Vacation rentals with a pool in Worcester County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Worcester County rentals with a pool

House rentals with a pool

Guest favorite
A private pool is surrounded by a paved patio, providing spacious outdoor lounging areas. Two vibrant green chairs are positioned beside the water, with gently swaying plants creating a relaxing ambiance.
Home in Ocean City
4.92 out of 5 average rating, 39 reviews

West OC Bayside Getaway w/ pool

ZacharyRating, 5 stars3 months ago
House is in one of the best spots for easy in and out of inlet access to beach, shopping, and restaurants. Gives you an extremely personal, and private way to thoroughly enjoy beach life environment. Doug was absolutely amazing from start to finish. Hospitality beyond expectations, which made the stay that much more enjoyable.
Guest favorite
A large swimming pool is surrounded by a concrete deck, with numerous white lounge chairs arranged along one side. The calm water reflects the clear blue sky, while the distant community homes are visible in the background, creating an inviting leisure space.
Home in Berlin
4.79 out of 5 average rating, 192 reviews

OC, Md great amenities, near national park/beaches

EmilyRating, 5 stars7 months ago
Shawn and Terri’s air bnb went above and beyond my expectations! We decided not to stay on the beach this year but I didn’t realize that we’d still be right on the bay! There’s a peer overlooking the ocean that was just a five minute walk away. Not only that, but the community itself was private, peaceful, and had everything you could ever need to stay busy! There were two pools, ball courts, and playgrounds all walking distance. The residents were kind and welcoming. Assateague beach was a five minute drive away and restaurants only a ten minute drive! The main strip of ocean city was super close. The air bnb itself was clean and beautifully decorated. There were extra blankets, amenities, my son loved the cards and coloring books! All in all this was the perfect place to stay.
Guest favorite
Home in Ocean City
4.93 out of 5 average rating, 28 reviews

Luxury OC Beach House w/ Deluxe Game Room & Pool!

OluwafemiRating, 5 stars1 month ago
Andrew's place was definitely everything we wanted and more. we will definitely be coming back soon.
Guest favorite
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.
Home in Ocean Pines
4.95 out of 5 average rating, 128 reviews

Little house in Berlin, Md.

JaredRating, 5 stars5 months ago
William's place was perfect for our three-night getaway and exactly as described. The house was a perfect fit for me, my wife, and two daughters and there was plenty to do for the kids. The house is conveniently located about 15 minutes from the beach, but the immediate area also had plenty in the way of dining and other things to do. We travel up to OC about once a year and looking forward to hopefully staying here again.
Top guest favorite
A two-story home is presented with a brick facade and light-colored siding. Green shutters frame the windows, while a small garden with shrubs and flowers is located at the front. A driveway leads up to the entrance steps, surrounded by well-maintained lawn and trees.
Home in Salisbury
5 out of 5 average rating, 52 reviews

Loch Raven Retreat/spacious home w/ private pool

ElizabethRating, 5 stars3 weeks ago
The cleanest AirBnB we’ve ever stayed in! Great location, easy communication with the host. Would not hesitate to book Loch Raven again.
Superhost
A spacious deck offers several white Adirondack chairs arranged for relaxation, overlooking a tranquil canal. Gentle reflections of trees in autumn colors can be seen on the water, enhancing the serene outdoor setting.
Home in Ocean Pines
5 out of 5 average rating, 3 reviews

Nautical at 82 Newport- private dock & waterfront

MARYANNRating, 5 stars4 months ago
My family if 12 had plenty of space. The house was immaculate and the views were amazing. great sunrise view from the back deck. Very prompt communication when ever i had questions. I would highly recommend this home. Hottub was used daily and enjoyed.
Top guest favorite
Home in Ocean City
5 out of 5 average rating, 19 reviews

Large beachy feel 4 Bedroom

RavenRating, 5 stars3 months ago
Brian's home was beautiful! we really enjoyed ourselves definitely be renting again
Superhost
An expansive outdoor pool is featured, showcasing clear blue water under bright sunlight. Surrounding lounge chairs are arranged neatly along the pool deck, and a gentle landscape of greenery is visible in the background.
Home in Berlin
4.92 out of 5 average rating, 37 reviews

Bayside 6BR 4.5 Bath w/2 Pools & Sep In-Law suite

LaurenRating, 5 stars2 weeks ago
We loved this spot - perfect location for adventures at Assateague and running into Ocean City. The house is in a great neighborhood, which was perfect for walking the dog early in the morning. The kids loved the indoor pool, and we enjoyed the quiet. Highly recommend staying here, and we plan on coming back!

Condo rentals with a pool

Superhost
An aerial view of the bayside condo highlights multiple white buildings, with balconies facing the water. The outdoor pool is visible beside the docks, and parking areas surround the complex. The shoreline gently meets the bay, creating an inviting waterside setting.
Condo in Ocean City
4.82 out of 5 average rating, 57 reviews

Bayside Boaters' Paradise | Pool | Family Fun

SusanRating, 5 stars5 months ago
Beautiful view on the bay. Ally was very thorough & communicative throughout the process. Only thing that is kind of a bummer is that linens are not included. But other than that, I highly recommend Ally's condo.
Guest favorite
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.
Condo in Ocean City
4.91 out of 5 average rating, 305 reviews

Ocean Front 802 Midtown Oasis Pool & Parking

MoniqueRating, 5 stars1 week ago
I enjoyed staying at this location. The view once you enter the condo is fantastic. Access to the beach and to other ocean city restaurants are great very walkable or very very short drive . The building is undergoing some kind of construction so when you walk into the building it’s clearly being worked on and is a bit dusty but once you get in the condo everything melts away. The condo also comes with some beach chairs and umbrellas.
Guest favorite
A rooftop pool area is highlighted, featuring a rectangular swimming pool surrounded by a spacious sun deck. Lounge chairs are positioned around the pool, and a clear blue sky is visible above, creating a serene outdoor environment.
Condo in Ocean City
4.89 out of 5 average rating, 27 reviews

Sunset Tranquility - 3/2.5 Midtown-1 block Ocean

LeandroRating, 5 stars8 months ago
We loved this place! beautiful unit with a Bay View, pool on the roof top, 2 parking spots and walking distance to everything. Violet was very responsive and showed that she cared if we got to the place safely and gave clear instructions on how to get into the space. we will be back, thank you!
Guest favorite
A covered patio area features a small table with two chairs, facing expansive canal views. String lights hang overhead, enhancing the tranquil setting. The surroundings include well-maintained grass and neighboring waterfront units, providing a peaceful outdoor space for relaxation.
Condo in Ocean City
4.97 out of 5 average rating, 34 reviews

2BR Waterfront | 1st Floor | Patio | Pool | W/D

ShannonRating, 5 stars2 weeks ago
The place was optimum for our mini vacay. We absolutely loved the area, it was peaceful and relaxing and the amenities were just right. Jaqueline remained open and available for communication and was very clear in her expectations of us as guest. Definitely 5 Stars!
Superhost
A swimming pool is surrounded by several lounge chairs, providing ample space for relaxation. The vibrant blue water invites swimming, while people are seen enjoying the pool. A nearby fence enhances safety, and pool floats are casually placed along the edge.
Condo in Ocean City
4.71 out of 5 average rating, 7 reviews

Time N Tide Condo - 2 BR w/Pool, Boardwalk/Beach

VickieRating, 5 stars7 months ago
The Time-n-Tide condo was great! Very well furnished, great decor, excellent amenities and great location. We felt very relaxed and comfortable during our stay, super cozy. Tina & Daryl we're very helpful with information and responsive to any questions we had. We hope to stay here again - great choice and value.
Superhost
Condo in Ocean City
4.69 out of 5 average rating, 29 reviews

OC's Only Private Resort

LauraRating, 5 stars7 months ago
Great place in a great spot! We enjoyed quiet mornings on the porch and being able to walk to nearby shops and restaurants with ease.
Superhost
A spacious outdoor pool is highlighted, surrounded by lounge chairs and with a scenic backdrop of clouds and blue sky. The pool area features multiple swim lanes, enhancing the inviting atmosphere of the gated community.
Condo in Ocean City
4.77 out of 5 average rating, 13 reviews

Paradise At Sunset Island In OC

JaniceRating, 5 stars8 months ago
We love staying at Sunset Island. This is the first time in a condo and it was perfect!
Superhost
An outdoor community pool is surrounded by a concrete deck, equipped with lounge chairs. Multiple balconies are visible from the adjacent buildings, adorned with pink flowers. The tranquil setting is complemented by soft lighting as the sun sets in the background.
Condo in Ocean City
4.88 out of 5 average rating, 40 reviews

Family Friendly Two BR OCMD Condo Bay Side

KirstenRating, 5 stars8 months ago
It was a great place with lots of space! Diane even had a helpful manual with local stores, restaurants, hospitals, and pharmacies around the area. Very easy check in and check out process.

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