Holiday rentals with a pool in Ocean Pines

4.97 out of 5 average rating, 201 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 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

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.

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, 109 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 three-story building with a light blue exterior is shown. Multiple balconies are visible, equipped with railings, and the entrance is marked by a sign. Underneath the structure, a private parking area is accessible, with a gate in the foreground.

4.84 out of 5 average rating, 137 reviews

Ocean Block - Clean, cozy 1 Bedroom. Pool, Wifi

Ocean Block / Convention Center, One bedroom, recently remodeled, with view of the beach. 1/2 Block to the beach. Across the street from the Convention Center. 12 blocks to the boardwalk. 10 Blocks to Jolly Roger Amusement Park. Ocean View from living room balcony. Quiet complex, great for romantic getaway. THIS COMPLEX DOES NOT ALLOW SMOKING, VAPING OR MARIJUANA. THE NEIGHBORS WILL SMELL IF EVEN WHEN YOU ARE INDOORS. ONCE WE GET A COMPLAINT, YOU WILL HAVE TO LEAVE WITHOUT A REFUND.

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.

4.95 out of 5 average rating, 257 reviews

A spacious master bedroom features a king-size bed layered with decorative bedding in soft hues. Natural light streams through multiple windows, illuminating the neutral walls and plush carpeting. A bedside table and a gray storage ottoman complement the tranquil atmosphere of the room.

Townhouse in Millville

⛱ Quiet 3 Bed Twinhome just 3 miles from Beach! ⛱

Enjoy this Beautiful 3 Bedroom & 2.5 Bath Twinhome in Millville, DE. Perfect for Families! This home is within walking distance or short drive to Restaurants, Shops, Grocery Store and other Attractions & Most Importantly - only 3 miles to THE BEACH!! There is a Community Pool in the neighborhood. Many Toys, Games, Puzzles available for children. Home is No Smoking of Any Kind. Also No Pets, No Large groups/parties (10 people max.) or Senior Week rentals permitted. Book Today!

4.86 out of 5 average rating, 110 reviews

A bright living room features a large sectional sofa and a decorative round coffee table on a colorful area rug. Natural light enters through a window adorned with light curtains, and a ceiling fan circulates air. A television setup is positioned on a media cabinet.

Townhouse in Ocean City

DownByTheBay 214-Sleeps 15/Downtown/Boardwalk/Pool

Come and enjoy this oasis, accommodates 15, this 3 BR 3.5 BA home is in the heart of Ocean City MD, minutes from the beach & located steps away from Ocean City most popular attraction, The BOARDWALK. There is everything you will need for a large group to retreat (fully equipped kitchen), 2 large balconies, 2 car parking plus community & street parking, outdoor pool *This property DOES NOT provide linens/towels* ***Please FIND us @ Down by the Bay OCMD For current Promotion**

4.84 out of 5 average rating, 222 reviews

Beachfront 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 a breathtaking view of the beach and ocean.

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*

Three condominium buildings rise against a clear blue sky, showcasing varied architectural styles with prominent glass and concrete facades. A sandy path leads toward the beach, bordered by a wooden fence that adds a natural touch to the coastal view.

4.95 out of 5 average rating, 111 reviews

Oceanfront Bldg.| 2 pools | Tennis | Game Room

Welcome to our beautifully renovated two-bedroom, two-bathroom ocean-view unit at the Quay in North OC. Located on the 5th floor, this condo offers stunning views of both the ocean and the bay. Step outside, and you will find yourself just moments away from the beach! The kitchen is fully equipped and has a fantastic ocean view from the countertop. This unit does not include sheets, towels, or toiletries. $75 registration fee from March to Nov.

4.98 out of 5 average rating, 265 reviews

A modern living area features a spacious gray sofa and a wooden coffee table, complemented by a cozy area rug. Large glass doors open to a private oceanfront balcony, allowing natural light to fill the space. Decorative accents include a wall-mounted surfboard and a round mirror.

Flat in Ocean City

OceanFront-Fireplace-sleeps4-Balcony-King-Disney+

Welcome to Salty Shark - direct oceanfront studio! This remodeled studio sleeps 4 and is in North Ocean City near great restaurants, bars, and 58 acre North Side Park. The park has sports fields, a recreation center, a walking/biking path, crabbing pier, playground, and outdoor fitness area. Building has outdoor pool in summer too! The unit features a King Murphy bed, and a Queen sofa bed. There's also an outdoor pool open in summer months!

Popular amenities for Ocean Pines rentals with a pool

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, 23 reviews

Beach Paradise 2101-Downtown Luxury Condo Bay View

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, 270 reviews

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

A light-filled living area features a comfortable blue sofa and two matching patterned armchairs. A woven coffee table sits in the center, while a television is positioned on a stand nearby. An outdoor balcony is accessible through sliding glass doors that enhance the open feel of the space.

4.85 out of 5 average rating, 39 reviews

Charming 2BR/2BA condo Oceanside, Midtown, Pool

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

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, 66 reviews

Ocean Pines, Waterfront Oasis

The expansive view showcases the sandy beach stretching along the Atlantic Ocean, gently reflecting the clouds above. Features include a shared pool bordered by lounge chairs and landscaped areas. The setting sun casts warm hues over the water, enhancing the serene coastal atmosphere.

4.8 out of 5 average rating, 15 reviews

Oceanfront | Pool | Steps to beach | Elevator

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

4.86 out of 5 average rating, 7 reviews

The Whale’s Tale Retreat w/ Beach Club Pass

Apartment rentals with a pool

A light-filled living area features a soft, neutral-toned sectional sofa facing a wooden coffee table. Floor-to-ceiling windows showcase ocean views, with sunlight reflecting off the water. A flat-screen TV is mounted on a wooden entertainment unit, complementing the room's modern design.

4.91 out of 5 average rating, 335 reviews

Oceanfront Family Oasis: Pool, Beach & Parking!

5 out of 5 average rating, 20 reviews

The Salty Tail @ Jamaica Bay 33rd Street - Midtown

The living area is spacious, featuring a light blue wall color and a large sectional sofa. Natural light floods through windows, illuminating the decorative rug. The outdoor porch includes dining furniture and offers views of the canal and neighboring buildings.

5 out of 5 average rating, 99 reviews

Beautiful waterview 2B condo w/Dock&Close to Beach

A spacious living area features a large sectional sofa in light beige fabric, complemented by a wooden coffee table with a rustic finish. A serene coastal photograph decorates the wall, while soft lighting from a nearby lamp creates a cozy ambiance.

4.95 out of 5 average rating, 59 reviews

Freshly renovated ! Steps to outdoor pool & beach

4.88 out of 5 average rating, 110 reviews

White Marlin 107 Renovated Amazing Bay Views Pool

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

An expansive view of the beach is captured, showcasing soft sand leading to calm ocean waves reflecting sunlight under a clear sky. The horizon stretches far into the distance, with a few distant figures visible on the beach, and a neighboring building is seen to the right.

4.99 out of 5 average rating, 80 reviews

Beautiful Ocean Front Condo 2b/2ba with pool

A spacious living room is depicted with a comfortable grey sectional sofa and a wooden coffee table. Large sliding glass doors provide unobstructed views of the ocean, allowing natural light to fill the room. A flat-screen TV is mounted on the wall opposite the seating area.

4.98 out of 5 average rating, 46 reviews

Extraordinary Oceanfront Penthouse - Unit 1209

Other holiday rentals with a pool

4.96 out of 5 average rating, 79 reviews

A cozy seating area is positioned on the waterfront, featuring plush cushions and decorative pillows. Two lanterns with candles add ambiance. Lush greenery and a clear sky are visible in the background, enhancing the serene view of the water.

Home in Berlin

Private pool, waterfront, kayaks, bikes, firepits!

A bright living area features a comfortable blue sofa and an armchair, with a decorative lamp beside them. A white coffee table sits atop a patterned rug, which complements the room's light decor. Two windows, adorned with blinds, allow natural light to filter in.

5 out of 5 average rating, 18 reviews

Stubbe's Beach House, Home in Ocean Pines, MD

5 out of 5 average rating, 23 reviews

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.

Home in Ocean View

Ocean View Paradise w/Hot Tub & Free Massages!

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

4.93 out of 5 average rating, 88 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

4.9 out of 5 average rating, 39 reviews

A spacious living area is depicted, featuring a large sectional sofa and two accent chairs. A coffee table sits at the center, with a modern stone fireplace adorned by a flat-screen television. Natural light enters through window panes, highlighting the plush area rug.

Home in Ocean View

Luxury Single Family, Waterfront w/Linens Included

5 out of 5 average rating, 4 reviews

An open floor plan is showcased, featuring a modern kitchen with a central island and white cabinetry. Large sliding glass doors allow for natural light and ocean views. A cozy seating area includes a coffee table and comfortable blue couches, inviting relaxation in a bright environment.

Flat in Ocean City

NEW: Oceanfront End-Unit Condo w/ 100ft Balcony

A cozy living area is featured, showcasing a comfortable sectional sofa adorned with decorative pillows. Natural light filters through sheer curtains, illuminating the space. A wooden coffee table sits center stage, complemented by a small potted plant and subtle wall décor.