Vacation rentals with a pool in West Ocean City

4.97 out of 5 average rating, 204 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 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

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!

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, 112 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 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

Welcome to The Jamaican Sand Turtle! We are located on the 4th floor(no elevator) at the north end of the boardwalk, in a quiet neighborhood. You can come in via 50 or 90 as we are halfway between the two. *WIFI *Full-sized kitchen with all essentials you need to prepare your favorite meals. *Stack washer/dryer in condo *Outdoor station for rinsing after beach visits *2 full-size beds -bedding not provided *Queen sleeper sofa *Bath towels provided-need laundered before leaving

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.

A wooden pier extends into calm waters, framed by posts topped with white caps. A vibrant sunset bathes the scene in warm hues of orange and yellow, reflecting beautifully on the water's surface. The distant silhouette of trees and community is visible against the dramatic sky.

4.81 out of 5 average rating, 212 reviews

Bayside community near OCMD 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 gated, beautiful community, is bayside, has 2 awesome pools, big splash pool, rec center, a fishing/crabbing pier, pond with paddle boats, 2 playgrounds+ more For kiddos of all ages, we are located right next door to Frontier Town, which has awesome water slides , western shows, mini golf, a rope course, ice cream shop..

Superhost

A bright living room features a comfortable sofa and a large, cozy bean bag. Natural light pours in through sliding glass doors, which lead to the outdoor space. A large area rug with a starfish design complements the decor, while a colorful wall art piece adds a playful touch.

4.86 out of 5 average rating, 42 reviews

NEW! Entire Townhouse, Minutes from Downton OC!

Stop right there!! This 2-bedroom, 1.5 bathroom beautifully renovated in 2022 - entire townhouse w/ a private outdoor patio is the perfect space for your Ocean City vacation. You are less than a 5-minute drive to the beach & downtown Ocean City Inlet. Walking distance to OC's most famous local bars/restaurants; Sunset Grille, Brass Monkey, Crab Alley, Harborside, and Sunset Marina. Tanger Outlets are less than 1 mile away! Access to community pool and free parking!

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!

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, 341 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.

Popular amenities for West Ocean City rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House 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

Waterfront Oasis with Ocean City Skyline Views!

A bright dining area is illuminated by natural light, featuring a circular table surrounded by four light-colored chairs with soft gray cushions. The room showcases window shutters and a decorative light fixture overhead, adding to the cheerful ambiance.

5 out of 5 average rating, 14 reviews

Meet at the Marina | Beach Club Parking

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

4.94 out of 5 average rating, 277 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

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

4.86 out of 5 average rating, 7 reviews

The Whale’s Tale Retreat w/ Beach Club Pass

4.97 out of 5 average rating, 138 reviews

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.

Home in Ocean City

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

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, 69 reviews

Coastal Oasis in Ocean Pines

Condo rentals with a pool

A modern living area is presented with a sleek white cabinet and a flat-screen television mounted on the wall. Comfortable ottomans with a geometric pattern are positioned nearby, and a globe and plant add subtle accents. Natural light enters through the door, which leads to a balcony.

4.77 out of 5 average rating, 168 reviews

Beach condo next to Seacrets

5 out of 5 average rating, 21 reviews

The Salty Tail @ Jamaica Bay 33rd Street - Midtown

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, 100 reviews

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

A spacious living area features a gray sofa and matching armchairs adorned with decorative pillows. The light-colored walls and wooden flooring create a bright, relaxing atmosphere. Doorways lead to other areas of the condo, enhancing accessibility and flow.

4.89 out of 5 average rating, 109 reviews

Summer Winds Condo D102 Bayside w Pool Sleeps 6

A clear view of a swimming pool surrounded by a fenced area, providing access to the bay. Multiple boats are docked nearby, with calm waters visible in the background. The condo building's exterior is visible, showcasing a light grey finish.

4.89 out of 5 average rating, 84 reviews

UNIQUE Bay Front Sanctuary Condo

A spacious balcony offers unobstructed ocean views, featuring two comfortable wooden chairs and a small circular table. The bright blue waters and clear sky create a serene backdrop, enhancing the feeling of open outdoor space.

4.98 out of 5 average rating, 101 reviews

Beautiful 2BR 2BA oceanfront condo at the Atlantis

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, 312 reviews

Direct Oceanfront with a View and Amenities Galore

An open-concept living space is visible, featuring light wood flooring and a welcoming sign above a dining table with turquoise chairs. A television is mounted on the wall opposite, with a cozy seating area and a clock near the entrance. Bright light enters through windows covered by patterned curtains.

4.94 out of 5 average rating, 33 reviews

2BR OCMD Condo | Pool | Linens Included

Other vacation rentals with a pool

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

4.98 out of 5 average rating, 51 reviews

Steps to the Ocean & boardwalk/3bedroom/2bath

5 out of 5 average rating, 58 reviews

Ocean Pines Fun – Arcade, Pools & Near O.C. Beach

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

The waterfront home is positioned along the canal, featuring a spacious deck with seating areas and landscaping. A stone pathway leads to the dock, which is equipped for boating. The exterior is complemented by greenery and a calm water view, providing a serene outdoor setting.

4.8 out of 5 average rating, 25 reviews

Ocean Pines 3BR 2BA Canal Front Home with Sunroom

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.

4.96 out of 5 average rating, 26 reviews

Robin Hood Retreat

Superhost

A modern kitchen features white cabinetry paired with a blue-tiled backsplash. Stainless steel appliances, including a refrigerator and stove, are complemented by open shelving above. Counter space provides functionality, with light streaming in, creating a bright and inviting cooking area.

Apartment in Ocean City

4.78 out of 5 average rating, 9 reviews

The Cottage - Waterfront

A spacious living area features a large gray sectional sofa, providing ample seating. A flat-screen TV is mounted on the wooden wall with a light-colored media console beneath. Natural light enters through sliding glass doors, complemented by curtains that frame the space against warm wooden ceilings.