Vacation rentals with a pool in Eastern Shore of Virginia

Find and book unique homes with a pool on Airbnb

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Popular amenities for Eastern Shore of Virginia rentals with a pool

House rentals with a pool

Top guest favorite
Home in Selbyville
5 out of 5 average rating, 15 reviews

Coastal Comfort: 4BR 3BH House Pool & Rooftop Deck

AnthonyRating, 5 stars6 months ago
Place was great...Host was easy to communicate with
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
Home in Montross
4.93 out of 5 average rating, 200 reviews

The Glebe

LynnRating, 5 stars1 month ago
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.
Guest favorite
A large, inviting pool area features clear blue water surrounded by lounge chairs and umbrellas. The pool is equipped for swimming laps, with marked lanes. A spacious building with numerous windows provides a welcoming atmosphere adjacent to the pool.
Home in Selbyville
5 out of 5 average rating, 5 reviews

Dogs Welcome Beaches| Nature Trails|Gym|Pool

AmyRating, 5 stars8 months ago
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!!
Guest favorite
A large outdoor pool area features a crystal-clear pool surrounded by a spacious stone patio. Multiple loungers are arranged around the pool, and a hot tub is positioned nearby. Lush greenery encircles the area, providing an inviting retreat.
Home in Rehoboth Beach
4.87 out of 5 average rating, 228 reviews

Dodd House Beach Home w/private pool and hot tub

AmandaRating, 5 stars2 months ago
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!
Superhost
A private pool is situated in a grassy yard, surrounded by a stone patio. The pool is framed by light-colored tiles and features a handrail for easy access. Nearby, a low fence and well-maintained shrubs provide a sense of enclosure and tranquility.
Home in Ocean View
4.87 out of 5 average rating, 67 reviews

PRiVATE Pool, Peaceful, and Close to Bethany Beach

Phil Rating, 5 stars1 week ago
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.
Superhost
Home in Ocean City
4.81 out of 5 average rating, 52 reviews

Amazing Large 4 Bedroom West OC Town House, Pool!

CarlaRating, 5 stars5 months ago
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.
Guest favorite
The backyard features a large swimming pool shaped like a heart, surrounded by a spacious deck. There is a sand area with a fire pit and lush, green turf for outdoor activities. The house provides access to the deck and sunlit spaces.
Home in Salisbury
4.9 out of 5 average rating, 60 reviews

The Bury Oasis: Pool◈Hot Tub◈Master Suite◈PingPong

DavidRating, 5 stars3 months ago
The Oasis was perfect for our needs . We will definitely book it again in the future!

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 stars4 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 stars4 days 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
The modern kitchen features sleek stainless-steel appliances, including a refrigerator and microwave. A breakfast bar with four stools invites casual dining, while pendant lights above add subtle illumination. Wall art enhances the space, complemented by neutral colors and wood-style flooring.
Condo in Ocean View
4.89 out of 5 average rating, 9 reviews

Waterfront Condo With Olympic size swimming pool

DawnRating, 5 stars8 months ago
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!
Guest favorite
An indoor pool area is captured, featuring a circular pool with swimmers enjoying the water. Colorful banners hang from the ceiling, and large windows provide views of the outside. Lounge chairs surround the pool, adding to the inviting atmosphere.
Condo in Ocean City
4.85 out of 5 average rating, 87 reviews

Ocean View Condo W/ Indoor and Outdoor Pool

KathleenRating, 5 stars1 week ago
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.
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 stars6 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 stars6 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 stars7 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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