House holiday rentals in Portsmouth

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.

4.96 out of 5 average rating, 132 reviews

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!

ValueFamilyHospitality

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, 130 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 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!

ValueFamilyAccuracy

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.

4.82 out of 5 average rating, 159 reviews

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.

FamilyValueQuiet

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.

4.92 out of 5 average rating, 166 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!

LocationFamilyBreakfast

4.78 out of 5 average rating, 133 reviews

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

Escape to this entertaining 3BR, 2-bath retreat in Portsmouth, VA. Just 4 mins from Rivers Casino and 15 mins from Waterside District. A 30-min drive takes you to VA Beach, ODU, NSU, HU, and CNU. Stay connected with WiFi & Smart TVs. The outdoor space is a treat with a grill & various activities. Indoors, there's a pool table, darts, table tennis, and board games. The renovated kitchen has stainless steel appliances. This home offers a wide range of amenities for a memorable getaway.

LocationFamilyBeach

4.96 out of 5 average rating, 131 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!

ValueFamilyQuiet

4.84 out of 5 average rating, 104 reviews

Home in Newport News

The Artist House

Welcome to the Art House! Enjoy stunning local artwork displayed throughout our property which is a perfect blend of comfort & creativity. Our ideal location places you three minutes from the Shipyard, ten minutes from Coliseum Central & Hampton University, & fifteen minutes from Christopher Newport University. You want more! We are twenty five minutes from Norfolk state and ODU. Let’s not forget the beach too! We are fifteen minutes from buckroe beach in Hampton.

FamilyValueCheckout

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, 103 reviews

The Pines- Family Entertainment Room

This ranch home is located in a quiet & safe neighborhood (Windy Pines) in an area we call “Churchland”. The area is comprised of tri-cities in the same area. (Portsmouth, Chesapeake & Suffolk) Near military installations, shipyards, hospitals, beaches, amusement parks, museums, casinos, and more Property is walking distant from Hoffler Creek Wildlife Preserve nature trail and less than a mile from Popular Harbour View Shopping area.

FamilyValueGetting around

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.

4.98 out of 5 average rating, 199 reviews

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!

FamilyValueQuiet

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, 280 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.

ValueFamilyComfort

The living area is designed with a mix of modern furnishings and artwork. A comfortable sectional sofa and an accent chair surround a coffee table. Light streams in through a window, highlighting a TV and a decorative cabinet. Artwork adds a pop of color to the neutral walls.

4.93 out of 5 average rating, 143 reviews

3BR Mid-Century Modern Home • Near Airport

Welcome to our beautifully updated 3-bed, 2-bath home in Norfolk. Featuring a spacious layout with cozy beds, it’s ideal for families or groups. Enjoy a gourmet kitchen, a huge dining space, Wi-Fi, a washer and dryer, and all the amenities needed for a relaxing stay. Located next to Norfolk Airport and the Botanic Gardens, you’ll have easy access to all of Hampton Roads. Book your extended getaway today!

FamilyLocationCleanliness

A charming two-story home is seen from the street, featuring a welcoming front porch with white railing. Large windows allow natural light to fill the space. The yard is well-maintained and bordered by a sidewalk, surrounded by trees that provide shade.

4.99 out of 5 average rating, 152 reviews

Ghent on the Corner: Cozy 3 bed 2.5 bath home

My cozy, 3 bed / 2.5 bath Norfolk home has a spacious 1st floor primary suite with a full bathroom, 2 bedrooms upstairs along with a 2nd full bathroom. No cleaning fee or checkout instructions. Pet-friendly! Free Wi-Fi, parking for 4 cars, grill & gazebo. Distances: CHKD - 5 min EVMS - 5 min Sentara Norfolk General - 5 min Waterside / Downtown - 10 min Ocean View - 20 min VB Oceanfront - 25 min

FamilyLocationAccuracy

Popular amenities for Portsmouth house rentals

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.

4.82 out of 5 average rating, 158 reviews

Retreat with Pool, Walk to Beach

LocationFamilyNearby

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.

4.96 out of 5 average rating, 118 reviews

Artful Retreat with a Private Pool

ValueFamilyCleanliness

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, 130 reviews

Country Comfort Close to the Beaches

LocationFamilyAccuracy

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, 124 reviews

Private Pool at the Oceanfront in a Spacious Home

ValueFamilyCleanliness

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, 131 reviews

Gorgeous Vacation House

FamilyValueKitchen

4.83 out of 5 average rating, 144 reviews

Home in Sandbridge

Bayfront Pool Retreat, Walk to Beach

LocationFamilyCheck-in

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, 239 reviews

Sunrise, North End Beach / Oceanfront Area

LocationValueQuiet

4.85 out of 5 average rating, 110 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!

LocationFamilySleep quality

Weekly house rentals

A modern gray sectional couch is positioned against a light gray wall. It features several decorative pillows in varying shades. Two table lamps with simple shades stand on either side on dark side tables, and a patterned area rug covers the hardwood floor.

4.76 out of 5 average rating, 17 reviews

The Mayfield

LocationValueBathroom

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.

4.7 out of 5 average rating, 172 reviews

Cozy Modern Cabin - Historic

ValueLocationCheckout

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.

4.96 out of 5 average rating, 90 reviews

R & R River House

ValueFamilyTV

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.

4.9 out of 5 average rating, 21 reviews

Home Away From Home

FamilyLocationView

4.83 out of 5 average rating, 36 reviews

The Main House

ValueFamilyAccuracy

4.9 out of 5 average rating, 10 reviews

Cozy Modern Retreat, Peaceful Stay Near Everything

CleanlinessCheck-inHospitality

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, 99 reviews

Hidden Gem.4/bedroom cozy home fenced in yard

ValueFamilyAccess

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.

4.97 out of 5 average rating, 135 reviews

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

FamilyLocationAccuracy

Private house rentals

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.

4.74 out of 5 average rating, 61 reviews

Portsmouth 3BR Near Casino | Spacious Yard Stay

ValueFamilyAir conditioning

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.

4.94 out of 5 average rating, 48 reviews

The Bartlett Inn

FamilyLocationSleep quality

4.83 out of 5 average rating, 60 reviews

Elegance Escape on Saunders Dr

ValueLocationAccess

4.76 out of 5 average rating, 25 reviews

Escape to a Waterfront Retreat

LocationValueView

4.84 out of 5 average rating, 62 reviews

Modern 2 bdrm home w/Firepit, game console, bikes

ValueFamilyCleanliness

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.

4.89 out of 5 average rating, 38 reviews

Cornick Corner near "Rivers Casino"

LocationFamilyAccuracy

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.

4.92 out of 5 average rating, 26 reviews

The Couple’s $pot @ The Dock Near Casino

LocationLayoutNearby