House holiday rentals in Portsmouth

4.97 out of 5 average rating, 305 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.

4.97 out of 5 average rating, 127 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, 122 reviews

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.

Home in Norfolk

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 space to spread out, this is IT! Convenient to VB Oceanfront, Downtown Norfolk, Rivers Casino, Waterside & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect family/friends group trips, 12 minutes from Carnival Cruise Port. Oh & bring your fishing poles, river is fully stocked!

4.85 out of 5 average rating, 147 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.

4.97 out of 5 average rating, 125 reviews

The three-story farmhouse-style home features a charming brick facade and a front porch with blue double doors. Lush greenery surrounds the entrance, while a path leads toward the driveway. Sunlight highlights the roof and front yard, creating a welcoming exterior.

Home in Colonial Place

Newport Nook: 5/2.5 Home in Norfolk - Sleeps 10!

5 bed / 2.5 bath - Sleeps 10! Our cozy, farmhouse-style Norfolk home is 5 min from Historic Ghent / ODU. Free Wi-Fi, parking for 4 cars. Coffee, grill, & fire pit provided. Pet-friendly! NO cleaning fee or checkout instructions! Driving Distances: ODU - 5 min Sentara Norfolk General - 5 min CHKD / EVMS - 8 min Norfolk Naval Station - 14 min Virginia Beach Oceanfront - 25 min Monthly: $4,200. Fully furnished rental with all utilities, Wi-Fi, weekly housekeeping, pest & lawn care included.

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.

4.94 out of 5 average rating, 155 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

Make yourself at home! This property offers a warm and welcoming environment for guests, 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!

The exterior of a single-story house is featured, with a well-maintained lawn and landscaped shrubbery. The entrance is framed by a small set of steps and a walkway leading to the front door. A concrete driveway provides access, with trees and a fenced area visible in the background.

4.82 out of 5 average rating, 106 reviews

Walk to the Casino! Sleeps 8, close to everything

Welcome to your perfect getaway! Centrally located with the casino within walking distance and easy highway access to Norfolk, VA Beach, and Chesapeake. Located on a quiet street. This beautifully remodeled and freshly painted 3-bedroom, 2-bath home features a primary suite with private en-suite bathroom, spacious living areas, and a private fenced backyard. Enjoy modern amenities including security cameras, washer/dryer, WiFi, and 4 Roku TVs. Comfortable and ready when you are — book today!

4.96 out of 5 average rating, 128 reviews

Home in Chesapeake

The Cozy Cottage Two Bedroom, King bed House

This is a charming and cozy Cape Cod style house. It’s decorations are eclectic and comfortable. There is a king size bed in the master bedroom and a queen size bed in the second bedroom. There are smart TV’s in each bedroom and the living room. This home has central heat and air conditioning, updated appliances, and carpeting. It’s centrally located and there is plenty of space for parking. This is a perfect place to recharge whether you’re visiting for work or a getaway!

4.85 out of 5 average rating, 108 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!

4.92 out of 5 average rating, 211 reviews

Home in Suburban

Sunset Sanctuary on the Water- Fast Wifi/Netflix

Escape to this 3 BEDS/2 BATH Sunset Sanctuary on the Water, a peaceful retreat where breathtaking sunsets meet serene waterfront views. Perfect for relaxation, this home offers comfort and charm with cozy living spaces and a welcoming atmosphere. Enjoy coffee on the deck, unwind by the water, or explore nearby attractions. Ideal for families or friends seeking a quiet getaway, our sanctuary blends natural beauty with modern convenience for a truly memorable stay.

4.98 out of 5 average rating, 185 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!

A charming, two-story home with a light blue exterior is surrounded by tall trees and a well-maintained lawn. The roof features dark shingles, while steps lead to a welcoming front door, framed by greenery. Sunlight filters through leaves, creating a serene atmosphere.

4.81 out of 5 average rating, 267 reviews

Waterfront Maryview/Naval Hosp Casino close to all

This lovely, quaint home has been completely updated for your comfort. The great room is bright and open. The home is located on the Elizabeth River in an upscale neighborhood with a large yard. This is perfect for a family vacation, or a long weekend. There is an attached mother-in-law suite in the rear of the house. This is rented out separately. It has a private entrance at the rear of the house.

Popular amenities for house rentals in Portsmouth

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A charming coastal cottage exterior is depicted, featuring a white clapboard façade and a shingled roof. The blue front door is framed by decorative shutters, with a welcoming wreath displayed. An American flag hangs proudly, completing the inviting entrance.

4.83 out of 5 average rating, 150 reviews

Retreat with Pool, Walk to Beach

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, 106 reviews

Artful Retreat with a Private Pool

4.76 out of 5 average rating, 37 reviews

A single-story home is displayed, featuring a well-maintained lawn and circular driveway. The exterior is a combination of brick and siding, complemented by large windows. A series of trees in the background provide natural shade, and a chimney is visible on the roof.

Home in Northside

3 Bdrm home with Hot Tub

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 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.

4.86 out of 5 average rating, 119 reviews

Private Pool at the Oceanfront in a Spacious Home

4.93 out of 5 average rating, 127 reviews

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.

Home in Norfolk

Gorgeous Vacation House

4.83 out of 5 average rating, 140 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

Home in North Virginia 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, 228 reviews

Sunrise, North End Beach

Weekly house rentals

4.69 out of 5 average rating, 168 reviews

A spacious living area is presented with hardwood floors and neutral-colored walls. A comfortable couch and a coffee table are arranged on a soft area rug, while a large TV is mounted on the wall. Natural light filters through windows adorned with light curtains.

Home in Port Norfolk

Cozy Modern Cabin - Historic

A bright living area features a large flat-screen television mounted on the wall and a comfortable seating arrangement. Large sliding doors open to a view of the water outside, while a soft area rug adds warmth to the space.

4.95 out of 5 average rating, 83 reviews

R & R River House

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.

4.94 out of 5 average rating, 16 reviews

Home Away From Home

4.9 out of 5 average rating, 30 reviews

A serene view of a private beach is presented, bordered by a gently sloping green lawn. The tranquil water reflects the sky, while scattered stones and patches of marsh grass create a natural shoreline. A tree stands near the water's edge, adding to the peaceful ambiance.

Home in Suffolk

Respass Beach Cove Cottage

4.78 out of 5 average rating, 18 reviews

Escape to a Waterfront Retreat

A single-story bungalow features a welcoming brick exterior, surrounded by well-maintained landscaping. A spacious driveway leads to the house, which is framed by tall trees. The front porch, adorned with white railings, provides an inviting entryway. A detached garage is visible in the background.

4.88 out of 5 average rating, 33 reviews

Cornick Corner near "Rivers Casino"

4.66 out of 5 average rating, 32 reviews

Lighthouse Launch - Spacious 4 BR/2BA Retreat

A well-lit kitchen features stylish brass pendant lights with perforated designs, casting warm glows. Below, modern grey cabinetry and a countertop are complemented by a coffee maker near the window, offering a bright and inviting workspace.

5 out of 5 average rating, 52 reviews

Riverfront Home w/ Vintage Vibes

Private house rentals

4.78 out of 5 average rating, 132 reviews

Fun 3BR-2bath with a game room-Near Rivers Casino

A two-story home with a welcoming front porch is displayed, featuring white railings and steps leading to the entrance. The exterior is painted in light yellow, complemented by white detailing. A spacious fenced yard is visible, providing an outdoor area for relaxation.

4.73 out of 5 average rating, 56 reviews

Portsmouth 3BR Near Casino | Spacious Yard Stay

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, 53 reviews

Waterfront/Arcade/Fishing Fun

4.9 out of 5 average rating, 21 reviews

A wooden dock extends over a calm lake, framed by lush greenery. Two black chairs are positioned for relaxation, overlooking the water. A slide is visible in the background, accompanied by green and red kayaks, offering options for water activities.

Home in Cape Charles

Eden Lake House Cape Charles

The exterior of the home showcases a well-maintained façade with light-colored siding and a welcoming front porch. Lush green grass surrounds the entryway, flanked by neatly trimmed bushes. An American flag is displayed prominently, adding to the charming curb appeal.

4.56 out of 5 average rating, 9 reviews

Family and pet friendly!

4.96 out of 5 average rating, 55 reviews

Home in Norfolk

Norfolk Beach Bungalow • Cozy & Convenient

4.91 out of 5 average rating, 66 reviews

Home in Chesapeake

Comfy House! The Perfect Getaway

The living room features a vibrant orange sectional couch adorned with decorative pillows in front of a contemporary coffee table. Two framed wall art pieces add a touch of elegance, while large windows with sheer and blackout curtains allow natural light to fill the space.