Holiday rentals with outdoor seating in Ocean Pines

Guest suite in Ocean Pines

A cozy living area features a white couch and two accent chairs with a leaf pattern. A glass coffee table sits on a woven area rug. Large sliding doors provide a view of the outdoor patio, framed by greenery and water, enhancing the space's natural light.

4.95 out of 5 average rating, 392 reviews

Stunning private waterfront suite

Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City. Park in the driveway and step into your own private escape!

4.97 out of 5 average rating, 198 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

Ocean Pines Winter Retreat

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 open living area is highlighted by large windows that offer views of the bay and pool. A comfortable sectional sofa is positioned adjacent to a smart TV, while a modern dining table for four is visible next to the kitchen. The space features light-colored walls and natural wood flooring.

4.96 out of 5 average rating, 107 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! 🌊☀️

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, 137 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!

4.84 out of 5 average rating, 103 reviews

The living room features large windows adorned with floral-patterned drapes, allowing natural light to fill the space. Two comfortable chairs, including a recliner and a plush seating option, are positioned next to a coffee table. A television rests on a light-colored media unit, enhancing the room's functionality.

Home in Ocean City

Ocean City Townhome by Beach Bayside

If you're looking for a vacation home, consider this convenient duplex located just a few blocks from the beach. Situated on the second floor, this vacation rental offers all the necessary amenities for a comfortable stay with Food lion, Target and Marshalls nearby. Enjoy a short, seven-minute walk to Harpoon Hanna's, a local restaurant hotspot. For entertainment, Jolly Roger Amusement Park, James Farm Ecological Preserve, Roland Convention Center, host regular sports events and live shows.

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, 107 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!

A light-filled living room features a cozy sofa adorned with decorative pillows in warm colors. Artwork in simple frames complements the bright walls. A textured rug sits beneath a coffee table, enhancing the inviting space. A ceiling fan and light fixtures add functionality.

4.92 out of 5 average rating, 104 reviews

North OC|Fully Stocked 2 Bd 2 Bath

Welcome to Your Beach Lover's Paradise! Experience a vacation in a 2-bed, 2-bath condo, steps from Ocean City's shores. Stocked kitchen w/ new appliances, coffee, pots, pans, & dishes for all your meal needs. The condo features a washer/dryer, a cozy living room w/ a smart TV, and a balcony off the master. Sleeps 6 (twin bunk beds, twin, queen, pullout) Walk to the beach in 11 min & nearby attractions like Harpoon Hannah's, Fenwick Island, & Sunsations. Linens/towels provided. Book now!

4.96 out of 5 average rating, 485 reviews

The living area features large sliding doors that open to a porch with stunning bay views during sunset. A neutral-colored couch and a cozy chair create a welcoming space. A wooden dining table complements the serene atmosphere, illuminated by the warm glow from the setting sun.

Townhouse in Ocean City

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

A spacious bedroom features a king bed adorned with blue linens and a patterned blanket. Natural light filters through the window, which is covered by blackout shades. A vibrant surfboard art piece hangs above, adding a coastal touch to the serene atmosphere.

4.99 out of 5 average rating, 113 reviews

Perfect Wave-100 steps to Beach Sleeps 4

Step into Perfect Wave, your breezy beachside escape, mere moments from the tranquil Ocean City shores. Top floor no elevator. Strict no smoking no pets and no more than 4 guests. Imagine a tranquil retreat where the beach is just a whisper away. Welcome to Perfect Wave, your top-floor sanctuary, where the rhythm of the ocean sets the pace for your idyllic getaway. With a bevy of dining options and local attractions at your doorstep, you're poised to craft the vacation of your dreams.

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.

A cozy living area presents a light brown couch adorned with colorful cushions and a decorative throw. Two accent chairs sit across from the couch, positioned on a patterned area rug. Natural light filters through sheer curtains covering a large window, illuminating the space.

4.97 out of 5 average rating, 105 reviews

Sweet Retreat

Sweet Retreat is conveniently located in Ocean Pines, Maryland. The premiere residential and resort community of Ocean Pines is located eight miles inland from the ocean resort town of Ocean City. Ocean Pines has over 9 miles of waterfront property and 3,000 acres of wooded areas. Community amenities include beaches, a yacht club, golf course, community center, a Beach Club Pool and other community pools. Passes are available at ocean Pines Association.

An open-concept living space features comfortable seating, including a cozy sofa and accent chair. A dining area with modern chairs complements an equipped kitchen, showcasing stylish cabinetry and stainless-steel appliances. Large windows offer expansive views of the ocean and bright natural light.

4.93 out of 5 average rating, 138 reviews

WraparoundBalcony-2 Bed-Sleeps 8-Pool-Laundry-WiFi

Welcome to our stunning oceanfront retreat! This luxurious property offers the perfect combination of comfort, style, and breathtaking views. With a spacious J-shaped wraparound balcony, you can indulge in panoramic vistas of the sparkling ocean waves from every angle. Ideal for groups of up to 8 guests, this two-bedroom, two-bathroom getaway provides ample space for everyone to unwind. Book today for the vacation you'll never forget!

Popular amenities for outdoor seating rentals in Ocean Pines

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.9 out of 5 average rating, 608 reviews

A charming tiny house features wooden shingles and a welcoming front door. It is framed by colorful flowers in a garden, enhancing the outdoor landscape. A sign above the door adds a personal touch, while large windows allow natural light to fill the space.

Home in Ocean View

Tiny House at Good Earth, near Bethany Beach

4.85 out of 5 average rating, 198 reviews

The cottage exterior is seen with a large deck featuring white railings and a blue and white striped awning. A set of outdoor furniture is arranged on the deck, and steps lead down to a grassy area. The well-maintained, light-colored siding complements the serene environment.

Home in Fenwick Island

Hall Cottage, Fenwick Island, DE

4.97 out of 5 average rating, 29 reviews

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.

Home in Ocean City

Direct Bay Front Epic Sunsets Rooftop Pool

Superhost

A cozy living area features a leather armchair positioned next to a small side table with a lamp. A storage chest rests on the floor beneath a collection of framed artworks and a flat-screen television, enhancing the eclectic atmosphere of the space.

Home in Berlin

4.83 out of 5 average rating, 138 reviews

Joy in the Morning @ Berlin Boho Bungalow

4.81 out of 5 average rating, 212 reviews

The kitchen area showcases wooden cabinetry and a central island, with essential appliances visible. A round dining table with wooden chairs is positioned nearby. Natural light is introduced through a window, creating a bright and functional cooking space.

Home in Berlin

Bayside community, near OCMD, great rates

An open-concept living area features a well-equipped kitchen with modern appliances and a dining table surrounded by blue chairs. A spacious seating area is visible, leading to a staircase that ascends to an upper loft with a railing overlooking the main level.

4.96 out of 5 average rating, 117 reviews

Newly Renovated Ocean Pines Cottage

A vibrant living area is highlighted by tropical-patterned wallpaper and warm wooden flooring. Comfortable seating is arranged around a central coffee table, complemented by an accent table in the corner. A large mirror reflects the space, adding depth and light.

4.85 out of 5 average rating, 40 reviews

Cottage in the Pines

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.

Apartment rentals with outdoor seating

A light-filled room features a cozy gray sofa and a large bean bag chair with decorative pillows. Three framed ocean-themed prints decorate the walls, contributing to a calming ambiance. Natural light streams through two white-framed windows with light blinds, illuminating the space.

4.9 out of 5 average rating, 31 reviews

Mermaid Cove

A spacious living area features a modern sectional sofa adorned with soft green accent pillows. A light-colored coffee table sits in the center, accompanied by a woven tray. Sheer curtains frame the large windows, allowing natural light to fill the room.

4.91 out of 5 average rating, 58 reviews

Bright Condo Close to Beach w/ Parking

A light-filled living area features two armchairs and a spacious sectional sofa, complemented by a wooden coffee table. A large TV sits on a wooden console, while a plant adds a touch of greenery. Sunlight streams through the sliding doors leading to a balcony.

5 out of 5 average rating, 48 reviews

Renovated 1BR w Ocean View

A spacious covered deck features a hammock swaying gently, with ocean views under a colorful sunset. Light reflects off the water, creating a serene atmosphere. A white outdoor table is positioned nearby, providing a spot to enjoy the scenery and salt breeze.

4.94 out of 5 average rating, 62 reviews

Endless Summer With Ocean View & Large Deck

A cozy sleeping area is displayed with a queen-sized bed adorned with a light blue blanket and decorative pillows. Soft lighting is provided by a bedside lamp. Artwork is arranged on the walls, adding a touch of color and personality to the space.

4.92 out of 5 average rating, 113 reviews

West Ocean City: Private Studio, Close To Beach

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.

4.89 out of 5 average rating, 19 reviews

North OC- short walk 2 beaches and park

Superhost

A private covered back deck features two turquoise chairs, offering a view of a tidal lagoon. The scene includes a railing highlighting the outdoor space and includes vibrant green vegetation. Soft clouds are visible against a blue sky, enhancing the serene atmosphere.

4.88 out of 5 average rating, 8 reviews

Beachy Getaway

A bright bedroom features floor-to-ceiling windows providing panoramic ocean views. A queen bed is centered against a light-colored wall, complemented by a patterned quilt. A dresser and wall-mounted television complete the space, with natural light illuminating the calming atmosphere.

5 out of 5 average rating, 56 reviews

SuperHost! Amazing OceanFront View with 2 Pools!

Apartment rentals with outdoor seating

The living area showcases an open layout with high ceilings and modern furnishings. A light gray sofa and patterned accent chairs surround a coffee table. A wall-mounted television and a stylish fireplace are visible. The kitchen area offers bar seating and white cabinetry, complemented by beach-themed artwork.

4.86 out of 5 average rating, 100 reviews

Summer Palace in Ocean city .

A cozy bedroom features a full bed covered with a light blue quilt. A dark wooden nightstand holds a decorative tray and lamp. A vintage cabinet adorns the wall, while a large piece of ocean-themed artwork complements the space. Natural light illuminates the room from nearby windows.

4.9 out of 5 average rating, 126 reviews

☀️ Ocean block | Midtown OCMD

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.

4.87 out of 5 average rating, 114 reviews

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

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, 124 reviews

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

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, 303 reviews

Direct Oceanfront with a View and Amenities Galore

Two chairs are positioned beside a small round table, offering a serene view of the ocean through large windows. The sandy beach stretches out beneath a cloudy sky, with gentle waves lapping at the shore.

4.98 out of 5 average rating, 121 reviews

Ocean front condo with Balcony

The oceanfront view includes soft sandy beaches leading to calm waters. Dunes with sparse grass cover offer a natural barrier, while a small wooden walkway provides access to the beach. A building with a red roof and white exterior is positioned nearby, enhancing the coastal setting.

4.97 out of 5 average rating, 150 reviews

Renovated Ocean Front! Wake up to an Ocean View!

A bright living area features large windows that offer views of the ocean and a gentle breeze. Comfortable seating is arranged around a soft ottoman, with decorative pillows enhancing the space. Natural light floods in, creating an inviting and airy atmosphere.