Southern Pines, North Carolina

Vacation Rentals in Southern Pines, North Carolina

Discover 38 vacation rental properties in Southern Pines. From 1 to 4 bedrooms. Average $192/night. 100% have pools.

38 verified listings Book securely on VRBO Prices updated March 2026

38 properties available

52 Longleaf: 2 BR, 2 BA Condominium in Southern Pines, Sleeps 4

52 Longleaf: 2 BR, 2 BA Condominium in Southern Pines, Sleeps 4

2 beds 2 baths
PoolA/CWiFiBalcony
$108/night
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MCM Spanish Revival Estate across street from Southern Pines Golf Club

MCM Spanish Revival Estate across street from Southern Pines Golf Club

3 beds 2 baths
PoolA/CWiFiBalcony
$208/night
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Upstairs at the Estate - Across from SP Golf Club

Upstairs at the Estate - Across from SP Golf Club

2 beds 2 baths
PoolA/CWiFiBalcony
$141/night
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Beautiful 1920's Craftsman-Downtown Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines

3 beds 2 baths
PoolA/CWiFiBalcony
$198/night
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Mystical Cottage in Southern Pines

Mystical Cottage in Southern Pines

1 bed 1 bath
PoolA/CWiFiBalcony
$160/night
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Condo in the Pines! 2BR 2BA. Sleeps 4. Military discount available!

Condo in the Pines! 2BR 2BA. Sleeps 4. Military discount available!

2 beds 2 baths
PoolA/CWiFiBalcony
$95/night
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Loft Cottage on Ridge<br>? Short & Extended Stays?

Loft Cottage on Ridge<br>? Short & Extended Stays?

1 bed 1 bath
PoolA/CWiFiBalcony
$113/night
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The Flat Coat Cottage: Downtown Southern Pines

The Flat Coat Cottage: Downtown Southern Pines

3 beds 3 baths
PoolA/CWiFiBalcony
$366/night
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Charming Downtown Cottage

Charming Downtown Cottage

2 beds 1 bath
PoolA/CWiFiBalcony
$150/night
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SoPi Cottage - Walk to Town - King Bed

SoPi Cottage - Walk to Town - King Bed

2 beds 1 bath
PoolA/CWiFiBalcony
$180/night
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ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!

ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!

3 beds 2 baths
PoolA/CWiFiBalcony
$128/night
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Adorable 1 bedroom guest house in Southern Pines

Adorable 1 bedroom guest house in Southern Pines

1 bed 1 bath
PoolA/CWiFiBalcony
$131/night
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Slice of Seclusion in Downtown Southern Pines

Slice of Seclusion in Downtown Southern Pines

1 bed 1 bath
PoolA/CWiFiBalcony
$141/night
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Peaceful ground floor golf-front condo close to it all! Great for longer stays!

Peaceful ground floor golf-front condo close to it all! Great for longer stays!

2 beds 2 baths
PoolA/CWiFiBalcony
$165/night
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Sage at The Shire 255 - Unit A - Downtown!

Sage at The Shire 255 - Unit A - Downtown!

1 bed 1 bath
PoolA/CWiFiBalcony
$136/night
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New Pines Retreat - Brand New Home!

New Pines Retreat - Brand New Home!

3 beds 2 baths
PoolA/CWiFiBalcony
$142/night
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Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!

Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!

3 beds 3 baths
PoolA/CWiFiBalcony
$271/night
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Cottage on Ridge- Short & Extended Stays

Cottage on Ridge- Short & Extended Stays

1 bed 1 bath
PoolA/CWiFiBalcony
$137/night
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Historic 1890 Cottage in the Heart of Downtown Southern Pines, NC!

Historic 1890 Cottage in the Heart of Downtown Southern Pines, NC!

3 beds 2 baths
PoolA/CWiFiBalcony
$241/night
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Golf Retreat -Walk or Bike to Downtown - Golf, Breweries, Restaurants!

Golf Retreat -Walk or Bike to Downtown - Golf, Breweries, Restaurants!

3 beds 2 baths
PoolA/CWiFiBalcony
$174/night
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Extended Stays welcome!

Extended Stays welcome!

4 beds 1 bath
PoolA/CWiFiBalcony
$420/night
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Historic Hidden Gem - Downtown Southern Pines

Historic Hidden Gem - Downtown Southern Pines

3 beds 1 bath
PoolA/CWiFiBalcony
$236/night
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Cozy Southern Pines Retreat 1 Mi to Downtown!

Cozy Southern Pines Retreat 1 Mi to Downtown!

3 beds 2 baths
PoolA/CWiFiBalcony
$124/night
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Guest House on 7 acres in horse country

Guest House on 7 acres in horse country

2 beds 2 baths
PoolA/CWiFiBalcony
$113/night
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Walk to Downtown - 5 min. to MidPines, So. Pines & PineNeedles - Sleeps 6-8

Walk to Downtown - 5 min. to MidPines, So. Pines & PineNeedles - Sleeps 6-8

3 beds 2 baths
PoolA/CWiFiBalcony
$116/night
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Downtown Townhome; Walk to Dine & Shop on Broad St

Downtown Townhome; Walk to Dine & Shop on Broad St

3 beds 2 baths
PoolA/CWiFiBalcony
$203/night
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The Gallery - 2 bd Boutique Southern Pines Cottage

The Gallery - 2 bd Boutique Southern Pines Cottage

2 beds 1 bath
PoolA/CWiFiBalcony
$160/night
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Most relevant reviews

Most relevant reviews

1 bed 1 bath
PoolA/CWiFiBalcony
$131/night
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Peaceful Southern Pines Home w/ Pool + Yard!

Peaceful Southern Pines Home w/ Pool + Yard!

4 beds 3 baths
PoolA/CWiFiBalcony
$396/night
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The Pinecone Cottage - a Southern Pines escape

The Pinecone Cottage - a Southern Pines escape

3 beds 3 baths
PoolA/CWiFiBalcony
$264/night
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Cozy cottage close to it all - pet friendly!

Cozy cottage close to it all - pet friendly!

2 beds 2 baths
PoolA/CWiFiBalcony
$156/night
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Solitude at The Shire 255 D - Unit D - Downtown!

Solitude at The Shire 255 D - Unit D - Downtown!

1 bed 1 bath
PoolA/CWiFiBalcony
$126/night
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Reynolds Villa- Golf/Couples Retreat

Reynolds Villa- Golf/Couples Retreat

2 beds
PoolA/CWiFiBalcony
$226/night
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The Bungalow on Connecticut w/E scooter rental

The Bungalow on Connecticut w/E scooter rental

3 beds 2 baths
PoolA/CWiFiBalcony
$184/night
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Tanglewood Farm B&B-Horse & Hound Dog Friendly1 BR/2BA Private Apt on Horse Farm

Tanglewood Farm B&B-Horse & Hound Dog Friendly1 BR/2BA Private Apt on Horse Farm

1 bed 2 baths
PoolA/CWiFiBalcony
$140/night
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Southern Pines Getaway w/Theater, Fire Pit & Pool

Southern Pines Getaway w/Theater, Fire Pit & Pool

4 beds 3 baths
PoolA/CWiFiBalcony
$525/night
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Downtown So. Pines - sleeps 8, walk to town.

Downtown So. Pines - sleeps 8, walk to town.

3 beds 2 baths
PoolA/CWiFiBalcony
$150/night
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Firefly Cottage with Cozy Firepit in SouthernPines

Firefly Cottage with Cozy Firepit in SouthernPines

3 beds 2 baths
PoolA/CWiFiBalcony
$246/night
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