Vacation rentals with outdoor seating in Ocean Pines

4.94 out of 5 average rating, 275 reviews

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

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

After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

4.9 out of 5 average rating, 186 reviews

A single-story home sits nestled among lush greenery, featuring a welcoming front porch with a wooden railing. A set of steps leads up to the entrance, flanked by large windows adorned with green shutters, complementing the home's neutral exterior.

Cottage in Ocean Pines

Cozy Beach Getaway in the Lovely Ocean Pines North

Welcome to our Cozy Beach Getaway!! ☀️🌊👙⛱️🐚🏖️🌞🌅⛅️ This beautiful and peaceful home is located in Ocean Pines North. 3 bedrooms, 2 bathrooms. Peaceful front porch and back deck. 🏡🏝️ Whether you’re looking for a summer family vacation, girls weekend getaway, or just a break from reality, this is the perfect place! Washer/dryer 🧺, two smart TV’s 📺, driveway fits 4 cars comfortably 🚗. Enjoy the hustling city of Ocean City during the day and stay in the tranquility and peaceful Ocean Pines at night! 🏖️💞☀️

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, 395 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, 203 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.

Condo in Ocean Pines

Ocean Pines marina view 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

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.

4.85 out of 5 average rating, 106 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.

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

Completely remodeled beach home with brand new furnishings in Ocean Pines. Open concept living on main level with beautiful well-equipped kitchen, seating for 10 total at island/dining table and a relaxing living room. Off the hallway is the king bedroom and separate full bathroom with bathtub. Spacious mud/laundry room with beach chairs, umbrella and wagon available for use. Open loft area upstairs with arcade game, lounging area, 2 additional bedrooms and full bath with stand-up shower.

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, 111 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, 310 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 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.

A charming house with large windows is situated by the water, framed by lush greenery. A wooden dock leads from the house to the water's edge, surrounded by tall grass. Soft evening light highlights the structure, creating a serene ambiance.

4.99 out of 5 average rating, 136 reviews

Charming Waterfront Cottage w/2 King Suites + Dock

Newly renovated, sparkling, spacious house with room for seven and waterfront views is waiting for you. Perfect for a single or double family getaway, girls weekend, or quiet retreat. *Please note this is a No Smoking and No Pet Property. **We are located in a quiet, residential neighborhood with lovely neighbors in close proximity. Please consider this when booking. ***We do not supply sheets and towels. Rental License #2162

Popular amenities for Ocean Pines outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

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, Delaware

5 out of 5 average rating, 58 reviews

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

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.

4.83 out of 5 average rating, 41 reviews

Cottage in the 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.

4.8 out of 5 average rating, 25 reviews

Ocean Pines 3BR 2BA Canal Front Home with Sunroom

A converted garage features a game room setup with a pool table and a dart board on the wall. Light filters through the windows, illuminating the patterned rugs on the floor. Two folding tables are positioned, awaiting use for gatherings or games.

4.9 out of 5 average rating, 63 reviews

Private, pet-friendly, w/game room & new kitchen

A living area is characterized by a spacious sectional sofa, positioned under a vaulted ceiling with exposed beams. Natural light enters through a skylight and a window, illuminating a mounted television and a decorative side table, enhancing the room's clean and inviting design.

5 out of 5 average rating, 18 reviews

Cozy Coastal Home in Ocean Pines

4.86 out of 5 average rating, 7 reviews

The Whale’s Tale Retreat w/ Beach Club Pass

4.98 out of 5 average rating, 44 reviews

The front exterior of The Cedar Cottage is showcased, featuring a gravel driveway leading to the entrance. A wooden deck is adorned with an umbrella and patio table, complemented by greenery and a wooden fence in the background.

Home in Ocean City

Cedar Cottage - 3 BR, 3 full bath, family-friendly

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 studio apartment showcases a king-size bed with a plush blanket, accompanied by nightstands and a smart TV mounted on the wall. A cozy seating area with a green sofa and a round coffee table is present, along with a dining table for four and access to a private balcony.

4.93 out of 5 average rating, 54 reviews

Studio Condo Steps to the Beach

4.89 out of 5 average rating, 19 reviews

Direct Oceanfront • Sunrise Views • Steps to Sand

A spacious balcony offers a relaxing view of the sandy beach and ocean. Colorful Adirondack chairs in vibrant hues are positioned for comfort alongside a round table, creating an inviting outdoor space. The horizon meets the gently rolling waves under a partly cloudy sky.

5 out of 5 average rating, 13 reviews

Oceanfront and on the Boardwalk!

4.97 out of 5 average rating, 33 reviews

The Shook Shack - Perfect Bayside & Beach Stay

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, 64 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

Condo rentals with outdoor seating

An open living area features a comfortable gray sofa, arranged on a colorful area rug. A dining table with seating for six is positioned nearby, and a bright kitchen with modern appliances is visible in the background. Natural light fills the space through windows adorned with cheerful curtains.

4.99 out of 5 average rating, 102 reviews

Ocean Aire Elegant Beach Getaway

4.93 out of 5 average rating, 104 reviews

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

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, 244 reviews

Cozy oceanfront condo with stunning ocean views

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 spacious living area features a blue sofa and chairs, complemented by a decorative area rug. A dining table and kitchen area are visible in the background, highlighting the open layout. Natural light illuminates the room through the windows.

4.96 out of 5 average rating, 155 reviews

Mid-Town OC! Ocean Block... Steps to the Beach!

A spacious efficiency is shown with a large bed dressed in neutral linens. A television is mounted on the wall, and modern wall sconces provide lighting. A comfortable seating area includes a gray couch. Floor-to-ceiling windows overlook the scenic view outside.

4.88 out of 5 average rating, 123 reviews

Oasis by the Ocean - Direct Oceanfront