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Southern Pines Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
96 rentals 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 in Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Upstairs at the Estate - Across from SP Golf Club, holiday rental in Southern Pines
Upstairs at the Estate - Across from SP Golf Club, holiday rental in Southern Pines
Upstairs at the Estate - Across from SP Golf Club, holiday rental in Southern Pines

Upstairs at the Estate - Across from SP Golf Club

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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3BR Townhome - Walk to Downtown Southern Pines, holiday rental in Southern Pines
3BR Townhome - Walk to Downtown Southern Pines, holiday rental in Southern Pines
3BR Townhome - Walk to Downtown Southern Pines, holiday rental in Southern Pines

3BR Townhome - Walk to Downtown Southern Pines

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Southern Pines Getaway for 8 with Pool and Theater Room!, holiday rental in Southern Pines
Southern Pines Getaway for 8 with Pool and Theater Room!, holiday rental in Southern Pines
Southern Pines Getaway for 8 with Pool and Theater Room!, holiday rental in Southern Pines

Southern Pines Getaway for 8 with Pool and Theater Room!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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The Enchanted Castle- Right Downtown with Hot Tub & Fenced Backyard, holiday rental in Southern Pines
The Enchanted Castle- Right Downtown with Hot Tub & Fenced Backyard, holiday rental in Southern Pines
The Enchanted Castle- Right Downtown with Hot Tub & Fenced Backyard, holiday rental in Southern Pines

The Enchanted Castle- Right Downtown with Hot Tub & Fenced Backyard

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Charming home in the heart of Downtown Southern Pines, holiday rental in Southern Pines
Charming home in the heart of Downtown Southern Pines, holiday rental in Southern Pines
Charming home in the heart of Downtown Southern Pines, holiday rental in Southern Pines

Charming home in the heart of Downtown Southern Pines

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 9
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 2
Match: Sleeps
More info
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The Flat Coat Cottage!, holiday rental in Southern Pines
The Flat Coat Cottage!, holiday rental in Southern Pines
The Flat Coat Cottage!, holiday rental in Southern Pines

The Flat Coat Cottage!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Fore Seasons – Unbeatable Golf Experience! - Available for 2024 Open!, holiday rental in Southern Pines
Fore Seasons – Unbeatable Golf Experience! - Available for 2024 Open!, holiday rental in Southern Pines
Fore Seasons – Unbeatable Golf Experience! - Available for 2024 Open!, holiday rental in Southern Pines

Fore Seasons – Unbeatable Golf Experience! - Available for 2024 Open!

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!, holiday rental in Southern Pines
Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!, holiday rental in Southern Pines
Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!, holiday rental in Southern Pines

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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
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Downtown Southern Pines Townhome with Deck!, holiday rental in Southern Pines
Downtown Southern Pines Townhome with Deck!, holiday rental in Southern Pines
Downtown Southern Pines Townhome with Deck!, holiday rental in Southern Pines

Downtown Southern Pines Townhome with Deck!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Hot Tub Retreat -Walk or Bike to Downtown - Golf, Breweries, Restaurants!, holiday rental in Southern Pines
Hot Tub Retreat -Walk or Bike to Downtown - Golf, Breweries, Restaurants!, holiday rental in Southern Pines
Hot Tub Retreat -Walk or Bike to Downtown - Golf, Breweries, Restaurants!, holiday rental in Southern Pines

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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!

Holiday Rental House
4 bedrooms
0 bathrooms
Sleeps 10
Match: Sleeps
More info
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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
More info
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Charming, newly updated Downtown Cottage, holiday rental in Southern Pines
Charming, newly updated Downtown Cottage, holiday rental in Southern Pines
Charming, newly updated Downtown Cottage, holiday rental in Southern Pines

Charming, newly updated Downtown Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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
More info
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Peaceful Southern Pines Home w/ Pool + Yard!, holiday rental in Southern Pines
Peaceful Southern Pines Home w/ Pool + Yard!, holiday rental in Southern Pines
Peaceful Southern Pines Home w/ Pool + Yard!, holiday rental in Southern Pines

Peaceful Southern Pines Home w/ Pool + Yard!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Cozy downtown cottage close to the park, holiday rental in Southern Pines
Cozy downtown cottage close to the park, holiday rental in Southern Pines
Cozy downtown cottage close to the park, holiday rental in Southern Pines

Cozy downtown cottage close to the park

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Charming Southern Pines Abode - Walk to Dtwn!, holiday rental in Southern Pines
Charming Southern Pines Abode - Walk to Dtwn!, holiday rental in Southern Pines
Charming Southern Pines Abode - Walk to Dtwn!, holiday rental in Southern Pines

Charming Southern Pines Abode - Walk to Dtwn!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Cozy cottage near downtown Southern Pines, holiday rental in Southern Pines
Cozy cottage near downtown Southern Pines, holiday rental in Southern Pines
Cozy cottage near downtown Southern Pines, holiday rental in Southern Pines

Cozy cottage near downtown Southern Pines

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Affiliated with FlipKey
52 Longleaf - Available during 2024 Open, holiday rental in Southern Pines
52 Longleaf - Available during 2024 Open, holiday rental in Southern Pines
52 Longleaf - Available during 2024 Open, holiday rental in Southern Pines

52 Longleaf - Available during 2024 Open

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Standard Guestroom (ADA) - 1 King · The Jefferson Inn Rm. 8, holiday rental in Southern Pines
Standard Guestroom (ADA) - 1 King · The Jefferson Inn Rm. 8, holiday rental in Southern Pines
Standard Guestroom (ADA) - 1 King · The Jefferson Inn Rm. 8, holiday rental in Southern Pines

Standard Guestroom (ADA) - 1 King · The Jefferson Inn Rm. 8

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Standard Guestroom 1 King  · The Jefferson Inn Rm. 10, holiday rental in Southern Pines
Standard Guestroom 1 King  · The Jefferson Inn Rm. 10, holiday rental in Southern Pines
Standard Guestroom 1 King  · The Jefferson Inn Rm. 10, holiday rental in Southern Pines

Standard Guestroom 1 King · The Jefferson Inn Rm. 10

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Standard Guest Room- 2 Queens  · The Jefferson Inn Rm. 13, holiday rental in Southern Pines
Standard Guest Room- 2 Queens  · The Jefferson Inn Rm. 13, holiday rental in Southern Pines
Standard Guest Room- 2 Queens  · The Jefferson Inn Rm. 13, holiday rental in Southern Pines

Standard Guest Room- 2 Queens · The Jefferson Inn Rm. 13

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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11-Standard Guest Room - 2 Queens  · The Jefferson Inn Rm. 11, holiday rental in Southern Pines
11-Standard Guest Room - 2 Queens  · The Jefferson Inn Rm. 11, holiday rental in Southern Pines
11-Standard Guest Room - 2 Queens  · The Jefferson Inn Rm. 11, holiday rental in Southern Pines

11-Standard Guest Room - 2 Queens · The Jefferson Inn Rm. 11

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Deluxe Guestroom - 2 Queens  · The Jefferson Inn Rm. 5, holiday rental in Southern Pines
Deluxe Guestroom - 2 Queens  · The Jefferson Inn Rm. 5, holiday rental in Southern Pines
Deluxe Guestroom - 2 Queens  · The Jefferson Inn Rm. 5, holiday rental in Southern Pines

Deluxe Guestroom - 2 Queens · The Jefferson Inn Rm. 5

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Deluxe Guestroom-2 Queens  · The Jefferson Inn Rm. 14, holiday rental in Southern Pines
Deluxe Guestroom-2 Queens  · The Jefferson Inn Rm. 14, holiday rental in Southern Pines
Deluxe Guestroom-2 Queens  · The Jefferson Inn Rm. 14, holiday rental in Southern Pines

Deluxe Guestroom-2 Queens · The Jefferson Inn Rm. 14

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Standard Guestroom - 1 King  · The Jefferson Inn Rm. 6, holiday rental in Southern Pines
Standard Guestroom - 1 King  · The Jefferson Inn Rm. 6, holiday rental in Southern Pines
Standard Guestroom - 1 King  · The Jefferson Inn Rm. 6, holiday rental in Southern Pines

Standard Guestroom - 1 King · The Jefferson Inn Rm. 6

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Deluxe Guest Room - 1 King + · The Jefferson Inn Rm. 7, holiday rental in Southern Pines
Deluxe Guest Room - 1 King + · The Jefferson Inn Rm. 7, holiday rental in Southern Pines
Deluxe Guest Room - 1 King + · The Jefferson Inn Rm. 7, holiday rental in Southern Pines

Deluxe Guest Room - 1 King + · The Jefferson Inn Rm. 7

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Deluxe Suite · The Jefferson Inn Rm. 1, holiday rental in Southern Pines
Deluxe Suite · The Jefferson Inn Rm. 1, holiday rental in Southern Pines
Deluxe Suite · The Jefferson Inn Rm. 1, holiday rental in Southern Pines

Deluxe Suite · The Jefferson Inn Rm. 1

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Deluxe Guestroom-2 Queens  · The Jefferson Inn Rm. 12, holiday rental in Southern Pines
Deluxe Guestroom-2 Queens  · The Jefferson Inn Rm. 12, holiday rental in Southern Pines
Deluxe Guestroom-2 Queens  · The Jefferson Inn Rm. 12, holiday rental in Southern Pines

Deluxe Guestroom-2 Queens · The Jefferson Inn Rm. 12

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Deluxe Guestroom - 2 Queens  · The Jefferson Inn Rm. 4, holiday rental in Southern Pines
Deluxe Guestroom - 2 Queens  · The Jefferson Inn Rm. 4, holiday rental in Southern Pines
Deluxe Guestroom - 2 Queens  · The Jefferson Inn Rm. 4, holiday rental in Southern Pines

Deluxe Guestroom - 2 Queens · The Jefferson Inn Rm. 4

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Junior Suite - 1 King  · The Jefferson Inn Rm. 15, holiday rental in Southern Pines
Junior Suite - 1 King  · The Jefferson Inn Rm. 15, holiday rental in Southern Pines
Junior Suite - 1 King  · The Jefferson Inn Rm. 15, holiday rental in Southern Pines

Junior Suite - 1 King · The Jefferson Inn Rm. 15

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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The Jefferson Inn Rm. 2 | Standard Suite, holiday rental in Southern Pines
The Jefferson Inn Rm. 2 | Standard Suite, holiday rental in Southern Pines
The Jefferson Inn Rm. 2 | Standard Suite, holiday rental in Southern Pines

The Jefferson Inn Rm. 2 | Standard Suite

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Standard Suite - 2 Queens · The Jefferson Inn Rm. 9, holiday rental in Southern Pines
Standard Suite - 2 Queens · The Jefferson Inn Rm. 9, holiday rental in Southern Pines
Standard Suite - 2 Queens · The Jefferson Inn Rm. 9, holiday rental in Southern Pines

Standard Suite - 2 Queens · The Jefferson Inn Rm. 9

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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The best of Southern Pines, right at your doorstep!, holiday rental in Southern Pines
The best of Southern Pines, right at your doorstep!, holiday rental in Southern Pines
The best of Southern Pines, right at your doorstep!, holiday rental in Southern Pines

The best of Southern Pines, right at your doorstep!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Adorable 1 bedroom guest house in Southern Pines, holiday rental in Southern Pines
Adorable 1 bedroom guest house in Southern Pines, holiday rental in Southern Pines
Adorable 1 bedroom guest house in Southern Pines, holiday rental in Southern Pines

Adorable 1 bedroom guest house in Southern Pines

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Downtown Southern Pines: The Shire 255, holiday rental in Southern Pines
Downtown Southern Pines: The Shire 255, holiday rental in Southern Pines
Downtown Southern Pines: The Shire 255, holiday rental in Southern Pines

Downtown Southern Pines: The Shire 255

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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A Slice of Seclusion in The Middle of Downtown SP!, holiday rental in Southern Pines
A Slice of Seclusion in The Middle of Downtown SP!, holiday rental in Southern Pines
A Slice of Seclusion in The Middle of Downtown SP!, holiday rental in Southern Pines

A Slice of Seclusion in The Middle of Downtown SP!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Cottage on Ridge ? Short Stays? Extended Stays, holiday rental in Southern Pines
Cottage on Ridge ? Short Stays? Extended Stays, holiday rental in Southern Pines
Cottage on Ridge ? Short Stays? Extended Stays, holiday rental in Southern Pines

Cottage on Ridge ? Short Stays? Extended Stays

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Check-out
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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
More info
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Historic Carriage House Southern Pines - Weymouth, holiday rental in Southern Pines
Historic Carriage House Southern Pines - Weymouth, holiday rental in Southern Pines
Historic Carriage House Southern Pines - Weymouth, holiday rental in Southern Pines

Historic Carriage House Southern Pines - Weymouth

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Secret Cottage, holiday rental in Southern Pines
Secret Cottage, holiday rental in Southern Pines
Secret Cottage, holiday rental in Southern Pines

Secret Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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
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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The Bungalow on Connecticut w/E scooter rental, holiday rental in Southern Pines
The Bungalow on Connecticut w/E scooter rental, holiday rental in Southern Pines
The Bungalow on Connecticut w/E scooter rental, holiday rental in Southern Pines

The Bungalow on Connecticut w/E scooter rental

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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As seen on
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Affiliated with FlipKey
Renovated Golf Front! Short commute to Ft.Bragg - Pets Allowed Upon Approval, holiday rental in Southern Pines
Renovated Golf Front! Short commute to Ft.Bragg - Pets Allowed Upon Approval, holiday rental in Southern Pines
Renovated Golf Front! Short commute to Ft.Bragg - Pets Allowed Upon Approval, holiday rental in Southern Pines

Renovated Golf Front! Short commute to Ft.Bragg - Pets Allowed Upon Approval

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Luxury Golf Front Condo, holiday rental in Southern Pines
Luxury Golf Front Condo, holiday rental in Southern Pines
Luxury Golf Front Condo, holiday rental in Southern Pines

Luxury Golf Front Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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As seen on
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Cloverfield Retreat - Private Barn Rental, holiday rental in Southern Pines
Cloverfield Retreat - Private Barn Rental, holiday rental in Southern Pines
Cloverfield Retreat - Private Barn Rental, holiday rental in Southern Pines

Cloverfield Retreat - Private Barn Rental

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
HolidayLettings.co.uk logo
Affiliated with FlipKey
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
More info
Check-in
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Showing results 1-50 of 96
Frequently Asked Questions about Southern Pines