Family-friendly holiday rentals in Portsmouth

Guest suite in Western Branch

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.

4.96 out of 5 average rating, 370 reviews

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

Welcome to The Purple Room, get ready for an AirBnB experience unlike any others. This one of a kind AirBnB not only offers a memorable staying experience, but will be a welcome end to an exciting day at the beach, dinner and drinks at a local restaurant or bar, or an adventurous day exploring all the culture and history the area has to offer. We are centrally located, offer free parking, wifi and kitchenette. We have local art, free wine and food samples. Come see what the excitement is about!

4.93 out of 5 average rating, 119 reviews

A couple relaxes on the deck of the sailboat, enjoying drinks against a vibrant sunset backdrop of pink and purple hues. Soft blankets and a cozy atmosphere are present, with the marina and boats gently reflected in the calm water.

Boat in Willoughby

Romantic Sailboat Experience + Seafood Restaurant

We can't adequately describe how romantic & carefree it feels to step aboard our sail boat. The perfect stay begins by treating yourselves to dinner at the marina's seafood restaurant, then snuggle up together on deck to watch the sunset turn the sky pink & purple. The marina atmosphere is simply magical & you'll love rocking with the gentle sway of calm waters. Come enjoy a weekend aboard this amazingly cozy & romantic sail boat. Convenient to Norfolk & Virginia Beach, the location is prime!

4.95 out of 5 average rating, 146 reviews

A cozy living area is furnished with a beige sofa and a blue armchair. A coffee table with a decorative runner sits in front, surrounded by wooden paneling. Natural light enters from a nearby window, complemented by patterned curtains. Wall art adds subtle character to the space.

Flat in Portsmouth

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

Lots of Great Concerts going on close by!! Ponderosa B, 500 Sq.Ft., One Bedroom Garage Apartment for 2 Adults, family oriented neighborhood about 1/2 mile Rivers Casino! -, Kick back and relax in this calm, stylish space. Private entrance and nice, safe, free parking for 1 vehicle. Large Sign for each Visitor Parking Space. One Bedroom w/very comfortable 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.

4.85 out of 5 average rating, 151 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.

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, 113 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!

4.94 out of 5 average rating, 156 reviews

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.

Home in Portsmouth

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!

4.96 out of 5 average rating, 301 reviews

A fully stocked kitchen is presented, featuring a gas stove, a refrigerator, and a microwave. A dark wooden hutch displays dishes and glassware, while a Keurig coffee maker is located on the countertop. Natural light filters in through a nearby window, illuminating the tiled floor.

Flat in Olde Towne

Cozy Ground Floor Apt in Historic Home

Charming 1st floor apartment with private entrance in circa 1795 home in the Olde Towne historic neighborhood. Guests enjoy an easy walk to downtown shops, restaurants, breweries, museums, and a movie theater. The waterfront is close with marinas, restaurants, and the Elizabeth River ferry to transport you to Norfolk to enjoy events on the waterfront. Business or military travelers are two blocks from the Renaissance Hotel and a 15-minute walk from the Portsmouth Naval Hospital.

Farm stay in Cape Charles

The Airstream is surrounded by tall trees, with a spacious deck featuring comfortable seating arrangements. Oversized Adirondack chairs and a large sofa face the natural scenery. Soft lighting adds warmth, enhancing the outdoor experience in a peaceful, wooded setting.

4.96 out of 5 average rating, 271 reviews

Airstream Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning Airstream retreat 10 mins from Cape Charles. The 1969 Airstream has been converted into a contemporary studio with all the comforts of a luxury hotel room. Wake up to the birds singing in the trees that completely surround the huge front deck. Take a walk on our trails. Enjoy watching the animals. Take a trip into Cape Charles for restaurants and shopping, then enjoy a movie in the Airstream at night.

4.94 out of 5 average rating, 127 reviews

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.

Flat in Portsmouth

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!

4.94 out of 5 average rating, 129 reviews

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.

Flat in Olde Towne

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.

4.89 out of 5 average rating, 158 reviews

A light-filled living area features a sectional sofa adorned with decorative pillows. An area rug with blue floral patterns anchors the space. A flat-screen television is mounted on the wall next to a fireplace, while two doors lead to other areas of the home.

Flat in Olde Towne

Charming cozy apt historic in Old Towne Portsmouth

Newly renovated, newly furnished, cozy and relaxing 1 bd 1 bath apt is available for your stay. Coffee shops, museums, restaurants, bars and the Commodore Theater are all within steps. The ferry to downtown Norfolk is a quick 5 minute walk and every Saturday morning the Farmers Market is literally around the corner. If you are in town for a concert, the Amphitheater is a short walk away. Let us make your stay stress free and enjoyable.

4.98 out of 5 average rating, 188 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!

Popular amenities for Portsmouth family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.76 out of 5 average rating, 222 reviews

Home in Willoughby

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

4.97 out of 5 average rating, 89 reviews

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.

Home in Willoughby

Stylish Beach House, Hot Tub, Pet Friendly

4.93 out of 5 average rating, 105 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

Guest house in Chuckatuck

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.

4.96 out of 5 average rating, 169 reviews

Country Living Guest House (Upstairs/Downstairs)

4.96 out of 5 average rating, 102 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!

The entrance features a light-colored door adorned with a welcoming wreath. To the right, a sign displays the property name 'All4One' alongside the Virginia shape. The brick facade showcases a warm, inviting exterior, complemented by a traditional lantern mounted beside the door.

4.8 out of 5 average rating, 168 reviews

All 4 One | Beach Living

4.87 out of 5 average rating, 261 reviews

A wide, sandy beach is outlined by spacious condos in soft pastel colors against a clear blue sky. Fishing rods are positioned in the sand near beach carts, indicating a relaxed atmosphere. Waves gently lap at the shoreline, creating a tranquil coastal setting.

Apartment in Sandbridge

Ocean Escape

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.

4.85 out of 5 average rating, 115 reviews

Comfortable 3 bedroom house with deck with hot tub

Family- and pet-friendly home rentals

Cottage in East Ocean View

A tranquil beach scene is captured, featuring smooth sandy stretches bordered by green grass and gentle dunes. The horizon reveals a calm ocean meeting a partly cloudy sky, creating a serene atmosphere that invites relaxation and reflection.

4.99 out of 5 average rating, 294 reviews

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

4.91 out of 5 average rating, 160 reviews

A modern living area features a light-toned design with a spacious sofa and a round coffee table. The dining area, equipped with high-backed stools, complements a well-appointed kitchen. Outdoor seating surrounds a fire pit, while a sandy path leads to the beach, framed by lush grass and water views.

Home in East Ocean View

Beautiful renovated 2Bed home!

5 out of 5 average rating, 148 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!

4.91 out of 5 average rating, 219 reviews

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.

Home in East Ocean View

@Whit’s End? Come in and Relax

Guest suite in Virginia Beach

4.9 out of 5 average rating, 716 reviews

Quiet Neighborhood 7 Miles From the Beaches

5 out of 5 average rating, 128 reviews

A modern living room is showcased with light hardwood flooring and elegant furnishings. A large flat-screen TV is mounted on a marble feature wall, while a plush sofa is positioned nearby. Natural light flows in through large windows adorned with sheer curtains.

Home in Norfolk

Beach Stay

4.97 out of 5 average rating, 373 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

4.98 out of 5 average rating, 238 reviews

A spacious studio apartment features a queen-size bed adorned with a colorful coral-themed quilt. Nearby, a small seating area is visible, alongside a well-equipped kitchen. Warm wood flooring enhances the inviting atmosphere, complemented by a modern ceiling fan and natural light entering through the window.

Flat in Newport News

Centrally Located Sleek Studio Apartment

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 280 reviews

Cottage in Norfolk

Positano Villa

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, 151 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, 109 reviews

Artful Retreat with a Private Pool

5 out of 5 average rating, 111 reviews

The waterfront view captures a serene sunset over the canal, with soft golden light reflecting on the water. Lush grasses and reeds line the shore, enhancing the tranquil atmosphere. Nearby homes are silhouetted against the vibrant sky, creating a peaceful retreat.

Cottage in Sandbridge

Sanctuary on Sandpiper - Bayfront in Sandbridge

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

Apartment in Virginia Beach

The outdoor pool area features a well-maintained pool surrounded by lounge chairs. A clear blue sky is noted above, with clouds adding texture. Nearby greenery and structures contribute to the atmosphere, allowing for a relaxing outdoor experience.

4.98 out of 5 average rating, 106 reviews

Paradise at the Beach

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