Holiday rentals with a pool in Chesapeake

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Chesapeake

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Apartment in Williamsburg

4.95 out of 5 average rating, 129 reviews

Kingsmill 1bed/1ba on Golf Course 9th Fairway

This beautiful 1 bed-1 bath unit is a cozy 400 sq.ft. and is located in the exclusive Kingsmill neighborhood. This first floor unit offers a king-size bed with a private patio that walks out onto the 9th Fairway of the River Course at Kingsmill. You'll enjoy the luxurious full bathroom with shower/tub combination and upgraded finishes. In the bedroom, you'll also find a computer desk, an over-sized sitting chair, a mini-fridge, a microwave, a Keurig coffee maker, and 50" Roku Smart TV w cable!

13–20 Oct

₹13,146 per night

Superhost

Home in Virginia Beach

4.83 out of 5 average rating, 105 reviews

Stunning Views of Back Bay & Seconds to the Beach

Be our guest and enjoy some of the most spectacular views in all of Virginia Beach. Lounge in the pool and watch the sun set over Back Bay or enjoy exploring Back Bay with fishing and site seeing. With the beach being a block away, you can get your feet wet with surfing or snorkeling or simply relax on the beach with your favorite beverage. Little Island Park, Back Bay Wildlife Refuge & The Baja are just a few minutes away as well. This 6 bedroom home, with 11 beds will be the perfect get away.

5–12 Dec

₹43,887 per night

Guest favourite

Flat in Cape Charles

4.98 out of 5 average rating, 182 reviews

Cape Charles Plantation Home “Nevill’s Nook Suite”

Sorry We do NOT cook Breakfast, We offer a SELF catered SUITE & INCLUDES a welcome package of champagne, wine, OJ, 1/2 & 1/2, butter Bagel, Eng. muffins, crm. cheese, yogurt, jam,coffee. Counter top convection oven *Lge. microwave *Keurig coffee * ENLARGE pics 2 read captions w/needed info Click show more We help guests stay safe by disinfecting frequent touch surfaces* light switches, doorknobs, cabinet knobs, remotes, etc. before arrival. Under kitchen & bathroom sinks are Disinfectant wipes

15–22 Oct

₹17,039 per night

Guest favourite

Home in Gloucester Point

4.99 out of 5 average rating, 146 reviews

York River Vacation Home

This lovely, spacious waterfront home is located on the York River in Gloucester County Virginia. It is the perfect get away to enjoy the relaxing sounds and sights of nature. The views are spectacular! Keep an eye out for osprey and dolphins as you enjoy watching the sunrise and set over the water. There is plenty to do! Relax in the salt water pool overlooking the water, bring a pole & fish and crab right off of the private dock, or venture out on the kayaks. 16 ton boat lift, Jet ski lifts.

29 Jan – 5 Feb

₹29,975 per night

Guest favourite

Flat in Hampton

4.96 out of 5 average rating, 364 reviews

"Shangri-La", of Hampton, Virginia

2nd story 1200 square foot apartment with 2 BR's, Wi-Fi, microwave, fridge and bar with sink. Walk in glass enclosed shower & soaker tub. Private deck with gas grill down the spiral stairs below on ground level patio. Pool table in BnB. We share our pool with our BnB guests seasonally. Please inquire about pool availability if important to your booking. Local history, sites, nature and beaches abound. Security cameras surround the exterior of our home for our protection as well as yours!

26 Aug – 2 Sep

₹11,797 per night

Guest favourite

Guest suite in Chesapeake

4.95 out of 5 average rating, 479 reviews

Sweet Suite!

Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

26 Dec – 2 Jan

₹9,709 per night

Guest favourite

Apartment in Virginia Beach

4.88 out of 5 average rating, 175 reviews

Oceanfront Gem VaB Studio Exceptional Views

Newly renovated modern studio condo, owners personal getaway now open to guests. This corner unit, the largest and most private in Oceans ll Condominium complex, is on the 3rd floor and offers beautiful, expansive views at both sunrise and sunset. Just off the boardwalk with community pool, this unit sleeps three. Right on the oceanfront, you won't find a more peaceful getaway! Beach chairs and towels provided. Please note: due to the open layout of the building, there is no elevator.

7–14 Jan

₹15,322 per night

Guest favourite

Apartment in Virginia Beach

4.83 out of 5 average rating, 101 reviews

Oceanfront, beachfront, boardwalk, fun, dolphins

Fantastic condo on the beach. Floor to ceiling windows in living-room, master bedroom. Watching ocean waves, sunrise/moonrise, dolphins swimming by. Enjoy the ocean, boardwalk, beach gym, beach playground right downstairs. Extra-large end-unit with fully equipped kitchen, saves you $$$ on meals. One free parking. Walking distance to restaurants, stores, bars, beach concerts. New 65” smart QLED TV in living room, new sofa, new dining room set. Up to 45% off Winter Special Deals!

14–21 Nov

₹47,457 per night

Guest favourite

Apartment in Virginia Beach

4.86 out of 5 average rating, 207 reviews

Ocean Escape

Ocean Escape, 4th floor condo in the luxuriously upscale Sanctuary Resort at False Cape in Virginia Beach, Virginia, breathtaking views of both the Atlantic Ocean and Back Bay and is a leisurely 100 step stroll to the beautiful beach and surf. Beach chairs, coolers, umbrellas, sand toys for the kids, boogie boards and two beach cruiser bikes. Expansive community pool area, complete with Jacuzzi tub, lounge furniture, stainless steel gas grills and picnic tables.

14–21 Nov

₹13,264 per night

Guest favourite

Flat in Virginia Beach

4.87 out of 5 average rating, 151 reviews

Va.Beach/Oceanfront Studio, Boardwalk, Beach, Pool

Nestled on the desirable north end of the boardwalk, close to the area’s best attractions, the top restaurants and bars. Just steps to the boardwalk, beach and ocean. Enjoy a nice meal or a early morning cup of coffee while enjoying a beautiful view of the Atlantic Ocean. Our studio includes a reserved parking space, saltwater pool, large BBQ deck area and a lawn on the beach. This small oceanfront complex is a great place for couples or a small family.

3–10 Dec

₹12,681 per night

Guest favourite

Cottage in Norfolk

4.97 out of 5 average rating, 201 reviews

Positano Villa

This recently remodeled home build in 1933 and located on the Chesapeake Bay is a perfect place to vacation. Direct private beach access with a beautiful salt water pool to enjoy. Around the pool there is plenty of space for games, grilling, and relaxing. Use the newly renovated kitchen or visit one of several local restaurants serving fresh local seafood to satisfy your appetite. Williamsburg, Jamestown and Yorktown are only a short drive away.

18–25 Mar

₹26,250 per night

Guest favourite

Home in Virginia Beach

4.96 out of 5 average rating, 161 reviews

Salida del Sol, North End Beach

The beach AND privacy! Wide open residential beaches, with plenty of "distancing space"! Best kept secret at the beach! Fully stocked, fully furnished, immaculate Vacation rental on Va Beach North End. 5 star rating says it all. Atlantic Ocean across the street. Public beach access. 3 flat screen TVs, Wifi, cable, beach cart, chairs &'umbrella. Outdoor grill. Private parking. 2024 Pool Season... May 10-September. 15. NO HAIR DYE!

11–18 Jan

₹17,476 per night