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Southern Pines vacation rentals

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Best Southern Pines vacation rentals

Most recommended vacation rentals in Southern Pines

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Cozy Southern Pines Retreat 1 Mi to Downtown! - Southern Pines - Building
Cozy Southern Pines Retreat 1 Mi to Downtown!
Southern Pines, NC
Free Wi-Fi
$179+
Check availability
Slice of Seclusion in Downtown Southern Pines - Southern Pines - Bedroom
Slice of Seclusion in Downtown Southern Pines
Southern Pines, NC
10Wonderful(2)
Free Wi-Fi
$165+
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Downtown Townhome Walk to Dine and Shop on Broad St - Southern Pines - Living room
Downtown Townhome Walk to Dine and Shop on Broad St
Southern Pines, NC
9.6Wonderful(22)
Free Wi-Fi
$308+
Check availability
Condo in the Pines! 2BR 2BA. Sleeps 4. Military discount available! - Southern Pines - Bedroom
Condo in the Pines! 2BR 2BA. Sleeps 4. Military discount available!
Southern Pines, NC
Free Wi-Fi
$219+
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Southern Pines Vacation Rental with Deck and Grill! - Southern Pines - Balcony
Southern Pines Vacation Rental with Deck and Grill!
Southern Pines, NC
10Wonderful(7)
Free Wi-Fi
$208+
Check availability
Sienna at The Shire 255 - Unit B - Downtown! - Southern Pines - Restaurant
Sienna at The Shire 255 - Unit B - Downtown!
Southern Pines, NC
Free Wi-Fi
$261+
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The Downtown Ace - Southern Pines - Living room
The Downtown Ace
Southern Pines, NC
9.5Wonderful(9)
Parking
Free Wi-Fi
$337+
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The Cottage at Knollwood Manor - Southern Pines - Bedroom
The Cottage at Knollwood Manor
Southern Pines, NC
9.7Wonderful(12)
Parking
Free Wi-Fi
$199+
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52 Longleaf: 2 Br, 2 Ba Condominium In Southern Pines, Sleeps 4 - Southern Pines - Kitchen
52 Longleaf: 2 Br, 2 Ba Condominium In Southern Pines, Sleeps 4
Southern Pines, NC
$312+
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Peaceful Southern Pines Home with Pool and Yard! - Southern Pines - Living room
Peaceful Southern Pines Home with Pool and Yard!
Southern Pines, NC
9.4Wonderful(23)
Free Wi-Fi
Pool
Pet friendly
$663+
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Sweet Southern Pines Abode w/ Yard & Covered Porch - Southern Pines - Living room
Sweet Southern Pines Abode w/ Yard & Covered Porch
Southern Pines, NC
9.6Wonderful(12)
Free Wi-Fi
$1,398+
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The Enchanted Castle- Right Downtown with Hot Tub & Fenced Backyard - Southern Pines
The Enchanted Castle- Right Downtown with Hot Tub & Fenced Backyard
Southern Pines, NC
Pet friendly
$515+
Check availability
The Shire 255 D - Solitude - Downtown - Southern Pines
The Shire 255 D - Solitude - Downtown
Southern Pines, NC
9.6Wonderful(6)
Free Wi-Fi
Pet friendly
$188+
Check availability
'Wyndham Championship'Condo- Golf Cottage at Longleaf Country Club. Sleeps 2+ - Southern Pines
'Wyndham Championship'Condo- Golf Cottage at Longleaf Country Club. Sleeps 2+
Southern Pines, NC
$176+
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Ask Me About Discounts Before You Book! - Southern Pines
Ask Me About Discounts Before You Book!
Southern Pines, NC
Pet friendly
$157+
Check availability
Ask Me About Discounts Before You Book! - Southern Pines
Ask Me About Discounts Before You Book!
Southern Pines, NC
9.8Wonderful(5)
Pet friendly
$149+
Check availability
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$0 - $1,209$1,209 - $2,417$2,417 - $3,625$3,625 - $4,833$4,833+ per night

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Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

May

High season

April

Average price (weeknight)

$215

Average price (weekend night)

$207
Cheapest month to stay with an average 18% drop in price.
Most expensive month to stay with an average 9% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Southern Pines vacation rental deals

  • Vacation rentals in Southern Pines are around 53% more expensive than hotels on average. Search here to compare prices for all accommodation types in Southern Pines.
  • The best vacation rental properties in Southern Pines are Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See! (10.0, 27 reviews), A Cinderella Story -Downtown Southern Pines (10.0, 26), and Knollwood Manor - Historic Mansion Overlooking the Famous Mid Pines Golf Course (9.9, 21), based on ratings and reviews from real travelers.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Southern Pines for 4 days.
  • The cheapest Southern Pines vacation rental found on KAYAK in the last 2 weeks was $216, while the most expensive was $1,169.
See more tips

FAQs when booking a vacation home in Southern Pines

  • How much is a vacation rental for a week in Southern Pines?

    The average price for a weekly Southern Pines vacation rental found by KAYAK users in the last 2 weeks is $1,389.

  • How much is a vacation rental for a month in Southern Pines?

    The average price for a monthly Southern Pines vacation rental found by KAYAK users in the last 2 weeks is $5,951.

  • What types of vacation rentals are available in Southern Pines?

    There are loads of different property types that you can make your vacation home in Southern Pines. You’ll find apartments, caravans, condos, houses and villas.

  • What are some of the most-loved vacation rentals available in Southern Pines?

    If you’re looking for something special, the vacation rental most loved by KAYAK users is The Jefferson Inn.

  • Are there any pet-friendly vacation rentals in Southern Pines?

    There are a number of dog and pet-friendly Southern Pines vacation rentals, with around 17% allowing you to bring your pet along with you.

  • How much is a vacation rental in Southern Pines for tonight?

    In the last 72 hours, users have found Southern Pines vacation rentals for tonight for as low as $165. Search here for similar prices

  • How can I find vacation rentals near me in Southern Pines?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

See more FAQs

Where to stay in Southern Pines?

Our map will help you find the perfect place to stay in Southern Pines by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Southern Pines

Southern Pines vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Southern Pines. Find cheap vacation homes to rent in Southern Pines. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Southern Pines that suits you best.

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