House holiday rentals in Portsmouth

4.97 out of 5 average rating, 297 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!

4.86 out of 5 average rating, 132 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, 118 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.

4.93 out of 5 average rating, 147 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!

4.98 out of 5 average rating, 128 reviews

The exterior of a two-story home is showcased, featuring natural wooden siding and two private balconies. Each balcony is equipped with a railing and simple seating, providing a comfortable space to enjoy the outdoors. A surrounding green area offers a touch of nature.

Home in Willoughby

One block from the Beach

Stay at one of the highest rated homes in Willoughby Beach. It has everything you need to have a relaxing getaway. Enjoy the breezes of the Willoughby Bay on the back 2 decks, and the Chesapeake Bay on the front 2 decks. 500 ft walk to Chesapeake beach access, and an outdoor shower ready when you return. We have been hosting since 2018 and you can read our reviews to see that this property is our pride and joy. Let us show you what a five star experience is on Airbnb... Mandy and Kevin

5 out of 5 average rating, 138 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.

A three-story house features a light gray exterior with a welcoming yellow front door. Flanking the entrance are neatly trimmed shrubs and small trees, complementing the spacious front porch. The surrounding area includes well-maintained neighboring houses and a glimpse of a fenced backyard.

4.92 out of 5 average rating, 169 reviews

5 Min to Downtown & Ghent, Fenced Yard, Firepit

Welcome to Norfolk! This is a large 3 story, 4 BR/3.5 BA house located just outside of the popular Ghent district in and walking distance to many breweries, restaurants & coffee shops! This is a fast growing area of town and for good reason, we’re so exited to host you! 15 min drive to Norfolk International Airport 12 min drive to Naval Base 8 min drive to Downtown/waterside district/freemason historic district 6 min drive to ODU campus 4 min drive to Virginia Zoo

4.93 out of 5 average rating, 125 reviews

A cozy living space features a blue couch with white pillows, accentuated by warm wood beams. A round coffee table and light-colored curtains allow natural light to brighten the room, while a ceiling fan adds a touch of comfort. Soft textures contribute to a welcoming atmosphere.

Home in Buckroe Beach

Condo in Buckroe Beach

Welcome to our beautiful, newly renovated two bedroom condos. Perfectly located just 1 block distance to the beach. Our condos feature modern beach home designs and are equipped with all the amenities you need for a relaxing stay. With comfy home vibes and proximity to the best restaurants, bars, and tourist attractions, this condo is the perfect place to experience all that Hampton has to offer. Book today and enjoy an unforgettable stay in Buckroe Beach.

4.98 out of 5 average rating, 181 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 beach scene at sunset features individuals playing volleyball in the sand. The calm water reflects shades of pink and orange from the setting sun. Silhouettes of a pier and distant structures are visible along the horizon, framed by beach grass in the foreground.

4.93 out of 5 average rating, 287 reviews

Quilted Quarters by the Bay with Private Entrance

Enjoy beach life, hiking and biking near the Chesapeake Bay in a spacious fully furnished studio with a private entrance and private bath in a very safe and quiet neighborhood with one dedicated parking space as well. Five minute walk to the beach and First Landing State Park with hiking, biking, running trails, locally owned restaurants, bars, shops, breweries, grocery, pharmacy, farmer's market and yoga studio.

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.

4.8 out of 5 average rating, 260 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 Portsmouth house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.82 out of 5 average rating, 38 reviews

A private pool is surrounded by a spacious patio area, featuring lounge chairs and shaded seating. The clear water reflects the blue sky, while a white fence offers privacy. Decorative elements such as lights and tropical decor enhance the leisure space.

Home in Willoughby

The Blue Octopus~Private Pool~HotTub~Beach~FirePit

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, 118 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.

4.93 out of 5 average rating, 122 reviews

Gorgeous Vacation House

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, 225 reviews

Sunrise, North End Beach

4.85 out of 5 average rating, 107 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!

The entrance to Unit 4 features a blue door framed by a white pergola. A shadow pattern from the structure falls across the light-colored deck, which includes several outdoor chairs. Fenced areas filled with greenery are visible in the background.

4.86 out of 5 average rating, 137 reviews

THE OLD BEACON 4 I Beach Living

4.89 out of 5 average rating, 141 reviews

Half house w/pool & new patio all to yourself

Weekly house rentals

4.76 out of 5 average rating, 210 reviews

A spacious living area features a large sectional sofa in neutral tones, complemented by vibrant yellow and blue pillows. A wooden coffee table sits in front, with a patterned area rug enhancing the warmth of the space. Large windows allow natural light to fill the room.

Home in Willoughby

Beach House~Hot Tub~3 Min to Sand~HUGE Kitchen

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, 36 reviews

The Bartlett Inn

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.

4.72 out of 5 average rating, 215 reviews

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

An outdoor seating area is presented on a wooden deck, featuring a table surrounded by rattan chairs and an additional bench. Colorful floral murals embellish the wooden fence, while a black umbrella offers shade. Lush grass surrounds the area, creating a serene environment.

4.96 out of 5 average rating, 46 reviews

Norfolk Beach Bungalow • Cozy & Convenient

A modern kitchen features light cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator, oven, and dishwasher, are visible. Soft lighting highlights the spacious layout, which is complemented by tiled flooring and a seamless flow into the adjacent dining area.

5 out of 5 average rating, 86 reviews

Hidden Gem.4/bedroom cozy home fenced in yard

4.84 out of 5 average rating, 25 reviews

An open living space is shown, featuring a comfortable gray sectional sofa and a stylish white coffee table. A modern kitchen bar is visible with three stools, while a dining area with two chairs is situated near the window. Natural light illuminates the room, enhancing the soft color palette.

Home in Buckroe Beach

The Iverson: Cozy 2 Bdrm Home by the Beach

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

5 out of 5 average rating, 21 reviews

Home in Ocean View

Casa del Sol – Game Room, Firepit & Walk to Beach!

Private house rentals

4.81 out of 5 average rating, 127 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, 42 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

4.78 out of 5 average rating, 27 reviews

Home in Chesapeake

Cozy Ranch Retreat.

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, 55 reviews

PureLife Portsmouth 3BR | Fenced Yard, Near Casino

4.97 out of 5 average rating, 39 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

The spacious sunroom features comfortable seating arranged around a central coffee table. A basketball hoop and trampoline provide recreational options. Colorful wall decorations and a vibrant rug enhance the playful atmosphere. Large screens allow views of the private backyard, while windows offer natural light.

4.93 out of 5 average rating, 96 reviews

The Pines- Family Entertainment Room

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!

A modern kitchen is featured, showcasing sleek white cabinetry and stainless-steel appliances. Ample counter space complements a deep farmhouse sink. Light is provided by recessed lighting and a window, which leads into an open dining area visible in the background.