
Vacation rentals with a pool in Chesapeake Beach
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Top-rated rentals with a pool in Chesapeake Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Chesapeake Beach rentals with a pool
House rentals with a pool

Coastal Retreat @ Coliseum| Pool, Bonus Rm, Gazebo
Erin's place was awesome! The home was gorgeous, the amenities, everything was well worth the price! Will definitely rebook!

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!

Milk 'N' Honey at the 4X4 Carova Beach
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!

Stunning Views of Back Bay & Seconds to the Beach
Great location and host. The home was the perfect size for my family and friends.

Coconut Cottage-Sleeps 2,Pool,Beach
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.

Beach Home, Upscale Croatan Resort + Private Pool
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

Casita View Get Away
Had a great stay.

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

Beach Luxury Beachfront
Great location! Clean, comfortable stay and the host was helpful and responsive. Would recommend for others.

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

2BD2BA Condo w/Pool2Blocks2Beach
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!

Good Vibes at the Beach
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

Ocean & Bay Views - Local Family Owned & Operated
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.

Paradise at the Beach
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.

Dolphin Beach condo-amazing view and indoor pool
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!!

Paradise Cove
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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