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Vacation rentals with a pool in Chesapeake Beach

Find and book unique homes with a pool on Airbnb

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Popular amenities for Chesapeake Beach rentals with a pool

House rentals with a pool

Guest favorite
Home in Hampton
4.86 out of 5 average rating, 44 reviews

Coastal Retreat @ Coliseum| Pool, Bonus Rm, Gazebo

AshleyRating, 5 stars3 weeks ago
Erin's place was awesome! The home was gorgeous, the amenities, everything was well worth the price! Will definitely rebook!
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 stars1 week 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 newly built coastal home stands elevated on stilts, featuring a spacious lower deck with a pool and hot tub enclosed by a wooden fence. Multiple balconies extend from the upper floors, inviting views of the surrounding natural landscape.
Home in Corolla
4.8 out of 5 average rating, 10 reviews

Milk 'N' Honey at the 4X4 Carova Beach

ElizabethRating, 5 stars8 months ago
Absolutely loved the home and the whole experience! Our only issue was in our arrival and not being aware that high tide would impact when you should attempt getting to the house. More information regarding the tide schedule and if the roads within the houses are accessible would be very helpful. Recommendation to stop at the grocery store before you each the beach access road and what types of things are not supplied at the house would be good, too. Overall we were so very pleased with our stay and Misty was great when we needed her. I would absolutely recommend this house to my friends and family and would love to visit again!
Superhost
The image presents a large outdoor pool surrounded by a deck, sun loungers, and a gazebo. Lush greenery lines the background, complementing the serene waters of Back Bay visible in the distance under a bright blue sky with scattered clouds.
Home in Virginia Beach
4.84 out of 5 average rating, 129 reviews

Stunning Views of Back Bay & Seconds to the Beach

GregRating, 5 stars2 weeks ago
Great location and host. The home was the perfect size for my family and friends.
Top guest favorite
A refreshing pool is visible in the foreground, surrounded by several lounge chairs in pastel colors. An orange umbrella shades a dining table with additional seating. A casual bar area is located behind the pool, offering a convenient space for relaxation and refreshments.
Home in Virginia Beach
5 out of 5 average rating, 21 reviews

Coconut Cottage-Sleeps 2,Pool,Beach

LoriRating, 5 stars1 week ago
The Pool House was exactly as described — clean, comfortable, and welcoming! Denise had thoughtful touches like snacks, water, and coffee ready for us when we arrived. Both she and her sweet dog Murphy made us feel right at home. We were also able to check in when we arrived in Sandbridge a little early. The Pool House was ready and waiting. We were in town for a wedding, and when a last-minute issue came up with the newlyweds’ accommodations, Denise was incredibly gracious and allowed us to turn the Pool House over to them. It ended up being the perfect space for the couple to relax for a couple of days before leaving on their honeymoon. The couple and their parents were very grateful for Denise’s kindness and willingness to help. The stress of not having a place to stay on their wedding night melted away. I would absolutely recommend staying here — Denise is a wonderful host, and Murphy is a joy! God bless you, Denise.
Superhost
Home in Virginia Beach
4.86 out of 5 average rating, 134 reviews

Beach Home, Upscale Croatan Resort + Private Pool

DylanRating, 5 stars1 month ago
Such a wonderful place!! Beverly was more than accommodating and was very responsive to all of our questions🙌🏽 we would love to stay here again in the future
Guest favorite
An outdoor area features a floral-patterned rug, two black wicker chairs, and tall potted plants. The space is framed by a railing and a welcome mat at the entrance, with a clear blue sky visible above.
Home in Norfolk
5 out of 5 average rating, 16 reviews

Casita View Get Away

JohnRating, 5 stars3 weeks ago
Had a great stay.
Superhost
A vibrant outdoor space features a private saltwater pool surrounded by lounge chairs and umbrellas. An orange daybed sits next to the water, while a colorful mural with the text 'SANDBRIDGE, VA' adds a cheerful touch to the backdrop.
Home in Virginia Beach
4.85 out of 5 average rating, 48 reviews

Designer 7BR w/ Pool and Hot Tub. Pets welcome!

RobertRating, 5 stars2 weeks ago
This rental property was the ideal spot for our family reunion of 16, ages 8 to 78. This was one of the most well-equipped properties we have stayed at. We have stayed at several rental properties in Sandbridge Beach, VA in previous years, and this is our favorite. The kitchen was well equipped and stocked with essentials (coffee, sugar, creamers, paper towels, toilet paper, regular and beach towels, etc.) The kids loved the game room and outdoor pool. The adults enjoyed the hot tub and ping pong room. Two big dining tables easily accommodated our group size (8 adults at one and 8 kids at the other). The beds and pillows were all comfortable. Amy, the Operations Manager, was most helpful and very responsive to any of our questions. We plan to return to this property sometime in the future. Definitely a 5-star experience for everyone in our family.

Condo rentals with a pool

Guest favorite
The image captures a serene view of the ocean during sunrise, with soft waves lapping at the sandy beach. The sun reflects off the water, creating a shimmering effect across the surface. Gentle clouds float in the sky, enhancing the tranquil atmosphere.
Condo in Virginia Beach
4.91 out of 5 average rating, 55 reviews

Beach Luxury Beachfront

SteveRating, 5 stars2 weeks ago
Great location! Clean, comfortable stay and the host was helpful and responsive. Would recommend for others.
Superhost
An indoor pool area features a clear view of the ocean through large windows. Bright blue walls complement the sparkling water. Light blue rocking chairs line the room, inviting relaxation alongside the pool and hot tub.
Condo in Virginia Beach
5 out of 5 average rating, 4 reviews

Boardwalk Resort & Villas - 1BR/1BA - Oceanfront!

AldoRating, 5 stars11 months ago
We stayed a week at Kerri’s place in Virginia. She went above and beyond our expectations, very communicative and organized. She offered a ton of information and insights before and during our stay. Her place offers a delightful and relaxing getaway experience. The resort's picturesque location by the ocean provides stunning views and a serene atmosphere. The rooms are spacious, well-appointed, and comfortable, ensuring a pleasant stay. The resort amenities such as the pool, spa, and on-site restaurants add to the overall wonderful experience. The staff is friendly, accommodating, and dedicated to providing top-notch service to guests. Whether you're looking to relax by the beach or explore the nearby attractions, Boardwalk Resort is a fantastic choice for a vacation in Virginia. I would definitely recommend and revisit Kerri’s place.
Guest favorite
A spacious living area is displayed, featuring a gray sofa and blue armchairs. A large TV is mounted on the wall. Light shines from overhead fixtures, highlighting the open layout between the living space and kitchen, which includes a breakfast bar with seating.
Condo in Virginia Beach
4.85 out of 5 average rating, 20 reviews

2BD2BA Condo w/Pool2Blocks2Beach

ConnieRating, 5 stars1 week ago
Susan's Airbnb is the place to be in Virginia Beach. We felt at home right away and loved to short walk to the beach. We would definitely come back!
Guest favorite
A clear view of a rectangular pool surrounded by a patio area. Lounge chairs are positioned near the pool, and a hot tub is visible adjacent to the water. Greenery and potted plants line the space, and a building with large windows is in the background.
Condo in Virginia Beach
4.87 out of 5 average rating, 86 reviews

Good Vibes at the Beach

BevRating, 5 stars2 weeks ago
Colin is an impeccable host! He’s caring-he’s honest- he answers all concerns immediately- His “home” is one of the nicest beautifully decorated homes we have stayed in-and so clean!!! Thank you for the privilege of staying at your place
Guest favorite
A spacious pool area is surrounded by a vibrant blue building, with sun loungers arranged around a shimmering pool. Wooden tables and chairs provide seating options for guests, while well-maintained landscaping enhances the inviting atmosphere of the outdoor space.
Condo in Virginia Beach
4.92 out of 5 average rating, 131 reviews

Ocean & Bay Views - Local Family Owned & Operated

MarieRating, 5 stars1 week ago
We had a lovely stay at Crystal’s while in town for a graduation. Crystal was proactive with directions, recommendations, and instructions, and she responded quickly to questions. The place was nicely decorated, and well-stocked with kitchen gadgets, beach chairs, games, and other necessities. This is a nice place for a getaway.
Guest favorite
The outdoor pool area features a well-maintained pool surrounded by lounge chairs. A clear blue sky is noted above, with clouds adding texture. Nearby greenery and structures contribute to the atmosphere, allowing for a relaxing outdoor experience.
Condo in Virginia Beach
4.98 out of 5 average rating, 92 reviews

Paradise at the Beach

BlakeRating, 5 stars1 day ago
Overall this a great find, close to the beach, nice pool, easy access. Kattia was very fast to respond and had some great suggestions. She left us water bottles and rain ponchos which thankfully we didn't need. We found the unit to be very clean and fresh and she has thought of everything. The only issue we had was the TV in the master would not connect to the wifi but we didn't really need it. Loved having access to the pool from the sliding door in the master bedroom. We met some of the other owners and they were all very nice. It was also nice to be so close to Harris Teeter.
Superhost
An indoor pool area is featured, with large skylights allowing natural light to illuminate the space. Bright blue walls complement the pale tiles surrounding the pool. Comfortable lounge chairs are positioned nearby, creating a relaxing environment for guests.
Condo in Virginia Beach
4.85 out of 5 average rating, 41 reviews

Dolphin Beach condo-amazing view and indoor pool

O'KeylaRating, 5 stars5 days ago
Nikola’s place was actually great, better than expected honestly. I recommend he upload updated quality pictures. No longer have carpet, rooms are very spacious. Every time I travel I be so nervous about the space and cleaning and even tho I clean again the place was very clean. I wasn’t expecting that. Only little issue is when it came to the hot water….the hot water didn’t last long for the showers for everyone to shower and, couldn’t get the water hot coming out the sinks. Nikola place is located in a more quieter end of the beach and not the main center strip area of the beach. Great oceanfront view. Nikola was a great communicator and responded sooner than 10mints. Gave straight forward step by step directions. Especially compared to other places reviews for this exact same building. We had no major issues(other than the water) we enjoyed our trip and stay. We would book again. Thank you Nikola!!
Top guest favorite
An aerial view showcases the surrounding area of the condo complex, with a direct line of sight to the beachfront. Nearby buildings and establishments are visible, providing a visual reference for the convenient location relative to the beach and boardwalk.
Condo in Virginia Beach
5 out of 5 average rating, 22 reviews

Paradise Cove

ValentinaRating, 5 stars2 weeks ago
We had a great stay ! The condo had everything we needed and more. It’s in a great walkable location very close to the beach .

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