Vacation 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 favorite

Condo in Williamsburg

4.95 out of 5 average rating, 130 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!

Aug 22 – 29

ﺩ.ﺇ567 per night

Guest favorite

Apartment in Cape Charles

4.98 out of 5 average rating, 183 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

Sep 30 – Oct 7

ﺩ.ﺇ736 per night

Guest favorite

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.

Mar 15 – 22

ﺩ.ﺇ1,292 per night

Guest favorite

Condo in Virginia Beach

4.88 out of 5 average rating, 150 reviews

Oceanfront Jewel VB Studio Mesmerizing Ocean View

Newly remodeled, stunning panoramic oceanfront views from the 3rd floor at the peaceful north end of Va Beach boardwalk. Perfect for two, this cozy 355 sq ft studio with wireless internet, large screen TV and full kitchen, has a community pool, back patio, charming beach lawn with tables & lounge chairs and is walking distance to outstanding restaurants, attractions and shopping. Beach chairs and towels provided. Please note: due to the open layout of the building, there is no elevator.

Sep 15 – 22

ﺩ.ﺇ1,013 per night

Guest favorite

Apartment 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!

Dec 2 – 9

ﺩ.ﺇ508 per night

Guest favorite

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.

Mar 19 – 26

ﺩ.ﺇ419 per night

Guest favorite

Home in Virginia Beach

4.88 out of 5 average rating, 115 reviews

Half house w/pool & new patio all to yourself

PLEASE READ TO THE END!!!!!! Our home is close to restaurants, parks, the resort oceanfront and art and culture. You’ll love our place because of the location and the ambiance. Our space is good for couples, solo adventurers, business travelers or small families. Please know that my wife and I live in the other half of the house. There is NO shared space!!! You have a private entrance with full & private access to all amenities. Our home is LGBTQ+ friendly because LOVE IS LOVE!

Feb 13 – 20

ﺩ.ﺇ455 per night

Guest favorite

Condo 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.

Oct 7 – 14

ﺩ.ﺇ641 per night

Guest favorite

Apartment 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.

Jan 6 – 13

ﺩ.ﺇ417 per night

Guest favorite

Cottage in Norfolk

4.97 out of 5 average rating, 202 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.

Mar 27 – Apr 3

ﺩ.ﺇ1,486 per night

Superhost

Guest suite in Virginia Beach

4.92 out of 5 average rating, 104 reviews

"Forget About It" Guest Suite- 300 STEPS TO BEACH!

Come and "Forget About It" in a 1000 sqft 2 bedroom guest suite on the first floor. Quietly and conveniently located on a cul-de-sac. Only a short walk (approximately 300 steps) to the beach! Listen to the ocean waves as you relax out back by the pool. Enjoy the quiet north end of Sandbridge Beach where there is no public parking. Virginia Beach Oceanfront is only 7 miles away. Owners live upstairs and are here to help and assist as needed.

Jun 8 – 15

ﺩ.ﺇ1,371 per night

Guest favorite

Home in Virginia Beach

4.96 out of 5 average rating, 163 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!

Oct 30 – Nov 6

ﺩ.ﺇ805 per night