House holiday rentals in Portsmouth

4.97 out of 5 average rating, 289 reviews

A well-appointed bedroom features a spacious bed with a textured white cover. Colorful accent pillows add depth to the decor. A wooden dresser stands against one wall, while a bedside lamp illuminates the space. Natural light filters through a window adorned with light curtains.

Home in Smithfield

Mason Manor - Downtown Smithfield next to WCP

Historic Smithfield 233 S Mason Street 2 Bedrooms 1 Bath Located in the heart of historic Smithfield boasts old world charm and character with a touch of today’s conveniences. The living room has gas fireplace for cool evenings & leads to dining area & updated fully equipped kitchen. The full bath is updated with jetted tub. Front porch swing for relaxing and back deck for entertainment. Windsor Castle Park just steps away. Located just around the corner from restaurants, shopping & more.

4.98 out of 5 average rating, 121 reviews

A welcoming living area features two orange armchairs and a matching sofa, arranged around a glass coffee table. A colorful area rug provides warmth to the space, while framed artwork adorns the walls. A floor lamp and a plant enhance the inviting atmosphere.

Home in Olde Towne

Mid-Century Modern Old Town Portsmouth 3bd/2.5 bth

In the heart of Colonial Portsmouth, VA, on a quiet one-way street -- nestled among homes that date back to the American Revolution & Underground Railroad -- you have found this unique gem... classic and unassuming on the outside, newly rebuilt and designed within. Glasgow Modern, the perfect home-away-from-home. Adjacent to an amazing park, blocks away from the water. We live here 6 months of the year, so the house has everything you need. Dine, Play, Explore, Enjoy... Our home is your home!

4.97 out of 5 average rating, 143 reviews

A two-story blue home is surrounded by trees, featuring a spacious deck with railings accessible from the upper level. A gravel patio area with chairs and a fire pit is visible on the ground level, complemented by neatly maintained greenery.

Home in Gloucester Point

Charming coastal home w/ outdoor area and river views

Tucked away at the end of a quiet road, our home welcomes you. This spacious, thoughtfully designed 1 BR/1.5 BA home on 4 acres is ideal for those looking to relax and get away from it all while still being just minutes away from some of the areas best dining and attractions. Whether you want to watch the sun rise over the York River, spend the day exploring the Williamsburg historic triangle (Busch Gardens), or just take it easy around the house and enjoy the outdoor area, the choice is yours.

4.87 out of 5 average rating, 122 reviews

The bedroom features soft blue walls and a spacious bed with a light blue quilt. A decorative painting of flowers hangs above the bed. Natural light enters through the window, highlighting the room's warm-toned carpet and modern furnishings, including a nightstand and a mirror.

Home in West Park View

Penny’s Palace 1 Bed/1 Bath Home

Welcome to Penny’s Palace! A charming home nestled in quiet community of Portsmouth, VA. Entire home for you with sectioned off suite and bathroom. Penny’s Palace is vibrant & elegantly furnished yet practically designed to sleep 2 people comfortably. This bungalow offers an outdoor sitting area with a dreamy lighted canopy & outdoor grill. It’s perfectly located minutes from major Hampton Roads attractions: Olde Town Portsmouth, Children’s Museum, Downtown Norfolk, Casino, and Virginia Beach.

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.

4.93 out of 5 average rating, 137 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!

4.9 out of 5 average rating, 127 reviews

Home in Buckroe Beach

Home-Sweet-Home

ADORABLE RANCH-STYLE-HOME! ONLY 1.5 Miles to Buckroe Beach! FIRE-PIT OUT BACK GARAGE w/ WORKOUT SPACE HAVE a great time at this adorable 3BR 1BA ranch home with large detached garage. Fully Renovated and Fully Furnished. Kitchen features new cabinets, stainless steel appliances and opens to family room. New flooring. Nice neighborhood. Ceiling fans throughout. Garage with workout bench and dumb-bells. Back yard with sail-shade, chairs, grill and fire-pit. Make this your GETAWAY home!!!

Large windows provide stunning views of the lake, reflecting vibrant colors of the sunset. A small potted plant sits on a table beside a white chair, while light from the setting sun casts a warm glow across the interior space.

4.96 out of 5 average rating, 110 reviews

THE POINT! Private waterfront Oasis!

Enjoy breath taking views & a fully equipped home w/ many amenities. Looking for a private & intimate experience of quality time & a relaxing retreat w/ nature & ample spacw to spread out, this is IT! Convenient to Virginia Beach Oceanfront, Downtown Norfolk, Rivers Casino, Waterside District & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect for holiday family & group trips, 12 minutes from Carnival Cruise Half Moon port.🛳🌊🚢🏠😊!

5 out of 5 average rating, 131 reviews

A modern kitchen features white cabinetry and a granite countertop, equipped with stainless steel appliances including a stove and a refrigerator. Under-cabinet lighting enhances the space, and ample storage is provided by multiple upper and lower cabinets. A sink is positioned near a window, allowing natural light.

Home in East Ocean View

Quiet East Beach Bungalow, 1 block to beach!

Brand new construction located exactly one block from the beautiful Chesapeake Bay at East Beach in Oceanview! A quick walk to the beach or Bay Oaks Park, this bungalow is perfect for relaxing getaways. Fireplace, patio, grill, spacious front porch, new appliances, washer/dryer, private off-street parking. A quick trip to the Naval Bases! Guests are provided with linens, towels, toiletries, and high speed internet(SmartTV). Additional rooms available case by case basis. Please ask.

4.84 out of 5 average rating, 131 reviews

A coffee table is adorned with a lit candle, a notebook, and two books. Comfortable blue chairs are positioned in the background, while a patterned rug adds warmth to the space. Soft natural light illuminates the room, enhancing the decor.

Home in Willoughby

Bungalow at the Bay

This wonderfully decorated home is the perfect spot for a beach getaway with the whole family. Inside you will find a spacious living room, kitchen, bathroom, and two guest rooms with one queen, and a full. Outside there is a backyard porch, perfect for socializing, and a sizable backyard protected by a fence that stretches the property! Free parking is available inside and outside the property. Beach access and free parking is located on 11th view street about a two-minute walk away!

4.9 out of 5 average rating, 147 reviews

A modern living area features a light-toned design with a spacious sofa and a round coffee table. The dining area, equipped with high-backed stools, complements a well-appointed kitchen. Outdoor seating surrounds a fire pit, while a sandy path leads to the beach, framed by lush grass and water views.

Home in East Ocean View

Beautiful renovated 2Bed home!

Your next unforgettable beach getaway awaits with a stay at this charming and completely renovated 2-bedroom, 1-bathroom vacation rental centrally located in Norfolk. Spend sunny summer days at Ocean View Beach, or explore the sights and sounds of nearby First Landing State Park, followed by a quick bite to eat at a local seafood restaurant. At dusk, retreat back to 'Castaway Cottage' for a family BBQ on the propane grill and s'mores shared around the fire pit………………………………

4.85 out of 5 average rating, 105 reviews

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

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!

4.98 out of 5 average rating, 170 reviews

The living room features comfortable navy sofas with decorative cushions and an ottoman in a warm tone. A lamp stands beside a built-in bookshelf adorned with books and decor. Light streams through the windows, and a decorative fireplace adds to the room's character.

Home in Olde Towne

Gorgeous Olde Towne historic home - modern updates

Full of historic charm, modern in all the right places! This 1880s home is located in the heart of Olde Towne Portsmouth, just one block from the Elizabeth River harbor. Walk 3 minutes to the ferry stop and ride across the river to Norfolk's downtown and waterfront restaurants, or walk 5 minutes to Portsmouth's High Street to enjoy Olde Towne's charming coffee shops, restaurants, museums, and theaters. This location is unbeatable!

Popular amenities for house rentals in Portsmouth

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 203 reviews

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

York River Vacation Home

A private pool area features comfortable lounge chairs with floral cushions, surrounded by a clean concrete patio. A screened-in porch is visible in the background, with two inviting chairs for relaxing. The fenced yard offers additional privacy and space for outdoor enjoyment.

4.95 out of 5 average rating, 88 reviews

Paint The Beach Pink! Full House | Private Pool

A spacious brick home is surrounded by well-maintained landscaping featuring lush green grass and mature trees. The front porch, adorned with potted plants, provides a welcoming entrance. Natural light filters through the windows, enhancing the overall charm of the property.

4.95 out of 5 average rating, 121 reviews

Country Comfort Close to the Beaches

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.

4.81 out of 5 average rating, 48 reviews

Elegance Escape on Saunders Dr

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.

4.85 out of 5 average rating, 117 reviews

Private Pool at the Oceanfront in a Spacious Home

A two-story house features a light-colored exterior with a peaked roof. A spacious driveway leads to a garage door, framed by manicured grass and trees. A balcony extends from the top floor, providing outdoor space above the ground level.

4.92 out of 5 average rating, 118 reviews

Gorgeous Vacation House

4.82 out of 5 average rating, 136 reviews

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 Sandbridge

Stunning Views of Back Bay & Seconds to the Beach

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.

4.97 out of 5 average rating, 221 reviews

Sunrise, North End Beach

Weekly house rentals

4.71 out of 5 average rating, 7 reviews

Cozy 3Bed/3Bath Home near Portsmouth Naval-Casino

A modern dining area features a round table with a sleek black surface, surrounded by stylish chairs. A small potted plant sits at the center. The open-concept kitchen is visible in the background, showcasing light cabinetry and stainless steel appliances.

4.93 out of 5 average rating, 15 reviews

Portsmouth's Finest

A classic Cape Cod home is surrounded by well-maintained greenery. The brick exterior is complemented by a gravel pathway leading to the front steps. A concrete driveway provides access to an attached garage, while flags are displayed on the front porch, enhancing the home's welcoming appearance.

4.97 out of 5 average rating, 35 reviews

The Bartlett Inn

A fire pit surrounded by five colorful Adirondack chairs is set on a gravel circle by the water's edge. The calm waters of Hampton Roads Bay stretch out in the background, providing scenic waterfront views under a clear blue sky.

4.94 out of 5 average rating, 48 reviews

Waterfront/Arcade/Fishing Fun

5 out of 5 average rating, 26 reviews

Home in Ocean View

Cozy Home Near Hospitals & Beach

A modern living room is presented, featuring a spacious sectional sofa with light fabric. A wall-mounted smart TV dominates the area, and a glass coffee table is placed in front. Two black bar stools are positioned near a kitchen counter in the background, enhancing the open layout.

4.93 out of 5 average rating, 15 reviews

Home Away From Home

A spacious living area is highlighted by a grey sectional sofa adorned with colorful throw pillows. A rectangular coffee table is centered on a striped area rug. Natural light enters through windows, illuminating the room, while a ceiling fan enhances airflow.

4.86 out of 5 average rating, 94 reviews

Cozy Retreat

4.88 out of 5 average rating, 8 reviews

Escape to a Waterfront Retreat

Private house rentals

4.82 out of 5 average rating, 120 reviews

A spacious living room is featured, containing a large sectional sofa and a coffee table. A flat-screen TV is positioned against the wall, with natural light coming in through two windows. Decorative touches on the wall and a rug add comfort to the space.

Home in Downtown Hampton

The "Bison" contemporary retreat (King Bed)+

5 out of 5 average rating, 30 reviews

A spacious living area is displayed with a dark blue sectional sofa adorned with decorative pillows. A round wooden coffee table is positioned in front, accompanied by a remote control. Two wall hangings, including a world map, enhance the ambiance, along with a plant and a standing lamp.

Home in Hampton

*Spacious Cozy Home* near Beach in Hampton

4.97 out of 5 average rating, 37 reviews

A charming brick residence showcases classic architecture with a distinctive green-roofed entrance and large, bright windows. Lush landscaping surrounds the home, featuring manicured grass and flowering shrubs. A tall tree provides shade in the front yard, adding to the inviting appeal of the property.

Home in Olde Towne

Tudor Treasure in Olde Towne

5 out of 5 average rating, 20 reviews

Relaxing 3BR River Stay • 8 Mins to Casino!

A cozy living area is presented with a comfortable gray sofa adorned with decorative pillows. A flat-screen television is mounted on the wall, and a marble coffee table sits on a patterned rug. Natural light filters through a large window covered with vertical blinds.

4.71 out of 5 average rating, 206 reviews

Modern, Homely 3-bdrm|wParking|Centrally located.

A modern living room is showcased with light hardwood flooring and elegant furnishings. A large flat-screen TV is mounted on a marble feature wall, while a plush sofa is positioned nearby. Natural light flows in through large windows adorned with sheer curtains.

5 out of 5 average rating, 91 reviews

Beach Stay

4.95 out of 5 average rating, 38 reviews

Norfolk Beach Base • Cozy & Convenient

A cozy living area is furnished with a gray sectional couch adorned with decorative pillows. A small black table sits on a patterned rug, complemented by floor lamps and wall-mounted greenery. Natural light enters through a window, enhancing the inviting space.