Holiday rentals with a pool in Worcester County

Find and book unique homes with a pool on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Worcester County rentals with a pool

House rentals with a pool

Superhost
Home in Berlin
5 out of 5 average rating, 4 reviews

Mins to Golf & Beach! Private Pool & Luxe Firepit

CaroleRating, 5 stars3 weeks ago
Lindsay and Andrew’s Summer Breeze home in Berlin met all of our expectations. We particularly enjoyed the pool, grill and outdoor amenities - which made it perfect for our family holiday weekend getaway. The house is well kept, comfortable, neatly stocked with all essential amenities as described and, is staged and modeled exactly as pictured in the photos. We appreciated a quiet retreat, off the beaten path, yet we had an easy and quick drive to stores, restaurants and to the Ocean City boardwalk. As hosts, they were very responsive and efficiently communicated what we needed to know in advance, making our stay easy and smooth. From the booking process to assisting us with a couple of adjustments, they did not hesitate to help us. If there is an opportunity for us in the future, we’d love to stay again. Thank you Lindsey and Andrew!
Guest favourite
Home in Ocean City
4.95 out of 5 average rating, 255 reviews

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

ErikaRating, 5 stars3 weeks ago
Beautiful spot! Great location, close to all the happenings of Ocean City, but peaceful and quiet at the house…perfect set up. Great neighborhood. The house is beautiful, all the beds very comfortable. The back deck is gorgeous, thoroughly enjoyed that space and taking the kayaks out on the canal! It’s worth bringing your own linens and towels, we packed everything into a large tote and it worked out perfectly. Very responsive and friendly host! We had a great time here and plan to return. Highly recommend!
Top guest favourite
Home in Ocean City
5 out of 5 average rating, 5 reviews

TwoBlockstoBeach&Boardwalk! Pool! PingPong! Bikes!

DesireaRating, 5 stars1 week ago
This home was perfect for our family getaway! Shawn was an excellent host! The home had great amenities and things for our family to do! We really appreciated the beach gear, chairs, wagon, pool toys and games. You can tell Shawn put a lot of thought into this home and what it has to offer to its guests. We recommend this home for sure! Beautiful home!
Top guest favourite
Home in Ocean Pines
5 out of 5 average rating, 48 reviews

Ocean Pines Fun – Arcade, Pools & Near O.C. Beach

KarenRating, 5 stars1 month ago
The host was so accommodating and respectful! always responded quickly! Location was perfect for where our family needed to be! Host allowed us to checkin early on day of arrival after very long trip! Excellent, and beautiful property! Thank you so much!
Guest favourite
Home in Ocean Pines
4.95 out of 5 average rating, 129 reviews

Little house in Berlin, Md.

AmandaRating, 5 stars2 months ago
Great for a few days getaway! Comfortable and cozy!
Guest favourite
Home in Salisbury
4.9 out of 5 average rating, 60 reviews

Bury Oasis: Pool, Hottub, Movie Theatre, Game Room

DavidRating, 5 stars5 months ago
The Oasis was perfect for our needs . We will definitely book it again in the future!
Guest favourite
Home in Ocean City
4.9 out of 5 average rating, 126 reviews

Beautiful Cottage W/ shared pool & close 2 beach

TerryRating, 5 stars2 weeks ago
Everything was as described. Jennifer was very responsive and left excellent instructions on everything. We will stay there again.
Top guest favourite
Home in Ocean Pines
4.99 out of 5 average rating, 87 reviews

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines

MiaRating, 5 stars6 days ago
My family really enjoyed our stay here. The house was so quaint, clean, well stocked, and all on one floor. There was plenty of space for my multi-generational family. Also, the beaches and other area attractions were nearby (just a short drive). I’d definitely recommend staying here!

Apartment rentals with a pool

Top guest favourite
Apartment in Ocean City
4.92 out of 5 average rating, 110 reviews

Steps from Seacrets Beach House Getaway

jondaRating, 5 stars8 months ago
Andrew could not have been a better host. He was especially responsive even when were checking in late. It was truly a great experience
Superhost
Apartment in Ocean City
5 out of 5 average rating, 3 reviews

New Updated Direct Oceanfront Condo - Pool & Wifi!

KaraRating, 5 stars2 weeks ago
Listing is better than you think it is! Great location (I was nervous about it because we usually stay closer to 120th St) it was very private and peaceful. Big bonus that it is right over the bridge (no extra traffic lights!) The kitchen is fully stocked - we wound up bringing a lot that we didn’t need. The pullout couch is also one of the most comfortable I’ve ever been on. Beautifully decorated and updated. Might book again this season!
Guest favourite
Apartment in Ocean City
4.91 out of 5 average rating, 35 reviews

Cozy 1 BR Condo - 5 Minute walk to Beach, w/ Pool!

DanielleRating, 5 stars2 weeks ago
Our stay was very peaceful and relaxing all thanks to Clint’s place! We were able to walk to the boardwalk and restaurants. The place itself was clean and has everything you would need on vacation. Thank you Clint!
Top guest favourite
Apartment in Ocean City
5 out of 5 average rating, 44 reviews

Top Rated! Beautful Sunsets! Midtown Bayside Condo

LandonRating, 5 stars1 week ago
Raphaelle is a great host and our stay was amazing. With great views and an accommodating place, would certainly return!
Superhost
Apartment in Ocean City
4.87 out of 5 average rating, 77 reviews

Oceanview Oasis with 2 private balconies

AmyRating, 5 stars2 days ago
Beautiful place with the best views!!! Great area. The pool was awesome and heated most days and with the cold/cloudy days we had, that was a treat especially for my daughter. It was never busy or crowded and had very friendly staff. All VERY nice families/couples stayed here- no noise or ruckus at night. Julie was responsive and quick. My only “concern” Would be no screen door on deck but luckily we didn’t get many flies/birds up that high (14th floor). Still I would have loved to sleep with the sliding door open listening to the ocean. It had two bed rooms and all was decorated nicely. We had such a GREAT time and absolutely LOVED Fountainhead and would definitely stay again!!
Top guest favourite
Apartment in Ocean City
4.91 out of 5 average rating, 22 reviews

The Coastal Condo

ChelsieRating, 5 stars1 week ago
We loved our stay at The Marylander in Colleen & Joe’s condo. From the very start she was very responsive, understanding and kind. The condo was the perfect amount of space which was well cared for & clean, we enjoyed the amenities that came with the building and the short walk to the beach! I’m already looking forward to booking another stay here!
Guest favourite
Apartment in Ocean City
4.9 out of 5 average rating, 202 reviews

Prime Condo North OC 2 Blocks to Beach w/ Pool

AndreaRating, 5 stars1 week ago
Place was great to stay at ! Very nice host and clear instructions. 10/10 👍🏽
Guest favourite
Apartment in Ocean City
4.93 out of 5 average rating, 41 reviews

127th Bayside-pool-short walk 2 beach-By Park!

KellyRating, 5 stars1 month ago
Erin was super easy to talk to and responded right away to any questions I had. She gave clear directions upon check-in and check out and her place was super clean and comfortable. We found a really cool Mexican restaurant located in the shopping complex beside the condo which had really great margaritas and tacos. We would definitely stay here again!

Destinations to explore