Portsmouth, Virginia

Vacation Rentals in Portsmouth, Virginia

Discover 22 vacation rental properties in Portsmouth. From 1 to 7 bedrooms. Average $221/night. 100% have pools.

22 verified listings Book securely on VRBO Prices updated March 2026

22 properties available

Historic Old Towne Southern Charm

Historic Old Towne Southern Charm

2 beds 2 baths
PoolA/CWiFiBalcony
$154/night
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Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

3 beds 2 baths
PoolA/CWiFiBalcony
$154/night
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Cheerful 2 bedroom 2 full bathroom townhouse

Cheerful 2 bedroom 2 full bathroom townhouse

2 beds 2 baths
PoolA/CWiFiBalcony
$132/night
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New listing! Charming, Waterfront Home-3 br,2 bath-sleeps 10!

New listing! Charming, Waterfront Home-3 br,2 bath-sleeps 10!

3 beds 2 baths
PoolA/CWiFiBalcony
$304/night
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Coastal family sized! Central to attractions! Long term ask for rate. Workspace

Coastal family sized! Central to attractions! Long term ask for rate. Workspace

3 beds 2 baths
PoolA/CWiFiBalcony
$226/night
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Portsmouth Waterfront Vacation Rental w/ Deck

Portsmouth Waterfront Vacation Rental w/ Deck

3 beds 2 baths
PoolA/CWiFiBalcony
$323/night
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Private Estate on 4 Acres

Private Estate on 4 Acres

7 beds 4 baths
PoolA/CWiFiBalcony
$987/night
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Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.

2 beds 1 bath
PoolA/CWiFiBalcony
$126/night
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Clev’s collage place

Clev’s collage place

1 bed 1 bath
PoolA/CWiFiBalcony
$70/night
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Parkside Suites minutes away from Downtown!

Parkside Suites minutes away from Downtown!

2 beds 1 bath
PoolA/CWiFiBalcony
$99/night
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The Mermaids Lair 🧜‍♀️

The Mermaids Lair 🧜‍♀️

1 bed 1 bath
PoolA/CWiFiBalcony
$105/night
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Newly updated private studio

Newly updated private studio

1 bed 1 bath
PoolA/CWiFiBalcony
$137/night
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Beautiful 4bedroom vacation pool home, where relaxation & indulgence intertwine.

Beautiful 4bedroom vacation pool home, where relaxation & indulgence intertwine.

4 beds 2 baths
PoolA/CWiFiBalcony
$246/night
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Wooded Wonderland

Wooded Wonderland

3 beds 2 baths
PoolA/CWiFiBalcony
$347/night
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Family friendly! 3 bd/2 ba, full house, sleeps 8

Family friendly! 3 bd/2 ba, full house, sleeps 8

3 beds 2 baths
PoolA/CWiFiBalcony
$180/night
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3D Theater plus Dock on Small Lake

3D Theater plus Dock on Small Lake

2 beds 1 bath
PoolA/CWiFiBalcony
$201/night
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3 Bdrm GEM in Portsmouth, Sleeps 6! Close to Casino & All.

3 Bdrm GEM in Portsmouth, Sleeps 6! Close to Casino & All.

3 beds 2 baths
PoolA/CWiFiBalcony
$163/night
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Charming, Waterfront Townhome with a View of Downtown. Pet-Friendly!

Charming, Waterfront Townhome with a View of Downtown. Pet-Friendly!

2 beds 2 baths
PoolA/CWiFiBalcony
$169/night
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Portsmouth Perfection Downtown- historic Parkview

Portsmouth Perfection Downtown- historic Parkview

3 beds 1 bath
PoolA/CWiFiBalcony
$175/night
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Newly remodeled - Safe area - Large Bedrooms

Newly remodeled - Safe area - Large Bedrooms

3 beds 1 bath
PoolA/CWiFiBalcony
$166/night
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5 Minutes to the Casino!Family sized home 3 bedroom with patio and a game room

5 Minutes to the Casino!Family sized home 3 bedroom with patio and a game room

3 beds 2 baths
PoolA/CWiFiBalcony
$144/night
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Love Boat Adventurer

Love Boat Adventurer

2 beds 1 bath
PoolA/CWiFiBalcony
$260/night
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