
Vacation rentals with a pool in Worcester County
Find and book unique homes with a pool on Airbnb
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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Popular amenities for Worcester County rentals with a pool
House rentals with a pool

West OC Bayside Getaway w/ pool
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.

OC, Md great amenities, near national park/beaches
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.

Luxury OC Beach House w/ Deluxe Game Room & Pool!
Andrew's place was definitely everything we wanted and more. we will definitely be coming back soon.

Little house in Berlin, Md.
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.

Loch Raven Retreat/spacious home w/ private pool
The cleanest AirBnB we’ve ever stayed in! Great location, easy communication with the host. Would not hesitate to book Loch Raven again.

Nautical at 82 Newport- private dock & waterfront
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.

Large beachy feel 4 Bedroom
Brian's home was beautiful! we really enjoyed ourselves definitely be renting again

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

Bayside Boaters' Paradise | Pool | Family Fun
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.

Ocean Front 802 Midtown Oasis Pool & Parking
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.

Sunset Tranquility - 3/2.5 Midtown-1 block Ocean
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!

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

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

OC's Only Private Resort
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.

Paradise At Sunset Island In OC
We love staying at Sunset Island. This is the first time in a condo and it was perfect!

Family Friendly Two BR OCMD Condo Bay Side
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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- Ocean City Beach
- Broadkill Beach
- Assateague Island National Seashore
- Deauville Beach
- Ocean City Boardwalk
- Jolly Roger Amusement Park
- Dewey Beach Access
- Northside Park
- Heritage Shores
- Jolly Roger at the Pier
- Cape Henlopen State Park
- Peninsula Golf & Country Club
- Bayside Resort Golf Club
- Delaware Seashore State Park
- Towers Beach
- Gerry Boyle Park
- Bow Beach
- Baywood Greens Golf Maintenance
- Poodle Beach
- Guard Shore
- Wallops Beach
- Langford Sand
- Saint Jerome Beach
- Plantation Lakes Golf and Country Club
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