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Vacation rentals with a pool in Hampton Roads

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Hampton Roads

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, 201 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.

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, 134 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!

Top guest favorite

An aerial view of a two-story home with a red roof, surrounded by lush green lawns. A sparkling pool is situated in the backyard, accompanied by lounge chairs, a patio area, and a gazebo. The property features a well-maintained outdoor space with nearby landscaping.

Apartment in Hampton

4.96 out of 5 average rating, 396 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!

A charming private balcony offers a dining setup for two with white Adirondack chairs and a table, overlooking the beach. A stunning sunset illuminates the horizon, while the seaside view provides a serene backdrop for the table adorned with floral centerpiece and tableware.

Condo in Virginia Beach

4.88 out of 5 average rating, 241 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.

The exterior of a private attached suite is shown, featuring a welcoming entrance with white steps and a small porch. Lush greenery and colorful flowers frame the walkway, leading to a paved driveway. A wooden fence provides privacy, while a well-maintained lawn enhances the setting.

Guest suite in Chesapeake

4.95 out of 5 average rating, 595 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 charming two-story cottage is set on a lush green lawn, with a clear view of the Chesapeake Bay in the background. The cottage features large windows and a sloped roof, with a small wooden addition on one side, surrounded by well-maintained grass.

Tiny home in Cape Charles

4.98 out of 5 average rating, 339 reviews

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

A two-story house featuring a welcoming porch with white railings and steps leading to the front door. The exterior is clad in light siding, complemented by well-kept landscaping and a driveway leading to a garage on the right. Trees provide a natural backdrop.

Home in Suffolk

4.85 out of 5 average rating, 104 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!

Top guest favorite

A lush field is filled with blooming yellow flowers under a clear blue sky. In the background, a red barn is situated near a fence, surrounded by trees that provide a natural border to the landscape.

Farm stay in Williamsburg

4.97 out of 5 average rating, 375 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.

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, 114 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 view of the beach stretches towards the horizon, framed by green grass and a flower pot. White lounge chairs are arranged for relaxation, while colorful umbrellas dot the sandy shore, providing shade to beachgoers enjoying the ocean.

Condo in Virginia Beach

4.96 out of 5 average rating, 148 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

Cottage in Norfolk

4.97 out of 5 average rating, 269 reviews

Villa Positano

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.

Home in Hampton

4.93 out of 5 average rating, 122 reviews

4BD home w/ game room & pool near Langley & PTC!

Welcome Home! Be the next to rent this beautifully renovated, modernized home with beautiful kitchen, amazing bathrooms and generous bedrooms and closets. Come in and relax in this centrally located neighborhood - convenient ten minute trip for shopping, restaurants and military bases. Great for families coming in town for Boo Williams tournaments! This is the one! DONT FORGET TO ASK ABOUT OUR YACHT RENTAL OPTIONS!!!

Vacation rentals for every style

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A space thats all yours, with room for everyone

Popular amenities for Hampton Roads rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious backyard features a large, unheated swimming pool surrounded by a concrete patio. The two-story blue cottage is visible in the background, complemented by greenery and a fence that provides privacy.

Home in Norfolk

4.83 out of 5 average rating, 18 reviews

Nautical Cottage

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, 13 reviews

Spacious 4BR Home w/ Pool • Family Friendly

An aerial view of the backyard showcases a large pool with a sun ledge, a lazy river with vibrant umbrellas, and a splash pad. Surrounding seating areas are arranged for relaxation. Fixed and floating piers provide access to the water, complemented by water equipment visible in the background.

Home in Virginia Beach

4.93 out of 5 average rating, 15 reviews

8br, Pool,Lzy Rvr,Pier,Pool,Hot Tub (Sandbridge)

Top guest favorite

A cozy living area features a brown sofa adorned with decorative pillows against a warm yellow wall. A small desk holds books and a decorative item, while natural light fills the space through sheer curtains. A doorway leads to a bathroom area.

Home in Norfolk

4.96 out of 5 average rating, 70 reviews

The Seaglass Cottage

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, 117 reviews

Private Pool at the Oceanfront in a Spacious Home

The image presents a large outdoor pool surrounded by a deck, sun loungers, and a gazebo. Lush greenery lines the background, complementing the serene waters of Back Bay visible in the distance under a bright blue sky with scattered clouds.

Home in Virginia Beach

4.85 out of 5 average rating, 134 reviews

Stunning Views of Back Bay & Seconds to the Beach

Top guest favorite

A modern kitchen area is visible, featuring stainless steel appliances and a granite countertop with bar seating. Two stylish light fixtures hang above, while the space is illuminated by natural light from large windows covered with light curtains. A seating arrangement includes sleek black bar stools.

Home in Virginia Beach

4.97 out of 5 average rating, 217 reviews

Salida del Sol, North End Beach

Top guest favorite

An aerial view captures a vibrant Victorian-style home featuring teal and yellow siding. A striped awning provides shade over the front porch, where two chairs sit beside potted plants. Neatly trimmed hedges line the walkways, and a neighboring home adds to the charming streetscape.

Home in Cape Charles

5 out of 5 average rating, 34 reviews

East of the Sun Victorian - Private Pool

Condo rentals with a pool

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, 65 reviews

Beach Luxury Beachfront

A living area features two pull-out sofas, one adorned with decorative pillows. A patterned rug covers the tile floor, and two framed black-and-white photographs hang on the walls. A light pendant illuminates the adjacent kitchenette and dining area, enhancing the open layout.

Condo in Virginia Beach

4.89 out of 5 average rating, 88 reviews

Oceanfront Condo with Spectacular Beach View

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

4.84 out of 5 average rating, 38 reviews

2BD2BA Condo w/Pool2Blocks2Beach

The exterior of a charming three-story building is showcased, featuring red brick walls and a steeply pitched roof. Large windows with white railings overlook a landscaped courtyard with fountains and blooming trees, creating a welcoming ambiance surrounded by greenery.

Condo in Williamsburg

4.96 out of 5 average rating, 47 reviews

Marriott's Manor Club Ford's Colony 2BD Villa Slee

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, 104 reviews

Paradise at the Beach

A sunset view over the ocean is captured from a balcony, where warm colors blend in the sky. Gentle waves lap at the shore, and silhouettes of distant boats are visible on the horizon. The sandy beach offers a serene atmosphere.

Condo in Virginia Beach

4.87 out of 5 average rating, 153 reviews

Oceanfront, beach, boardwalk, fun, dolphin, sunris

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

4.97 out of 5 average rating, 29 reviews

Back Bay Breeze

A sweeping view of a lush green golf course is presented, featuring gently curving pathways and sand traps. Tall trees provide shade along the course, and a few golfers are visible in the distance, contributing to the serene landscape.

Condo in Williamsburg

4.95 out of 5 average rating, 77 reviews

Lovely 2 Bedroom Condo in 4Diamond Historic Resort

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

4.91 out of 5 average rating, 75 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, 12 reviews

Ava’s Estuary

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

4.9 out of 5 average rating, 69 reviews

The Green Bean Bungalow

Top guest favorite

A roller coaster is depicted in motion, showcasing riders on a track that curves downwards, next to a large wooden structure resembling a water ride. Surrounding green trees provide a natural backdrop, contributing to the lively atmosphere of the amusement area.

Townhouse in Williamsburg

5 out of 5 average rating, 25 reviews

3bdr Williamsburg Townhouse, sleeps 8

A spacious guest room features a king bed with crisp white linens and a neutral-colored bed skirt. Two bedside lamps illuminate the dark wood nightstands. A dresser and a chair are positioned near a window that allows natural light to brighten the room.

Apartment in Williamsburg

5 out of 5 average rating, 4 reviews

Beautiful 1BR at Williamsburg + Amenities

Two wooden adirondack chairs are placed on a stone patio, each adorned with a green tropical patterned pillow. A calm waterway is visible in the background, flanked by trees and a building. Bright blue skies add natural light to the scene.

Tiny home in Virginia Beach

4.96 out of 5 average rating, 26 reviews

Key Lime Cabana at Surfside

A balcony offers a view of the sandy beach and ocean waves. Two black chairs are positioned beside a round table, inviting relaxation. The sky is partly cloudy, and the beachfront promenade is visible below.

Apartment in Virginia Beach

4.88 out of 5 average rating, 59 reviews

Oceanfront Views! 2 BR, 2 BATH!

A modern kitchen and dining area features a round marble table surrounded by black chairs. White cabinetry and stainless steel appliances are visible, with natural light illuminating the space. A framed art piece is displayed on the wall, and a potted plant adds a touch of greenery.

Apartment in Virginia Beach

4.92 out of 5 average rating, 37 reviews

Newly Built Apt Near Oceanfront

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