Holiday rentals with a pool in West Ocean City

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

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!

5.0 out of 5 average rating, 4 reviews

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.

5.0 out of 5 average rating, 10 reviews

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

Spacious luxury condo on Harbour Island Marina, just two blocks from the beach and boardwalk . Relax and enjoy all Ocean City has to offer . Nearly 2,000 sq ft, 3 bedrooms, 3.5 baths, and a private balcony overlooking the marina . Enjoy luxury bedding, linens, bath & beach towels, beach chairs, and a beach wagon. Enjoy Indoor pool, fitness center, and private parking. Home of the White Marlin Open. Steps to fishing, boardwalk, watersports, and great restaurants. Sleeps 8 comfortably .

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.

4.86 out of 5 average rating, 120 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, 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*

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.

4.81 out of 5 average rating, 120 reviews

Mosaic Life Escapes -Bayfront Million Dollar Views

At Mosaic Life Escapes the BAYFRONT is our back yard! Safe gated community home. Water access for paddle boards & kayaks. Community fishing/crabbing pier 2 pools 3 ponds arcade room, playgrounds, paddle boats. 2 bd home w/a million dollar view. Minutes from Ocean City, Assateague Island & Casino. WiFi + 3 smart TVs We have implemented additional sanitizing procedures between guest stays to ensure a clean house! Perfect for a family or romantic get away!

5.0 out of 5 average rating, 4 reviews

Private Oasis | Backyard Pool

Welcome to Private Oasis! Enjoy a freshly updated getaway featuring a new upstairs bath with walk-in shower, new carpets, and renovated kitchen and baths. Relax in your private backyard pool, grill on the patio, or unwind in spacious living areas with plenty of sleeping options. Includes an Ocean Pines Beach Club parking pass and access to community amenities. The perfect spot for fun, sun, and family memories. NEW RENOVATED PHOTOS COMING SOON.

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!

Escape to your dream family vacation in this amazing 2-bedroom condo on the 8th floor! Enjoy incredible ocean views, direct beach access, and proximity to Ocean City's top attractions like the vibrant OC Boardwalk and thrilling amusement parks. This condo offers modern amenities, a refreshing seasonal outdoor pool, and the convenience of free parking. Perfect for families seeking fun and relaxation near the ocean.

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!

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!

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 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, 286 reviews

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

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, 165 reviews

Tortuga Cottage: Your All- Season Getaway

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, 231 reviews

Bayside community great amenities & rates

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

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, 62 reviews

Waterfront w/Dock, Rooftop Terrace & 2 Kings

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

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!

A light grey two-story house features a large front porch with white railings and multiple seating areas. Bright turquoise shutters frame the windows, and an American flag is displayed on the porch. Lush green landscaping complements the inviting facade.

4.95 out of 5 average rating, 56 reviews

West OC Bayside Getaway w/ pool

Condo rentals with a pool

An open-concept living space features comfortable seating, including a cozy sofa and accent chair. A dining area with modern chairs complements an equipped kitchen, showcasing stylish cabinetry and stainless-steel appliances. Large windows offer expansive views of the ocean and bright natural light.

4.92 out of 5 average rating, 155 reviews

WraparoundBalcony-2 Bed-Sleeps 8-Pool-Laundry-WiFi

4.83 out of 5 average rating, 249 reviews

Beachfront with a View and Amenities Galore

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, 287 reviews

Oceanfront Paradise | Pool | Hot Tub | Beach

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, 105 reviews

Completely Renovated Luxury Bay Front Condo

A spacious bedroom showcases a large window offering panoramic views of the ocean. The room features a king-sized bed with light, patterned bedding, complemented by a nightstand and a dresser. A cozy chair is positioned near the window, inviting relaxation.

4.97 out of 5 average rating, 102 reviews

Designer Oceanfront Condo | Pool, Hot Tub & Deck

A private balcony is showcased overlooking the ocean, featuring two comfortable chairs and a small table. The scene is framed by large sliding doors, allowing natural light to brighten the space. Green turf flooring complements the outdoor seating area.

4.97 out of 5 average rating, 100 reviews

Luxury Oceanfront Oasis!

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

A view from a balcony showcases the bay with vibrant waters and a clear blue sky. In the foreground, a small seating area with a table and two chairs overlooks a tree and landscaped area. Nearby, colorful cars are parked along the street.

4.91 out of 5 average rating, 109 reviews

Double Decker by de Bay

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

5.0 out of 5 average rating, 23 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!

5.0 out of 5 average rating, 39 reviews

Apartment in Ocean City

SeaGate Serenity | Oceanfront Condo with Balcony

4.9 out of 5 average rating, 51 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

4.98 out of 5 average rating, 45 reviews

A well-lit bedroom features a spacious bed with light bedding and a decorative throw. A small TV is mounted on the wall, and large windows provide views of the outdoors. A separate area includes a small table and chairs, with a private bathroom visible in the background.

Apartment in Ocean Pines

Coastal Retreat in Ocean Pines fall kayaking steps

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

5.0 out of 5 average rating, 11 reviews

Beachy Pines l Sleeps 6, Sunroom, Beach Club Pass

The exterior of a multi-story building is displayed, featuring light gray siding and multiple windows. A landscaped area with flowering shrubs is visible in the foreground, and a paved pathway leads up to the entrance. Clear blue skies enhance the inviting atmosphere.