Vacation rentals with a patio in Ocean Pines

4.97 out of 5 average rating, 98 reviews

A vibrant neon sign reading 'Sea Glass Sunrise' is framed by lush green foliage, set against a backdrop of a serene beach at dawn. The soft pastel colors of the sky create a peaceful atmosphere, enhancing the welcoming ambiance of the space.

Condo in Ocean City

Gorgeous New Beachfront! King Bed, Direct Sea View

Stunning beachfront condo with direct view of the ocean! Your vacation home away from home! Everything you need right ON the beach. All linens, supplies and a well-stocked kitchen! New 65" TV w/free 4K Netflix provided! Modern serene decor in the heart of OC! Feel like getting out? Enjoy walking distance to Seacrets, Mackey's, and Fager's Island, Subway, Candy Kitchen or Dumsers' Dairyland! More adventure? Walk to minigolf, pontoon boats and jetski rentals! Only 4 minute drive to the boardwalk!!

5 out of 5 average rating, 108 reviews

The living area features comfortable electric reclining sofas facing a coffee table. Large windows provide views of the ocean, while a dining area and modern kitchen are visible in the background, creating a spacious and inviting atmosphere.

Condo in Ocean City

2BRCapri: Indoor Pool, Game Room, Massage Chair

ALL THE COMFORTS OF HOME AT THE BEACH! BRAND NEW RENOVATED BATHROOMS! -ALL LINENS INCLUDED -Comfortable electric-reclining sofas -65-in smart Roku TV with soundbar. -Massage chair in master bedroom -Balcony & Dining Area w/ Ocean +Bay Views -In-unit W/D -Many conventional & USB Outlets -Arcade level features b-ball hoop, pool tables, ping-pong, shuffleboard, air-hockey -Outdoor tennis court -Large heated indoor pools -can swim full laps -Sauna and Gym -Board games in unit -Fast Wifi

4.93 out of 5 average rating, 117 reviews

A back deck features a seating area composed of a sofa and ottoman with soft cushions, facing a calm canal. A wooden table is positioned nearby. A red umbrella is closed and stands beside the seating, while a sunset casts gentle hues across the water.

Home in Ocean City

3 BR Waterfront Home, Minutes to the Beach

Recently updated waterfront house located in the family-friendly Montego Bay community. Enjoy beautiful sunsets on the back deck or hop in one of the kayaks for a paddle around the wide-open canal. Try your hand at crabbing or fishing off the dock to catch your dinner. Within easy walking distance of the beach and Northside Park (about 10 minutes walk to both). Beach chairs, toys, boogie boards, and umbrellas are yours to use for fun in the sand and surf. The dock is available for boat tie-ups.

The exterior of the Ocean Pines Chalet features a spacious deck with wooden railings, surrounded by trees. The A-frame structure showcases large windows that invite natural light. A wide driveway leads up to the property, providing ample parking space in a serene, wooded setting.

4.95 out of 5 average rating, 37 reviews

Ocean Pines Chalet

Nestled in the tranquil Ocean Pines, MD, Ocean Pines Chalet is a picturesque 4-bedroom, 3.5-bath haven exuding coastal charm. This delightful retreat is surrounded by a plethora of local amenities including community pools, parks, tennis and basketball courts, skate parks, golf, and a yacht club. A 15-minute drive from the bustling Ocean City beaches, it offers the perfect blend of serene living and beachside excitement, making it an ideal getaway for those seeking both relaxation and adventure

4.94 out of 5 average rating, 131 reviews

A living room features light blue seating arranged around a coffee table, complemented by a decorative cabinet and a large television. Natural light filters through the window, enhancing the tranquility of the space, which is accented by a ceiling fan and wall art above the entrance.

Home in Selbyville

Central Haven with Great Fenced Yard

You will be close to everything when you stay in this centrally-located home. The rear deck and grill are great for enjoying time outside. There's a fenced rear yard, making this home a perfect choice for man's best friend. We welcome dogs of any breed, size, and weight. We do offer size-specific pet amenities, so please share a photo of your dog when booking, or provide a basic description so we can set out appropriate amenities. For those traveling with cats, please inquire before booking.

4.92 out of 5 average rating, 78 reviews

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, >3 guests may apply.

4.99 out of 5 average rating, 179 reviews

Cottage in Frankford

19th Century Coastal Cottage with Modern Amenities

Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. Exposed wood beams and interior brick walls as well as all the luxuries required for a rural escape. This charming cottage near the beach & is surrounded by enchanted gardens. You will swoon over the carved marble bathtub and gorgeous living areas. Perfect for a romantic getaway, Hobbs and Rose Cottage is waiting to create a memorable experience for you! NEW for 2025, our mediation room!

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, 97 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!

Superhost

A beach-front balcony features two comfortable lounge chairs and a matching ottoman, all adorned with light green and white striped cushions. A small lamp sits on the floor beside the chairs. A view of the ocean with clear blue skies and a sandy beach is visible in the background.

Condo in Ocean City

4.81 out of 5 average rating, 102 reviews

Lovely beach-front condo with pool and views

Kick back and relax in this calm, stylish space. This one-bedroom condo is the perfect space for 1-2 couples, or a family. You have floor-to-ceiling beach views, plus amazing sunrises and sunsets from the two separate balconies. The kitchen is well equipped to cook every meal, or eat out at Ocean City's many restaurants. Your stay also comes with 4 pool passes for accessing the onsite seasonal outdoor pool (viewable from the unit) and access to the building’s tennis/pickleball courts!

A family-friendly home is nestled among trees, featuring a cozy outdoor area with a hammock and fire pit. The interior includes a spacious living room with a Smart TV and a welcoming layout that captures natural light, presenting a relaxing environment for guests.

5 out of 5 average rating, 56 reviews

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

Escape to a serene family retreat in Ocean Pines, MD! Our peaceful home offers the best of both worlds—quiet wooded relaxation with access to seasonal community pools and amenities, plus proximity to Ocean City beaches (less than 10 miles), Golf Club (2 miles), historic Berlin, and Assateague’s wild horses. Perfect for family getaways, with an arcade system, trails, playgrounds, restaurants, and more nearby. Book your stay today and follow us on IG @OceanPinesVacation for more!

A welcoming living room features a cozy sofa and two armchairs arranged around a circular coffee table. A flat-screen TV is mounted above a fireplace, while a decorative area rug with floral patterns adds warmth to the space. Natural light streams through sheer curtains.

4.96 out of 5 average rating, 69 reviews

Cozy home in Ocean Pines

Relax with the whole family at this peaceful place to stay, just 15 minutes away from Ocean City Beach. Our beautiful, comfortable rancher is conveniently located in the heart of Ocean Pines community, perfect for families and adults looking for a quiet, relaxing stay. This is a single-story home and accommodates up to 6 guests. We offer 3 bedrooms and 2 bathrooms, located in the south side of the Ocean Pines community.