Vacation rentals with a pool in Ocean City

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Ocean City

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favourite
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
4.94 out of 5 average rating, 283 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!

Top guest favourite
Condo in Ocean City
5 out of 5 average rating, 21 reviews

BeachBox II • The One with Wraparound Water Views

Just looking? ❤️ Add us to your Wishlist. Questions? 💬 Message for a quick reply. 4th-floor corner unit with breathtaking views of the bay, ocean & inlet—2 blocks from the boardwalk, beach & all of OC's downtown attractions. Guests rave that it's clean, well-stocked, & family-friendly with thoughtful touches throughout. Relax by the bayside pool or spot Assateague Island's wild horses from the balcony. Walk everywhere, sleep soundly, & make memories! Perfect for couples & small families alike.

Top guest favourite
The image captures a serene view of the bay, with calm waters extending toward the horizon. A wooden pier can be seen jutting into the water, complemented by a nearby tree that adds a touch of greenery. The sky is partly cloudy, enhancing the natural setting.
Condo in Ocean City
4.91 out of 5 average rating, 287 reviews

Wight Bay Unit 245

2 bedroom, 2 bath, sleeps 6 *2nd bedroom will have twin bunk beds & 1 queen bed for 2025! Beautiful recently renovated condo! Bay-side 47th street on the canal with an amazing bay view. The building is in a prime location right next door to Seacrets! There is a pool, two piers, and it’s only a block from the beach. Perfect for getaways with friends or family! Bedroom 1: 1 Queen bed Bedroom 2: Twin bunk beds, 1 Queen Bed Living room: 1 Queen pull out couch 1 Parking Pass, Pool, Elevator

Top guest favourite
Condo in Ocean City
5 out of 5 average rating, 11 reviews

Downtown Condo, Parking, Walk to Beach & Boardwalk

Modern 2BR/2BA downtown Ocean City condo with bay view, balcony, elevator, pool, and parking. Sleeps 6 with 1 king and 2 queen beds. Walk about 1,000 ft to the inlet beach, boardwalk, rides, pier, dining, festivals, and downtown events. Enjoy a full kitchen, dishwasher, washer/dryer, smart TVs, WiFi, linens, bath towels, beach towels, chairs, umbrella, and cooler. Includes 1 assigned parking space plus 1 shared first-come space with passes. Perfect for families, couples & event-goers year-round.

Top guest favourite
Apartment in Ocean City
5 out of 5 average rating, 13 reviews

SeaGate Serenity | Oceanfront Condo with Balcony

Wake up to the sound of the waves crashing outside your window and finish your days relaxing on the private balcony as you watch the pastel skies over the ocean at sunset. Come find your serenity by the sea in our newly renovated oceanfront condo. Located in midtown, you can keep your car parked in our reserved spot and walk to many of the towns best restaurants, bars, and entertainment as well as the World Famous Ocean City Boardwalk. Morning beach strolls, pool days, and evening sips await :)

Top guest favourite
A spacious living area features comfortable seating arrangements, including a large sectional sofa and recliners. A flat-screen television is positioned on an entertainment unit, and ample natural light is provided by multiple windows and a sliding door leading to the sunroom. Wooden flooring enhances the open atmosphere.
Home in Ocean City
4.95 out of 5 average rating, 101 reviews

Spacious waterfront home & boat access!

Waterfront getaway, easy beach access (0.3 mile walk), pool, restaurants, and more. Linens & towels included! Bring your boat! Pier tie up available. Spacious 3 bedroom + bonus room with sleeping arrangements for 10(8 beds). This well-maintained home is close to dining, shopping, NorthsidePark & all the fun activities Ocean City has to offer. Beach chairs, toys, kayaks & paddleboard available. Fireworks from Northside Park can be viewed every Sunday summer night - right from the driveway!

Guest favourite
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.
Condo in Ocean City
4.92 out of 5 average rating, 104 reviews

Renovated Oceanside Modern Boho Beach Retreat

Escape to Grace's Getaway in the heart of desirable Midtown Ocean City. **NOW OFFERING MINI WEEK RENTALS DURING SELECT PEAK SUMMER WEEKS** Mini Week Rentals are offered Sunday-Wednesday or Wednesday-Sunday. This fully renovated 3 bed/3 bath condo complete with ***COMPLIMENTARY LINEN SERVICE*** is the perfect escape. Prime oceanside location is 100 steps to the beach and offers sunset views from the balcony overlooking the pool. Condo is equipped with cable/high speed internet & Roku.

Guest favourite
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.
Condo in Ocean City
4.98 out of 5 average rating, 247 reviews

Cozy oceanfront condo with stunning ocean views

Fully updated 1 bed/1 bath oceanfront condo in a quiet, mid-rise building with a beachfront pool in uptown OC. The perfect unit for a quick romantic getaway, long weekend, or family vacation. We are happy to accommodate the dates and timeframes that meet the needs of our guests. If possible, please consider these recommended timeframes for your booking: Memorial Day - Labor Day -7 Nights, Fri-Fri or Mon-Mon -3 Nights, Fri-Mon -4 Nights, Mon-Fri Labor Day - Memorial Day -Any 2 Nights

Guest favourite
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.
Condo in Ocean City
4.95 out of 5 average rating, 176 reviews

Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool

Opal Osprey: This OVERSIZE one-bedroom condo has been completely remodeled... giant oceanfront balcony PLUS a large patio room on the bayside! Expansive ocean views from every angle, super easy beach access, wonderful atmosphere in the quiet north end of OC. 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 - Keyless check-in 24/7

Guest favourite
Condo in Ocean City
4.84 out of 5 average rating, 233 reviews

Beachfront 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 a breathtaking view of the beach and ocean.

Guest favourite
A spacious living area is displayed featuring comfortable navy blue sofas and patterned armchairs. A large coffee table rests on a textured rug, with a view of the ocean visible through floor-to-ceiling windows. An electric fireplace adds warmth, while a dining table invites gatherings.
Condo in Ocean City
4.86 out of 5 average rating, 231 reviews

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

Book 4 nights, get 1 night FREE stays thru June 11. inquire before booking This is a Ocbeachfrontrentals .com premier property 24/7 SUPPORT LINEN & TOWELS PROVIDED 8TH FLOOR PENTHOUSE! This stunning top floor 3 b 2.5 ba unit is the ULTIMATE friends & family beach trip, located in a premier building in Ocean City. Enjoy the ocean breeze and stunning views from over 150 square ft of private balcony. Wake up to ocean views from every room!

Guest favourite
Condo in Ocean City
4.94 out of 5 average rating, 109 reviews

Boutique Moments OC • Pool • Walk to Boardwalk

Absolutely no parties! Stylish, spotless boutique getaway just 2 blocks from the beach and minutes from the Boardwalk, downtown restaurants, and local attractions. Enjoy a beautiful pool, fast WiFi, cable TV, and a thoughtfully designed modern stay made for comfort and relaxation. Primary guest must be at least 21 to book. Adults-only stay, no parties, and no pets allowed. 🚪🚪 I’m here to help anytime—I live just 2 doors down.

Popular amenities for Ocean City rentals with a pool

When is the best time to visit Ocean City?

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Quick stats about vacation rentals with a pool in Ocean City

  • Total vacation rentals

    Explore 3,230 vacation rentals in Ocean City

  • Nightly prices starting at

    Ocean City vacation rentals start at $14 CAD per night before taxes and fees

  • Verified guest reviews

    Over 59,350 verified reviews to help you choose

  • Family-friendly vacation rentals

    2,460 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 180 rentals that welcome pets

  • Rentals with dedicated workspaces

    1,650 properties have a dedicated workspace

  • Wifi availability

    3,170 of Ocean City vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Ocean City rentals

  • 4.7 Average rating

    Ocean City stays receive an average rating of 4.7 out of 5 from guests

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