Cottage
10.0(22 Reviews)
1 Bedroom
4 Guests
Parking
Kitchen
Air Conditioner
Internet
CA $331/Night
7 Nights - CA $2,317
Pinehurst Winter Rentals & Holiday Homes
Discover winter rentals Pinehurst - We found 282 exact matches
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Compare Winter Rental in Pinehurst
10.0
House
9.7(3 Reviews)
1 Bedroom
4 Guests
- Parking
Balcony/Terrace
View- Kitchen
CA $235/Night
7 Nights - CA $1,642
House
1 Bedroom
- Internet
Child Friendly
Sports/Activities
Entertainment
CA $673/Night
7 Nights - CA $4,713
Condo
10.0(6 Reviews)
2 Bedrooms
4 Guests
Hot Tub- Parking
Pool
Ocean View
CA $393/Night
7 Nights - CA $2,749
House
9.4(13 Reviews)
3 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $252/Night
7 Nights - CA $1,765
House
10.0(4 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $242/Night
7 Nights - CA $1,698
Resort
8.8(187 Reviews)
81 Guests
- Hot Tub
Breakfast- Parking
- Pool
CA $1,103/Night
7 Nights - CA $7,720
Condo
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
CA $393/Night
7 Nights - CA $2,750
House
6.6(14 Reviews)
3 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $241/Night
7 Nights - CA $1,687
Condo
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $238/Night
7 Nights - CA $1,663
House
5 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $1,446/Night
7 Nights - CA $10,126
House
10.0(2 Reviews)
2 Bedrooms
6 Guests
Private Pool
Oceanfront- Hot Tub
- Parking
CA $385/Night
7 Nights - CA $2,697
CA $177/Night
7 Nights - CA $1,243
House
10.0(2 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $277/Night
7 Nights - CA $1,940
Condo
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
CA $258/Night
7 Nights - CA $1,809
Villa
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $225/Night
7 Nights - CA $1,576
Villa
10.0(1 Review)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
Spa
CA $640/Night
7 Nights - CA $4,477
Condo
10.0(1 Review)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
CA $334/Night
7 Nights - CA $2,337
Condo
10.0(1 Review)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $260/Night
7 Nights - CA $1,824
Condo
10.0(1 Review)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
CA $234/Night
7 Nights - CA $1,638
Villa
10.0(1 Review)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
CA $208/Night
7 Nights - CA $1,453
House
9.8(147 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- View
CA $174/Night
7 Nights - CA $1,215
House
9.6(29 Reviews)
2 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $319/Night
7 Nights - CA $2,230
Villa
9.4(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $293/Night
7 Nights - CA $2,048
About Pinehurst Winter Rental on BedroomVillas.ca
At BedroomVillas, we feature a wide range of listings for accommodations in Pinehurst, FL that are perfect for your winter trip or seasonal escape. Our listings include hotels, private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that travelers are sure to love. BedroomVillas winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you are escaping the snow or running to it, BedroomVillas helps connect you to the best cabins, bungalows, lodges, and villas, as well as the best places to stay in both sun and ski resorts. BedroomVillas will make your winter getaway an unforgettable experience.
BedroomVillas offers luxury finds for travelers planning on renting a place in Pinehurst, to enjoy these benefits and to book your winter vacation homes, go to the BedroomVillas filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of incredible winter vacation rentals without hassle. Our interactive map is also available, so you can view destinations spanning the globe or around Pinehurst and unlock even more amazing deals. Relax with BedroomVillas.
Winter Rental: Explore Top Destinations
Frequently Asked Questions About Pinehurst Winter Rentals
What are the top rated 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:
- Modern 3 bedroom, 2 bath getaway with HEATED private pool and jacuzzi
- Spacious 4 BR Retreat w/3 Ensuites, Pool & Spa
- Newly remodeled 3-bedroom condo in a bundled community
- Super Clean, Comfortable, & Centrally Located near RSW and FGCU
- 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.
- 3 BR, 2 Bath W/Community Pool & Exercise Rm Located In A Quiet Gated Community
- New Remodeled and Quiet 4 bed pool home by Coconut Point - Close to Beaches!
- Modern Oasis Estero Bay - a serene retreat for the ultimate vacation experience
- Riverfront Retreat with Pool, Spa & Dock
How much does it cost to rent a place to stay near Pinehurst in the wintertime?
The average cost for winter rentals in Pinehurst is $312 per night. BedroomVillas.ca has a wide list of great winter places to stay near Pinehurst that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Pinehurst that allow pets?
Yes, here are the top cottage/chalet rentals in Pinehurst that allow you to bring your pet or dog:
- River Ranch Oaks
- Zen Container Tiny Home with Fenced-in Yard, Fire Pit, Centrally located and Pet Friendly
- Fort Myers Coastal Retreat Hot Tub Yard Games
- Completely renovated in fantastic community & location!
See all pet-friendly vacation rentals in Pinehurst on BedroomVillas.ca
Do you have any winter rentals in Pinehurst that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Pinehurst to find what works for you.
Are there winter accommodations in Pinehurst that have indoor swimming pools?
As of 2026, the data from BedroomVillas.ca shows that there are over 282 private swimming pools or indoor pools accommodations near Pinehurst along with other great amenities.
Do any winter holiday rentals in Pinehurst have hot tubs?
About 282 holiday rentals in Pinehurst boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Pinehurst?
Yes, there are many luxury places to stay in Pinehurst for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Pinehurst with all the best amenities for your next trip.
