
Vacation rentals with a pool in Eastern Shore of Virginia
Find and book unique homes with a pool on Airbnb
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
Get the amount of space that is right for you
Popular amenities for Eastern Shore of Virginia rentals with a pool
House rentals with a pool

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

York River Vacation Home
We had a wonderful stay here! Everything was exactly as described. Eugene was really responsive when communicating and super friendly! I would highly recommend staying here if you get the chance. Thank you again for such a relaxing place to stay!

The Blue Octopus~Private Pool~HotTub~Beach~FirePit
Family vacation for almost a week and everyone loved it! We definitely recommend families to come to the Blue Octopus for their next visit to Ocean View-Willoughby Spit. Friendly, clean and with all the amenities for the whole family.

Paint The Beach Pink! Full House | Private Pool
Check in was super easy, the AC was on when we arrived which was great after a long Uber. The pool felt nice and the whole backyard area was fantastic. We ended up using the bikes a lot more than we thought which was a lot of fun. It's a quick bike ride to the boardwalk and walking didn't take too much longer. Bradley was very quick to respond whenever I had a question about anything. If we come back to Virginia Beach we will definitely be checking the availability of this house!

Hot Tub - Massage Chair - Golf Cart - Beach Gear
Nate was very responsive from booking , all the way through our stay. He was very flexible due to our circumstances and juggling vacation with 2 young children and 2 labradors. I would recommend this home to anyone with a family or pets as it offers the interior space that cape Charles historic homes lack while maintaining the same proximity to the town’s attractions.

Country Comfort Close to the Beaches
I can't say enough positive things about Alice and her home. She was incredibly welcoming, and made my entire weekend a delight. Her home is beautiful, and it was a very comfortable stay. But Alice's kindness and generosity really went above and beyond. Thank you again!

Stunning waterfront panoramic view getaway house
We loved our stay in Captain’s Cove! Nick was a very responsive host with wonderful local suggestions. Do be aware that there is really not much in the way of gas stations, grocery stores or restaurants in the immediate area. We knew that going in, though, and it wasn’t an issue for us. Just know you will need to drive a bit or prepare with those items on your way in (which Nick told us in advance as well!) The view is beautiful! The Airbnb is exactly as pictured. It was very quiet as well. Loved that it was pet friendly so we could bring our dog! Would definitely stay again!

Blue Oyster: Perfect Getaway, Pool, Kayaks, Quiet
The gothic style cottage is a perfect, inviting, poetic, lovely setting. Three of us stayed. With three bedrooms and baths it was the perfect size. We all loved it. We played games, went out to remarkable local restaurants and use the bikes. Super fun place to take a mini vacation. Irvington is a very culturally rich, yet quaint area. The meadow in front of the house is picturesque as well as the view from the screened in porch. In the morning having my coffee, listening to the birds was a memorable highlight. Thank you for providing a quality, clean, well-appointed, refreshing stay for us. Will keep this on my list of stays to repeat, thank you again. Debra
Condo rentals with a pool

Kingsmill 1bed/1ba on Golf Course 9th Fairway
Crystal's condo was spotless and an easy place to stay. Crystal was very proactive and made us feel welcome. her dinner suggestions were superb too! perfect for a weekend getaway in a resort atmosphere. Thank you so much, we highly recommend!

Luxury Oceanfront Getaway!
Shiri's place was perfect. My wife and I have both frequented OC since we were kids, and we both agreed that this was the nicest place we have ever stayed. Far enough from the boardwalk to be peaceful, close enough to travel to the boardwalk if we wanted. The condo was clean, there is a washer and dryer in the unit which is a plus, and a tv in both the living room and bedroom, which is something we always look for. There is plenty to do in the area! Unfortunately, it rained during our whole stay, but you have beach access just outside of the building! We are excited to stay at Shiri's place again (hopefully when it's not raining 😂) and spend some time on the beach! We sat on the balcony every morning and night and it was so peaceful. Shiri was always very helpful and kind - she is such a wonderful host!

Oceanfront Family Oasis: Pool, Beach & Parking!
Great place to stay in Ocean City! clean and wonderful place situated right off the beach secluded and quiet. had lots of beach materials for use. would stay again.

Oceanfront, beach, boardwalk, fun, dolphin, sunris
We enjoyed staying at Kelly's place in VB. Its an ideal location for anyone who wants to stay right at the boardwalk. We witnessed amazing sunrises and moonrises. The ocean was right in front of us and from the 6th floor, the view was expansive. A lot of restaurants were also nearby. Kelly was always very communicative, polite and professional. The apartment was clean with the kitchen well stocked with utensils The bedrooms were of a pretty large size. And parking was on the premises. Overall, it was a wonderful experience and holiday for us. We strongly recommend Kelly's place.

Bay Creek Blessed at The Fairways
Book this condo! It was the cleanest AirBnB I’ve ever rented but was still warm and comfortable. You can tell the condo is well taken care of. The neighborhood was charming. The pool was closed but the beach within the community was nearby and quiet. We were a short drive from Cape Charles town center and parking was a breeze. The host was incredibly accommodating; her restaurant recommendations were spot on. I wish we could’ve stayed longer!

Romantic Beach Inscape-Best Ocean View+Heated Pool
The view and easy access to the beach make this perfect for a weekend getaway. Quiet in the offseason and close to tons of great local restaurants.

BaysideGetaway | 2 Blk to Beach & Boardwalk | Pool
Was an adorable place! It was perfect for the weekend away! It was within walking dostance of the beach and boardwalk. Matthew was amazing with his instructions on how to locate the home. He was very quick to respond and extremely kind. Highly recommend this place!

Direct Ocean Front/Gorgeous Views/Indoor Pool
My husband and I decided to go on a getaway last minute. We found Seth’s place and were able to book the unit for the days we had available. It was great and met all of our expectations. We have been to OC and Fenwick many times and knew this is where we wanted to stay. It did not disappoint and we hope to rent again in the near future.
Destinations to explore
- Ocean City Vacation rentals
- Outer Banks Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- Pocono Mountains Vacation rentals
- South Jersey Vacation rentals
- Jersey Shore Vacation rentals
- New York Vacation rentals
- East River Vacation rentals
- Plainview Vacation rentals
- Long Island Vacation rentals
- The Hamptons Vacation rentals
- Rentals with breakfast Eastern Shore of Virginia
- Beachfront rentals Eastern Shore of Virginia
- Rentals with a hot tub Eastern Shore of Virginia
- Rentals with an accessible height bed Eastern Shore of Virginia
- Rentals with a washer and dryer Eastern Shore of Virginia
- Apartment rentals Eastern Shore of Virginia
- Rentals with an EV charger Eastern Shore of Virginia
- Condo rentals Eastern Shore of Virginia
- Rentals with a fire pit Eastern Shore of Virginia
- Bed and breakfasts Eastern Shore of Virginia
- Waterfront rentals Eastern Shore of Virginia
- Rentals with a kayak Eastern Shore of Virginia
- Fitness-friendly rentals Eastern Shore of Virginia
- Rentals with a patio Eastern Shore of Virginia
- Family-friendly rentals Eastern Shore of Virginia
- Cottage rentals Eastern Shore of Virginia
- Pet-friendly rentals Eastern Shore of Virginia
- Hotel rentals Eastern Shore of Virginia
- Rentals with a fireplace Eastern Shore of Virginia
- Townhouse rentals Eastern Shore of Virginia
- Kid-friendly rentals Eastern Shore of Virginia
- House rentals Eastern Shore of Virginia
- Villa rentals Eastern Shore of Virginia
- Rentals with an accessible height toilet Eastern Shore of Virginia
- Rentals with beach access Eastern Shore of Virginia
- Rentals with outdoor seating Eastern Shore of Virginia
- Cabin rentals Eastern Shore of Virginia
- Rentals with lake access Eastern Shore of Virginia
- Rentals with pools Virginia
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Chesapeake Bay
- Virginia Beach Oceanfront
- Resort Beach
- Assateague Island National Seashore
- Busch Gardens Williamsburg
- Buckroe Beach
- First Landing State Park
- Water Country USA
- Buckroe Beach and Park
- Grandview Beach
- Assateague Beach
- Outlook Beach
- Haven Beach
- Snead Beach
- Sarah Constant Beach Park
- Norfolk Botanical Garden
- Wilkins Beach
- Little Creek Beach
- Kiptopeke Beach
- Wallops Beach
- Salt Ponds Public Beach
- Cape Charles Beachfront
- Bow Beach
- Parramore Beach