
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

Wooded Wonderland Miniature Golf Hot tub Pool
We rented this property to visit the Virginia Tattoo and the beach and had a great trip!

THE OLD BEACON 1 | Beach Living
Old Beacon is a cozy beach spot. The property consists of 4 units - two in front and two in back. The shared pool is a great place to relax on a windy afternoon and be out of the wind and featured plenty of seating and tables with umbrellas. Bedrooms are cozy and welcoming and the beds were comfortable. Bathrooms were clean and bright! Great place for a weekend or week long getaway! Matt is very responsive and gives clear instructions on how to park at the property and when you can access the house. Hope to be back soon!

Breathtaking Ocean views at Pinch Me, 8bdrm, 6bath
Beautiful place, such a great view of the beach. Beach access right across the street. Loved it. Spacious area, lots of room.

Elegance Escape on Saunders Dr
Clean Place with thoughtful touches from the host. Place has a pool and mini cinema. Would definitely book this place again when am next in Virginia

Stunning Views of Back Bay & Seconds to the Beach
Great place for families walking distance from the beach. I’ll love to visit in the summer when we can enjoy the beach and everything Virginia Beach has to offer.

Pool, hot tub, walk to beach, family friendly home
We had a wonderful stay at the Great Escape. The home was very clean and comfortable with plenty of space. The amenities were perfect and the beach is just a short walk with easy access. Cody was a wonderful host with quick responses. Thank you for sharing your home. We made wondrful memories in Virgina Beach.

Coral Point - Updated Cozy 4 bedroom w/ Salt Water
Lovely CLEAN beach home. Easy 5 min walk ( with toddler) to a beautiful beach. The short walk made it easy for us to go to the beach several times/day. Gorgeous sunrise! We really appreciated how kid/family friendly the home was! Our young kids felt safe just across the hall from us and my parents were able to have their own bedroom and bathroom on the other side of the house. Thank you Pip and Sheryl! We hope to be back in the future!

Beach Home, Upscale Croatan Resort + Private Pool
This is a wonderful beach home within walking distance of the oceanfront. Our extended family enjoyed a fantastic visit. The house is set up perfectly for multiple families with a large gathering space on the top floor next to the kitchen. There are several decks throughout the home to catch the sea breeze and air. Beverly was a great host and responsive to our needs.
Condo rentals with a pool

Beach Luxury Beachfront
Amazing place. Recommended.

Sandbridge Beach - DeepSeaSide Retreat
We loved our stay here in sandbridge! Bill and Anne were great hosts, with a lovely home that had everything we needed. Highly recommend!

2BD2BA Condo w/Pool2Blocks2Beach
Came with my girls for a conference at the Beach. Salt and Serenity was super peaceful, felt private and quiet. Beds were super comfy and the water pressure in the showers was awesome. We had everything we needed in the kitchen and all amenities were as described. Susan was a great, responsive host and made accommodations for our early check-in. And all the restaurant suggestions were a hit! Would definitely come again!

Good Vibes at the Beach
A great find. Everything we needed, including a grocery store, was walkable and convenient. Loved being 2 blocks from the ocean and boardwalk. Excellent space and very comfortable. Colin is an excellent host. Always addressed our questions and needs in a timely fashion. We will be back!

Oceanfront Gem VaB Studio Exceptional Views
We really enjoyed our stay! Was really amazing to be able to view the sunrise from bed! Also sitting on the private deck watching the ocean was very peaceful! The apartment was very well stocked and the kitchen worked well for preparing our meals! The charcoal grill on the back porch was very handy! It was a wonderful beachfront experience! Thanks

Ocean & Bay Views - Local Family Owned & Operated
We had a great weekend at Crystal’s place. The condo was clean, the furniture comfortable and it had everything we needed for a weekend stay-our family especially enjoyed the selection of games. The location was perfect and the beach just beautiful!

Beach Quarters Resort- Oceanfront 1 bdrm sleeps 6
Clean, comfortable and conveniently located. Steps from the beach and minutes from Grommet Island Park, a big hit with our grandson. Brooke’s prompt and professional responses made this impromptu stay uncomplicated and enjoyable

Upscale condo with Golf Course views
The condo is well appointed with everything I needed. Kingsmill is a special place. Rodica was very quick to reply when I had a few different questions. Very comfortable bed and reading chairs. Top notch.
Destinations to explore
- Virginia Beach Vacation rentals
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- Rentals with a washer and dryer Chesapeake Beach
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- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Bethel Beach
- Buckroe Beach
- First Landing State Park
- Kingsmill Resort
- Currituck Beach Lighthouse
- Virginia Beach National Golf Club
- Water Country USA
- Sarah Constant Beach Park
- Buckroe Beach and Park
- Grove Beach
- Golden Horseshoe Golf Club
- Haven Beach
- Wilkins Beach
- Cape Charles Beachfront
- Norfolk Botanical Garden
- Grandview Beach
- Kiptopeke Beach
- Jamestown Settlement
- Bonito St. Public Beach Access