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
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.
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 stars2 weeks 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 Deale
4.94 out of 5 average rating, 16 reviews

Modern Bay Dream

Olani Rating, 5 stars2 months ago
Rick was very supportive and his communication was superb. Great host with a beautiful cozy home. 5 star all across the board.
Top guest favorite
A community pool area is highlighted, featuring an outdoor seating arrangement with white chairs around a circular table. An orange patio umbrella provides shade. The pool is surrounded by a white fence with nearby houses in the background, accented by green trees.
Home in Rehoboth Beach
5 out of 5 average rating, 72 reviews

Spacious Living in Rehoboth, with a Pool

ClaireRating, 5 stars4 months ago
Lovely place to stay! My family and I had our Christmas here and it was the perfect space. It was comfortable, came well stocked, and had nice touches throughout the home.
Top guest favorite
The image captures a serene pool area featuring a large, sparkling blue pool. Six lounge chairs are arranged on a stone deck, positioned near a vibrant red cottage with large windows. Surrounding greenery complements the inviting outdoor space.
Home in Rehoboth Beach
4.97 out of 5 average rating, 86 reviews

Modern Beach House w/ Private Pool

LaurenRating, 5 stars7 months ago
We had an amazing stay and we loved the pool! It's definitely not your average Airbnb and felt like home. We had 5 adults & 1 toddler. The upstairs was great for the toddler/my husband and I since it was larger and had the private bathroom but was still usable to other guests, if needed because of the separate doors. There also had all the beach amenities you would need, which was so helpful - along with the Rehoboth parking pass. We can't thank M&M enough for this great option!
Top guest favorite
A private pool is framed by a stone patio, with several lounge chairs positioned nearby. Lush greenery surrounds the area, providing a relaxing atmosphere. A potted plant adds a touch of color to the space, inviting guests to unwind by the water.
Home in Rehoboth Beach
5 out of 5 average rating, 50 reviews

Charming 4bd beach house- Private pool in BayVista

JoergRating, 5 stars2 weeks ago
Danielle’s place was just awesome. From the minute we walked in we felt right at home. Very spacious, bright and just lovely overall! The kitchen had everything that you could dream of. Whenever we thought, oh we need this and that, it was right there. The sunroom is a dream to enjoy your morning coffee or afternoon drink. The bedrooms upstairs are spacious, very comfortable and the bathrooms had all amenities that you needed. We didn’t really use the backyard due to the weather but I am convinced that you will have a great time outdoors if the temperatures are right!! We will definitely try to come back!! Thank you!!!
Superhost
A tranquil outdoor space showcases a sparkling blue pool surrounded by lush greenery and natural stone features. A hot tub is positioned next to the pool, and lounge chairs are thoughtfully placed on the patio for relaxation amid the serene landscaping.
Home in Port Republic
4.75 out of 5 average rating, 20 reviews

Family Friendly: Hot Tub, Grill, Pool & More!

JosueRating, 5 stars2 weeks ago
Me and some friends stayed here and we all loved it. More than enough space and so much stuff/activities from movie nights to playing pool to hitting the hot tub and more to do in the house! We would definitely stay here again and the host was great.
Guest favorite
Home in Fort Washington
4.91 out of 5 average rating, 149 reviews

5 BEDR, Inground Pool+Billiard Table, Close To D.C

AndreaRating, 5 stars1 week ago
It was simply amazing. Daniel was a fantastic host. The house was incredible. Spacious, beautiful and peaceful felt just like home. The family and I enjoyed every inch of it. Family vacation home for every trip we take to DC.

Condo rentals with a pool

Guest favorite
Condo in Rehoboth Beach
4.98 out of 5 average rating, 83 reviews

Lovely 2BR Condo - Rehoboth/ Dewey

LatiaRating, 5 stars7 months ago
Michelle's place was spacious and well-appointed for myself and four other people. The water pressure was great, there was plenty of hot water for showers, and it was conveniently located. The neighborhood was quiet, and while we didn't have time to enjoy the amenities, the screened-in porch was lovely to enjoy and, best of all, free! The beds were firm and comfortable; the apartment was very clean! Thanks for a great stay, Michele!
Guest favorite
A heated pool is surrounded by a white fence and lounge chairs, offering a relaxing space for guests. Blue umbrellas provide shade, and the clear sky and sunlight enhance the open atmosphere. The pool reflects the bright blue hues of the sky.
Condo in Ocean City
4.87 out of 5 average rating, 31 reviews

Ocean View, Large Condo, Heated Pool

DavidRating, 5 stars8 months ago
We had a great stay at Valerie’s condo, it was a great space for our group of 6 and had everything we needed. Valerie was very responsive for any questions we had!
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 stars5 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
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, 88 reviews

Ocean View Condo W/ Indoor and Outdoor Pool

KathleenRating, 5 stars2 weeks 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.
Guest favorite
The image captures a community pool with clear blue water and a curved edge, surrounded by a spacious deck. Lounge chairs are arranged on the deck, and a few umbrellas provide shade. In the background, a three-story condo building is visible, framed by greenery.
Condo in Rehoboth Beach
4.96 out of 5 average rating, 93 reviews

Beautifully renovated 2BR 2BA Condo w/ pool!

ApurvaRating, 5 stars8 months ago
Enjoyable stay near the beaches and outlets. Clean living space with ample amenities including a nice pool. Host was friendly, accommodating, and prompt to respond to questions/requests.
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
A private balcony is shown, featuring two black wicker chairs and a small table positioned on a tiled floor. The view overlooks a serene body of water, with greenery and landscaped buildings visible in the background.
Condo in Rehoboth Beach
4.86 out of 5 average rating, 79 reviews

Lovely Two bedroom condo with community pool.

LaurenRating, 5 stars6 months ago
Airui was a great host. Beautiful place, nice view, very close to stores and restaurants. Airui was very responsive and the apartment was super clean :)

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