House vacation rentals in Ocean Pines

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.

4.94 out of 5 average rating, 275 reviews

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!

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.

4.95 out of 5 average rating, 39 reviews

Salty Serenity

Relax and recharge at our cozy 3 bed/2 bath home in Ocean Pines, a peaceful community near Ocean City, MD. Enjoy bikes, kayaks, and a fire pit in the large backyard, or use the pools, marina, yacht club, and golf course in the neighborhood. Beach parking at the Ocean Pines Beach Club in Ocean City is included. You can explore the boardwalk, casino, outlets, and the many nearby restaurants. Or, visit Berlin, or see the wild horses at Assateague Island. Come experience all the area has to offer!

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, 137 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.

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!

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.

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.

4.85 out of 5 average rating, 106 reviews

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!

A wooden pier extends into calm waters, framed by posts topped with white caps. A vibrant sunset bathes the scene in warm hues of orange and yellow, reflecting beautifully on the water's surface. The distant silhouette of trees and community is visible against the dramatic sky.

4.81 out of 5 average rating, 212 reviews

Bayside community near OCMD great rates

Welcome to MERMAID DREAMS where you can have FUN or just RELAX! We are ONLY 5 miles from OC, MD beaches/boardwalk & Assateague National Park/beaches. Our gated, beautiful community, is bayside, has 2 awesome pools, big splash pool, rec center, a fishing/crabbing pier, pond with paddle boats, 2 playgrounds+ more For kiddos of all ages, we are located right next door to Frontier Town, which has awesome water slides , western shows, mini golf, a rope course, ice cream shop..

A barn-style exterior of the condo is showcased, featuring a metal roof and three large garage doors at ground level. The second floor includes a deck with an entrance door. Expansive green space surrounds the property, with trees visible in the background under a clear blue sky.

4.95 out of 5 average rating, 82 reviews

SpaciousCondo nearOcean City|Winery|Golf on 5Acres

Come stay in our 2nd Floor Condo on our private 5-Acre Property! Enjoy the Barn-Like look from the outside, but inside, find a modern & spacious condo with a fully-equipped kitchen. Located in Berlin, Maryland, you are minutes to Historic Berlin and only 15 minutes to all the fun that Ocean City, Maryland has to offer! Have your morning coffee on the deck and soak in the scenic views or pitch a tent, light up the fire pit, let the kids run wild! We'll see you soon!

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, 137 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*

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.

Popular amenities for Ocean Pines house rentals

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.

4.96 out of 5 average rating, 24 reviews

Beach Paradise 2101-Downtown Luxury Condo Bay View

A charming ranch-style home is set against a backdrop of greenery, featuring a welcoming front deck with seating. The light-colored exterior is complemented by clear glass windows and a decorative front door. A well-maintained lawn and pathway enhance the inviting curb appeal.

4.6 out of 5 average rating, 10 reviews

Pet friendly with fenced in backyard!

5 out of 5 average rating, 106 reviews

Home in Frankford

Quiet 3BR Coastal Home Minutes to Bethany Beach

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

4.89 out of 5 average rating, 38 reviews

Cozy Stay by the Bay

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.

4.97 out of 5 average rating, 69 reviews

Coastal Oasis in Ocean Pines

5 out of 5 average rating, 22 reviews

A canal-front lodge is illuminated by a sunset, with boats gently moored along the waterfront. Inset is a vibrant community pool area, featuring sunbathers enjoying the water and surrounding deck. The inviting structure displays a welcoming ambiance, highlighted by an American flag and umbrellas on the deck.

Home in Selbyville

Waterfront | Pet Friendly w Pool Access | Crabbing

A pair of teal Adirondack chairs sits on a wooden dock overlooking calm water. Decorative pillows add a touch of comfort. Boat slips are visible in the background, with a soft reflection on the water's surface as the sun sets behind scattered clouds.

4.95 out of 5 average rating, 39 reviews

Cottage on the water

House rentals with a hot tub

A front porch features two white rocking chairs and a small side table, set against a backdrop of textured green wall panels. Soft lighting from a nearby lamp casts a warm glow, while decorative elements add charm alongside gravel and grassy landscaping.

4.95 out of 5 average rating, 66 reviews

Charming Cottage-Private Hot tub, Dock&Pool Access

4.97 out of 5 average rating, 30 reviews

A spacious swimming pool reflects the clear blue sky, surrounded by lounge chairs and umbrellas. Several tall trees provide subtle shade, while well-maintained pathways lead to various seating areas. The pool is designed for relaxation and leisure activities.

Home in Selbyville

Mallard Lakes 258

A spacious living room features a large brown sectional sofa adorned with colorful throw pillows. A round coffee table sits in the center, surrounded by a light-colored woven rug. Natural light floods the space from multiple windows, highlighting the decorative wall mirrors and neutral tones.

5 out of 5 average rating, 30 reviews

Cottage on Snug Harbor with hot tub!

A modern kitchen features a spacious island with four black bar stools positioned around it. White cabinetry is paired with stainless steel appliances, including a refrigerator and microwave. Natural light is provided by recessed lighting and a large window, creating a bright, inviting cooking space.

5 out of 5 average rating, 26 reviews

Ocean View Paradise w/Hot Tub & Free Massages!

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.

4.9 out of 5 average rating, 40 reviews

Boho Beach Golf Villa- 2026 booking fast!

The exterior view captures a two-story house situated by the waterfront, surrounded by expansive wetlands and serene ponds. The vibrant green landscape contrasts with the blue water, providing a picturesque backdrop for relaxation. Nearby, the distant skyline is faintly visible.

4.97 out of 5 average rating, 66 reviews

Hot Tub & Pool Table Waterfront Home | 4King Beds

A two-story home is presented with a light yellow exterior and white accents. A welcoming front porch features steps leading to the entrance. Lush greenery frames the property, while a garage is visible on the left. The surrounding area is well-maintained with a neat lawn.

4.81 out of 5 average rating, 100 reviews

Bethany Beach House, Bear Trap Dunes Golf Course!

A large, multi-story beach mansion is showcased in the early evening light. The exterior features a mix of blue siding and white trim. Lush greenery and colorful plants surround the entrance, while multiple balconies are visible on the upper levels.

4.96 out of 5 average rating, 52 reviews

Epic Luxurious Mansion Bayside Pools Tennis

Weekly house rentals

A dining area displays a wooden table set for six, featuring white plates, silver cutlery, and sparkling glasses. A vibrant centerpiece of sunflowers and decorative pumpkins is placed on a bright red runner. The adjoining kitchen is visible, showcasing modern cabinetry.

4.97 out of 5 average rating, 64 reviews

Summer By The Sea

An airy living space is highlighted by a high ceiling and large windows, inviting natural light. A gray sectional sofa faces a stone fireplace and a mounted television. Light blue cabinetry marks the kitchen area, with a dining table positioned nearby for flexibility.

5 out of 5 average rating, 11 reviews

Family Oasis - 4BR 3BA on Golf Course

4.8 out of 5 average rating, 10 reviews

The Ultimate Bayside Beach Escape

4.5 out of 5 average rating, 4 reviews

Bayfront on Brighton~Waterfont~No Pet Fee

A tranquil waterfront scene captures a canal-side home surrounded by lush greenery. A private boat slip is visible alongside the property, accommodating boats up to 23' long. The sun-filled exterior features a light-colored facade and a cozy patio, enhancing the serene atmosphere.

5 out of 5 average rating, 21 reviews

Waterfront Vacation Home in Ocean Pines

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

A spacious living area features a soft sectional sofa, positioned for cozy relaxation. A gas fireplace, framed by a white mantel, adds a warm touch. A smart TV is mounted on the wall, and a glass door leads to a dining area with natural light.

4.89 out of 5 average rating, 37 reviews

Serene OP cottage perfect for families!

The open-concept living room features two dark sofas adorned with decorative pillows, centered around a round coffee table. Bright overhead lighting illuminates the space, which leads into a modern kitchen visible in the background, creating a welcoming and functional gathering area.