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Southern Pines Holiday Apartments

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64 rentals in Southern Pines.
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Quaint Cottage in the heart of downtown Southern Pines, holiday rental in Southern Pines
Quaint Cottage in the heart of downtown Southern Pines, holiday rental in Southern Pines
Quaint Cottage in the heart of downtown Southern Pines, holiday rental in Southern Pines

Quaint Cottage in the heart of downtown Southern Pines

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Condo in the Pines! 2BR/2BA (sleeps 4), holiday rental in Southern Pines
Condo in the Pines! 2BR/2BA (sleeps 4), holiday rental in Southern Pines
Condo in the Pines! 2BR/2BA (sleeps 4), holiday rental in Southern Pines

Condo in the Pines! 2BR/2BA (sleeps 4)

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tanglewood Farm B&B - Fox Den Suite 1 BR/1BA Private Apartment on Horse Farm, holiday rental in Southern Pines
Tanglewood Farm B&B - Fox Den Suite 1 BR/1BA Private Apartment on Horse Farm, holiday rental in Southern Pines
Tanglewood Farm B&B - Fox Den Suite 1 BR/1BA Private Apartment on Horse Farm, holiday rental in Southern Pines

Tanglewood Farm B&B - Fox Den Suite 1 BR/1BA Private Apartment on Horse Farm

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Downtown Townhome; Walk to Dine & Shop on Broad St, holiday rental in Southern Pines
Downtown Townhome; Walk to Dine & Shop on Broad St, holiday rental in Southern Pines
Downtown Townhome; Walk to Dine & Shop on Broad St, holiday rental in Southern Pines

Downtown Townhome; Walk to Dine & Shop on Broad St

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Golf Condo in Longleaf Country Club, holiday rental in Southern Pines
Luxury Golf Condo in Longleaf Country Club, holiday rental in Southern Pines
Luxury Golf Condo in Longleaf Country Club, holiday rental in Southern Pines

Luxury Golf Condo in Longleaf Country Club

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mystical Cottage in Southern Pines, holiday rental in Southern Pines
Mystical Cottage in Southern Pines, holiday rental in Southern Pines
Mystical Cottage in Southern Pines, holiday rental in Southern Pines

Mystical Cottage in Southern Pines

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tanglewood Farm B&B - Tally Ho Suite 1 BR/1BA Private Apartment on Horse Farm, holiday rental in Southern Pines
Tanglewood Farm B&B - Tally Ho Suite 1 BR/1BA Private Apartment on Horse Farm, holiday rental in Southern Pines
Tanglewood Farm B&B - Tally Ho Suite 1 BR/1BA Private Apartment on Horse Farm, holiday rental in Southern Pines

Tanglewood Farm B&B - Tally Ho Suite 1 BR/1BA Private Apartment on Horse Farm

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tanglewood Farm B&B-Horse & Hound Dog Friendly1 BR/2BA Private Apt on Horse Farm, holiday rental in Southern Pines
Tanglewood Farm B&B-Horse & Hound Dog Friendly1 BR/2BA Private Apt on Horse Farm, holiday rental in Southern Pines
Tanglewood Farm B&B-Horse & Hound Dog Friendly1 BR/2BA Private Apt on Horse Farm, holiday rental in Southern Pines

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

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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AOS VACATION COTTAGE, holiday rental in Southern Pines
AOS VACATION COTTAGE, holiday rental in Southern Pines
AOS VACATION COTTAGE, holiday rental in Southern Pines

AOS VACATION COTTAGE

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Prime location - sleeps 8 with golf view and pool table., holiday rental in Southern Pines
Prime location - sleeps 8 with golf view and pool table., holiday rental in Southern Pines
Prime location - sleeps 8 with golf view and pool table., holiday rental in Southern Pines

Prime location - sleeps 8 with golf view and pool table.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful 1920's Craftsman-Downtown Southern Pines, holiday rental in Southern Pines
Beautiful 1920's Craftsman-Downtown Southern Pines, holiday rental in Southern Pines
Beautiful 1920's Craftsman-Downtown Southern Pines, holiday rental in Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Mid-Century Modern House in Southern Pines NC  minutes to Pinehurst  NC, holiday rental in Southern Pines
Mid-Century Modern House in Southern Pines NC  minutes to Pinehurst  NC, holiday rental in Southern Pines
Mid-Century Modern House in Southern Pines NC  minutes to Pinehurst  NC, holiday rental in Southern Pines

Mid-Century Modern House in Southern Pines NC minutes to Pinehurst NC

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cozy Escape Close to It All, holiday rental in Southern Pines
Cozy Escape Close to It All, holiday rental in Southern Pines
Cozy Escape Close to It All, holiday rental in Southern Pines

Cozy Escape Close to It All

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Sweet Southern Pines Abode w/ Yard & Covered Porch, holiday rental in Southern Pines
Sweet Southern Pines Abode w/ Yard & Covered Porch, holiday rental in Southern Pines
Sweet Southern Pines Abode w/ Yard & Covered Porch, holiday rental in Southern Pines

Sweet Southern Pines Abode w/ Yard & Covered Porch

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Serenity House Pet Friendly Southern Pines, holiday rental in Southern Pines
Serenity House Pet Friendly Southern Pines, holiday rental in Southern Pines
Serenity House Pet Friendly Southern Pines, holiday rental in Southern Pines

Serenity House Pet Friendly Southern Pines

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!, holiday rental in Southern Pines
ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!, holiday rental in Southern Pines
ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!, holiday rental in Southern Pines

ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Downtown Bungalow Near Base, Golf, Dining, Brewery, holiday rental in Southern Pines
Downtown Bungalow Near Base, Golf, Dining, Brewery, holiday rental in Southern Pines
Downtown Bungalow Near Base, Golf, Dining, Brewery, holiday rental in Southern Pines

Downtown Bungalow Near Base, Golf, Dining, Brewery

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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The Fairway Villa at Talamore Golf Resort, holiday rental in Southern Pines
The Fairway Villa at Talamore Golf Resort, holiday rental in Southern Pines
The Fairway Villa at Talamore Golf Resort, holiday rental in Southern Pines

The Fairway Villa at Talamore Golf Resort

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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NEW! Downtown Southern Pines Townhome with Deck!, holiday rental in Southern Pines
NEW! Downtown Southern Pines Townhome with Deck!, holiday rental in Southern Pines
NEW! Downtown Southern Pines Townhome with Deck!, holiday rental in Southern Pines

NEW! Downtown Southern Pines Townhome with Deck!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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The Tudor Cottage Sum, holiday rental in Southern Pines
The Tudor Cottage Sum, holiday rental in Southern Pines
The Tudor Cottage Sum, holiday rental in Southern Pines

The Tudor Cottage Sum

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Top Of The Hill - Southern Pines/Pinehurst NC , holiday rental in Southern Pines
Top Of The Hill - Southern Pines/Pinehurst NC , holiday rental in Southern Pines
Top Of The Hill - Southern Pines/Pinehurst NC , holiday rental in Southern Pines

Top Of The Hill - Southern Pines/Pinehurst NC

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Fairway Villa at Talamore Golf Resort, holiday rental in Southern Pines
The Fairway Villa at Talamore Golf Resort, holiday rental in Southern Pines
The Fairway Villa at Talamore Golf Resort, holiday rental in Southern Pines

The Fairway Villa at Talamore Golf Resort

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Downtown Bungalow Near Base, Golf, Dining, Brewery, holiday rental in Southern Pines
Downtown Bungalow Near Base, Golf, Dining, Brewery, holiday rental in Southern Pines
Downtown Bungalow Near Base, Golf, Dining, Brewery, holiday rental in Southern Pines

Downtown Bungalow Near Base, Golf, Dining, Brewery

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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The Clubhouse, holiday rental in Southern Pines
The Clubhouse, holiday rental in Southern Pines
The Clubhouse, holiday rental in Southern Pines

The Clubhouse

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Private Barn Rental, holiday rental in Southern Pines
Private Barn Rental, holiday rental in Southern Pines
Private Barn Rental, holiday rental in Southern Pines

Private Barn Rental

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!, holiday rental in Southern Pines
ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!, holiday rental in Southern Pines
ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!, holiday rental in Southern Pines

ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!, holiday rental in Southern Pines
ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!, holiday rental in Southern Pines
ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!, holiday rental in Southern Pines

ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Birdsong House- In the heart of downtown Southern Pines, holiday rental in Southern Pines
Birdsong House- In the heart of downtown Southern Pines, holiday rental in Southern Pines
Birdsong House- In the heart of downtown Southern Pines, holiday rental in Southern Pines

Birdsong House- In the heart of downtown Southern Pines

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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The Maine House - Downtown Southern Pines, holiday rental in Southern Pines
The Maine House - Downtown Southern Pines, holiday rental in Southern Pines
The Maine House - Downtown Southern Pines, holiday rental in Southern Pines

The Maine House - Downtown Southern Pines

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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NEW! Artsy Southern Pines Home ~ 1 Mi to Downtown!, holiday rental in Southern Pines
NEW! Artsy Southern Pines Home ~ 1 Mi to Downtown!, holiday rental in Southern Pines
NEW! Artsy Southern Pines Home ~ 1 Mi to Downtown!, holiday rental in Southern Pines

NEW! Artsy Southern Pines Home ~ 1 Mi to Downtown!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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NEW! Quaint Southern Pines Home < 1 Mi to Downtown, holiday rental in Southern Pines
NEW! Quaint Southern Pines Home < 1 Mi to Downtown, holiday rental in Southern Pines
NEW! Quaint Southern Pines Home < 1 Mi to Downtown, holiday rental in Southern Pines

NEW! Quaint Southern Pines Home < 1 Mi to Downtown

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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NEW! Chic Southern Pines Retreat: Walk to Downtown, holiday rental in Southern Pines
NEW! Chic Southern Pines Retreat: Walk to Downtown, holiday rental in Southern Pines
NEW! Chic Southern Pines Retreat: Walk to Downtown, holiday rental in Southern Pines

NEW! Chic Southern Pines Retreat: Walk to Downtown

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Stylish Southern Pines Home w/ Screened Porch, holiday rental in Southern Pines
NEW! Stylish Southern Pines Home w/ Screened Porch, holiday rental in Southern Pines
NEW! Stylish Southern Pines Home w/ Screened Porch, holiday rental in Southern Pines

NEW! Stylish Southern Pines Home w/ Screened Porch

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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NEW! Peaceful Southern Pines Home w/ Pool + Yard!, holiday rental in Southern Pines
NEW! Peaceful Southern Pines Home w/ Pool + Yard!, holiday rental in Southern Pines
NEW! Peaceful Southern Pines Home w/ Pool + Yard!, holiday rental in Southern Pines

NEW! Peaceful Southern Pines Home w/ Pool + Yard!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Evolve | Cozy Apt w/ Yard: 1 Mi to Nature Preserve, holiday rental in Southern Pines
Evolve | Cozy Apt w/ Yard: 1 Mi to Nature Preserve, holiday rental in Southern Pines
Evolve | Cozy Apt w/ Yard: 1 Mi to Nature Preserve, holiday rental in Southern Pines

Evolve | Cozy Apt w/ Yard: 1 Mi to Nature Preserve

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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2 BR/2 BA Townhouse in Downtown Southern Pines with Grill + Fenced-in Back Yard, holiday rental in Southern Pines
2 BR/2 BA Townhouse in Downtown Southern Pines with Grill + Fenced-in Back Yard, holiday rental in Southern Pines
2 BR/2 BA Townhouse in Downtown Southern Pines with Grill + Fenced-in Back Yard, holiday rental in Southern Pines

2 BR/2 BA Townhouse in Downtown Southern Pines with Grill + Fenced-in Back Yard

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Albatross Abode: Renovated Condo in Talamore!, holiday rental in Southern Pines
Albatross Abode: Renovated Condo in Talamore!, holiday rental in Southern Pines
Albatross Abode: Renovated Condo in Talamore!, holiday rental in Southern Pines

Albatross Abode: Renovated Condo in Talamore!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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A Cinderella Story -Downtown Southern Pines, holiday rental in Southern Pines
A Cinderella Story -Downtown Southern Pines, holiday rental in Southern Pines
A Cinderella Story -Downtown Southern Pines, holiday rental in Southern Pines

A Cinderella Story -Downtown Southern Pines

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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NEW! Charming Southern Pines Abode - Walk to Dtwn!, holiday rental in Southern Pines
NEW! Charming Southern Pines Abode - Walk to Dtwn!, holiday rental in Southern Pines
NEW! Charming Southern Pines Abode - Walk to Dtwn!, holiday rental in Southern Pines

NEW! Charming Southern Pines Abode - Walk to Dtwn!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Reynolds Villa- Golf/Couples Retreat, holiday rental in Southern Pines
Reynolds Villa- Golf/Couples Retreat, holiday rental in Southern Pines
Reynolds Villa- Golf/Couples Retreat, holiday rental in Southern Pines

Reynolds Villa- Golf/Couples Retreat

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Upstairs at The Estate-Across from SP Golf Club, Sleeps 6, holiday rental in Southern Pines
Upstairs at The Estate-Across from SP Golf Club, Sleeps 6, holiday rental in Southern Pines
Upstairs at The Estate-Across from SP Golf Club, Sleeps 6, holiday rental in Southern Pines

Upstairs at The Estate-Across from SP Golf Club, Sleeps 6

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Poolside at Walsh Lane Farmhouse - minutes to downtown Southern Pines, holiday rental in Southern Pines
Poolside at Walsh Lane Farmhouse - minutes to downtown Southern Pines, holiday rental in Southern Pines
Poolside at Walsh Lane Farmhouse - minutes to downtown Southern Pines, holiday rental in Southern Pines

Poolside at Walsh Lane Farmhouse - minutes to downtown Southern Pines

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Golfer’s Oasis - Welcome to The Southern Place!, holiday rental in Southern Pines
Golfer’s Oasis - Welcome to The Southern Place!, holiday rental in Southern Pines
Golfer’s Oasis - Welcome to The Southern Place!, holiday rental in Southern Pines

Golfer’s Oasis - Welcome to The Southern Place!

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Enjoy being 2 blocks from downtown in the Pastry Townhouse!, holiday rental in Southern Pines
Enjoy being 2 blocks from downtown in the Pastry Townhouse!, holiday rental in Southern Pines
Enjoy being 2 blocks from downtown in the Pastry Townhouse!, holiday rental in Southern Pines

Enjoy being 2 blocks from downtown in the Pastry Townhouse!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Serenity at Yadkin Horse Farm in Southern Pines Horse Country, holiday rental in Southern Pines
Serenity at Yadkin Horse Farm in Southern Pines Horse Country, holiday rental in Southern Pines
Serenity at Yadkin Horse Farm in Southern Pines Horse Country, holiday rental in Southern Pines

Serenity at Yadkin Horse Farm in Southern Pines Horse Country

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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New! SoPi Cottage - Walk to Town - Sleeps 6, holiday rental in Southern Pines
New! SoPi Cottage - Walk to Town - Sleeps 6, holiday rental in Southern Pines
New! SoPi Cottage - Walk to Town - Sleeps 6, holiday rental in Southern Pines

New! SoPi Cottage - Walk to Town - Sleeps 6

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Downtown Cottage on Ridge � Short Stays � Extended Stays, holiday rental in Southern Pines
Downtown Cottage on Ridge � Short Stays � Extended Stays, holiday rental in Southern Pines
Downtown Cottage on Ridge � Short Stays � Extended Stays, holiday rental in Southern Pines

Downtown Cottage on Ridge � Short Stays � Extended Stays

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Bicycle Lane - nestled between golfing and equestrian communities, holiday rental in Southern Pines
Bicycle Lane - nestled between golfing and equestrian communities, holiday rental in Southern Pines
Bicycle Lane - nestled between golfing and equestrian communities, holiday rental in Southern Pines

Bicycle Lane - nestled between golfing and equestrian communities

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Home w/hot tub, steps from everything!, holiday rental in Southern Pines
Historic Home w/hot tub, steps from everything!, holiday rental in Southern Pines
Historic Home w/hot tub, steps from everything!, holiday rental in Southern Pines

Historic Home w/hot tub, steps from everything!

Condo/Apartment
0 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Loft Cottage on Ridge � Short & Extended Stays�, holiday rental in Southern Pines
Loft Cottage on Ridge � Short & Extended Stays�, holiday rental in Southern Pines
Loft Cottage on Ridge � Short & Extended Stays�, holiday rental in Southern Pines

Loft Cottage on Ridge � Short & Extended Stays�

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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