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Portsmouth Holiday Rentals

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50 rentals in Portsmouth.
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Live history, dont just visit!, holiday rental in Portsmouth

Live history, dont just visit!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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GRANDMAs QUIET WATERFRONT HOME, holiday rental in Portsmouth

GRANDMAs QUIET WATERFRONT HOME

2 bedrooms
2 bathrooms
Sleeps 6
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Welcome Military Welcome Civilians Welcome All, holiday rental in Portsmouth

Welcome Military Welcome Civilians Welcome All

3 bedrooms
1 bathroom
Sleeps 6
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Immaculate ocean front 3 story beauty, holiday rental in Portsmouth

Immaculate ocean front 3 story beauty

4 bedrooms
4 bathrooms
Sleeps 11
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Gorgeous Beachfront Home With Stunning Views Of The Chesapeake Bay!!!, holiday rental in Portsmouth

Gorgeous Beachfront Home With Stunning Views Of The Chesapeake Bay!!!

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beach Side HideAway - Pet Friendly, WiFi, Smart TV, Central AC, holiday rental in Portsmouth

Beach Side HideAway - Pet Friendly, WiFi, Smart TV, Central AC

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Bay Escape - A TOGAR Vacation Rental, holiday rental in Portsmouth

Bay Escape - A TOGAR Vacation Rental

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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*BEACHFRONT * 25 STEPS TO BEACH *PETS* KAYAKS * 2 BEACHES *, holiday rental in Portsmouth

*BEACHFRONT * 25 STEPS TO BEACH *PETS* KAYAKS * 2 BEACHES *

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Beach Vacation Home 1.5 Blocks from Beach, holiday rental in Portsmouth

Beach Vacation Home 1.5 Blocks from Beach

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Home Away From Home. Great Beach Neighborhood!Comfy Beds, Cable, Wi-Fi, Grill!, holiday rental in Portsmouth

Home Away From Home. Great Beach Neighborhood!Comfy Beds, Cable, Wi-Fi, Grill!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beach House The Real Thing!  Direct Beachfront!, holiday rental in Portsmouth

Beach House The Real Thing! Direct Beachfront!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Town home Located 20 Minutes from the Virginia Beach Ocean Front., holiday rental in Portsmouth

Spacious Town home Located 20 Minutes from the Virginia Beach Ocean Front.

3 bedrooms
3 bathrooms
Sleeps 6
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Beautiful Waterfront Cottage Near Downtown Norfolk with Private Dock and Sunroom, holiday rental in Portsmouth

Beautiful Waterfront Cottage Near Downtown Norfolk with Private Dock and Sunroom

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Bay Breeze Seashell Suite, holiday rental in Portsmouth

Bay Breeze Seashell Suite

1 bedroom
1 bathroom
Sleeps 2
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Beach Cottage Coral Suite, holiday rental in Portsmouth

Beach Cottage Coral Suite

1 bedroom
1 bathroom
Sleeps 4
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Bay Breeze Compass Suite, holiday rental in Portsmouth

Bay Breeze Compass Suite

1 bedroom
1 bathroom
Sleeps 2
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Beach Cottage Wave Suite, holiday rental in Portsmouth

Beach Cottage Wave Suite

1 bedroom
1 bathroom
Sleeps 4
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Sea Shack Coast Suite, holiday rental in Portsmouth

Sea Shack Coast Suite

2 bedrooms
1 bathroom
Sleeps 4
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Your Home Away From Home, holiday rental in Portsmouth

Your Home Away From Home

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Minutes to Bay Beaches and Base! Spread out in this Spacious Mid-Century Ranch, holiday rental in Portsmouth

Minutes to Bay Beaches and Base! Spread out in this Spacious Mid-Century Ranch

4 bedrooms
2 bathrooms
Sleeps 8
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☀ Adorable Norfolk Cottage- Dogs welcome! ☀, holiday rental in Portsmouth

☀ Adorable Norfolk Cottage- Dogs welcome! ☀

3 bedrooms
2 bathrooms
Sleeps 6
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Sea Shack Island Suite, holiday rental in Portsmouth

Sea Shack Island Suite

2 bedrooms
1 bathroom
Sleeps 4
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Sea Shack Cape Suite, holiday rental in Portsmouth

Sea Shack Cape Suite

2 bedrooms
1 bathroom
Sleeps 4
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Murphy's Beach House on The Chesapeake Bay!, holiday rental in Portsmouth

Murphy's Beach House on The Chesapeake Bay!

4 bedrooms
4 bathrooms
Sleeps 8
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Sea Shack Lagoon Suite, holiday rental in Portsmouth

Sea Shack Lagoon Suite

2 bedrooms
1 bathroom
Sleeps 4
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Bay Breeze Anchor Suite, holiday rental in Portsmouth

Bay Breeze Anchor Suite

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Ship’s Inn; The Lighthouse Cottage (Beach View), holiday rental in Portsmouth

Ship’s Inn; The Lighthouse Cottage (Beach View)

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Welcome to Our Cozy Home in Chesapeake, holiday rental in Portsmouth

Welcome to Our Cozy Home in Chesapeake

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beach Side Studio #5 - Pet Friendly, holiday rental in Portsmouth

Beach Side Studio #5 - Pet Friendly

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beach Side Studio #3 - Beach Side, Pet Friendly with WiFi, holiday rental in Portsmouth

Beach Side Studio #3 - Beach Side, Pet Friendly with WiFi

1 bedroom
1 bathroom
Sleeps 3
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Cozy Mother-in-Law Suite, holiday rental in Portsmouth

Cozy Mother-in-Law Suite

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stately Norfolk Home w/Yard + Grill: Walk to Beach, holiday rental in Portsmouth

Stately Norfolk Home w/Yard + Grill: Walk to Beach

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beach Cottage Sand Suite, holiday rental in Portsmouth

Beach Cottage Sand Suite

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Sea Shack Harbor Suite, holiday rental in Portsmouth

Sea Shack Harbor Suite

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Ships Inn: The Captain's Cabin (Beach View), holiday rental in Portsmouth

Ships Inn: The Captain's Cabin (Beach View)

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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*WATERFRONT* SPACIOUS* 25 STEPS TO BEACH*, holiday rental in Portsmouth

*WATERFRONT* SPACIOUS* 25 STEPS TO BEACH*

4 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Furnished 1BR/1.5BA Luxury Condo, holiday rental in Portsmouth

Furnished 1BR/1.5BA Luxury Condo

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy 1 br near the Beach, holiday rental in Portsmouth

Cozy 1 br near the Beach

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stunning Contemporary Home on the Water in the heart ofVirginia Beach, holiday rental in Portsmouth

Stunning Contemporary Home on the Water in the heart ofVirginia Beach

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious 3600SF 6BR 4BA home ideal for large groups., holiday rental in Portsmouth

Luxurious 3600SF 6BR 4BA home ideal for large groups.

6 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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Rustic Beach Front Apt - Cozy and right on the beach, holiday rental in Portsmouth

Rustic Beach Front Apt - Cozy and right on the beach

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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⭐️The Great Ghent Experience⭐️   *closes to beaches, holiday rental in Portsmouth

⭐️The Great Ghent Experience⭐️ *closes to beaches

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Updated Coastal Home w/Grill, Blocks to Beach, holiday rental in Portsmouth

NEW! Updated Coastal Home w/Grill, Blocks to Beach

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Affordable Home 15 mins from the Oceanfront!!, holiday rental in Portsmouth

Spacious Affordable Home 15 mins from the Oceanfront!!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Classic Chesapeake Beachside Cottage w/ Porch!, holiday rental in Portsmouth

Classic Chesapeake Beachside Cottage w/ Porch!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Luxury Home - Hampton Road - Tidewater, holiday rental in Portsmouth

Luxury Home - Hampton Road - Tidewater

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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The Perfect space by AIRPORT STORES & RESTAURANTS, holiday rental in Portsmouth

The Perfect space by AIRPORT STORES & RESTAURANTS

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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NEW! Vivid Home w/ Porch: Walk to Ocean View Beach, holiday rental in Portsmouth

NEW! Vivid Home w/ Porch: Walk to Ocean View Beach

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New for 2022 - The Sailor's Valentine - Sleeps 4, holiday rental in Portsmouth

New for 2022 - The Sailor's Valentine - Sleeps 4

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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❤️ Beautiful Ocean Front Cottage near Naval Base and Ocean View Beach!, holiday rental in Portsmouth

❤️ Beautiful Ocean Front Cottage near Naval Base and Ocean View Beach!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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