Vacation 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, 279 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 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.

4.81 out of 5 average rating, 212 reviews

Bayside community for OCMD trip great rates

Welcome to MERMAID DREAMS where you can have FUN or just RELAX! We are ONLY 5 miles from OC, MD beaches/boardwalk & Assateague National Park/beaches. Our beach cottage provides you with all the essentials needed, including a washer/drier! Our gated community is bayside, has 2 awesome pools, big splash pool, rec center, a fishing/crabbing pier, pond with paddle boats, 2 playgrounds We are located next door to Frontier Town water slides , western shows, mini golf, a rope course, ice cream shop.

4.97 out of 5 average rating, 207 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

Vacation by the Bay: Condo with Marina View

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, 140 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.

The exterior of a two-story house is framed by lush greenery and neatly arranged flower beds. A covered front porch with white railings invites guests, while the clean lawn extends towards the street. The sky above showcases a mix of clouds and blue.

5 out of 5 average rating, 115 reviews

Stay Salty OC Beach House

Welcome to your ultimate getaway near Assateague State Park & Ocean City! Our spacious retreat sleeps 14 guests and boasts resort-style amenities including pools, a gym, kayaks, and tennis courts. Located just moments from beaches, charming towns, and exciting attractions, you'll have everything you need for an unforgettable vacation. With a fully stocked kitchen, game rooms, cozy reading nooks, puzzles, and a balcony, there's something for everyone. Book now and let the relaxation begin!

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, 118 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!

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.

4.87 out of 5 average rating, 112 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*

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, 113 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!

4.95 out of 5 average rating, 167 reviews

Steps to Beach, Pool, Family Friendly with Linens

Welcome to Surf House at Island Cabana, a spacious 3-bedroom, 2-bath condo just steps from the beach in North Ocean City. This elevator building offers a pool, secure lobby, and easy beach access just steps away. Perfect for families, the condo includes beach gear, a fully stocked kitchen, organic bedding, and kid-friendly amenities—plus parking and in-unit laundry for a comfortable, stress-free stay.

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 welcoming living room features a light-colored sectional sofa and two accent chairs. Natural light fills the space through several windows, illuminating a decorative rug. A wooden cabinet and wall decor complement the modern design, creating a comfortable area for relaxation.

4.94 out of 5 average rating, 17 reviews

NEW Beautiful Peaceful Costal Getaway

A cozy living area is presented with a neutral color palette, featuring a comfortable gray sofa, two matching chairs, and a wooden coffee table. Natural light fills the space through sliding glass doors, which offer access to an outdoor deck, while a framed artwork enhances the decor.

4.89 out of 5 average rating, 19 reviews

Bayside Townhome with Ample Parking

A welcoming exterior view of the home is showcased, featuring a covered front porch with white railings and blue shutters. An American flag is displayed, and the driveway is paved with ample space for parking. Surrounding trees offer natural privacy among the foliage.

4.94 out of 5 average rating, 18 reviews

The Beach Nut- w/ Beach Club Pass and No Pet Fee

4.92 out of 5 average rating, 26 reviews

Seaside Village Beach House

A spacious living area features two sofas, one in dark leather and the other in a light fabric, arranged around a low wooden coffee table. A flat-screen TV is mounted on a light wall above a stone fireplace, adding a cozy touch to the room.

4.97 out of 5 average rating, 141 reviews

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.

A private patio is featured, equipped with a stylish outdoor table and chairs under a large umbrella. Lush greenery is visible alongside the seating area, while a serene waterfront with moored boats can be seen in the background.

5 out of 5 average rating, 9 reviews

Peaceful place to escape.

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.

5 out of 5 average rating, 11 reviews

Bayside West

The exterior of a two-story home is shown, surrounded by lush greenery and mature trees. A wooden deck with railings is featured at the entrance, overlooking a pathway made of stones, while a large tree stands prominently beside the house.

4.84 out of 5 average rating, 19 reviews

Cozy Corner Retreat

Condo rentals with a pool

Double glass doors open onto a private balcony, allowing ample natural light to fill the space. Outside, two comfortable chairs are positioned for relaxation, while a potted plant adds a touch of greenery to the interior.

4.86 out of 5 average rating, 101 reviews

Lovely Condo Steps 2Beach+Pool Unlimited Parking

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, 347 reviews

Oceanfront Family Oasis: Pool, Beach & Parking!

A comfortable living area features a gray sofa with blue accent pillows and a textured rug. Large sliding glass doors offer a view of the ocean and access to a private balcony with outdoor seating. Natural light fills the space, creating a welcoming atmosphere.

4.98 out of 5 average rating, 244 reviews

Cozy oceanfront condo with stunning ocean views

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, 103 reviews

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

A panoramic view of the ocean is visible, with gentle waves lapping at the sandy beach. Below, an outdoor pool is surrounded by lounge chairs and clear pathways, providing a peaceful atmosphere. Skies are blue, enhancing the serene coastal setting.

4.86 out of 5 average rating, 118 reviews

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

A four-story building named Jamaica Bay is depicted, showcasing a light-colored exterior and balconies on each level. The surrounding landscape includes grassy areas and trees, contributing to the tranquil setting of the property.

4.95 out of 5 average rating, 104 reviews

The Jamaican Sand Turtle

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, 316 reviews

Direct Oceanfront with a View and Amenities Galore

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.

4.79 out of 5 average rating, 229 reviews

DirectOceanFront on Boardwalk/Newly Remodeled/Pool

Other vacation rentals with a pool

An aerial view of a spacious waterfront property showcases a well-manicured yard with a private boat dock. The surrounding neighborhood is visible, featuring a variety of homes, some with outdoor amenities like pools and decks. The serene bay can be seen in the background.

4.79 out of 5 average rating, 14 reviews

Ocean City Waterfront Home with Skyline Views!

4.88 out of 5 average rating, 33 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

4.97 out of 5 average rating, 39 reviews

A view of a serene waterway is captured, with various boats docked along the banks. Charming homes in soft colors line the waterfront, and the sky is clear with a few scattered clouds, creating a tranquil atmosphere.

Townhouse in Ocean City

3BR/Den/3.5B/boat dock/2 blocks to beach/boardwalk

5 out of 5 average rating, 34 reviews

The kitchen area features a wooden countertop with a modern sink and stylish faucet. Shelves hold various glassware and dinnerware, while a spacious dining area is visible in the background, showcasing a large table surrounded by natural lighting.

Apartment in Ocean City

Bayside Bungalow - Waterfront

4.91 out of 5 average rating, 92 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

5 out of 5 average rating, 13 reviews

A private dock extends over calm waters, accompanied by two blue adirondack chairs positioned for relaxation. Lush green grass borders the waterway, with trees providing a serene backdrop under a partly cloudy sky.

Townhouse in Ocean Pines

Canal Front Golf Retreat w/Dock

4.63 out of 5 average rating, 8 reviews

The Whale’s Tale Retreat w/ Beach Club Pass

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.