Holiday rentals with a pool in West Ocean City

4.94 out of 5 average rating, 286 reviews

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.

Home in Ocean City

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!

LocationFamilyBeach

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, 145 reviews

Newly built bright and airy guest suite!!!!

FREE oceanfront parking pass with bookings. 2 PERSON MAX. 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.

ValueFamilyNearby

The inviting living area features a cozy couch and an armchair, adorned with decorative pillows. Bright blue walls complement the light streaming through multiple windows with white blinds. A coffee table with a boat decor piece rests on a patterned rug that evokes a beach theme.

4.82 out of 5 average rating, 229 reviews

Bayside community great amenities & rates

Welcome! Perfectly located for all your beach fun in our gated, amenity filled, community! Close drive to beaches (5 miles OC and Assateague) & to water parks, boardwalk, brewery, quaint town of Berlin, awesome restaurants and more! Short walk to our community pools, pier, rec center, playgrounds, paddle boats at no extra charge! Our beach cottage provides you with all essentials! We are located next door to Frontier Town where they have themed shows, water park, ice cream, and a big arcade!

FamilyLocationBeach

4.97 out of 5 average rating, 221 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

FamilyLocationDecor

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, 149 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!

FamilyLocationDecor

5.0 out of 5 average rating, 4 reviews

Home in Ocean City

Salty Sunrise

Welcome!! Come relax in a large quiet townhouse. West OC has a laid back harborside feel, but yet just minutes to the boardwalk, great beaches and loads of fun. You'll have the entire place to yourself, 3 bedrooms, 2 full bathrooms on the 2nd floor and half bath on 1st floor. Full working kitchen and large dining room table. Full access to the indoor and outdoor pools, weight room, playground and tennis/ basketball courts. Enjoy sitting on one of the two back decks, grill out and chill.

LocationDecorCleanliness

4.88 out of 5 average rating, 108 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 may apply.

LocationFamilyAccuracy

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, 143 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*

LocationFamilyCheckout

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, 131 reviews

Ocean Pines Retreat with Beach Club

Escape to our peaceful Ocean Pines retreat! This updated, single-level rancher comfortably sleeps 6 and is perfect for families. Enjoy a quiet street just minutes from Ocean City. Features a modern kitchen, cozy fireplace, and exclusive access to the Ocean Pines Beach Club with a private pool, restaurant, and ocean access. Your serene beach getaway awaits!

FamilyLocationCheckout

4.92 out of 5 average rating, 119 reviews

A large pool is framed by a wooden gazebo, offering shaded seating areas and views of tropical palm plants. The surrounding area features well-maintained landscaping and a spacious poolside deck, inviting relaxation in a serene environment.

Townhouse in Berlin

Bayside Townhouse w/ amazing amenities

Vacation memories are made in the 3BR townhome situated in quiet private community. The property features an indoor and outdoor pool, clubhouse, basketball and tennis courts, kayak dock, crabbing fishing dock and much more! We are 10 minutes drive to OC and about 12 minutes to assateague island. Sleeps 8 Now includes an EV (J1772) charger!

ValueLocationParks

4.98 out of 5 average rating, 219 reviews

Cottage in Berlin

Bayfront Cottage w/ Amazing Views

Whether you’re enjoying time by the firepit or sipping coffee on the couch, the views of Sinepuxent Bay and Assateague Island make this cottage the ideal spot for your next vacation. The cottage is located in a quiet neighborhood and is only a short drive from Assateague Island, the historic town of Berlin, and the Ocean City Boardwalk.

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A row of upscale townhouses with contemporary architecture is displayed. Each unit features a garage with a clear driveway leading to the front entrance. Multiple windows allow ample natural light, and well-maintained landscaping lines the street.

4.91 out of 5 average rating, 64 reviews

Luxury Townhome WestOC -4 BRS / golf / asssateague

Welcome to your perfect coastal retreat! This spacious 2,700 sq. ft. luxury townhouse is ideal for a relaxing getaway filled with golf, fishing, and nearby adventures to Assateague Island and Frontier Town. Designed with comfort and convenience in mind, it’s the perfect home base for families and groups looking to unwind and explore.

ValueFamilyKitchen

Popular amenities for West Ocean City rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A bright living area features a comfortable blue sofa and a cozy armchair, with a gas fireplace as the focal point. Natural light floods the space through large windows, while a dining table and chairs are visible in the background, creating an inviting atmosphere for gatherings.

4.87 out of 5 average rating, 163 reviews

Tortuga Cottage: Your All- Season Getaway

FamilyValueCheck-in

A serene view of Sinepuxent Bay stretches across the horizon, showcasing expansive grasslands and soft green vegetation. The sky transitions to warm hues of sunset, creating a calming atmosphere. A glimpse of the fishing pier is visible in the distance, enhancing the waterfront scenery.

4.82 out of 5 average rating, 119 reviews

Mosaic Life Escapes -Bayfront Million Dollar Views

ValueLocationCondition

4.92 out of 5 average rating, 96 reviews

The townhouse complex stands amidst vibrant trees, their leaves reflecting the colors of the season. The multicolored façades of the homes suggest a welcoming atmosphere, enhanced by the white railings of the porches. A clear blue sky frames the scene, creating a serene setting.

Home in Ocean City

Beachy Sunset Island Townhouse!

LocationValueBeach

A wooden welcome sign with a pineapple motif is displayed alongside a vase of white and pink flowers. The smooth countertop reflects natural light from nearby windows, creating a bright and welcoming kitchen atmosphere.

4.94 out of 5 average rating, 17 reviews

Bayside West

ValueFamilyOutdoor spaces

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.

4.97 out of 5 average rating, 86 reviews

Private pool, waterfront, kayaks, bikes, firepits!

LocationFamilyHiking

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, 75 reviews

Coastal Oasis in Ocean Pines

FamilyValueGetting around

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.

4.95 out of 5 average rating, 20 reviews

Cozy beach home away from home!

LocationValueBeach

A waterfront home is surrounded by green lawns and trees, featuring multiple outdoor seating areas. The spacious deck overlooks the water and is equipped with a gas grill. A dock is visible, allowing for easy access to the bay.

5.0 out of 5 average rating, 61 reviews

Waterfront w/Dock, Rooftop Terrace & 2 Kings

LocationFamilyAccess

Condo rentals with a pool

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.

4.95 out of 5 average rating, 186 reviews

Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool

FamilyLocationIndoor spaces

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.

4.9 out of 5 average rating, 364 reviews

Oceanfront Family Oasis: Pool, Beach & Parking!

FamilyLocationSleep quality

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.

4.94 out of 5 average rating, 332 reviews

Direct Oceanfront with a View and Amenities Galore

FamilyLocationDecor

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.

5.0 out of 5 average rating, 115 reviews

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

LocationFamilyView

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, 141 reviews

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

LocationValueQuiet

A modern kitchen is displayed with white cabinetry and granite countertops. An L-shaped island with four chrome swivel stools offers additional seating. Stainless steel appliances, including a microwave and refrigerator, complement the space. A window provides a view of the water outside.

4.97 out of 5 average rating, 102 reviews

Completely Renovated Luxury Bay Front Condo

LocationFamilyBarbecue

A private balcony features two turquoise adirondack chairs facing the ocean. The oceanfront view showcases the sandy beach and rolling waves, inviting moments of relaxation and enjoyment. A decorative 'Seaside' sign is displayed on the wall, enhancing the coastal ambiance.

4.78 out of 5 average rating, 238 reviews

DirectOceanFront on Boardwalk/Newly Remodeled/Pool

LocationValueLaundry

A spacious living area features a large wall-mounted entertainment center with a flat-screen TV. Comfortable seating options include a striped sofa and a patterned armchair. Sliding glass doors provide unobstructed ocean views and natural light, enhancing the inviting atmosphere of the space.

4.8 out of 5 average rating, 121 reviews

Luxe Oceanfront 1BR | Pool, Hot Tub, Sun Deck

FamilyValueAir conditioning

Other holiday rentals with a pool

4.83 out of 5 average rating, 40 reviews

The exterior of the townhome showcases a welcoming facade with a combination of light brown siding and white trim. Large windows are visible on the upper floors, allowing for abundant natural light. The attached one-car garage is featured at the base, contributing to the home's modern aesthetic.

Townhouse in Berlin

Large Townhouse In GlenRiddle Community #102

LocationFamilyAccuracy

5.0 out of 5 average rating, 7 reviews

Luxury 3BR/4BA Condo: Indoor Pool, Walk to Beach

FamilyLocationWalkability

4.82 out of 5 average rating, 77 reviews

The exterior of a multi-unit townhome is shown, featuring a light blue façade with white accents. A spacious balcony extends across the front, and the ground level includes two garage doors. Clear blue skies provide a bright backdrop.

Townhouse in Ocean City

Amazing Large 4 Bedroom West OC Town House, Pool!

LocationFamilyCleanliness

5.0 out of 5 average rating, 17 reviews

Downtown Condo, Parking, Walk to Beach & Boardwalk

ValueLocationAccuracy

5.0 out of 5 average rating, 22 reviews

A three-story townhome showcases a blend of stone and shingles in a contemporary design. The exterior is complemented by large windows, and well-maintained landscaping creates an inviting approach. Two garage doors are visible, and a driveway accommodates additional parking.

Townhouse

Luxury Townhome close to OC beach & boardwalk!

FamilyLocationCondition

4.98 out of 5 average rating, 59 reviews

A modern three-story townhouse is displayed, featuring a light blue and gray exterior with white railings. The entrance is accented by a covered porch and stairs leading to the second floor. A garage is visible on the lower level, completing the inviting facade.

Townhouse in Ocean City

The Bowline with Direct Bay Views

ValueFamilyNearby

4.9 out of 5 average rating, 49 reviews

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.

Apartment in Ocean City

Mermaid Cove

ValueLocationParking