Short Term Vacation Rentals Locally Managed by Stay Well

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Laptop Friendly workspacePets allowedFenced yardKids amenities

Our top properties

- Foxfire
  4.85 ★
- Foxfire
  4.85 ★
- Foxfire
  4.85 ★
- Foxfire
  4.85 ★
- Foxfire
  4.85 ★
- Foxfire
  4.85 ★
- Foxfire
  4.85 ★
- Foxfire
  4.85 ★
- Foxfire
  4.85 ★
- Foxfire
  4.85 ★
Luxurious Pine Manor: Golf Front Estate with Pool!
- 14 guests
- 6 bedrooms
- 6 baths
- Private pool
- Golf course view
- Swimming pool
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
Flat Coat Cottage
- 8 guests
- 3 bedrooms
- 3 baths
- Pets allowed
- Suitable for children
- Free WiFi
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
Mulligan Manor: Downtown Southern Pines
- 6 guests
- 3 bedrooms
- 3 baths
- Pets allowed
- Suitable for children
- Free WiFi
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
The Shire 255 C - Slate
- 4 guests
- 2 bedrooms
- 1 bath
- Suitable for children
- Free WiFi
- Kitchen
- Pinehurst
  5.00 ★
- Pinehurst
  5.00 ★
- Pinehurst
  5.00 ★
- Pinehurst
  5.00 ★
- Pinehurst
  5.00 ★
- Pinehurst
  5.00 ★
- Pinehurst
  5.00 ★
- Pinehurst
  5.00 ★
- Pinehurst
  5.00 ★
- Pinehurst
  5.00 ★
Perfect Pinehurst Getaway - Ideal for Groups
- 8 guests
- 5 bedrooms
- 3 baths
- Suitable for children
- Free WiFi
- Kitchen
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
- Southern Pines
  5.00 ★
Serene South Henley
- 8 guests
- 4 bedrooms
- 2 baths
- Pets allowed
- Suitable for children
- Free WiFi
- AberdeenDucks Landing 🏡
  5.00 ★
- AberdeenDucks Landing 🏡
  5.00 ★
- AberdeenDucks Landing 🏡
  5.00 ★
- AberdeenDucks Landing 🏡
  5.00 ★
- AberdeenDucks Landing 🏡
  5.00 ★
- AberdeenDucks Landing 🏡
  5.00 ★
- AberdeenDucks Landing 🏡
  5.00 ★
- AberdeenDucks Landing 🏡
  5.00 ★
- AberdeenDucks Landing 🏡
  5.00 ★
- AberdeenDucks Landing 🏡
  5.00 ★
The Magnolia at Ducks Landing
- 6 guests
- 3 bedrooms
- 2 baths
- Pets allowed
- Suitable for children
- Free WiFi
- Pinehurst
  5.00 ★
- Pinehurst
  5.00 ★
- Pinehurst
  5.00 ★
- Pinehurst
  5.00 ★
- Pinehurst
  5.00 ★
- Pinehurst
  5.00 ★
- Pinehurst
  5.00 ★
- Pinehurst
  5.00 ★
- Pinehurst
  5.00 ★
- Pinehurst
  5.00 ★
Lakefront Treehouse in Pinehurst
- 2 guests
- 1 bedroom
- 2 baths
- Free WiFi
- Kitchen
- Air conditioning
- Southern Pines
  4.95 ★
- Southern Pines
  4.95 ★
- Southern Pines
  4.95 ★
- Southern Pines
  4.95 ★
- Southern Pines
  4.95 ★
- Southern Pines
  4.95 ★
- Southern Pines
  4.95 ★
- Southern Pines
  4.95 ★
- Southern Pines
  4.95 ★
- Southern Pines
  4.95 ★
Maine Avenue: Downtown Southern Pines
- 6 guests
- 3 bedrooms
- 2 baths
- Suitable for children
- Free WiFi
- Kitchen
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
The Shire 255 B - Sienna
- 4 guests
- 1 bedroom
- 1 bath
- Suitable for children
- Free WiFi
- Kitchen
- Carthage
  4.95 ★
- Carthage
  4.95 ★
- Carthage
  4.95 ★
- Carthage
  4.95 ★
- Carthage
  4.95 ★
- Carthage
  4.95 ★
- Carthage
  4.95 ★
- Carthage
  4.95 ★
- Carthage
  4.95 ★
- Carthage
  4.95 ★
Full Stop Landing
- 4 guests
- 2 bedrooms
- 1 bath
- Suitable for children
- Free WiFi
- Kitchen
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
- Southern PinesThe Shire 🏡
  4.95 ★
The Shire 255 A - Sage
- 4 guests
- 1 bedroom
- 1 bath
- Suitable for children
- Free WiFi
- Kitchen
- Southern PinesThe Shire 🏡
  4.90 ★
- Southern PinesThe Shire 🏡
  4.90 ★
- Southern PinesThe Shire 🏡
  4.90 ★
- Southern PinesThe Shire 🏡
  4.90 ★
- Southern PinesThe Shire 🏡
  4.90 ★
- Southern PinesThe Shire 🏡
  4.90 ★
- Southern PinesThe Shire 🏡
  4.90 ★
- Southern PinesThe Shire 🏡
  4.90 ★
- Southern PinesThe Shire 🏡
  4.90 ★
- Southern PinesThe Shire 🏡
  4.90 ★
The Shire 255 D - Solitude
- 2 guests
- 1 bedroom
- 1 bath
- Pets allowed
- Suitable for children
- Kitchen
- Pinebluff
  4.95 ★
- Pinebluff
  4.95 ★
- Pinebluff
  4.95 ★
- Pinebluff
  4.95 ★
- Pinebluff
  4.95 ★
- Pinebluff
  4.95 ★
- Pinebluff
  4.95 ★
- Pinebluff
  4.95 ★
- Pinebluff
  4.95 ★
- Pinebluff
  4.95 ★
The Loft and Mane Cottage
- 4 guests
- 1 bedroom
- 2 baths
- Suitable for children
- Free WiFi
- Kitchen
- Southern Pines
  4.75 ★
- Southern Pines
  4.75 ★
- Southern Pines
  4.75 ★
- Southern Pines
  4.75 ★
- Southern Pines
  4.75 ★
- Southern Pines
  4.75 ★
- Southern Pines
  4.75 ★
- Southern Pines
  4.75 ★
- Southern Pines
  4.75 ★
- Southern Pines
  4.75 ★
Slice of Seclusion in Downtown Southern Pines
- 2 guests
- 1 bedroom
- 1 bath
- Suitable for children
- Free WiFi
- Kitchen

Explore all properties (38)