Holiday rentals with a pool in Ocean Pines

An A-frame structure is set amidst lush greenery, featuring a welcoming front porch with steps leading up to the entrance. Two bicycles are positioned nearby, and vibrant flowers adorn the edges. Sunlight filters through the leafy trees, enhancing the natural surroundings.

5 out of 5 average rating, 52 reviews

hi-A-tus A-frame

Charming A-frame nestled in the heart of Ocean Pines. Open floor plan, softest sheets, flat screen TVs, high speed WiFi, in an amenity filled community surrounded by multiple beaches. 10 min from Ocean City and 15 min from Assateague! Sleeps 4 comfortably. Perfect for 4 adults or family. Must be 25 yrs old. Enjoy all that Ocean Pines has to offer including 5 pools, multiple playgrounds, yacht club and farmers market. Weekly rental during the high season. Please inquire about longer stays.

A spacious living area features two sofas, one in dark leather and the other in a light fabric, arranged around a low wooden coffee table. A flat-screen TV is mounted on a light wall above a stone fireplace, adding a cozy touch to the room.

4.97 out of 5 average rating, 133 reviews

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.

Relax with the family in this comfortable and charming home. There is room for 8 to sleep comfortably. The dining room and breakfast nook offer plenty of seating for all with a spacious kitchen. Our corner lot offers the option for outdoor fun like slip and slide, corn hole, frisbee, and more! Nearby: Beach, Bay, Wildlife sanctuary surrounded by a walking trail, Pool, Tennis, restaurants & Eventful Northside Park! Quiet and peaceful location to make family or romantic memories of a lifetime.

4.97 out of 5 average rating, 196 reviews

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.

Apartment in Ocean Pines

Pines Getaway - Berlin Tree Light & Ice Ice 11/28

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

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.

4.98 out of 5 average rating, 136 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.

4.96 out of 5 average rating, 138 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.

A charming cottage exterior is showcased, featuring a distinctive A-frame design. The front porch is framed by wooden railings, while a path of stepping stones leads to the entrance. Surrounding trees provide a natural backdrop, enhancing the serene outdoor environment.

5 out of 5 average rating, 21 reviews

Ocean Pines 2BR 1BA Cottage with Fire Pit

Pint-sized, pet friendly cottage close to everything, the perfect, quiet little sanctuary. Full kitchen in case you wish to cook in one night. Dining table and a cozy living room. Board games, yard games, pickle ball equipment, outdoor seating, fire pit and a grill round out this amazing cottage. Accommodates 6 people, recommend no more than 4 adults. Close to the Woodlands Restaurant & the Pines Public House. Not far from the Ocean Pines Sports Core Pool and the Ocean Pines Golf Club.

5 out of 5 average rating, 115 reviews

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.

Home in Berlin

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!

A spacious living room features a comfortable dark sofa, two brown chairs, and a cozy fireplace. Natural light enters through large windows adorned with light blue drapes. A ceiling fan and recessed lighting contribute to a bright and airy atmosphere, complemented by modern decor.

4.99 out of 5 average rating, 102 reviews

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines

Beautifully updated and recently renovated, rancher on a great street in Ocean Pines perfect for families and adults looking for a relaxing stay. We offer 3 bedrooms and 2 bathrooms on one level, with new large flat screen TV's, stainless appliances, and everything you'll need for your stay. We have a large driveway and a screened patio. Ocean Pines boasts over a dozen parks and walking trails, a public Yacht Club, 5 pools, 2 marinas, and a championship golf course - 10 min to the beach!

Guest suite in Ocean Pines

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.

4.99 out of 5 average rating, 135 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.

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.

4.95 out of 5 average rating, 300 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.

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.

4.96 out of 5 average rating, 280 reviews

Caramar Couples Retreat

This cute little first floor efficiency condo is ocean front for a perfect vacation to the beach. It’s an older building but has been partially renovated and updated. You can get to the beach by a very short walk through a private walkway from the condo building. The view from the private balcony is perfect and relaxing. WiFi provided upon check in- xfinity, Netflix, and internet. Indoor and outdoor dining areas and a full kitchen. Closet and dresser for storage use.

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.

4.85 out of 5 average rating, 136 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*

Popular amenities for Ocean Pines rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The living room features two plush sofas and two accent chairs, arranged around a circular coffee table. A flat-screen TV is mounted above a gas fireplace, and large windows allow natural light to fill the space, showcasing views of the bay.

4.95 out of 5 average rating, 21 reviews

Beach Paradise 2101-Downtown Luxury Condo Bay View

A spacious living area features large windows revealing expansive ocean views. A cozy seating arrangement is positioned near a modern fireplace. Light-colored walls and a neutral coffee table complement the calming atmosphere, while sliding doors provide access to a balcony with additional seating.

4.96 out of 5 average rating, 26 reviews

Direct Bay Front Epic Sunsets Rooftop Pool

4.93 out of 5 average rating, 14 reviews

Bayside Breeze Getaway @ the Makai

A charming bayside home features a covered porch adorned with twinkle lights, creating a welcoming entry. The exterior showcases light-colored siding, large windows, and landscaped greenery, complemented by playful flamingo decorations on the front lawn.

4.97 out of 5 average rating, 106 reviews

Beach Oasis w/ King Suite + Outdoor Shower & Pool

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.

4.95 out of 5 average rating, 42 reviews

Beautiful Spacious 4 Bedroom Home in Ocean Pines

4.9 out of 5 average rating, 39 reviews

The living room features ample seating on a sectional couch, complemented by an area rug and coffee table. Natural light streams through large windows, illuminating the space. A TV and sound bar are mounted on the wall, enhancing the entertainment options.

Home in Ocean View

Boho Beach Golf Villa

The expansive view showcases the sandy beach stretching along the Atlantic Ocean, gently reflecting the clouds above. Features include a shared pool bordered by lounge chairs and landscaped areas. The setting sun casts warm hues over the water, enhancing the serene coastal atmosphere.

4.79 out of 5 average rating, 14 reviews

Oceanfront | Beachfront | Elevator | eFireplace

5 out of 5 average rating, 54 reviews

A cozy family room is presented with a large flat-screen TV mounted above a stone fireplace, featuring comfortable seating options, including a spacious sofa and a futon. Vibrant arcade games are visible against the textured wall, enhancing the entertainment options.

Home in Bethany Beach

Coastal Cottage! Walk to Beach!

Apartment rentals with a pool

A comfortable living area features a light-colored table surrounded by ocean-themed upholstered seating. Large glass doors allow natural light to fill the space while offering a view of the balcony and ocean beyond. A flat-screen television is mounted on the wall.

4.9 out of 5 average rating, 116 reviews

Oceanfront Carousel building, Swimming Pools!

Apartment in Bethany Beach

A circular swimming pool is surrounded by sun loungers and shaded umbrellas, inviting relaxation. The beach lies in the background, with a stretch of sandy shore and blue umbrellas, while guests enjoy the sun and water nearby.

4.88 out of 5 average rating, 189 reviews

Beautiful Beach-View Condo

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.

4.91 out of 5 average rating, 330 reviews

Oceanfront Family Oasis: Pool, Beach & Parking!

A comfortable living area features a gray sofa with blue accent pillows and a textured rug. Large sliding glass doors offer a view of the ocean and access to a private balcony with outdoor seating. Natural light fills the space, creating a welcoming atmosphere.

4.98 out of 5 average rating, 242 reviews

Cozy oceanfront condo with stunning ocean views

A three-story building with a light blue exterior is shown. Multiple balconies are visible, equipped with railings, and the entrance is marked by a sign. Underneath the structure, a private parking area is accessible, with a gate in the foreground.

4.84 out of 5 average rating, 136 reviews

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

Three condominium buildings rise against a clear blue sky, showcasing varied architectural styles with prominent glass and concrete facades. A sandy path leads toward the beach, bordered by a wooden fence that adds a natural touch to the coastal view.

4.95 out of 5 average rating, 108 reviews

Oceanfront Bldg.| 2 pools | Tennis | Game Room

An open-concept living and dining area features a wooden dining table set for six, complemented by modern chairs. A comfortable seating arrangement with light-colored couches is situated near large windows, offering views of the surrounding area. A mounted TV and decorative elements enhance the space.

4.96 out of 5 average rating, 122 reviews

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

An open-concept living area is featured with beach-inspired decor, a spacious sofa, and a dining table for six. Large sliding glass doors provide access to an oceanfront balcony with stunning views. A ceiling fan is installed for added comfort.

4.99 out of 5 average rating, 145 reviews

🌊Carousel Oceanfront 2 Bedroom Amazing Amenities

Other holiday rentals with a pool

A comfortable living room features a light-colored sectional sofa adorned with blue and patterned cushions. A coffee table displays decorative items, and a side table holds a lamp. Natural light is filtered through sheer curtains, illuminating artwork on the walls and indoor plants.

4.88 out of 5 average rating, 8 reviews

Spacious seashore getaway.

4.96 out of 5 average rating, 79 reviews

A cozy seating area is positioned on the waterfront, featuring plush cushions and decorative pillows. Two lanterns with candles add ambiance. Lush greenery and a clear sky are visible in the background, enhancing the serene view of the water.

Home in Berlin

Private pool, waterfront, kayaks, bikes, firepits!

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.

5 out of 5 average rating, 18 reviews

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

A cozy living area features a comfortable grey sofa adorned with beach-themed pillows. Light wood flooring complements the dining area, which includes a small table and four chairs. The open kitchen is visible in the background, equipped with white cabinetry and modern appliances.

5 out of 5 average rating, 59 reviews

Top Rated! Beautful Sunsets! Midtown Bayside Condo

4.89 out of 5 average rating, 18 reviews

The kitchen features wooden cabinets and a mosaic tiled backsplash. A center island with three rattan bar stools is present, alongside full-sized appliances, including a refrigerator and stove. A staircase is visible in the background, leading to the upper level.

Flat in Ocean City

North OC- short walk 2 beaches and park

4.96 out of 5 average rating, 28 reviews

An aerial view of a well-appointed beach club showcases a spacious outdoor pool surrounded by lounge chairs and umbrellas. A tennis and pickleball court is visible, along with a serene pond nearby. The surrounding landscape features neatly arranged homes and lush greenery.

Townhouse in Ocean View

OceanViewBeachClub-minutes from Bethany Beach/Golf

Holiday home in Ocean Pines

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.

4.91 out of 5 average rating, 94 reviews

Bayside Blue Getaway near Ocean City

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.