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!

4.97 out of 5 average rating, 175 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.

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.

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, 164 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!

4.78 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.

4.89 out of 5 average rating, 106 reviews

Dog Friendly, Large Yard, Spacious & Sleeps 6!

Experience the perfect blend of tranquility and convenience in this charming 3-bed, 2-bath Norfolk home. With a spacious layout and cozy beds, it’s ideal for families and their four-legged friends (pre-approval required; inquire for rules before booking). Features include a fenced yard, a fully stocked kitchen, Wi-Fi, and a quiet cul-de-sac setting. Just a short walk to the beach, you’ll have easy access to the sand and nearby attractions. Book your extended getaway today!

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

Take a break and unwind at your private pool! Stylish, updated interior and a spacious backyard with pool and lounge area. Rinse off at the outdoor shower after a day at the beach and enjoy your private retreat! The Rudee Inlet is less than a block away with great restaurants, fishing, and water activities. A path along the Rudee Inlet leads to the beach and shops - a quick 4 block trip with the included bikes! Outdoor seating and gas fire pit added for the cooler months!

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.

A spacious living room features a comfortable sectional sofa, a wooden entertainment center with a large TV, and a decorative console table. Light-colored walls complement the area rug, and framed artwork adds interest. A staircase is visible, leading to the upper level.

4.89 out of 5 average rating, 206 reviews

3 bedroom private home a block from the beach!

Relax with the whole family at this peaceful home. A block to the beach! 3 bedrooms and 2 bathrooms, with an outdoor shower and finished basement with extra living space. Outdoor patio with gas grill and patio furniture. All amenities included sheets, towels, cooking utensils, etc. Fast Wi-Fi throughout the home. Can sleep up to 8! Pets always welcome. All bedrooms are on main level no stairs required. Weekly and monthly discounted rates upon inquiry.

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, 197 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!

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.

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, 142 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!

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.

4.82 out of 5 average rating, 158 reviews

Retreat with Pool, Walk to Beach

4.99 out of 5 average rating, 213 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 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, 129 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, 123 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, 131 reviews

Gorgeous Vacation House

4.83 out of 5 average rating, 144 reviews

Home in Sandbridge

Bayfront Pool Retreat, Walk to 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, 239 reviews

Salida del Sol, North End Beach / Oceanfront Area

4.85 out of 5 average rating, 109 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!

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

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, 89 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.

4.9 out of 5 average rating, 21 reviews

Home Away From Home

4.9 out of 5 average rating, 10 reviews

Cozy Modern Retreat, Peaceful Stay Near Everything

4.76 out of 5 average rating, 25 reviews

Escape to a Waterfront Retreat

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

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.

4.96 out of 5 average rating, 25 reviews

The Couple’s $pot @ The Dock Near Casino

5 out of 5 average rating, 5 reviews

1.5 Miles to Rivers! 3 br 5 beds

Private house rentals

4.96 out of 5 average rating, 96 reviews

A spacious living area features a soft sectional sofa adorned with decorative pillows. A glass-top coffee table is centered on a patterned rug, flanked by side tables with lamps. Natural light streams through two large windows, complemented by light curtains.

Home in Chesapeake

2 Master Suites, Sleeps 6-8, King bed, 2.5 baths

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, 171 reviews

Cozy Modern Cabin - Historic

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

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.

4.93 out of 5 average rating, 58 reviews

Waterfront/Arcade/Fishing Fun

4.83 out of 5 average rating, 59 reviews

Elegance Escape on Saunders Dr

4.95 out of 5 average rating, 66 reviews

Beach Bungalow • Navy Base • Quiet St • Dogs OK

4.84 out of 5 average rating, 62 reviews

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

A grand staircase with black and floral-patterned steps ascends gracefully. Soft pink walls surround the space, while natural light filters through a large window. A colorful stained glass window adds a vibrant touch, enhancing the historic charm of the home.