
House holiday rentals in Portsmouth
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Top-rated house rentals in Portsmouth
Guests agree: these houses are highly rated for location, cleanliness and more.

Charming Home by the Sea, a block from the beach!
Single family home steps from the beach. Parking for vehicles including garage. Outdoor/indoor dining areas. Gas grill & fully equipped kitchen with cooking essentials for stay at home meals. 3 bedrooms sleeps 8. Can accommodate additional guests for an up charge with air mattress and sheets provided. Pets welcome! Hardwood flooring and central AC/heat throughout. Walking distance to restaurants in the local area. 15 minutes to Norfolk Naval Station, 10 mins to Airport, 20 mins to VB boardwalk.

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!

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!

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.

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.

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!

Walk to Beach! Fully Updated + Hot tub!
Welcome to a fully renovated 3-bedroom, 2-bath rancher in Hampton Roads. Perfect for families or groups, it offers cozy beds plus a pullout couch in the versatile recreation room. Unwind with top-tier amenities like a fire pit and a climate-controlled game room/office. Located just one block from the beach (and complete with beach gear!), you’ll enjoy effortless access to the shore and local attractions. Whether for a weekend or an extended stay, this home has it all!

Sunset Sanctuary on the Water- Fast Wifi/Netflix
Escape to this 3 BEDS/2 BATH Sunset Sanctuary on the Water, a peaceful retreat where breathtaking sunsets meet serene waterfront views. Perfect for relaxation, this home offers comfort and charm with cozy living spaces and a welcoming atmosphere. Enjoy coffee on the deck, unwind by the water, or explore nearby attractions. Ideal for families or friends seeking a quiet getaway, our sanctuary blends natural beauty with modern convenience for a truly memorable stay.

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.

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!

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.

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
House rentals with a pool

Retreat with Pool, Walk to Beach

Artful Retreat with a Private Pool

Country Comfort Close to the Beaches

Private Pool at the Oceanfront in a Spacious Home

Gorgeous Vacation House

Bayfront Pool Retreat, Walk to Beach

Sunrise, North End Beach / Oceanfront Area

Half house w/pool & new patio all to yourself
Weekly house rentals

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

Tudor Treasure in Olde Towne

Home Away From Home

Family and pet friendly!

Escape to a Waterfront Retreat

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

Cornick Corner near "Rivers Casino"

YES Queen! The Bridgerton House
Private house rentals

SpacComf-4bd2ba-sleeps8-parking-I164-hosp-3daysmin

Blessed and peaceful home

Eden Lake House Cape Charles

Beach Bungalow • Navy Base • Quiet St • Dogs OK

Comfy House! The Perfect Getaway

3BR Gem Near Rivers Casino | Comfort & Convenience

Relaxing Luxurious Waterfront

*NEW* Cozy & Very Stylish home for your family!
When is the best time to visit Portsmouth?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $134 SGD | $128 SGD | $144 SGD | $146 SGD | $150 SGD | $160 SGD | $174 SGD | $153 SGD | $130 SGD | $142 SGD | $136 SGD | $139 SGD |
| Avg. temp | 6°C | 7°C | 10°C | 16°C | 20°C | 25°C | 27°C | 26°C | 23°C | 18°C | 12°C | 8°C |
Quick stats about house rentals in Portsmouth

Total holiday rentals
Explore 310 holiday rentals in Portsmouth

Nightly prices starting at
Portsmouth holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 9,840 verified reviews to help you choose

Family-friendly holiday rentals
170 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 80 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
190 properties have a dedicated workspace

Wifi availability
300 of Portsmouth holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Portsmouth rentals

4.7 Average rating
Portsmouth stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Portsmouth’s top spots include Chrysler Museum of Art, Nauticus and Cinemark Chesapeake Square
Destinations to explore
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- Rentals with beach access Portsmouth
- Family-friendly rentals Portsmouth
- Rentals with a washing machine and dryer Portsmouth
- Rentals with a kayak Portsmouth
- Rentals with an EV charger Portsmouth
- Rentals with pools Portsmouth
- Waterfront rentals Portsmouth
- Rentals with a firepit Portsmouth
- Flat rentals Portsmouth
- Fitness-friendly rentals Portsmouth
- Apartment rentals Portsmouth
- Pet-friendly rentals Portsmouth
- Rentals with a patio Portsmouth
- Rentals with a fireplace Portsmouth
- Rentals with breakfast Portsmouth
- Rentals with lake access Portsmouth
- Rentals with outdoor seating Portsmouth
- House rentals Virginia
- House rentals United States
- Chesapeake Bay
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
- Grommet Island Park
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Old Dominion University
- Neptune's Park
- Currituck Beach Lighthouse
- Regent University
- Colonial Williamsburg's Merchants Square
- First Landing Beach
- Nauticus
- The Mariners' Museum
- Currituck Club
- Town Point Park





