
Holiday rentals with a pool in Chesapeake Beach
Find and book unique homes with a pool on Airbnb
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
Superhost

Home in Currituck County
5 out of 5 average rating, 4 reviewsCorova Beaches 5BR w/Heated Pool & Hot Tub!
ColinRating, 5 stars3 weeks ago
Our family had a wonderful time and couldn’t have asked for a nicer property. NorthStar was beautifully furnished, clean as a whistle, very well-stocked and is run by a top-notch management company. Grace was proactive and extremely responsive. We will return next summer when the water is warmer. Thanks Grace and all at Oak Realty for a wonderful weekend of memories and allowing us such a nice home to call ours for Memorial Day Weekend 2025!
Top Guest favourite

Home in Gloucester Point
4.99 out of 5 average rating, 184 reviewsYork River Vacation Home
AdamRating, 5 stars5 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

Home in Corolla
4.78 out of 5 average rating, 9 reviewsMilk '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

Home in Virginia Beach
4.87 out of 5 average rating, 31 reviewsVA Beach-Town Center Escape
KaylaRating, 5 stars1 week ago
This is my 2nd stay in Krystal’s Air BNB. This was the place I knew where I feel safe and comfortable at. The location is close great restaurants and shopping locations. The neighborhood is very quiet. Krystal is responsive, friendly, and respectful. When I do visit VA again I’ll probably be at this particular Air BNB!
Superhost

Home in Virginia Beach
4.84 out of 5 average rating, 129 reviewsStunning Views of Back Bay & Seconds to the Beach
GregRating, 5 stars1 week ago
Great location and host. The home was the perfect size for my family and friends.
Guest favourite

Home in Suffolk
4.84 out of 5 average rating, 94 reviewsPerfect Getaway!
JimRating, 5 stars1 week ago
We had a great family visit at this house. We really enjoyed the pool and whole house was very comfortable and clean! It was nice to just hang all day by the pool or top for a sanctuary from a long day of events. Sabrina was very attentive and responsive with questions and situations, appreciate her flexibility as a host!
Top Guest favourite

Home in Virginia Beach
5 out of 5 average rating, 21 reviewsCoconut Cottage-Sleeps 2,Pool,Beach
LoriRating, 5 stars5 days 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 reviewsBeach 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
Condo rentals with a pool
Superhost

Condo in Virginia Beach
4.84 out of 5 average rating, 286 reviewsBeautiful Beachfront Condo
JeffreyRating, 5 stars4 days ago
The only issue we had was our code for the building and parking did not work at first! Pam was very quick to resolve! There are no elevators in parking garage, I would take my stuff in at the entrance and then park! Dolphin run staff was not much help! We had a second car that we were supposed to get a parking permit for. They just told us to park and not worry about signs that clearly stated towed with no permit. Our car did NOT get towed!
Guest favourite

Condo in Virginia Beach
4.91 out of 5 average rating, 54 reviewsBeach Luxury Beachfront
JamesRating, 5 stars1 month ago
This place was great! The view is amazing, very clean, and was described to a T. Very nice!
Superhost

Condo in Virginia Beach
5 out of 5 average rating, 4 reviewsBoardwalk 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 favourite

Condo in Virginia Beach
4.84 out of 5 average rating, 19 reviews2BD2BA Condo w/Pool2Blocks2Beach
ConnieRating, 5 stars5 days 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 favourite

Condo in Virginia Beach
4.87 out of 5 average rating, 86 reviewsGood 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 favourite

Condo in Virginia Beach
4.92 out of 5 average rating, 131 reviewsOcean & 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 favourite

Condo in Virginia Beach
4.97 out of 5 average rating, 92 reviewsOceanfront Studio: Boardwalk, Beach, & Pool Views
HannahRating, 5 stars2 weeks ago
Frances’ condo was in a great location right at the end of the boardwalk. We were able to get up in the morning and walk to breakfast with multiple other restaurants within walking distance. The view of the pool and ocean was nice and the condo felt bright and sunny. There was one dedicated parking spot which was nice. Everything in the condo was clean and nicely decorated. We enjoyed our stay and highly recommend!
Guest favourite

Condo in Virginia Beach
4.98 out of 5 average rating, 91 reviewsParadise at the Beach
Qy'DarriusRating, 5 stars2 weeks ago
Our stay at Kattia's was excellent! One of the cleanest airbnb's we've ever stayed in, and Kattia was responsive and intentional from check in through check out. Genuinely one of my family's best experiences with booking and staying at an Airbnb, can't say enough good things.
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- Chesapeake Bay
- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- First Landing State Park
- Water Country USA
- Buckroe Beach and Park
- Kingsmill Resort
- Grandview Beach
- Currituck Beach Lighthouse
- Outlook Beach
- Jamestown Settlement
- Haven Beach
- Ocean Breeze Waterpark
- Sarah Constant Beach Park
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Wilkins Beach
- Bonito St. Public Beach Access
- Little Creek Beach
- Kiptopeke Beach