
Holiday rentals with a pool in Chesapeake
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Top-rated rentals with a pool in Chesapeake
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Popular amenities for Chesapeake rentals with a pool
House rentals with a pool

New fully loaded, Firepit, pool/hottub, ocean view
My family came together for a 3-day stay at Nomad Dunes. It was everyone's 1st time to the OBX. There's 16 of us ranging in age from 9-74! There are 3 levels to this home with sleeping areas on all levels which was great for us. I think we used every entertaining and relaxing spot in this house!! You can see the ocean from the top floor and it truly is easy enough to walk to the beach or hop in the car and drive back and forth. Having the pool was perfect for our family. It is about 5ft deep at most so all the kids could access the pool without worry. And the hot tub was VERY popular with our group! Hardly anyone picked up a phone or devise other than to take photos or videos and we watched one movie. The drive on the beach to get to the home was a LOT more than we expected!! Videos do not do this justice. It's long, and bumpy, and feels out of control at times. SHOP beforehand!! Beds and furnishings are comfy and pretty. I suggest mentioning if you plan to use the bunks and sofa bed.

Aloha Beaches OBX
This home was incredible! The 4x4 experience was really fun and we saw horses everyday, at one point the horses were under the house cooling off in the shade. It’s hard to put into words 🙂 Sarah was responsive and helpful throughout the trip!

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!

New! Boat Dock /Pool /HotTub/ Waterfront/ Beach
I had a fantastic experience staying at Sandbridge Stay. The property was exactly as described—clean, cozy, and well-equipped with everything I needed. The location was perfect, close to beach, but still quiet and peaceful for a good night’s rest.

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

Sunrise, North End Beach
Mark is a great host. The house is immaculate. Every little detail is perfect. By far the nicest AirBNB I have ever rented. Mark made sure everything was perfect for our visit with our son in the Navy.

Splash of Lime Carova 4x4 Beach Cottage
What a great place to stay. Splash of lime worked great for our group. The house is set up nicely and has lots of storage available. We were lucky enough to get daily visits from the wild horses throughout the day. Martin is an excellent host and responded very quickly to answer any questions we had.

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.
Apartment rentals with a pool

Beautiful Beachfront Condo
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!

Beach Luxury Beachfront
We frequently go to Virginia Beach and now that our boys are grown, it was nice to have the space of an apartment on the beach instead of 2 hotel rooms. The location is right where we usually stay when we go to Virginia Beach. Walkable to all of our favorite restaurants, clean, comfortable beds… just perfect!

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.

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.

Oceanfront Studio: Boardwalk, Beach, & Pool Views
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!

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.

Oceanfront, beach, boardwalk, fun, dolphin, sunris
We enjoyed staying at Kelly's place in VB. Its an ideal location for anyone who wants to stay right at the boardwalk. We witnessed amazing sunrises and moonrises. The ocean was right in front of us and from the 6th floor, the view was expansive. A lot of restaurants were also nearby. Kelly was always very communicative, polite and professional. The apartment was clean with the kitchen well stocked with utensils The bedrooms were of a pretty large size. And parking was on the premises. Overall, it was a wonderful experience and holiday for us. We strongly recommend Kelly's place.
Quick stats about holiday rentals with a pool in Chesapeake
Total rentals
130 properties
Nightly prices starting at
$26Â SGD before taxes and fees
Total number of reviews
2.8K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Destinations to explore
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- Rentals with beach access Chesapeake
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- 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
- Golden Horseshoe Golf Club