Holiday rentals with a pool in West Ocean City

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, 287 reviews

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!

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, 117 reviews

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

Welcome to the Canal Bungalow! A stylish 1000 sq. foot retreat to enjoy all the fun & relaxation of the coastal lifestyle in North Oc. Bring your boat with you and dock alongside your back porch, enjoy pool access in a private gated community, or bring your sports gear for Northside Park. We are tucked away on the quiet bayside of OC & only a few minutes walk to the beach. Unwind on our beautiful balcony while watching the boats go by & finally understand the true meaning of a coastal lifestyle!

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.

4.97 out of 5 average rating, 152 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 .

4.86 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**

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, 335 reviews

Direct Oceanfront 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 full 100% 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, 144 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, 122 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!

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, 167 reviews

Tortuga Cottage: Your All- Season Getaway

This is an escape to reacquaint with family, nature, and your best self. Come home from the beach just a few miles away to enjoy the gas fire place, outdoor fire pit, and hot tub on chilly nights, fenced in back yard. Take advantage of the parks indoor outdoor pools golf yacht club, just moments from the cottage. Dogs are part of our family, and we are happy to consider canine guests on a case by case basis. Please see policies for breeds.

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, 134 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!

Popular amenities for West Ocean City rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 232 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, 65 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, 64 reviews

Waterfront w/Dock, Rooftop Terrace & 2 Kings

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!

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.

5.0 out of 5 average rating, 54 reviews

Large beachy feel 4 Bedroom

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

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!

5.0 out of 5 average rating, 19 reviews

Cabin in the Pines I Luxury Touches + EV Charging

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, 187 reviews

Oceanfront 1 Bedroom, Balcony, Sitting Room, 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.

4.9 out of 5 average rating, 365 reviews

Oceanfront Family Oasis: Pool, Beach & Parking!

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, 110 reviews

Double Decker by de Bay

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.

4.95 out of 5 average rating, 103 reviews

Luxury Oceanfront Oasis!

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, 107 reviews

Completely Renovated Luxury Bay Front Condo

A bright living area features a blue sofa, a striped armchair, and a wooden coffee table. Natural light flows through sliding glass doors that lead to a balcony with ocean views. Light curtains frame the view, and a TV is mounted on a light-colored media console.

4.96 out of 5 average rating, 113 reviews

21st Floor Carousel - 2 BR Oceanfront & Bay View

The living area features a modern design with a sleek Italian leather sofa and a wall-mounted flat-screen TV. An electric fireplace is installed beneath the TV, while a coffee table and a single chair complement the space. Ample natural light enters through a nearby window.

4.97 out of 5 average rating, 316 reviews

Bluewater Couples Escape

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, 143 reviews

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

Other holiday rentals with a pool

4.96 out of 5 average rating, 25 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!

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, 17 reviews

Downtown Condo, Parking, Walk to Beach & Boardwalk

4.81 out of 5 average rating, 81 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!

5.0 out of 5 average rating, 44 reviews

Apartment in Ocean City

SeaGate Serenity | Oceanfront Condo with Balcony

4.91 out of 5 average rating, 53 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

4.77 out of 5 average rating, 108 reviews

An inground pool is centrally located within a fenced backyard, surrounded by a grassy area. A seating arrangement is visible near the pool, along with a grill positioned nearby. Sunlight reflects off the water, creating a bright and inviting space.

Cottage in Ocean City

Our Little Cottage