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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Superhost

The living area features a spacious layout with two light-colored sofas positioned around a central white coffee table. Natural light fills the room through multiple windows, illuminating the hardwood floor. A dining table is visible in the background, complemented by a decorative area rug.

Home in Virginia Beach

4.83 out of 5 average rating, 23 reviews

The VIBE House with POOL!

This amazing home located in the happening ViBe district of the Virginia Beach Oceanfront has it all! Personal in-ground pool and backyard dining table! Walking distance to the Virginia Beach Convention Center and Sports center. Also, on 6 blocks off all the action at the Virginia Beach boardwalk and oceanfront. Amazing restaurants, beautiful beach and waves, and all the local hot spots for shopping are all walkable from this home. A farmers market located on 19th street is steps away from the h

Top guest favorite

Home in Gloucester Point

4.99 out of 5 average rating, 177 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

The pool area is showcased with a clear blue water feature and adjacent Jacuzzi. Surrounding lounge furniture and a nearby seating arrangement provide space for relaxation. The backdrop features a low, stone wall and buildings with a warm color palette, enhancing the community atmosphere.

Condo in Virginia Beach

4.87 out of 5 average rating, 232 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. Community pool area, complete with Jacuzzi tub, lounge furniture, and stainless steel gas grills. The elevator is just across from dedicated parking spot.

Superhost

An aerial view captures the expansive backyard setting, featuring a large blue swimming pool and a spillover hot tub. The area is surrounded by well-maintained greenery and palm trees, with outdoor furniture arranged for relaxation. Spacious outdoor areas are visible, complementing the nearby structures.

Home in Virginia Beach

4.83 out of 5 average rating, 42 reviews

Luxury Home, 50' pool, hot tub, grill & pool house

Reunion Paradise! Upscale 5300 SQ FT PLUS Hot Tub, Sauna, Steam Shower, 50' Pool. Quiet & safe when you want to walk, bike or go for a jog at any time. This home is furnished with Ethen Allan tables & chairs, Restoration Hardware and Pottery Barn Bedrooms. Plenty of room in the backyard for a great family reunion. Enough grass space for put up a volleyball. 50' pool, 8 foot deep end, 3.5' shallow end (over 1/2 the pool) Spill over hot tub to enjoy watching the stars or family in the pool.

Guest favorite

A saltwater pool is bordered by white lounge chairs, offering a view of the Atlantic Ocean in the distance. A deck with beach umbrellas is visible beyond the pool, while the sunny sky features a few scattered clouds.

Condo in Virginia Beach

4.89 out of 5 average rating, 210 reviews

Va Beach Oceanfront Studio, Boardwalk, Pool, Beach

Nestled in the heart of the coastal city of Virginia Beach where all of the area’s greatest attractions will be right at your fingertips. This coastal beach studio offers a space-maximizing layout which includes kitchenette with full size appliances. All on the desirable north end of the Virginia Beach boardwalk. This small oceanfront complex is one of a kind, a great place for couples or a small family. Enjoy an early morning cup of coffee while enjoying beautiful views of the Atlantic Ocean.

Guest favorite

A spacious pool area is highlighted, featuring a clear blue pool surrounded by a decorative fence. Brightly colored lounge chairs are positioned on the patio, with a shaded gazebo and lush greenery visible in the background.

Home in Virginia Beach

4.99 out of 5 average rating, 70 reviews

The Golden Hour Pool is Open!

The Golden Hour is a third row beach house with a private beach access just off the pool deck! 5BR/3.5BA completely remodeled beach house in the heart of Sandbridge with a 16x32 pool AND baby pool! Custom kitchen and baths with personalized touches throughout. Lots of outdoor spaces to go and enjoy the Sandbridge Beach lifestyle! Pool opens May 2nd and closes October 15th! Pets on a case by case basis. Some breed restrictions for insurance purposes. Must provide docs after booking

Guest favorite

A spacious backyard features a saltwater inground pool surrounded by manicured grass. A two-level deck is visible with patio furniture, offering comfortable seating options. The exterior of the two-story house is seen in the background, under a partly cloudy sky.

Home in Suffolk

4.84 out of 5 average rating, 87 reviews

Perfect Getaway!

Home away from home!! Beautiful 2 story house with 3 bedrooms, 3 bathrooms, and a huge playroom over the garage. The master suite has a beautiful bathroom with a jacuzzi tub, and huge walk in shower. The fenced in backyard has plenty of space to run around, and has an awesome saltwater inground pool for fun! In addition, there is a 2 level, new deck, and patio furniture to sit and relax on. There is something for everyone to do here.. I’m positive you will love it!

Guest favorite

A bright outdoor pool area is surrounded by lounge chairs, with a cabana featuring a bar in the background. Modern multi-story buildings with vibrant yellow and orange accents create a lively atmosphere near the water's edge. Clear blue skies enhance the inviting scene.

Condo in Virginia Beach

4.94 out of 5 average rating, 62 reviews

Cher's Place @ The Beach

Relax with the whole family at this peaceful place to stay in Sandbridge! This property is ON the beach (unit itself is not facing the ocean) with access to 3 pools, a gym, local restaurants and much more! As you can see, guests LOVE my place! I frequently travel for work, spending a lot of time in hotel rooms. I know the NECESSITIES! ** I am currently replacing furniture and bedding so pics may not match perfectly. Need more room?? See my other property!

Top guest favorite

A lagoon-style saltwater pool is framed by a spacious deck, featuring multiple lounge chairs. Beyond the pool, serene water views are observed, and lush greenery adds a natural touch to the setting.

Home in Virginia Beach

4.95 out of 5 average rating, 22 reviews

Sandbridge- Great Escape Saltwater Pool &Boat Ramp

Stunning panoramic water views! Enjoy this classic cozy coastal home with an open floor plan, fully stocked kitchen & lagoon style saltwater pool. Lots of covered deck space, including a screened-in porch for relaxing after a day in the sun. 3 bedrooms, 2 full baths, an enclosed outdoor shower. Located on quiet neighborhood street with easy walk to the beach. Bring your water toys for this is a waterfront home with private boat ramp and pool. Sunday check-in.

Top guest favorite

A private saltwater pool is depicted, surrounded by a spacious patio area. The pool's clear blue water is inviting, with a ladder providing easy access. Lush greenery and a white fence frame the background, enhancing the serene ambiance near the Chesapeake Bay.

Cottage in Norfolk

4.97 out of 5 average rating, 240 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.

Top guest favorite

An outdoor swimming pool is surrounded by a spacious deck area. Several white lounge chairs are arranged neatly along the poolside, providing spots for relaxation. Shade umbrellas are positioned at intervals, enhancing the leisure space. The pool is bordered by landscaped greenery and residential buildings.

Home in Virginia Beach

4.96 out of 5 average rating, 194 reviews

Sunrise, 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

A bright sleeping area features a spacious bed with light bedding, flanked by two armchairs. Natural light fills the space through large windows, revealing a view of trees outside. Soft, warm tones are complemented by a piece of art above the headboard.

Condo in Virginia Beach

4.85 out of 5 average rating, 141 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.