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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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Top guest favorite

A spacious waterfront home is showcased with a well-maintained lawn and blooming yellow flowers near the entrance. A large driveway leads to a brick facade, complemented by a garage. Clear blue skies can be seen in the background, enhancing the welcoming appearance of the property.

Home in Gloucester Point

4.99 out of 5 average rating, 198 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.

A private pool is surrounded by a spacious patio, featuring lounge chairs and a shaded gazebo. Lush greenery encircles the pool area, providing a sense of privacy. The clear blue water reflects the sky, inviting relaxation and enjoyment.

Home in Virginia Beach

4.85 out of 5 average rating, 115 reviews

Private Pool at the Oceanfront in a Spacious Home

Private Pool at the Oceanfront in a spacious 2600 sq ft home. 3 blocks from the Virginia Beach Boardwalk, Vibe District. 4 bedrooms in a three-story Private Home. 1st Flr: 2 bathrms, a bedrm with Full-bunk bds, kitchen, dining rm & living rm. 2nd lvl contains a lux Mstr ste with massive jacuzzi, dbl shwr and living rm . 3rd Lvl: 2+ bedrms, bathrms & prvt balconies (queen in 1 room and 2 doubles in the other). Two-car garage and driveway, NOT a duplex. Pool unheated. Modern Tvs and cable!

An aerial view of the property reveals a spacious backyard featuring a swimming pool surrounded by lounge chairs and inflatable pool toys. Lush greenery encircles the area, enhancing the sense of privacy, and the house is seen with its inviting deck and patio area.

Home in Portsmouth

4.93 out of 5 average rating, 130 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

Make yourself at home! This property offers a warm and welcoming environment for guest, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!

A well-appointed backyard patio features a dining table accompanied by several chairs. A swimming pool is situated nearby, surrounded by a wooden fence and trees. Sunlight illuminates the area, creating a bright and inviting outdoor space.

Home in Norfolk

4.94 out of 5 average rating, 113 reviews

Gorgeous Vacation House

This is is the perfect home away from home! Enjoy cozy furnishings and modern amenities in this 3bed/2.5 bath house located in the vibrant city of Norfolk oceanview. The house is renovated with top notch material and artistic touch. The kitchen, living room, and private backyard with deck/patio swimming pool make it the ideal place to relax. Shopping, restaurants, and entertainment are all within minutes; plus onsite parking and self-check-in make this an ideal destination for travelers.

Top guest favorite

Cottage in Virginia Beach

5 out of 5 average rating, 109 reviews

Sanctuary on Sandpiper - Bayfront in Sandbridge

Relax in this renovated 1950's flat-top beach cottage in gorgeous Sandbridge Beach. This waterfront home, on a canal off the beautiful Back Bay, is an easy five-minute, two-block walk to the ocean and the perfect setting for your family beach vacation. With three king beds, a custom-built bunk room, two full baths, a well-equipped kitchen, a spacious backyard, saltwater pool, and all linens and beach gear included, it's got everything you need to spend quality time away with your family.

A community pool is visible, featuring a clear blue water surface and surrounded by a spacious pool deck. Lounge chairs are positioned along the perimeter, with ocean views and a white fence providing a boundary. A building with a light exterior stands nearby, contributing to a serene environment.

Condo in Virginia Beach

4.88 out of 5 average rating, 237 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.

A private backyard pool area is highlighted, featuring a large in-ground pool surrounded by a concrete deck. Lush greenery and trees provide a natural backdrop, while a wooden fence offers privacy. Pool accessories are visible, indicating a space for relaxation and enjoyment.

Guest suite in Chesapeake

4.95 out of 5 average rating, 588 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.

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

4.97 out of 5 average rating, 212 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! June 22-24 2025 MUST INQUIRE.

A serene outdoor area features a sparkling blue pool surrounded by a sunlit patio. Comfortable seating arrangements are positioned beneath a white pergola, enhancing the inviting space. The building's light-colored siding and a mural in the background create a relaxed atmosphere of leisure and comfort.

Home in Virginia Beach

4.82 out of 5 average rating, 140 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!

Top guest favorite

A saltwater pool is surrounded by lounge chairs, with the Atlantic Ocean visible in the background. The pool area features a white railing, potted plants, and blue skies dotted with clouds. Colorful flags add a festive touch to the scene.

Apartment in Virginia Beach

4.89 out of 5 average rating, 197 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.

A clear blue saltwater pool is framed by a smooth beige deck. Sun loungers are positioned around the pool, offering space for relaxation. Nearby buildings create a simple backdrop, with bright blue skies overhead enhancing the inviting atmosphere.

Condo in Virginia Beach

4.97 out of 5 average rating, 108 reviews

Oceanfront Studio: Boardwalk, Beach, & Pool Views

Atlantic Ocean views from the comfort of an Oceanfront studio, perfect for beach-loving travelers. Reserved parking space just steps from the beach, indulge in the sand & surf without having to cross a street. Park your car, & let your toes sink into the sand for a truly relaxing stay. Equipped with Wi-Fi & Roku TV, you can stay connected throughout your visit. Take a refreshing dip in the saltwater pool or lounge on the lawn just steps from the beach.

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, 264 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.

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Popular amenities for Chesapeake Beach rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

A private pool is situated on a spacious wooden deck, with inviting blue water reflecting the landscape. Lounging chairs are placed nearby, and the ocean view is visible in the background, extending to a sandy shore under a bright blue sky.

Home in Virginia Beach

4.67 out of 5 average rating, 12 reviews

Oceanfront | 7BR | Pool | Hot Tub | Sleeps 20

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, 79 reviews

The Golden Hour Pool is Open until October 5th!

A spacious living area is highlighted by a cozy sofa positioned near a wooden coffee table. Large windows provide natural light and views of the outdoors, while a decorative fireplace adds a charming focal point. Neutral tones enhance the welcoming ambiance.

Home in Hampton

4.88 out of 5 average rating, 51 reviews

Coastal Retreat @ Coliseum| Bonus Room, Gazebo

An outdoor space is shown featuring green grass and a view of the ocean. White tables and chairs are arranged on the lawn, while a cluster of trees stands nearby. A pathway along the beach can be seen in the distance, leading to the sandy shore.

Home in Virginia Beach

4.79 out of 5 average rating, 24 reviews

Ocean Front Studio on Boardwalk

Top guest favorite

Home in Norfolk

4.96 out of 5 average rating, 69 reviews

The Seaglass Cottage

A single-story brick house is framed by a well-maintained lawn and colorful bushes. The covered front porch features white railings and two entrances. Large windows allow natural light to fill the living spaces, while trees provide shade in the background.

Home in Portsmouth

4.87 out of 5 average rating, 46 reviews

Elegance Escape on Saunders Dr

Home in Virginia Beach

4.77 out of 5 average rating, 26 reviews

Coral Point - Updated Cozy 4 bedroom w/ Salt Water

A clear blue pool is depicted, bustling with activity. A child is seen jumping into the water, wearing a safety vest. Surrounding the pool, a spacious deck provides ample room for lounging. A building is visible in the background, offering changing facilities and amenities.

Home in Cape Charles

4.93 out of 5 average rating, 84 reviews

Bay Creek (Pool!) Meets Historic Cape Charles!

Condo rentals with a pool

A spacious living area is displayed, featuring a gray sofa and blue armchairs. A large TV is mounted on the wall. Light shines from overhead fixtures, highlighting the open layout between the living space and kitchen, which includes a breakfast bar with seating.

Condo in Virginia Beach

4.86 out of 5 average rating, 35 reviews

2BD2BA Condo w/Pool2Blocks2Beach

A clear view of a rectangular pool surrounded by a patio area. Lounge chairs are positioned near the pool, and a hot tub is visible adjacent to the water. Greenery and potted plants line the space, and a building with large windows is in the background.

Condo in Virginia Beach

4.86 out of 5 average rating, 102 reviews

Good Vibes at the Beach

Top guest favorite

The outdoor pool area features a well-maintained pool surrounded by lounge chairs. A clear blue sky is noted above, with clouds adding texture. Nearby greenery and structures contribute to the atmosphere, allowing for a relaxing outdoor experience.

Condo in Virginia Beach

4.98 out of 5 average rating, 102 reviews

Paradise at the Beach

A spacious balcony is shown with six white wooden chairs and a round table, offering views of the bay and distant clouds. A relaxed blue chair adds a touch of color, while the railing provides safety and an open feel to the outdoor space.

Condo in Virginia Beach

4.96 out of 5 average rating, 28 reviews

Back Bay Breeze

Top guest favorite

An aerial view showcases the surrounding area of the condo complex, with a direct line of sight to the beachfront. Nearby buildings and establishments are visible, providing a visual reference for the convenient location relative to the beach and boardwalk.

Condo in Virginia Beach

4.97 out of 5 average rating, 31 reviews

Paradise Cove

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, 249 reviews

Ocean Escape

Top guest favorite

The entrance to the resort showcases a stately brick facade with an arched entryway. Colorful flower beds and well-maintained landscaping surround the pathway, while a tall tree and flagpole add to the welcoming atmosphere. Ample natural light promotes a friendly ambiance.

Condo in Williamsburg

4.93 out of 5 average rating, 117 reviews

Colonial Williamsburg Spacious 4 Bedroom Suite!

Top guest favorite

A spacious balcony features several blue adirondack chairs, offering a view of the surrounding buildings and the outdoor area. Clear skies with a few clouds create a bright atmosphere. The ocean is visible in the distance, providing a scenic backdrop.

Condo in Virginia Beach

5 out of 5 average rating, 22 reviews

New! 4 BR/Oceanfront/Ocean & Bay views/3pools/Gym

Other vacation rentals with a pool

Top guest favorite

The exterior of a modern tiny home is illuminated by a radiant sunset, creating striking sun rays. The home features a spacious deck with steps leading to the ground. Nearby, similar structures are visible against a backdrop of vibrant sky colors.

Tiny home in Virginia Beach

4.9 out of 5 average rating, 72 reviews

Jen n John's Mini Mansion.

Top guest favorite

A vibrant sunset paints the sky in shades of orange and pink, reflecting beautifully on the calm water below. Silhouettes of trees and buildings outline the horizon, while the stillness of the scene evokes a serene atmosphere.

Tiny home in Virginia Beach

5 out of 5 average rating, 11 reviews

Ava’s Estuary

A modern living area features a dark sofa paired with a round wooden coffee table atop a neutral woven rug. A patterned armchair provides additional seating. A flat screen TV is mounted on the wall opposite, and a dining space with woven chairs and a table is visible in the background.

Apartment in Virginia Beach

5 out of 5 average rating, 5 reviews

Unit 901 - Luxury Living on the Oceanfront

A well-appointed guest room features a spacious bed with a light-colored quilt, complemented by two bedside tables with lamps. Decorative wall art is displayed above the headboard, and a comfortable bench sits at the foot of the bed. Soft natural light filters through the window with dark drapes.

Apartment in Williamsburg

4.92 out of 5 average rating, 63 reviews

2 Bedroom @ The Historic Powhatan Resort

Top guest favorite

A private in-ground pool glistens under clear blue skies, surrounded by a wooden fence. An umbrella provides shade next to a lounge area. In the background, a cabana is visible along with outdoor seating, enhancing the inviting space for relaxation.

Home in Virginia Beach

4.99 out of 5 average rating, 85 reviews

Great last minute deals! Message me! 8bdrm, 6bath

A spacious pool area is presented, featuring a large, inviting blue swimming pool with a built-in hot tub. Several lounge chairs and umbrellas provide shaded seating around the pool, while sliding glass doors lead to the interior of the house.

Guesthouse in Virginia Beach

4.73 out of 5 average rating, 126 reviews

POOL, Pool House, Hot Tub, Grill, 2 bedroom

A serene view of the pool area at sunset showcases warm hues filling the sky. White lounge chairs are arranged around the pool, which is enclosed by a safety fence. In the background, the beach and ocean can be seen, enhancing the tranquil atmosphere.

Apartment in Virginia Beach

4.77 out of 5 average rating, 166 reviews

Oceanfront Building Boardwalk Pool Beach 3 Beds

Top guest favorite

A wide sandy beach stretches alongside gentle ocean waves under a clear blue sky. Colorful resort buildings line the beach, creating a welcoming coastal atmosphere. Footprints in the sand suggest leisurely strolls along the shore, inviting relaxation in this serene setting.

Apartment in Virginia Beach

5 out of 5 average rating, 43 reviews

Bayside condo on the beach in Sandbridge

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