Family-friendly holiday rentals in Portsmouth

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, 107 reviews

Hidden Gem.4/bedroom cozy home fenced in yard

Make yourself at home!Hidden Gem offers a clean welcoming space for guests, located in a quiet established neighborhood. Guests should expect a clean and comfortable stay. Conveniently located near parks,shopping, and dining options. Attractions aren’t too far away Rivers casino.2.9. Virginia Beach Ocean Front.23miles. Waterside district Norfolk 8.5 miles. Town center 17.miles. Busch Gardens 40 miles. Old Dominion University 9.8 miles. Norfolk State University 8.8 miles.Hampton University23miles

Indoor spacesKitchenComfort

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, 169 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.

KitchenFamilyLocation

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, 173 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!

Indoor spacesFamilyLocation

A well-lit bedroom features a spacious bed with decorative pillows and a cozy throw blanket. Natural light enters through a window, while a standing lamp and a woven basket add functional elements. A ceiling fan and light fixture enhance the room's comfort.

4.85 out of 5 average rating, 155 reviews

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Enjoy easy access to everything from this perfectly located, fully furnished home. Walk to fine dining, museums, a historic theater. Visit the waterfront where you can view the Navy ships or ride the Ferry to Norfolk to experience Waterside & MacArthur Mall. This is a great place for traveling professionals or those in town for sightseeing or local events. Virginia Beach Oceanfront is 30 minutes away. Home is located in a beautiful, historic area and only 8 minutes from the new casino!

KitchenFamilyLocation

Guest suite in Portsmouth

A comfortable living room area is featured, showcasing a light-colored sectional sofa with dark blue accent pillows. A dark coffee table is set in front of the sofa. A vibrant world map painting adorns the wall, and natural light streams through a nearby window.

4.96 out of 5 average rating, 123 reviews

Historic Hideaway Private Apartment/Suite

You will be comfortable in this spacious, one bedroom suite. You have your own kitchen, washer/dryer, and living room space with large tvs in the bedroom and the living room. To wind down from your day step into your large beautiful shower that has endless hot water. Try living room sofa pulls out to a sleeper lay down while watching tv, or to use as an extra bed. Enter/exit thru a private entrance. Only you will have access to your space. Clean and inviting. Stay a day, or stay a while!

Indoor spacesKitchenQuiet

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.

KitchenIndoor spacesLaundry

A cozy living space features a light-colored sofa with blue cushions and an armchair. A wooden coffee table sits on a patterned rug, accompanied by two lamps providing soft light. Artwork adorns the walls, and a small plant adds a touch of greenery.

4.94 out of 5 average rating, 135 reviews

Lovely Two Bedroom, 1 1/2 bath, King bed Townhouse

Your family will be close to everything when you stay at this centrally-located place. Beautiful re-done townhouse. New carpet and luxury vinyl, new vanities and toilets, Maytag washer and dryer, central heat and air, brand new hot water tank, small patio in back. Close to shopping, Kroger, T J Maxx, Walmart, CVS, and other shops. Plenty of take out food, like chick-fil-A, Panda Express, Wendys, Rallys, Dunkin Donuts, and more. Brand new Rivers Casino less than a mile away!

KitchenIndoor spacesWi-Fi

A cozy living area features two dark couches with decorative pillows, a coffee table at the center, and a small desk against the wall. A potted plant adds greenery, and artworks are displayed across the walls. Soft carpeting enhances the comfortable atmosphere.

4.91 out of 5 average rating, 108 reviews

"The Ponderosa A" - Close to the Casino & Concerts

Lots of Great Concerts going on Check out the outdoor concerts at the Rivers Casino. Only 1/2 mile away. 600 Sq.Ft., One Bedroom Garage Apartment for 2 Adults, nice, quiet neighborhood 1/2 mile to the Private entrance and nice, free Private entrance parking for 1 vehicle. Large Sign Visitor Parking Space. One Bedroom w/Queen size bed, Full size Kitchen, One full Bathroom. Only 4 miles to Downtown Portsmouth , 5.9 miles to Norfolk, 22 mi to VB Oceanfront

Indoor spacesKitchenAccuracy

The exterior of a historic home features classic architectural details, including a covered porch with white columns. An American flag is prominently displayed, and mixed flower pots are arranged on the brick pathway. Large windows allow for natural light, showcasing the home’s inviting presence.

4.94 out of 5 average rating, 139 reviews

Best location in Olde Towne Portsmouth

This apartment is available for up to 6 months upon request. Perfect location for traveling medical professionals. Very convenient to the Naval Medical Center. Enjoy Historic Old Towne and stay in a home built in 1850. Stroll the neighborhood where you will see houses from the late 1700's. Take a short walk to numerous restaurants or take in a movie at the historic Commodore Theater. Two blocks away is the ferry terminal to Waterside in downtown Norfolk.

Indoor spacesKitchenComfort

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, 107 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.

Indoor spacesFamilyOutdoor spaces

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.

4.99 out of 5 average rating, 213 reviews

Historic Gem - Walk to Dining, Ferry & Waterfront

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!

KitchenFamilyDecor

Guest suite in Chesapeake

The Purple Room features a spacious bed with white linens and purple accents. A cozy seating area is visible beside large windows with light filtering through sheer curtains. Decorative elements, including wall art and a soft purple rug, enhance the vibrant atmosphere.

4.97 out of 5 average rating, 391 reviews

Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!

Welcome to The Purple Room, where every guest is made to feel like royalty. More than an Airbnb, it’s a one-of-a-kind boutique retreat intentionally designed to create unforgettable memories. From the peaceful atmosphere and thoughtful touches to your private entrance and relaxing escape, every detail has been curated to help you unwind, recharge, and experience something truly special. Come discover The Purple Room experience. 💜

KitchenFamilyComfort

Popular amenities for Portsmouth family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A modern living area features a comfortable sofa adorned with decorative pillows and a cozy throw. A large dining table with natural wood tones is visible in the background, contrasting against a blue accent wall decorated with serene artwork. Ample lighting brightens the space.

4.93 out of 5 average rating, 104 reviews

Stylish Beach House, Hot Tub, Pet Friendly

KitchenFamilyNearby

4.94 out of 5 average rating, 112 reviews

A single-story house is framed by vibrant flowering bushes and trees. A red flag is prominently displayed near the entrance. The front yard is spacious with grassy areas, and a paved driveway leads to a single-car garage.

Home in Newport News

1-Bedroom Home Near Christopher Newport University

KitchenIndoor spacesHiking

4.83 out of 5 average rating, 168 reviews

Cottage in Norfolk

902C Coastal King Retreat Steps from Beach + Sauna

KitchenIndoor spacesOutdoor spaces

4.97 out of 5 average rating, 178 reviews

An aerial view depicts the guest suite, nestled among lush greenery, with a spacious swimming pool nearby. The main house, along with various outdoor amenities, is visible, showcasing well-maintained landscaping and open fields surrounding the property.

Guesthouse in Suffolk

Country Living Guest House (Upstairs/Downstairs)

KitchenIndoor spacesHospitality

4.95 out of 5 average rating, 111 reviews

A grand deck is viewed, featuring two white rocking chairs overlooking a vibrant sunset over the water. The sky is filled with shades of pink and orange, reflecting on the calm ocean surface. A dark wicker seating area is visible to the right.

Home in Buckroe Beach

Exclusive Beachfront Home w/ 180° Views & Hot Tub!

FamilyKitchenHospitality

4.83 out of 5 average rating, 135 reviews

Walk to Beach! Fully Updated + Hot tub!

FamilyIndoor spacesAccess

4.85 out of 5 average rating, 103 reviews

An outdoor pool is positioned on a deck overlooking a tranquil canal. Surrounding the pool, several lounge chairs are arranged for relaxation. The landscape features houses lining the opposite bank, with greenery in view. A small boat dock is also visible in the distance.

Home in Sandbridge

Ocean Pearl- Canal View and Minutes to the beach

FamilyIndoor spacesWalkability

4.85 out of 5 average rating, 123 reviews

A spacious backyard is characterized by lush grass and towering trees. The back of the house features a modern deck leading to a hot tub, surrounded by a wooden railing. An additional structure is visible, presumably for storage, with a picnic table located nearby.

Home in Virginia Beach

Comfortable 3 bedroom house with deck with hot tub

FamilyIndoor spacesAccuracy

Family- and pet-friendly home rentals

A cozy living area features a striped sofa and two light armchairs, arranged around a soft, plush area rug. Natural light enters through two windows, and a mounted television is placed on the wall. A dining area is visible in the background, adorned with a simple floral centerpiece.

4.93 out of 5 average rating, 273 reviews

Cozy beach cottage! One block to the beach!

Indoor spacesFamilyDecor

A living area features a dark sectional sofa with a decorative pillow and a coffee table with a patterned surface. A soft area rug covers the hardwood floor. Light flows in through glass doors that lead to an outdoor space, while ceiling fans provide additional comfort.

4.91 out of 5 average rating, 231 reviews

@Whit’s End? Come in and Relax

Indoor spacesKitchenOutdoor spaces

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, 160 reviews

Ghent on the Corner: Cozy 3 bed 2.5 bath home

FamilyIndoor spacesWi-Fi

4.83 out of 5 average rating, 197 reviews

Norfolk Beach Casita | Fenced Yard | Dog Friendly

KitchenFamilyTV

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.

4.91 out of 5 average rating, 140 reviews

Gorgeous Vacation House

KitchenFamilyQuiet

4.96 out of 5 average rating, 393 reviews

A charming cottage is presented with a well-maintained front yard, featuring blooming trees and vibrant flower planters. A covered porch is visible, framed by decorative railings and welcoming steps that lead from a concrete driveway. The surrounding greenery adds a peaceful ambiance.

Cottage in Ocean View

Lovely Ocean View Cottage

Indoor spacesKitchenWi-Fi

4.85 out of 5 average rating, 115 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!

KitchenFamilyNearby

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, 143 reviews

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

KitchenFamilyCheck-in

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 295 reviews

Cottage in Norfolk

Villa Positano

KitchenFamilyGetting around

4.93 out of 5 average rating, 103 reviews

A bright outdoor pool area is surrounded by lounge chairs, with a cabana featuring a bar in the background. Modern multi-story buildings with vibrant yellow and orange accents create a lively atmosphere near the water's edge. Clear blue skies enhance the inviting scene.

Condo in Sandbridge

Cher's Place @ The Beach

FamilyIndoor spacesBarbecue

4.93 out of 5 average rating, 115 reviews

The exterior of a modern tiny home is illuminated by a radiant sunset, creating striking sun rays. The home features a spacious deck with steps leading to the ground. Nearby, similar structures are visible against a backdrop of vibrant sky colors.

Tiny home in Sandbridge

Jen n John's Mini Mansion.

FamilyKitchenOutdoor spaces

Cottage in Virginia Beach

A well-appointed kitchen features white cabinetry and a gray granite countertop. Essential appliances, including a stove and refrigerator, are present. Natural light enters through a window above the sink, where a small potted plant adds a touch of greenery.

4.88 out of 5 average rating, 139 reviews

Walk-to-Beach Apt with Shared Pool

KitchenIndoor spacesAccess

4.96 out of 5 average rating, 126 reviews

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.

Home in Virginia Beach

Artful Retreat with a Private Pool

FamilyIndoor spacesWi-Fi

4.96 out of 5 average rating, 137 reviews

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.

Home in Virginia Beach

Country Comfort Close to the Beaches

KitchenFamilyBeach

4.97 out of 5 average rating, 148 reviews

Condo in Virginia Beach

Oceanfront Studio: Boardwalk, Beach, & Pool Views

FamilyIndoor spacesBeach