
Vacation rentals with a pool in Eastern Shore of Virginia
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Top-rated rentals with a pool in Eastern Shore of Virginia
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Eastern Shore of Virginia rentals with a pool
House rentals with a pool

Coastal Comfort: 4BR 3BH House Pool & Rooftop Deck
Place was great...Host was easy to communicate with

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.

The Glebe
Excellent stay at RivahLife! The views were spectacular and the home was exactly as described. Easy to find with lots of stuff for the kids and adults. Looking forward to returning during the warmer months as the fishing, boating, and swimming would be more desirable. Thanks for the high chair and portable crib. Those things really help when traveling with kids.

Dogs Welcome Beaches| Nature Trails|Gym|Pool
My family and I enjoyed our stay in Delaware! The home was clean, beautiful, and just as described. Serena was easy to work with and very responsive. With the pool, access to the bay, walkable neighborhood, and close proximity to restaurants and the beach, we would love to stay here again!!

Dodd House Beach Home w/private pool and hot tub
Lynn & Brian were amazing Hosts! They were always responsive & available. They had plenty of things to do around the house & around town as well. The property was amazing & beautiful and was only a short little walk to the beach. I would highly recommend this place to all friends & family! Being pet friendly was an awesome addition as well!

PRiVATE Pool, Peaceful, and Close to Bethany Beach
We stayed at Trina’s place on a resent golf trip. She was great, and her place is exactly as described. She reached out days before we arrived with clear directions for check in, which was a breeze. Trina responded very quickly to my question and I would highly recommend stay with her if you are traveling to the area.

Amazing Large 4 Bedroom West OC Town House, Pool!
My family and I enjoyed our stay. We didn’t want to leave. The location was excellent. It was close to boardwalk, restaurants and the outlet mall. I loved not having to drive far to places. We will be back.

The Bury Oasis: Pool◈Hot Tub◈Master Suite◈PingPong
The Oasis was perfect for our needs . We will definitely book it again in the future!
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.

Waterfront Condo With Olympic size swimming pool
James was an amazing host. He was responsive, helpful, and kind. The condo was beautiful, clean, and perfect for our family. The neighbors were also very kind and welcoming. My children loved the pool and walking the bay. The views were second to none and the location was perfect since it was minutes away from restaurants, stores, and Bethany beach. We will definitely be booking again!

Ocean View Condo W/ Indoor and Outdoor Pool
We’ve stayed at Seawatch for many years so we’re already familiar with the great location. The condo was exactly as described and was a great place for our family. Would definitely book again.

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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