Holiday rentals with a fireplace in Ocean Pines

4.99 out of 5 average rating, 133 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 Beachfront! King Bed, Direct Ocean 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!!

A single-story home with a well-kept exterior is surrounded by trees, providing a serene setting. A covered porch with railings welcomes guests, while a gravel driveway leads to the entrance. The property features a reliable trash can and is nestled within a natural landscape.

4.98 out of 5 average rating, 46 reviews

Tranquil Waters, OceanPines, 3 br, Dog Friendly

Peaceful Coastal Getaway – Dog Friendly! Relax with the whole family at this peaceful beach retreat! This 1,500 sq. ft. home away from home is perfect for a laid-back vacation near the shore. Featuring 3 bedrooms (King, Queen, and 2 Twins), this home is spotlessly disinfected before each stay and includes a full linen package for your comfort and convenience. Enjoy a free parking pass to the Ocean Pines Beach Club on 49th Street, and make the most of the beautiful outdoor space—a low fenced-i

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 OP. Open floor plan, softest sheets, flat screen TVs, high speed WiFi, in an amenity filled community surrounded by multiple beaches. 10 min from OC & 15 min from Assateague! Sleeps 4 comfortably. Perf for 4 adults or fam. Must be 25 yrs old. Enjoy all that OP has to offer including 5 pools, multiple playgrounds, yacht club & farmers market. Weekly rental during the high season (6/6 - 8/29), Sat check-in/Sat check-out only! If you book diff, we'll cancel

4.97 out of 5 average rating, 218 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

Water view at Ocean Pines Yacht Club 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 cozy living area features a light gray sofa adorned with decorative pillows and a small blue ottoman. Natural light brightens the space, showcasing art on the walls and a dining area in the background, complemented by a wooden table and chairs.

4.87 out of 5 average rating, 103 reviews

Home Away from Home , Pet friendly retreat

Welcome to Ocean Pines Getaway, Enter home through a beautiful covered porch with swing for two and lovely seating area. This sweet home has 3 bedrooms & 2 full baths. A fully stocked kitchen , with eat in breakfast nook, Also proper dining room plenty of seating for family Cozy living room with working fireplace. All season sunroom plenty of seating, pub table & bar. Doggie door in sunroom large enough for 100 lb dog, leads to fenced in backyard. $100 pet fee and $125 linens & bath towels.

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, 145 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!

4.95 out of 5 average rating, 127 reviews

A modern living room features a comfortable sectional sofa in neutral tones, paired with a rustic wooden coffee table. A television is mounted above a stone accent wall. Glass doors open to a balcony, allowing natural light to fill the space.

Condo in Ocean City

Breezy Point #305 - Rooftop Deck Panoramic Sunsets

Welcome to Your Bayside Escape at Breezy Point! Step into style at this sleek bayside condo where modern comfort meets bayside views. Relax on the rooftop terrace and enjoy stunning sunset views and the fresh air. Tucked just off 28th Street, you're near restaurants, shops and quick bites. The boardwalk and beach are an easy walk or a quick drive away. A comfortable and convenient home base for couples and families. Hosting a bigger group? Ask about our other units in the same building!

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, 138 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 charming house with a light blue exterior is surrounded by lush greenery. A spacious deck features potted plants and outdoor seating. Colorful Adirondack chairs in red and blue are placed around a small fire pit on a patterned stone patio, inviting relaxation.

5 out of 5 average rating, 14 reviews

Cozy beach home away from home!

Welcome! Come enjoy a cozy experience at this centrally located home in the desired Ocean Pines Community! This home is near the playground and allows access to the on-site golf course, five pools (including indoor pool!) tennis courts, and marina for a small fee. Fun in the sun awaits 15 minutes away in downtown Ocean City, where you can stroll the boardwalk, lounge on the sand, or hit the amusement park. Plenty of restaurants, grocery stores and shopping within 15 minutes.

5 out of 5 average rating, 239 reviews

A charming cottage facade is framed by white columns and features a gabled roof. Two black rocking chairs, adorned with pillows, sit on a brick porch surrounded by colorful potted flowers. Lush greenery enhances the inviting atmosphere.

Cottage in Frankford

Hobbs & Rose | A Peaceful Cottage Escape

Built in 1941 from historic “clinker bricks,” this restored cottage is a dreamy place to slow down and reconnect. Surrounded by enchanted gardens and close to the beach, Hobbs & Rose is filled with charm—gorgeous living spaces, a carved marble soaking tub, and thoughtful details throughout. Enjoy a romantic getaway and unwind in our Sanctuary meditation room, where birdsong and forest friends welcome you. You relax—we’ve created every detail to help you feel restored.

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, 107 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 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, 16 reviews

Family Oasis - 4BR 3BA on Golf Course

TWO primary suites (4BR) and TWO living areas make this house double the fun! Our relaxed and beautiful home on a beautiful golf course is just 10 minutes from Ocean City. Enjoy all the amenities of Ocean Pines (pools, tennis courts, golf course, parks and walking trails). Parking for 6+ cars. House is loaded with well equipped spacious kitchen, great room with awesome entertainment setup, and tons of extra bedding options.

Popular amenities for Ocean Pines Accommodation with Fireplace

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a fireplace

Superhost

The front of the unit is showcased with a beige exterior and a contrasting red door. A welcoming porch is set off by white railings and steps leading to the yard. Surrounding greenery adds a natural touch to the entrance.

4.79 out of 5 average rating, 19 reviews

Cozy Home near OC & Assateague Park

The exterior of a three-bedroom home is showcased amidst tall pine trees. A gravel driveway leads to a garage, while two blue chairs are positioned on the front steps by the entrance, inviting relaxation in the natural surroundings.

4.95 out of 5 average rating, 56 reviews

Coastal Retreat: River View & Pine Haven

A light-colored home is featured, set against a backdrop of trees. The large front window allows natural light to enter the living space. A gravel driveway leads up to the entrance, with a small porch and railing providing access to the front door.

4.85 out of 5 average rating, 53 reviews

Amazing and peaceful family fun 4 bedroom home

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, 58 reviews

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

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, 25 reviews

Waterfront Vacation Home in Ocean Pines

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.

4.96 out of 5 average rating, 46 reviews

Beautiful Spacious 4 Bedroom Home in Ocean Pines

The exterior of the waterfront home is shown, with a spacious deck and screened porch overlooking the water. Lush landscaping and a pathway lead to the dock, while large windows create a welcoming atmosphere. A patio umbrella provides shade for outdoor seating.

5 out of 5 average rating, 65 reviews

Ocean Pines, Waterfront Oasis

4.86 out of 5 average rating, 72 reviews

Ocean Pines Escape

Apartment rentals with a fireplace

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, 42 reviews

Mermaid Cove

The kitchen area features a wooden countertop with a modern sink and stylish faucet. Shelves hold various glassware and dinnerware, while a spacious dining area is visible in the background, showcasing a large table surrounded by natural lighting.

5 out of 5 average rating, 37 reviews

Bayside Bungalow - Waterfront

5 out of 5 average rating, 20 reviews

Perfect, Cozy, Modern Beach Condo

The spacious living room is furnished with a large sectional sofa and a smaller couch, providing ample seating. A wooden coffee table sits centrally on a light area rug. Natural light fills the room through sliding doors, leading to the dining area visible in the background.

4.94 out of 5 average rating, 89 reviews

Jada Ocean & Bay view pool steps away to the beech

5 out of 5 average rating, 12 reviews

A dining area features a black wooden table surrounded by eight chairs, set against cheerful yellow walls adorned with framed coastal artwork. A cozy living space includes a light blue sofa and additional seating, complemented by large windows allowing natural light to fill the room.

Apartment in Selbyville

Luxurious Bayville Shores Home Close to the Beach!

A well-appointed bedroom features a plush king-sized bed with decorative bedding. Natural light floods the room through a large oceanfront window, leading to a private balcony. A ceiling fan adds comfort, while a mounted TV provides entertainment options.

4.93 out of 5 average rating, 40 reviews

Oceanfront Oasis | Indoor Pool | Hot Tub | Deck

The exterior of the Beach Winds condo building is shown, featuring three levels with several balconies, white railings, and an overhang. The structure is painted in soft green and beige tones, with stairs ascending to each floor, framed by neatly landscaped greenery.

4.85 out of 5 average rating, 248 reviews

Ocean view 2 Bed 2 bath CLEAN!

A tranquil bay view at dusk features a wooden pier extending over calm waters. The soft colors of the sunset reflect on the surface, while silhouettes of birds can be seen perched on the pier. Grassy areas border the water, enhancing the serene landscape.

4.96 out of 5 average rating, 137 reviews

Beautiful Bayfront Condo!

Villas with a fireplace

The exterior of a spacious home is surrounded by greenery, featuring large windows that invite natural light. A gravel driveway leads to the entrance, which is accented with steps and a circular front window.

Villa in Ocean Pines

4.43 out of 5 average rating, 72 reviews

Luxe Homey Get-Away Beach Cove

The living room offers comfortable seating with two upholstered chairs and a sectional sofa. A glass coffee table is centered on a plush carpet, while a gas fireplace and Smart TV are positioned on the wall. Natural light is welcomed through large front windows.

4.82 out of 5 average rating, 45 reviews

4 Mi to Bethany Beach: Sunny Escape w/ Porches!

New place to stay

Bear Trap. First-Floor, Pet-Friendly & Pond Views

The exterior of the condo unit is shown, featuring a covered deck and a screened porch. Green grass surrounds the building, while neatly trimmed hedges add to the landscaping. Steps lead up to the entrance, and the structure is painted in light tones with multiple windows.

4.9 out of 5 average rating, 155 reviews

Modern 3 BR 1st floor resort villa, near beach

4.99 out of 5 average rating, 93 reviews

Villa in Ocean City

Walk to the Beach! PingPong-Fenced Yard-N64-Bikes!

A comfortable living room is highlighted by a spacious gray sectional sofa and a circular wooden coffee table. A flat-screen TV is mounted above a modern fireplace, while large windows allow natural light to illuminate the space. A colorful area rug adds a cozy touch.

Villa in Millville

5 out of 5 average rating, 7 reviews

Screened Porch, Outdoor Shower: Millville Villa

Two adirondack chairs are positioned on a balcony, facing a golf course with lush green grass and a serene lake. A small table holds two cocktails, complemented by the backdrop of trees and a clear sky.

Villa in Ocean Pines

5 out of 5 average rating, 4 reviews

Lakeview/Golf course front home - 4 Bed/3 baths

The exterior of the villa is shown, featuring a modern design with a combination of stone and painted siding. The first-floor unit is highlighted, showcasing a private entrance and a small patio area. Large windows offer a view of the well-kept landscaping.