Vacation rentals in Portsmouth, VA

Best Vacation rentals and Airbnb offers in Portsmouth, VA

The Mermaids Lair 🧜‍♀️

Holiday Home, Portsmouth

The Mermaids Lair 🧜‍♀️ is a holiday home in Portsmouth, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About The Mermaids Lair 🧜‍♀️

The Mermaids Lair 🧜‍♀️ is a holiday home in Portsmouth, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $954.

From$136/night

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Cozy Portsmouth Retreat 2BR 1BA

Holiday Home, Portsmouth

Cozy Portsmouth Retreat 2BR 1BA is a holiday home in Portsmouth, with room for a group and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cozy Portsmouth Retreat 2BR 1BA

Cozy Portsmouth Retreat 2BR 1BA is a holiday home in Portsmouth, with room for a group and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, ac, air conditioning, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,387.

From$144/night

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Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Holiday Home, Portsmouth

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth is a holiday home in Portsmouth, with pet-friendly space, pool access, and kitchen access. This stay gives…

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About Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth is a holiday home in Portsmouth, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,092.

From$156/night

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Comfortable & Private 2 Bedrm Cottage w/ King bed.

Cottage, Portsmouth

Comfortable & Private 2 Bedrm Cottage w/ King bed. is a cottage in Portsmouth, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed. is a cottage in Portsmouth, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,099.

From$157/night

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Browse Vacation Rentals with a Pool in Portsmouth, VA

Add a pool to the search when you want an easy place to cool off between outings.

Cozy 2-bedroom condo in wonderful Chesapeake with fitness room, WiFi

Condo, Portsmouth

Cozy 2-bedroom condo in wonderful Chesapeake with fitness room, WiFi is a condo in Portsmouth, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a…

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About Cozy 2-bedroom condo in wonderful Chesapeake with fitness room, WiFi

Cozy 2-bedroom condo in wonderful Chesapeake with fitness room, WiFi is a condo in Portsmouth, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,067.

From$295/night

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Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!

Condo, Portsmouth

Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip! is a condo in Portsmouth, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!

Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip! is a condo in Portsmouth, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,869.

From$410/night

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5-bedroom Home in Chesapeake w/ Pool & Gym. Close to shopping and restaurants!

Holiday Home, Portsmouth

5-bedroom Home in Chesapeake w/ Pool & Gym. Close to shopping and restaurants! is a holiday home in Portsmouth, with pet-friendly space, pool access, and kitchen access. This stay gives…

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About 5-bedroom Home in Chesapeake w/ Pool & Gym. Close to shopping and restaurants!

5-bedroom Home in Chesapeake w/ Pool & Gym. Close to shopping and restaurants! is a holiday home in Portsmouth, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,724.

From$818/night

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Experience Timeless Luxury at Cavalier Manor on a Lake

Holiday Home, Portsmouth

Experience Timeless Luxury at Cavalier Manor on a Lake is a holiday home in Portsmouth, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Experience Timeless Luxury at Cavalier Manor on a Lake

Experience Timeless Luxury at Cavalier Manor on a Lake is a holiday home in Portsmouth, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,997.

From$1,142/night

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Best Portsmouth, VA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

The Magnolia JEM With A Private Entrance

Apartment, Portsmouth

The Magnolia JEM With A Private Entrance is a apartment in Portsmouth, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About The Magnolia JEM With A Private Entrance

The Magnolia JEM With A Private Entrance is a apartment in Portsmouth, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $912.

From$130/night

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Sojourn's Harborage S

Apartment, Portsmouth

Sojourn's Harborage S is a apartment in Portsmouth, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Sojourn's Harborage S

Sojourn's Harborage S is a apartment in Portsmouth, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,108.

From$158/night

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Sojourn's Harborage Pet-Friendly # 3

Apartment, Portsmouth

Sojourn's Harborage Pet-Friendly # 3 is a apartment in Portsmouth, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Sojourn's Harborage Pet-Friendly # 3

Sojourn's Harborage Pet-Friendly # 3 is a apartment in Portsmouth, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,148.

From$164/night

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\"The SmartHouse Getaway\" Cozy 2-bedroom house in Portsmouth with central AC/Heat

Holiday Home, Portsmouth

\"The SmartHouse Getaway\" Cozy 2-bedroom house in Portsmouth with central AC/Heat is a holiday home in Portsmouth, with parking, kitchen access, and room for a group. This stay gives…

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About \"The SmartHouse Getaway\" Cozy 2-bedroom house in Portsmouth with central AC/Heat

\"The SmartHouse Getaway\" Cozy 2-bedroom house in Portsmouth with central AC/Heat is a holiday home in Portsmouth, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,279.

From$183/night

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Best Pet-Friendly Vacation Rentals in Portsmouth, VA

Bring your pet along with stays that welcome four-legged travelers.

Guesthouse in ideal location with private entrance

Apartment, Portsmouth

Guesthouse in ideal location with private entrance is a apartment in Portsmouth, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Guesthouse in ideal location with private entrance

Guesthouse in ideal location with private entrance is a apartment in Portsmouth, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $829.

From$118/night

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Newly updated private studio

Apartment, Portsmouth

Newly updated private studio is a apartment in Portsmouth, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Newly updated private studio

Newly updated private studio is a apartment in Portsmouth, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,046.

From$149/night

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Sojourn's Harborage Pet-Friendly

Apartment, Portsmouth

Sojourn's Harborage Pet-Friendly is a apartment in Portsmouth, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Sojourn's Harborage Pet-Friendly

Sojourn's Harborage Pet-Friendly is a apartment in Portsmouth, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,093.

From$156/night

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Spacious modern 3-bedroom house in beautiful Portsmouth city.

Holiday Home, Portsmouth

Spacious modern 3-bedroom house in beautiful Portsmouth city. is a holiday home in Portsmouth, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a…

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About Spacious modern 3-bedroom house in beautiful Portsmouth city.

Spacious modern 3-bedroom house in beautiful Portsmouth city. is a holiday home in Portsmouth, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,372.

From$339/night

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Best Portsmouth, VA vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Cute Space Near TownCenter 15 Minutes from Beaches

Apartment, Portsmouth

Cute Space Near TownCenter 15 Minutes from Beaches is a apartment in Portsmouth, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Cute Space Near TownCenter 15 Minutes from Beaches

Cute Space Near TownCenter 15 Minutes from Beaches is a apartment in Portsmouth, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,055.

From$151/night

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Sojourn's Harborage | Pet-Friendly

Apartment, Portsmouth

Sojourn's Harborage · Pet-Friendly is a apartment in Portsmouth, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Sojourn's Harborage | Pet-Friendly

Sojourn's Harborage · Pet-Friendly is a apartment in Portsmouth, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,181.

From$169/night

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Sojourn's Harborage | Pet-Friendly

Apartment, Portsmouth

Sojourn's Harborage · Pet-Friendly is a apartment in Portsmouth, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Sojourn's Harborage | Pet-Friendly

Sojourn's Harborage · Pet-Friendly is a apartment in Portsmouth, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,197.

From$171/night

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Cozy 2BR Norfolk Stay • Pets Welcome • Wi-Fi

Holiday Home, Portsmouth

Cozy 2BR Norfolk Stay · Pets Welcome · Wi-Fi is a holiday home in Portsmouth, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Cozy 2BR Norfolk Stay • Pets Welcome • Wi-Fi

Cozy 2BR Norfolk Stay · Pets Welcome · Wi-Fi is a holiday home in Portsmouth, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,281.

From$183/night

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Our Favorite Family-Friendly Vacation Rentals in Portsmouth, VA

Plan a trip with stays that give families more room to spread out.

Charming 2-bedroom house with WiFi, AC in pleasant Norfolk - Close to beach

Holiday Home, Portsmouth

Charming 2-bedroom house with WiFi, AC in pleasant Norfolk - Close to beach is a holiday home in Portsmouth, with easy beach access, kitchen access, and room for a group. This stay gives…

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About Charming 2-bedroom house with WiFi, AC in pleasant Norfolk - Close to beach

Charming 2-bedroom house with WiFi, AC in pleasant Norfolk - Close to beach is a holiday home in Portsmouth, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,075.

From$154/night

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Beautiful, modern furnished 3-bedroom, 2-bathroom cottage near attractions.

Holiday Home, Portsmouth

Beautiful, modern furnished 3-bedroom, 2-bathroom cottage near attractions. is a holiday home in Portsmouth, with pet-friendly space, parking, and kitchen access. This stay gives travelers…

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About Beautiful, modern furnished 3-bedroom, 2-bathroom cottage near attractions.

Beautiful, modern furnished 3-bedroom, 2-bathroom cottage near attractions. is a holiday home in Portsmouth, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,491.

From$213/night

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Walkable to the Casino and Family friendly! 3 bd/2 ba, full house, sleeps 8

Holiday Home, Portsmouth

Walkable to the Casino and Family friendly! 3 bd/2 ba, full house, sleeps 8 is a holiday home in Portsmouth, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Walkable to the Casino and Family friendly! 3 bd/2 ba, full house, sleeps 8

Walkable to the Casino and Family friendly! 3 bd/2 ba, full house, sleeps 8 is a holiday home in Portsmouth, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,530.

From$219/night

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Sojourn Family Home Sleeps 6

Apartment, Portsmouth

Sojourn Family Home Sleeps 6 is a apartment in Portsmouth, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Sojourn Family Home Sleeps 6

Sojourn Family Home Sleeps 6 is a apartment in Portsmouth, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,757.

From$394/night

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