Vacation rentals with a pool in Worcester County

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Top-rated rentals with a pool in Worcester County

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, 272 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!

Guest favourite
A spacious living area is furnished with a light-colored couch and an armchair, complemented by a ceiling fan above. A flat-screen TV sits on a wooden media console, while a dining table is positioned in the background, leading towards an updated kitchen area.
Condo in Ocean City
4.83 out of 5 average rating, 176 reviews

☀️ Enjoy the Beachlife!! —>2Bed & 2Bath Condo ☀️

Relax with the whole family at this peaceful OCEANFRONT Condo in OCMD! Updated 2 Bedroom & 2 Full Bath on the 1st floor Atlantis High-Rise that sleeps 8. Most Importantly- Only Steps to THE BEACH! Unit is Self-Checkin & is walking distance/short drive to many Restaurants, Shops, Attractions, etc. Large Outdoor Pool is on site (seasonal). Toys, Games, Puzzles & is perfect for families with children. NO Smoking allowed. No Pets or Large groups(8 max) or senior week rentals permitted. Book Today!

Top guest favourite
The living area features comfortable electric reclining sofas facing a coffee table. Large windows provide views of the ocean, while a dining area and modern kitchen are visible in the background, creating a spacious and inviting atmosphere.
Condo in Ocean City
5 out of 5 average rating, 117 reviews

2BRCapri: Indoor Pool, Game Room, Massage Chair

ALL THE COMFORTS OF HOME AT THE BEACH! BRAND NEW RENOVATED BATHROOMS! -ALL LINENS INCLUDED -Comfortable electric-reclining sofas -65-in smart Roku TV with soundbar. -Massage chair in master bedroom -Balcony & Dining Area w/ Ocean +Bay Views -In-unit W/D -Many conventional & USB Outlets -Arcade level features b-ball hoop, pool tables, ping-pong, shuffleboard, air-hockey -Outdoor tennis court -Large heated indoor pools -can swim full laps -Sauna and Gym -Board games in unit -Fast Wifi

Guest favourite
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.
Condo in Ocean City
4.79 out of 5 average rating, 220 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.

Top guest favourite
An open living area is highlighted by large windows that offer views of the bay and pool. A comfortable sectional sofa is positioned adjacent to a smart TV, while a modern dining table for four is visible next to the kitchen. The space features light-colored walls and natural wood flooring.
Condo in Ocean City
4.96 out of 5 average rating, 107 reviews

Gone Coastal *Pool* Bayside with view* Top Floor

Welcome to Gone Coastal! Relax in this beautiful 2BR/2BA getaway featuring: 🛏 1 King (Master) | 1 Twin-over-Full Bunk | 1 Sleeper Sofa 🏊‍♂️ Outdoor Community Pools – Lap & Family Pool (Directly Across!) 🔑 Keyless, Contactless Check-in 🌅 Spacious Deck – Outdoor Dining + Bay & Pool Views 📺 Smart TVs + YouTube TV 🛒 1-Minute to Grocery Store 🍽 Fully Equipped Kitchen 📍 Prime Location – 120th St, Heron Harbor 🚗 Ample Free Onsite Parking A perfect retreat for families & beach lovers! 🌊☀️

Guest favourite
A spacious bedroom features a king-sized bed adorned with a patterned comforter. Large glass doors offer ocean views and open to a balcony with seating. A light-colored dresser and a wall-mounted TV complete the room, with soft natural light filling the space.
Condo in Ocean City
4.93 out of 5 average rating, 133 reviews

Oceanfront Studio, King bed, Sleeps 4, Pool, Wi-Fi

Wake up with ocean views right from your king-sized bed! This stunning ocean front studio comfortably sleeps 4 guests and offers a restful retreat in N. Ocean City. Whether you order carry-out or cook at home the kitchen has everything you need! Enjoy your coffee with the sun rise over the Atlantic or sip a cocktail on the balcony while gazing at the beach during the "golden hours" of evening. Located away from the hustle and bustle of the boardwalk, but only a short drive/bus ride away!

Top guest favourite
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.
Guest suite in Ocean Pines
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.

Guest favourite
Condo in Ocean City
4.84 out of 5 average rating, 222 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.

Top guest favourite
A bright living area features wooden beams and large windows adorned with plaid curtains. A variety of cushions decorate a sectional sofa and a leather couch. A television offers a view of a sports event, while an area rug adds pattern to the wooden floor.
Farm stay in Princess Anne
4.95 out of 5 average rating, 113 reviews

Farmhouse located on a horse farm

Farmhouse located just minutes off of Route 13 in Princess Anne, MD. Enjoy a peaceful farm experience while staying in a charming farmhouse with lots of character. You can walk the grounds of the farm, including a trail through the woods, or take a swim in the pool. We do not offer horseback riding lessons but you can interact with the horses. We are minutes to shopping, groceries, restaurants, UMES, and a short ride to Chincoteague (32 miles) and Ocean City (40 miles).

Top guest favourite
A cozy living area displays a light blue color scheme. A white sofa is positioned beside a coffee table on a patterned rug, while a dining table is set nearby. Floor-to-ceiling sliding doors open to a balcony, offering views of the ocean.
Condo in Ocean City
4.96 out of 5 average rating, 292 reviews

Caramar Couples Retreat

This cute little first floor efficiency condo is ocean front for a perfect vacation to the beach. It’s an older building but has been partially renovated and updated. You can get to the beach by a very short walk through a private walkway from the condo building. The view from the private balcony is perfect and relaxing. WiFi provided upon check in- xfinity, Netflix, and internet. Indoor and outdoor dining areas and a full kitchen. Closet and dresser for storage use.

Guest favourite
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
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!

Top guest favourite
The living room features a comfortable seating area with gray sofas and a round coffee table. A flat-screen TV is mounted on the wall. Large sliding glass doors provide expansive views of the ocean, complemented by a blue area rug on the tiled floor.
Condo in Ocean City
4.9 out of 5 average rating, 157 reviews

Oceanfront & Amazing views! Time to book for 2026!

Great Mid-Town location! Direct Ocean front, 3 bedroom 2 full bath condo. Breathtaking views from very room. Natural light flows in from sliding glass doors and new windows, brightening the entire condo. When the surf gets too rough, go for a swim in the outdoor pool. 3 elevators and 2 assigned parking spaces. Make our home your home for vacation. Come stay at the Sandpiper Dunes and make wonderful memories that will last a lifetime!

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