We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Some info has been automatically translated. Show original language

Airbnb your place

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.

0 of 0 items showing

1 of 3 pages

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, 190 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 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, 219 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.

A swimming pool is surrounded by a wooden fence, featuring two yellow umbrellas over lounge chairs. Sunlight reflects off the clear water, and nearby buildings are visible in the background against a clear blue sky.

Condo in Virginia Beach

4.87 out of 5 average rating, 143 reviews

Oceanfront, beach, boardwalk, fun, dolphin, sunris

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!

Aerial view of the property showcasing a fenced backyard with a sparkling blue pool surrounded by concrete. A seating area with lounge chairs and various floatation devices is visible beside the pool. Lush greenery from surrounding trees frames the scene, providing a sense of privacy.

Home in Portsmouth

4.93 out of 5 average rating, 121 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, 108 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, 104 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

4.89 out of 5 average rating, 228 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 light-colored house sits under a clear blue sky, showcasing a welcoming front porch with a sloped roof. Lush green grass surrounds the home, while a flower bed with blooming flowers adds a touch of color to the well-maintained yard.

Home in Virginia Beach

4.88 out of 5 average rating, 137 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!

Top guest favorite

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, 580 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.

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, 134 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!

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, 98 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.

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, 255 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.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations and amenities

Popular amenities for Chesapeake Beach rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Hampton

4.87 out of 5 average rating, 47 reviews

Coastal Retreat @ Coliseum| Pool, Bonus Rm, Gazebo

A pool cover in shades of green is neatly secured on a paved surface, surrounded by tall trees and a serene landscape. A river view is visible in the background, suggesting a tranquil outdoor environment.

Home in Newport News

5 out of 5 average rating, 9 reviews

Pool River House

A newly built coastal home stands elevated on stilts, featuring a spacious lower deck with a pool and hot tub enclosed by a wooden fence. Multiple balconies extend from the upper floors, inviting views of the surrounding natural landscape.

Home in Corolla

4.86 out of 5 average rating, 14 reviews

Milk 'N' Honey at the 4X4 Carova Beach

A private pool is visible, featuring a gentle slope entry and surrounded by a spacious yard. Lush greenery and trees provide shade while a wooden fence borders the area, ensuring privacy. The pool water appears clear and inviting, reflecting the sky above.

Home in Virginia Beach

4.8 out of 5 average rating, 40 reviews

4BR House w 2 King BEDS,2 kitchens, POOL & SAUNA

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, 108 reviews

Private Pool at the Oceanfront in a Spacious Home

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, 98 reviews

Perfect Getaway!

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, 207 reviews

Sunrise, North End Beach

A spacious beachfront property is set against a clear blue sky. A large pool is surrounded by seating areas and a manicured lawn, leading to a private dock. Nearby homes are visible, showcasing a relaxed coastal environment.

Home in Virginia Beach

4.95 out of 5 average rating, 19 reviews

NEW! Boat Ramp, Dock, Pool, Hot Tub, Waterfront

Condo rentals with a pool

An indoor pool is framed by large windows, allowing natural light to fill the space. Colorful lounge chairs are arranged around the pool area, complemented by green walls and vibrant decor. The water appears clear and inviting, with a calm atmosphere evident within the room.

Condo in Virginia Beach

4.83 out of 5 average rating, 294 reviews

Beautiful Beachfront Condo

The image captures a serene view of the ocean during sunrise, with soft waves lapping at the sandy beach. The sun reflects off the water, creating a shimmering effect across the surface. Gentle clouds float in the sky, enhancing the tranquil atmosphere.

Condo in Virginia Beach

4.92 out of 5 average rating, 59 reviews

Beach Luxury Beachfront

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

4.88 out of 5 average rating, 25 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

4.87 out of 5 average rating, 94 reviews

Good Vibes at the Beach

A spacious pool area is surrounded by a vibrant blue building, with sun loungers arranged around a shimmering pool. Wooden tables and chairs provide seating options for guests, while well-maintained landscaping enhances the inviting atmosphere of the outdoor space.

Condo in Virginia Beach

4.93 out of 5 average rating, 135 reviews

Ocean & Bay Views - Local Family Owned & Operated

A well-maintained swimming pool features a clear blue surface surrounded by a textured deck. Lush greenery is visible in the background, with tall trees framing the scene. The area is enclosed by a fence, providing a private atmosphere.

Condo in Williamsburg

4.95 out of 5 average rating, 73 reviews

Lovely 2 Bedroom Condo in 4Diamond Historic Resort

Top guest favorite

The exterior of a two-story house is shown, featuring a gray shingle facade and a welcoming front porch. Neatly trimmed shrubs and manicured lawns frame the driveway, while flowering plants add subtle color. A double garage with white doors is visible on the left.

Condo in Cape Charles

4.96 out of 5 average rating, 27 reviews

Bay Creek Blessed at The Fairways

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, 242 reviews

Ocean Escape

Other vacation rentals with a pool

The exterior of a modern tiny home is showcased, featuring a deck with an umbrella and steps leading to the entrance. Lush greenery and blooming flowers frame the home, which is situated near a waterfront. A clear blue sky adds to the inviting atmosphere.

Tiny home in Virginia Beach

4.89 out of 5 average rating, 53 reviews

The Green Bean Bungalow

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, 7 reviews

Ava’s Estuary

Apartment in Virginia Beach

4.67 out of 5 average rating, 3 reviews

Unit 302 - Oceanfront 2 Bedroom Overlooking Beach!

An open living space features a large wooden dining table surrounded by benches. A cozy seating area includes a pair of armchairs and a sofa. A foosball table and kitchen bar stools are visible, along with warm wooden flooring and soft lighting throughout the room.

Farm stay in Virginia Beach

4.92 out of 5 average rating, 12 reviews

Secluded Sanctuary with pool access

Top guest favorite

Home in Norfolk

4.97 out of 5 average rating, 61 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

4.85 out of 5 average rating, 41 reviews

Elegance Escape on Saunders Dr

Top guest favorite

A private dock extends over calm waters, where three white Adirondack chairs are situated for seating, accompanied by a potted palm. Reeds line the opposite shore, and sunlight enhances the serene atmosphere of this waterfront space.

Camper/RV in Virginia Beach

4.96 out of 5 average rating, 45 reviews

Waterfront On Back Bay In Sandbridge.

A two-story beach house is shown, featuring a wide front porch with outdoor seating and umbrellas. The driveway provides ample space for parking, and flags adorn the house, adding a coastal touch. Surrounding landscaping includes greenery, enhancing the inviting exterior.

Apartment in Virginia Beach

4.9 out of 5 average rating, 10 reviews

Works 4 Me: New listing

Destinations to explore