Vacation rentals with a pool in Ocean Pines

4.97 out of 5 average rating, 199 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 2-bedroom 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

An open living area is highlighted by large windows that offer views of the bay and pool. A comfortable sectional sofa is positioned adjacent to a smart TV, while a modern dining table for four is visible next to the kitchen. The space features light-colored walls and natural wood flooring.

4.96 out of 5 average rating, 107 reviews

Gone Coastal *Pool* Bayside with view* Top Floor

Welcome to Gone Coastal! Relax in this beautiful 2BR/2BA getaway featuring: 🛏 1 King (Master) | 1 Twin-over-Full Bunk | 1 Sleeper Sofa 🏊‍♂️ Outdoor Community Pools – Lap & Family Pool (Directly Across!) 🔑 Keyless, Contactless Check-in 🌅 Spacious Deck – Outdoor Dining + Bay & Pool Views 📺 Smart TVs + YouTube TV 🛒 1-Minute to Grocery Store 🍽 Fully Equipped Kitchen 📍 Prime Location – 120th St, Heron Harbor 🚗 Ample Free Onsite Parking A perfect retreat for families & beach lovers! 🌊☀️

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!

4.92 out of 5 average rating, 188 reviews

The exterior of the multi-story townhouse is presented along a serene waterway. Balconies are visible on the front, while a clear blue sky reflects onto the calm waters. Boat docks are positioned nearby, enhancing the waterfront atmosphere.

Townhouse in Ocean City

IslandCoveParadise:LuxNewlyBuilt-Brdwk pool/2CarGg

We welcome you, your family and friends to stay at our luxury, Newly Built, beautifully furnished, & decorated 3 BR 3.5 BA w/2 parking garage spaces plus free street parking, and an outdoor pool on 25th street. Relax and enjoy the AMAZING VIEW on the water front from our triple balconies, just 2 blocks (3-4 minutes walk) from the boardwalk & the beach. Steps from Jolly Rogers Amusement Park and many miniature golf courses. Within walking distance are restaurants/, shopping, & nightlife.

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, 108 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 modern kitchen is complemented by a spacious dining area and cozy living room with ocean views. White cabinetry and stainless steel appliances enhance the kitchen, while large windows allow natural light to fill the space, highlighting the wood-paneled ceiling.

4.96 out of 5 average rating, 162 reviews

Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool

Opal Osprey: This OVERSIZE one-bedroom condo has been completely remodeled... giant oceanfront balcony PLUS a large patio room on the bayside! Expansive ocean views from every angle, super easy beach access, wonderful atmosphere in the quiet north end of OC. Linens included! Property Amenities - King size bed & queen sleeper - Large outdoor pool - Elevators - Dedicated high-speed WiFi and router w/ ethernet (Xfinity 100Mbps) - 2 Smart TVS with Xfinity, Roku - Keyless check-in 24/7

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.

4.86 out of 5 average rating, 109 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**

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*

4.9 out of 5 average rating, 108 reviews

A neatly arranged sleeping area features a spacious bed dressed in soft, floral bedding. Light-colored nightstands with lamps are placed on either side. Two neatly folded towels are positioned at the foot of the bed. A light rug covers the hardwood floor.

Apartment in Ocean City

Fresh renovated beach home~12 street

Enjoy a stylish experience at this centrally-located place. Our brand new remodeled beach home is located on a quiet street. You don’t need to worry about driving because the beach and Ocean city’s famous Boardwalk are only 2 minutes walking away from us. Peaceful nights with no loud vehicles speeding around. Our residential area is quiet with lovely pool which you can enjoy. The unit is stylish and clean. Great for couples or small family.

An open-plan kitchen and living area feature a light wooden counter with three stools. A fully equipped kitchen is visible, including a refrigerator, while a comfortable seating area with a cream-colored armchair and a coffee table is also present. Natural light enhances the inviting space.

4.88 out of 5 average rating, 162 reviews

Water Front Condo w/Pool Short Walk to Beach

FIRST FLOOR UNIT Bayside Condominium Sleeps 4 - 6 max Walking Distance to Northside Park Walk to the Ocean , don't worry about beach parking NON SMOKING 1 Bedroom 1 Bath condo, First floor unit with an outside deck This Air Conditioned, One Bedroom Condo has a fully equipped kitchen, washer/dryer, full refrigerator. There is a Queen bed and a full bed along with 1 Queen Sleep sofa in the living room *MUST BE 21 OR OVER* No Pets!

A serene ocean view is presented from a private balcony, featuring two teal chairs. The sandy beach stretches into the distance, with gentle waves lapping at the shore. A clear sky completes the tranquil coastal scene, creating a peaceful atmosphere.

4.92 out of 5 average rating, 258 reviews

Sun, Sand & Sea | Your Cozy Oceanfront Hideaway

-Oceanfront -Indoor pool & Hot tub -Walk to local dining and shopping -Elevator accessible plus luggage carts -Full kitchen for cooking meals -Fast Wifi and Streaming TVs -Fully Stocked Home: Clean linens, towels, toilet paper, paper towels & more! **2026 guests: Our pool and hot tub are in the process of being renovated and will be closed during your stay. They will re-open after Memorial Day**

Popular amenities for Ocean Pines rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living area features large windows revealing expansive ocean views. A cozy seating arrangement is positioned near a modern fireplace. Light-colored walls and a neutral coffee table complement the calming atmosphere, while sliding doors provide access to a balcony with additional seating.

4.97 out of 5 average rating, 29 reviews

Direct Bay Front Epic Sunsets Rooftop Pool

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

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, 269 reviews

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

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

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.

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 spacious living area is furnished with two dark leather sofas, providing ample seating. A ceiling fan enhances airflow. The open layout connects to a dining area featuring wooden chairs, while the kitchen is visible in the background, showcasing modern appliances and cabinetry.

4.94 out of 5 average rating, 225 reviews

Right behind Alley Oops & Crab Bag. Walk to beach

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.

4.89 out of 5 average rating, 38 reviews

Cozy Stay by the Bay

Condo rentals with a pool

A comfortable living area features a light-colored table surrounded by ocean-themed upholstered seating. Large glass doors allow natural light to fill the space while offering a view of the balcony and ocean beyond. A flat-screen television is mounted on the wall.

4.89 out of 5 average rating, 118 reviews

Oceanfront Carousel building, Swimming Pools!

A balcony is shown featuring two red Adirondack chairs and a small table, positioned to overlook the vast ocean. The horizon is visible in the distance, with a sandy beach below, inviting relaxation and scenic views.

4.96 out of 5 average rating, 72 reviews

Luxury Oceanfront Getaway!

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, 334 reviews

Oceanfront Family Oasis: Pool, Beach & Parking!

4.93 out of 5 average rating, 104 reviews

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

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

A welcoming kitchen and dining area is displayed, with modern appliances and a wooden dining table. Colorful letters spelling 'Welcome' are arranged on a sideboard, while a refrigerator and seating area are visible in the background, enhancing the cozy atmosphere.

4.87 out of 5 average rating, 54 reviews

BaysideGetaway | 2 Blk to Beach & Boardwalk | Pool

The beachfront property is displayed, featuring a modern four-story structure with multiple balconies. Soft sandy pathways lead to the building, bordered by natural grasses and low fencing. Clear blue skies enhance the oceanfront setting.

4.94 out of 5 average rating, 142 reviews

Direct Ocean Front/Gorgeous Views/Indoor Pool

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, 307 reviews

Direct Oceanfront with a View and Amenities Galore

Other vacation rentals with a pool

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, 75 reviews

Cozy home in Ocean Pines

4.93 out of 5 average rating, 14 reviews

Peace in the Pines- 3BD, 2BA w/ Beach Club Pass

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!

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

An open living area is presented, featuring a spacious sectional sofa, a light wood dining table with seating for six, and a modern kitchen. Natural light floods the space through large windows, enhancing the neutral color palette and warm wood accents.

5 out of 5 average rating, 17 reviews

House with Fire Pit + Private Yard near Ocean City

4.93 out of 5 average rating, 87 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, 20 reviews

The kitchen features wooden cabinets and a mosaic tiled backsplash. A center island with three rattan bar stools is present, alongside full-sized appliances, including a refrigerator and stove. A staircase is visible in the background, leading to the upper level.

Apartment in Ocean City

North OC- short walk 2 beaches and park

The exterior of the home features a welcoming entrance with a covered porch and decorative seasonal wreath. A stone pathway leads to the front door, surrounded by lush plants and landscaping, framed by light-colored siding and a garage door.