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

Guest favorite
A light and airy deck features a rectangular dining table surrounded by aqua-colored chairs. A calm water view is visible beyond the railing, with flags gently waving in the breeze. Soft lighting is provided by string lights overhead, enhancing the inviting atmosphere.
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 favorite
A spacious waterfront home is showcased with a well-maintained lawn and blooming yellow flowers near the entrance. A large driveway leads to a brick facade, complemented by a garage. Clear blue skies can be seen in the background, enhancing the welcoming appearance of the property.
Home in Gloucester Point
4.99 out of 5 average rating, 184 reviews

York River Vacation Home

AdamRating, 5 stars4 days ago
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!
Superhost
A private pool is surrounded by a spacious patio area, featuring lounge chairs and shaded seating. The clear water reflects the blue sky, while a white fence offers privacy. Decorative elements such as lights and tropical decor enhance the leisure space.
Home in Norfolk
5 out of 5 average rating, 4 reviews

The Blue Octopus~Private Pool~HotTub~Beach~FirePit

AngelaRating, 5 stars5 days ago
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.
Top guest favorite
A private pool area features comfortable lounge chairs with floral cushions, surrounded by a clean concrete patio. A screened-in porch is visible in the background, with two inviting chairs for relaxing. The fenced yard offers additional privacy and space for outdoor enjoyment.
Home in Virginia Beach
4.94 out of 5 average rating, 65 reviews

Paint The Beach Pink! Full House | Private Pool

WyattRating, 5 stars2 days ago
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!
Guest favorite
A spacious living area features a large sectional couch, a coffee table, and a massage chair. Natural light floods the space through sliding glass doors, illuminating the wood flooring. The open layout connects to a kitchen and dining area, enhancing the communal feel.
Home in Cape Charles
4.9 out of 5 average rating, 10 reviews

Hot Tub - Massage Chair - Golf Cart - Beach Gear

ThomasRating, 5 stars1 week ago
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.
Top guest favorite
A spacious outdoor deck surrounds a large pool, offering seating under a vibrant green umbrella. Adjacent to the pool, a brick structure is visible, featuring several windows that invite natural light, while the surrounding trees create a serene environment.
Home in Virginia Beach
4.94 out of 5 average rating, 108 reviews

Country Comfort Close to the Beaches

MaryJaneRating, 5 stars1 month ago
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!
Guest favorite
Home in Greenbackville
4.91 out of 5 average rating, 86 reviews

Stunning waterfront panoramic view getaway house

AlanaRating, 5 stars1 month ago
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!
Top guest favorite
Home in Irvington
5 out of 5 average rating, 44 reviews

Blue Oyster: Perfect Getaway, Pool, Kayaks, Quiet

Debra MaryleeRating, 5 stars2 days ago
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

Top guest favorite
A cozy bedroom features a king-size bed with crisp white linens and decorative pillows. A large window offers a view of a green space beyond, with a sitting area including a chair and small table. A 50" TV and coffee station are positioned on a wooden dresser.
Condo in Williamsburg
4.95 out of 5 average rating, 164 reviews

Kingsmill 1bed/1ba on Golf Course 9th Fairway

AmyRating, 5 stars4 days ago
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!
Top guest favorite
A balcony is shown featuring two red Adirondack chairs and a small table, positioned to overlook the vast ocean. The horizon is visible in the distance, with a sandy beach below, inviting relaxation and scenic views.
Condo in Ocean City
5 out of 5 average rating, 38 reviews

Luxury Oceanfront Getaway!

ChristopherRating, 5 stars2 days ago
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!
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, 310 reviews

Oceanfront Family Oasis: Pool, Beach & Parking!

JasonRating, 5 stars1 month ago
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.
Guest favorite
A swimming pool is surrounded by a wooden fence, featuring two yellow umbrellas over lounge chairs. Sunlight reflects off the clear water, and nearby buildings are visible in the background against a clear blue sky.
Condo in Virginia Beach
4.86 out of 5 average rating, 138 reviews

Oceanfront, beach, boardwalk, fun, dolphin, sunris

AnitaRating, 5 stars2 months ago
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.
Top guest favorite
The exterior of a two-story house is shown, featuring a gray shingle facade and a welcoming front porch. Neatly trimmed shrubs and manicured lawns frame the driveway, while flowering plants add subtle color. A double garage with white doors is visible on the left.
Condo in Cape Charles
4.96 out of 5 average rating, 27 reviews

Bay Creek Blessed at The Fairways

KathrynRating, 5 stars1 month ago
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!
Superhost
A hanging egg chair with plush white cushioning faces the ocean view. A small table holds a bottle of wine and a glass near a decorative statue. The balcony's green carpeting and a motivational message on the floor mat enhance the relaxing atmosphere.
Condo in Ocean City
4.84 out of 5 average rating, 170 reviews

Romantic Beach Inscape-Best Ocean View+Heated Pool

AdamRating, 5 stars2 months ago
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.
Guest favorite
A welcoming kitchen and dining area is displayed, with modern appliances and a wooden dining table. Colorful letters spelling 'Welcome' are arranged on a sideboard, while a refrigerator and seating area are visible in the background, enhancing the cozy atmosphere.
Condo in Ocean City
4.9 out of 5 average rating, 40 reviews

BaysideGetaway | 2 Blk to Beach & Boardwalk | Pool

ReginaRating, 5 stars1 month ago
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!
Guest favorite
An outdoor pool area features a rectangular pool with a clear blue surface. Sun loungers are positioned around the pool, and a glass enclosure creates a barrier against the elements. The building's multiple floors are visible in the background under a sunny sky.
Condo in Ocean City
4.97 out of 5 average rating, 126 reviews

Direct Ocean Front/Gorgeous Views/Indoor Pool

DianeRating, 5 stars5 days ago
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.

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