4.9 out of 5 average rating, 366 reviews
Top guest favorite
A balcony is shown featuring two red Adirondack chairs and a small table, positioned to overlook the vast ocean. The horizon is visible in the distance, with a sandy beach below, inviting relaxation and scenic views.
Condo in Ocean City

Luxury Oceanfront Getaway!

4.96 out of 5 average rating, 104 reviews
Guest favorite
The living area features a modern design with a sleek Italian leather sofa and a wall-mounted flat-screen TV. An electric fireplace is installed beneath the TV, while a coffee table and a single chair complement the space. Ample natural light enters through a nearby window.
Condo in Ocean City

Bluewater Couples Escape

4.97 out of 5 average rating, 318 reviews
Top guest favorite
A bright living area features a blue sofa, a striped armchair, and a wooden coffee table. Natural light flows through sliding glass doors that lead to a balcony with ocean views. Light curtains frame the view, and a TV is mounted on a light-colored media console.
Condo in Ocean City

21st Floor Carousel - 2 BR Oceanfront & Bay View

4.96 out of 5 average rating, 120 reviews
Guest favorite
A spacious living area features a cozy arrangement of seating with patterned upholstery and soft textures. A circular coffee table is centered amidst the furniture, and a wall-mounted television is paired with a stone accent wall. Large sliding doors open to the private balcony.
Condo in Ocean City

Beach Paradise 202-Downtown Luxury Condo Bay View

4.91 out of 5 average rating, 200 reviews
Guest favorite
A serene ocean view is presented from a private balcony, featuring two teal chairs. The sandy beach stretches into the distance, with gentle waves lapping at the shore. A clear sky completes the tranquil coastal scene, creating a peaceful atmosphere.
Condo in Ocean City

Oceanfront Paradise | Pool | Hot Tub | Beach

4.92 out of 5 average rating, 292 reviews

Other vacation rentals with a pool

Guest favorite
Farm stay in Berlin

Lux Estate Near OCMD w. Pool-GameRoom-Gym-Firepit

4.93 out of 5 average rating, 27 reviews
Top guest favorite
A welcoming entryway features a white door with a decorative window. Light wood flooring extends into a spacious living area, complemented by soft beige walls. A ceiling fan hangs above, while a table lamp illuminates a seating area. A glimpse of a well-equipped kitchen is visible in the background.
Apartment in Ocean Pines

Be our guest

4.99 out of 5 average rating, 68 reviews
Superhost
Home in Ocean Pines

Large House and Beach Club Access.

4.62 out of 5 average rating, 81 reviews
Superhost
A screened-in porch features a table covered with a floral tablecloth surrounded by four red chairs. Sunlight filters through the screens, illuminating the space, while trees provide a natural backdrop. The concrete floor is complemented by a simple area rug.
Home in Ocean Pines

Cozy Coastal Cottage Ocean Pines

4.79 out of 5 average rating, 57 reviews
Top guest favorite
A bright living area features a comfortable blue sofa and an armchair, with a decorative lamp beside them. A white coffee table sits atop a patterned rug, which complements the room's light decor. Two windows, adorned with blinds, allow natural light to filter in.
Home in Ocean Pines

Stubbe's Beach House, Home in Ocean Pines, MD

4.96 out of 5 average rating, 27 reviews
Top guest favorite
Home in Ocean Pines

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

5.0 out of 5 average rating, 67 reviews
Guest favorite
The exterior features a spacious gravel driveway leading up to a single-story home. A wooden deck wraps around the entrance, surrounded by landscaped areas with plants. Trees provide shaded spots, contributing to a calm outdoor environment.
Home in Ocean Pines

Par 5(28)

4.92 out of 5 average rating, 13 reviews
Top guest favorite
Home in Ocean Pines

Beach Club Pass 3BD, 2BA Peace in the Pines

4.95 out of 5 average rating, 21 reviews

When is the best time to visit Ocean Pines?

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Avg. price€147€137€144€153€176€225€242€240€191€174€143€153
Avg. temp3°C4°C7°C13°C18°C23°C26°C24°C21°C15°C9°C5°C

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