Pinehurst Winter Rental
Villa
4 Bedrooms
2 Baths
8 Guests
Private Pool
Oceanfront
Hot Tub
Fireplace/Heating
CA $875/Night
7 Nights - CA $6,123
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
4 Guests
1302.43 ft²
- Hot Tub
Spa
Pool
Balcony/Terrace
CA $552/Night
7 Nights - CA $3,866
House
10.0(9 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
CA $971/Night
7 Nights - CA $6,800
New
House
3 Bedrooms
2 Baths
6 Guests
1503 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly
CA $199/Night
7 Nights - CA $1,391
House
9.7(3 Reviews)
1 Bedroom
1 Bath
4 Guests
344.45 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Pet Friendly
CA $230/Night
7 Nights - CA $1,612
Cottage
10.0(21 Reviews)
1 Bedroom
1 Bath
4 Guests
- Pet Friendly
Kitchen
Parking
Air Conditioner
CA $260/Night
7 Nights - CA $1,818
House
9.4(13 Reviews)
3 Bedrooms
2 Baths
5 Guests
1302.43 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
CA $165/Night
7 Nights - CA $1,153
Condo
10.0(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1250 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
CA $377/Night
7 Nights - CA $2,638
Resort
8.8(187 Reviews)
20 Baths
81 Guests
490.83 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
CA $748/Night
7 Nights - CA $5,235
Condo
10.0(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
CA $373/Night
7 Nights - CA $2,614
House
5.9(9 Reviews)
3 Bedrooms
2 Baths
10 Guests
1797.57 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
CA $241/Night
7 Nights - CA $1,689
Condo
10.0(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
CA $305/Night
7 Nights - CA $2,131
Why Choose Rent By Owner for your Pinehurst Winter Rental?
What makes our Winter Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Pinehurst
How to Book Your Pinehurst Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Pinehurst
Common Winter Rental Amenities
What amenities can you expect?
Our Winter Rental are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Frequently Asked Questions About Pinehurst Winter Rentals
1. What are the top Winter Rentals in Pinehurst?
There are a lot of options in Pinehurst. If you plan on staying in the Pinehurst area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Pinehurst:
- NEW Coastal Paradise GEM! Spacious 4BR, 3 Full Baths w/Pool! PET FRIENDLY!
- Beautiful updated pool home in a quiet, gated community.
- Newly remodeled 3-bedroom condo in a bundled community
- Country Creek -Lovely updated 3 bed/2 bath Estero home with hot tub and golf
- Fabulous home w/new pool & spa. Minutes to golf, shop, dine, and fun-in-sun.
- Super Clean, Comfortable, & Centrally Located near RSW and FGCU
- 3 BR, 2 Bath W/Community Pool & Exercise Rm Located In A Quiet Gated Community
- Modern Oasis Estero Bay - a serene retreat for the ultimate vacation experience
- Family-Friendly Pool Home
- Luxury Tropical Oasis: 4-Bedroom Retreat
2. How many Winter Rentals are available in Pinehurst?
Currently, the total number of properties listed by RBO in 2026 is over 263 in the Pinehurst area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Pinehurst.
More Rentals You May Like Near Pinehurst
House
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
CA $221/Night
7 Nights - CA $1,543
Condo
10.0(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
1850 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $223/Night
7 Nights - CA $1,563
House
10.0(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $178/Night
7 Nights - CA $1,249
Condo
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
CA $243/Night
7 Nights - CA $1,698
House
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Hot Tub
- Fireplace/Heating
- Pool
Ocean View
CA $202/Night
7 Nights - CA $1,413
Villa
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Pool
- Ocean View
- View
CA $156/Night
7 Nights - CA $1,089
Condo
10.0(1 Review)
2 Bedrooms
2 Baths
8 Guests
900 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
CA $1,056/Night
7 Nights - CA $7,392
Condo
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
1691 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
CA $308/Night
7 Nights - CA $2,157
Condo
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
CA $305/Night
7 Nights - CA $2,137
Condo
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
1300 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
CA $236/Night
7 Nights - CA $1,656
House
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
CA $236/Night
7 Nights - CA $1,653
Condo
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
1262 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
CA $230/Night
7 Nights - CA $1,611
