Vacation 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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Guest favorite

Home in Gloucester Point

4.99 out of 5 average rating, 171 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.

Guest favorite

Condo in Virginia Beach

4.84 out of 5 average rating, 121 reviews

Oceanfront, beachfront, boardwalk, fun, dolphins

Fantastic condo on the beach. Floor to ceiling windows in living-room, bedrooms. Watching waves, sunrise, dolphins. Enjoy the ocean, boardwalk, beach gym, playground right at downstairs. Extra-large end-unit with fully equipped kitchen, saves you $$$ on meals. One free parking. Walking distance to restaurants, bars, stores, beach concerts, activities, art shows, performance. New 65” QLED TV, new sofa and dining set. Ask for extended stay discount! Up to 45% off Winter Special Deals. Book now!

Guest favorite

Condo in Virginia Beach

4.88 out of 5 average rating, 175 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.

Guest favorite

Home in Virginia Beach

4.88 out of 5 average rating, 128 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!

Guest favorite

Guest suite in Chesapeake

4.95 out of 5 average rating, 532 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.

Superhost

Home in Virginia Beach

4.82 out of 5 average rating, 112 reviews

THE OLD BEACON 1 | Beach Living

The Old Beacon is the perfect vacation blend of beach time and poolside sunbathing. This is the downstairs unit of the front cottage and the largest of The Old Beacon units. Stylish and comfortable interior with access to the amazing outdoor common area - pool, cornhole, porch swings, outdoor dining area, and outdoor shower for when you return from the beach! Kick back and relax in this vacation home that’s two blocks to the beach and Virginia Beach boardwalk!

Guest favorite

Farm stay in Williamsburg

4.96 out of 5 average rating, 340 reviews

3 BR Cottage on Mallardee Farm in Williamsburg

Enjoy all the comforts of home during your Williamsburg vacation at Mallardee Farm! Allow us to make our home, your home while you explore all of Williamsburg’s attractions-just a 15 minute drive away! You’ll find that Mallardee Farm will serve as its own attraction with our friendly, rescued farm pets, walking trails through the 57 acre property, complimentary fishing poles, canoe, row boat & kayaks to use on our 7 acre pond. Covid-19 precautions followed.

Guest favorite

Condo in Virginia Beach

4.95 out of 5 average rating, 101 reviews

VB Condo,Boardwalk/Oceanfront,Beach, Pool,Kitchen

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

Guest favorite

Cottage in Norfolk

4.97 out of 5 average rating, 231 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.

Guest favorite

Rental unit in Hampton

4.88 out of 5 average rating, 123 reviews

Penthouse Paradise On The Harbor

Enjoy a stylish experience at our brand new, centrally-located , downtown penthouse suite. This property, directly overlooking the historic Docks @ Downtown Hampton features many attractions such as Virginia Air and Space Science Center, Hampton Coliseum, Buckroe Beach and Park. This space is also located within walking distance of many quaint restaurants and speakeasy's such as Pour Girls, Marker 20, Baked Bistro and Pizza, and Stillwater Tavern.

Guest favorite

Home in Virginia Beach

4.96 out of 5 average rating, 186 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. 2025 Pool Season... May 23–September 7. NO HAIR DYE!

Guest favorite

Condo in Virginia Beach

4.85 out of 5 average rating, 137 reviews

WOW Location! Beach Paradise on Boardwalk w/Pool

Enjoy a piece of the Oceanfront with this gorgeous updated condo! Walk out your front door to the beach, pool, boardwalk, the historic Cavalier hotel, restaurants, shops and many entertainments on the beach! Newly renovated, this beachy North End paradise is the perfect getaway for a couple. One parking spot, deck area , a lawn on the beach with lounge chairs and coin operated laundry available on premises.