Holiday rentals with a pool in Ocean City

A bright living area features a spacious gray sectional sofa adorned with blue and white pillows. A coffee table sits in front, with a small decorative display. Large sliding glass doors provide access to the outdoors, facilitating natural light, while a flat-screen TV and a fireplace enhance the cozy setting.

5 out of 5 average rating, 12 reviews

Sun, Swim & Serenity

🏡 Bayside Comfort Near the Beach. Welcome to your perfect coastal getaway! Unwind in this condo just a short walk from the beach. Enjoy a queen bed, two full-size bunk beds, a fully equipped kitchen, private balcony, and access to the community pool. Stay connected with Wi-Fi and Smart TV, and take advantage of free parking. Located in a quiet community near Ocean City’s boardwalk, shops, and restaurants, this retreat offers the perfect blend of relaxation & convenience for families or friends.

A spacious living area is furnished with a blue couch and two light-colored armchairs, set against a backdrop of large sliding glass doors. Natural light fills the room, highlighting the ocean view and access to the balcony. A decorative wall piece adds a touch of character.

4.98 out of 5 average rating, 42 reviews

Oceanfront condo with pool, sleeps 4, free Wi-Fi

Beautifully remodeled Oceanfront condo perfect for a couple or small family. Enjoy beautiful sunrises from your spacious oceanfront balcony and spectacular sunsets from second balcony facing bayside. One of OC's largest 1BR floorplans (800+ sq. ft), it has everything you could want from full-sized appliances inc washer/dryer, granite counters and new flooring. Prime beachfront location, large pool, close to restaurants/bars, groceries and shopping, it is a must-stay! Linens & Towels included.

The kitchen features modern white cabinetry and updated appliances, including a stove and refrigerator. A central island with seating for two provides additional workspace. Fresh fruit is displayed in a bowl on the counter, while light blue walls create a calm, coastal ambiance.

4.97 out of 5 average rating, 31 reviews

Bayside Condo in Midtown Ocean City MD

Enjoy your stay in this 1 bedroom condo in the middle of everything! Walking distance to Shotti's Point OC, Coconuts Bar & Grill, Barn 34, Jolly Roger... to name a few. Catch the sunrise on the beach just a block away, then watch the stunning sunset steps from the front door. In between, enjoy the outdoor pool or launch a kayak in the bay from the private beach. The kitchen is newly renovated and there is still more to come! This is the perfect location to relax and enjoy all of Ocean City.

Multiple Condo units stand adjacent to calm waters, featuring private boat slips. Each unit is accessible by a balcony, surrounded by well-kept greenery. Cloudy skies reflect on the water's surface, while a few boats are visible moored nearby.

4.86 out of 5 average rating, 148 reviews

Bayfront Family Friendly Beach Condo w/BoatSlip

Come enjoy our Cozy Bay/Canal Water Front Beach Condo. 1 bedroom, 1 bath condo with a Boat Slip & Pool and just a few blocks from the Beach and Northside Park, in the desired Hidden Harbor Community. Also just a short walk to the Beach Bus Stop. ** For July and August we try to rent Saturday to Saturday, 7 night stays! ** Contact me if you're interested in shorter stays. Pool Open Memorial Day to Labor Day Xfinity WiFi and Smart TV for your streaming needs. New Mattress and TV added 2024!

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, 225 reviews

DirectOceanFront on Boardwalk/Newly Remodeled/Pool

Newly renovated and beautifully decorated direct oceanfront condo 1BR/1BA on the 4th floor, 12th St. on the center of the Boardwalk. Enjoy AMAZING VIEWS of the sunrises over the ocean and refreshing ocean breeze from the top floor. You can watch Ocean City’s best access to entertainment like the air show, fireworks, car shows and more on your private balcony. Within walking distance are great restaurants, shopping, nightlife, amusement parks, and plenty of water activities, and Pet Friendly.

A large swimming pool is surrounded by a spacious deck featuring several lounge chairs. The clear blue water is inviting, and the area is enclosed by a fence. A few trees are visible in the background, providing a touch of greenery against the blue sky.

4.96 out of 5 average rating, 73 reviews

Canal Front Condo 2 Blocks 2 Beach & Park Sleeps 4

1 bed/1 bath bayside canal front condo on 123rd Street in Ocean City, Md. Walk 2 blocks to the BEACH, NORTHSIDE PARK/Restaurants/shopping/Starbucks/CVS/WAWA/Grocery FREE PARKING, Wi-Fi, 2 smart TVs, full kitchen and laundry. POOL open Memorial Day - Labor Day Comfy Ext Firm queen bed and MF queen sleeper NO SMOKING, PETS, DRUGS WE PROVIDE PLENTY OF PILLOWS & BLANKETS PLEASE PACK BED SHEETS BEACH/BATH TOWELS We are happy to host families and guests 25+. Weekly discount available

A living area features a spacious sofa and accent chairs arranged invitingly. Natural light filters in through large sliding glass doors, offering views of the ocean. Decorative artwork adorns the walls, and a light-colored area rug adds a touch of warmth to the hardwood floor.

4.98 out of 5 average rating, 133 reviews

Oceanfront 1 Bedroom, Pool, Ocean & Bay Views

OVERSIZE one-bedroom plus TWO large 3-season rooms! The back balcony is filled with expansive ocean views from every angle and sliding windows, and the front porch looks out to the bay - wonderful atmosphere in the quiet north end. Linens included! Property Amenities - King size bed & queen sleeper - Large outdoor pool - Elevators - Dedicated high-speed WiFi and router w/ ethernet (Xfinity 100Mbps) - 2 Smart TVS with Xfinity, Roku - Washer/Dryer in unit - Keyless check-in 24/7

The oceanfront studio condominium is positioned alongside a sandy pathway, leading to the beach. The building features multiple balconies on the second and third floors, allowing for views of the surrounding area. Vegetation and beach fencing can be seen framing the pathway.

5 out of 5 average rating, 14 reviews

Oceanfront apt with amazing view

Incredible views at this oceanfront studio perfect for couples or a small family. Just steps to the beach through a private walkway. The dedicated parking space means you don't have to worry about parking. From this amazing location you are not only steps to the beach but also the on-site pool in the summer months, restaurants, bars, activities and the fantastic Northside Park. Kitchen essentials and linens are included which means less to pack and more time to relax.

An outdoor courtyard features a round table surrounded by six mesh chairs under a blue umbrella. A patterned area rug adds color to the space. Wooden steps lead to the entrance of the unit, complemented by the blue siding of the building.

5 out of 5 average rating, 10 reviews

Welcome to Splash Pad-pools, beach + private patio

Welcome to Splash Pad at Harbour Club—your perfect bayside retreat in North Ocean City! Nestled off of 120th Street, this first-floor gem combines the comforts of home with the magic of a beach getaway Prime Location: Enjoy the serenity of a bayside stay while being just a short stroll to the beach. We even provide beach chairs, umbrellas and a beach wagon to make your walk to the beach a breeze. All you need to do is pack your sunscreen and beach towels!

4.94 out of 5 average rating, 36 reviews

A spacious outdoor deck offers stunning views of the beach and ocean under a clear blue sky. Sunlight reflects off the water, while seating areas are arranged around a small table. Surrounding buildings provide context to the vibrant atmosphere of the area.

Townhouse in Ocean City

4 Level Townhome w/ In-law Suite~Pool & Oceanview

Bring the whole family to enjoy this large four level townhome on Oceanside 47th st. Only steps away from the beach with a variety of spaces to satisfy everyones needs. From ocean view rooms w/ private decks to a poolside in-law suite, our home is the perfect beachy getaway. *Walk to Seacrets, Dumsers, Belly Busters and more at this Central/Midtown location* *4/5 bedrooms, 4 full baths, and 2 kitchens* *Pool open Memorial Day - Labor Day*

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, 340 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 light-colored sofa is adorned with various cushions, including a white fluffy pillow and blue accents. Above the sofa, three framed prints depict a sun rising over stylized waves. A coffee table with decorative items is positioned in front of the sofa.

5 out of 5 average rating, 15 reviews

Oceanblock Coastal Boho Condo~

Escape to coastal boho bliss at this ocean block condo, just a few steps to the beach! This one bedroom, two bathroom condo also features a small bunkroom and pull out couch. It is the perfect spot for your next getaway. Whether you’re here for a fun family vacation, a romantic getaway, or simply to unwind, this condo has everything you need for a comfortable and memorable stay.

Popular amenities for Ocean City rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.89 out of 5 average rating, 27 reviews

2 BR Ocean Front Condo w/Pool, Expansive Views

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, 277 reviews

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

5 out of 5 average rating, 106 reviews

Home in Frankford

Quiet 3BR Coastal Home Minutes to Bethany Beach

4.81 out of 5 average rating, 212 reviews

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.

Home in Berlin

Bayside community near OCMD great rates

A serene koi fish pond is framed by natural stone, with lush green lily pads floating on the water's surface. Various koi fish can be seen swimming in the clear water, adding a calming element to the outdoor space.

4.79 out of 5 average rating, 126 reviews

Welcome to our beach retreat!

4.88 out of 5 average rating, 144 reviews

Beautiful Cottage W/ shared pool & close 2 beach

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, 138 reviews

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

4.81 out of 5 average rating, 113 reviews

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.

Home in Berlin

Mosaic Life Escapes -Bayfront Million Dollar Views

Apartment rentals with a pool

An open-concept living area features floor-to-ceiling windows offering sweeping ocean views. A spacious kitchen with modern appliances is complemented by an island and breakfast bar. Comfortable seating is arranged around a coffee table, creating an inviting space for relaxation and gathering.

4.87 out of 5 average rating, 150 reviews

Gorgeous oceanfront Capri Beach and Bay Views!!!!

A bright living area features a large flat-screen television mounted above a fireplace. Comfortable seating is provided by a gray armchair and a striped sofa. Natural light floods the space through sliding glass doors, which lead to a balcony with a scenic bay view.

4.92 out of 5 average rating, 49 reviews

BIKINIS & MARTINIS! 3 bedrooms, 2 baths, bayfront

5 out of 5 average rating, 65 reviews

✨OC 123✨ Canal front 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

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.

Apartment in Ocean Pines

Ocean Pines marina view condo

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.

4.95 out of 5 average rating, 311 reviews

Direct Oceanfront with a View and Amenities Galore

Superhost

A dining area features a wooden table surrounded by metal chairs, complementing the open concept design. Natural light filters through a large window, illuminating the space. A staircase leads to the upper level, while decorative plants add a touch of greenery.

4.82 out of 5 average rating, 62 reviews

Renovated Downtown Townhome W/ Pool & Shuffleboard

The modern kitchen features white cabinetry with a large, white island at the center, equipped with seating for four. Stainless steel appliances and pendant lighting enhance the contemporary design. A window provides natural light, highlighting the open layout that connects to the living area.

4.92 out of 5 average rating, 104 reviews

Renovated Oceanside Modern Boho Beach Retreat

Other holiday rentals with a pool

The dining area features a spacious table with neutral placemats and six wooden chairs. A modern kitchen is visible in the background, showcasing wooden cabinetry and stainless steel appliances. Natural elements like potted plants and tall grasses add a refreshing touch to the open layout.

4.97 out of 5 average rating, 39 reviews

Luxury 3BR/4BA Oasis: Close to Beach, Indoor Pool

5 out of 5 average rating, 12 reviews

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.

Home in Ocean Pines

Cozy beach home away from home!

An open-concept living space features a dining area with wooden chairs surrounding a rectangular table, and a blue couch positioned toward a wall-mounted television. A modern kitchen with a breakfast bar and stools is visible, complemented by natural light from large windows.

4.88 out of 5 average rating, 24 reviews

Direct ocean front 3 bedroom condo with pools

An open kitchen and dining area is displayed, featuring a granite-topped island with bar seating. Light cabinets and stainless-steel appliances occupy the kitchen space. A dining table with wooden chairs is positioned nearby, while a cozy living area is visible in the background.

4.91 out of 5 average rating, 47 reviews

HUGE bayside condo just 2 blocks from the ocean

Superhost

A spacious living area features blue accent walls, striped sofas, and a light wooden coffee table. A modern kitchen is equipped with stainless steel appliances and white cabinetry. Natural light fills the space through multiple windows, highlighting the coastal-inspired décor.

4.82 out of 5 average rating, 38 reviews

On Beach Time - Downtown OCMD with Pool

Superhost

4.75 out of 5 average rating, 12 reviews

Bluewater Beachfront Bliss

5 out of 5 average rating, 10 reviews

Beach resort at The Carousel

A light-filled living area features a soft white sofa adorned with coral-themed pillows. Large sliding glass doors provide an unobstructed view of the bay, leading to a private balcony. A dining space is visible in the background, complementing the tranquil ambiance.