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Five Points Holiday Rentals

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Our top choices for Five Points holiday rentals

Located in # 6 golf community, close to First Health Moore Regional Hospital.

Located in # 6 golf community, close to First Health Moore Regional Hospital.
Pinehurst
10.0 out of 10, Exceptional, (67)
"Great stay in Pinehurst!"
United States
jb22901
The price is NZ$261
includes taxes & fees
2 Jan - 3 Jan 2026
Located in # 6 golf community, close to First Health Moore Regional Hospital.

Calhoun Clubhouse - 5 Bedroom Split Level Home Near Pinehurst #6 / Firepit 🔥

Calhoun Clubhouse - 5 Bedroom Split Level Home Near Pinehurst #6 / Firepit 🔥
2.0 star property
Pinehurst
10.0 out of 10, Exceptional, (7)
"Great hospitality and very nice place for an overnight or more stay. "
United States
Robbie B.
The price is NZ$871
includes taxes & fees
5 Jan - 6 Jan 2026
Calhoun Clubhouse - 5 Bedroom Split Level Home Near Pinehurst #6 / Firepit 🔥

The Lucky Lie - Entire Condo in Pinehurst

The Lucky Lie - Entire Condo in Pinehurst
Pinehurst
9.6 out of 10, Exceptional, (51)
"It was a lovely stay at the Lucky Lie! Super clean and the beds were amazingly comfortable. Wonderful communication with the host as well."
United States
Kelly K.
The price is NZ$399
includes taxes & fees
4 Jan - 5 Jan 2026
The Lucky Lie - Entire Condo in Pinehurst

The McCaskill Cottage in the Village of Pinehurst!

The McCaskill Cottage in the Village of Pinehurst!
Old Town Pinehurst
9.8 out of 10, Exceptional, (10)
"It was a perfect stay. It had everything I needed. Hosts were great communicators. Perfect for a short stay in pinehurst and close to the hospital and downtown. Will stay there again if I am in town. "
United States
Denise
The price is NZ$463
includes taxes & fees
4 Jan - 5 Jan 2026
The McCaskill Cottage in the Village of Pinehurst!

Gene's Green - Mins from downtown!

Gene's Green - Mins from downtown!
Pinehurst
10.0 out of 10, Exceptional, (37)
"Loved Gene’s Greens! Roomy kitchen and master bedroom. Great location. Condo was perfect for our family!"
United States
Kaylan L.
The price is NZ$632
includes taxes & fees
4 Jan - 5 Jan 2026
Gene's Green - Mins from downtown!

The Cottage at Knollwood Manor

The Cottage at Knollwood Manor
2.0 star property
West Southern Pines
9.8 out of 10, Exceptional, (15)
"Love it, was perfect for us. "
United States
Creative Technical Solutions
The price is NZ$313
includes taxes & fees
30 Dec - 31 Dec
The Cottage at Knollwood Manor

COMPLETELY REMODELED 3 BDR, 2 Bath, Golf Course View Condo

COMPLETELY REMODELED 3 BDR, 2 Bath, Golf Course View Condo
2.0 star property
Pinehurst
10.0 out of 10, Exceptional, (16)
"Excellent location and a fabulous property."
United Kingdom
ALAN N.
The price is NZ$618
includes taxes & fees
31 Dec - 1 Jan 2026
COMPLETELY REMODELED 3 BDR, 2 Bath, Golf Course View Condo

2BD Pinehurst Golf Condo on Fairway of No. 3. Near Village, Resort & Fair Barn

2BD Pinehurst Golf Condo on Fairway of No. 3. Near Village, Resort & Fair Barn
2.0 star property
Pinehurst
10.0 out of 10, Exceptional, (2)
"Our host was very accommodating and quick to respond. We loved the location of the condo. It was very convenient to all of the Pinehurst courses, dining and shopping."
United States
jadine r.
The price is NZ$456
includes taxes & fees
12 Jan - 13 Jan 2026
2BD Pinehurst Golf Condo on Fairway of No. 3. Near Village, Resort & Fair Barn

"Charming 3-Bedroom Home with Private Gym in Prime Neighborhood!"

"Charming 3-Bedroom Home with Private Gym in Prime Neighborhood!"
Westover
9.0 out of 10, Wonderful, (12)
"I would book again"
United States
Warren J.
The price is NZ$469
includes taxes & fees
4 Jan - 5 Jan 2026
"Charming 3-Bedroom Home with Private Gym in Prime Neighborhood!"

Newly Renovated Property.

Newly Renovated Property.
Pinehurst
10.0 out of 10, Exceptional, (132)
"Great place"
United States
Darron G.
The price is NZ$519
includes taxes & fees
4 Jan - 5 Jan 2026
Newly Renovated Property.

Great golf property - walking distance to Pinehurst Resort

Great golf property - walking distance to Pinehurst Resort
Pinehurst
10.0 out of 10, Exceptional, (103)
"Nice place great for golf trip"
United States
Eric M.
The price is NZ$507
includes taxes & fees
12 Jan - 13 Jan 2026
Great golf property - walking distance to Pinehurst Resort

Sweet Retreat w/ Fire Pit, Near Downtown & Golf

Sweet Retreat w/ Fire Pit, Near Downtown & Golf
2.0 star property
Southern Pines
10.0 out of 10, Exceptional, (4)
"4 buddies and I needed a place to stay for a golf tournament in the area. This house was perfect! The house was very clean, comfortable and a perfect fit for 4 men. The location is great, less than 5-10 minutes from all of the major golf venues in the area. Lastly, Deanna was amazing to deal with! Great communication before, during and after our stay. I highly recommend this house!"
United States
Ray L.
The price is NZ$749
includes taxes & fees
31 Dec - 1 Jan 2026
Sweet Retreat w/ Fire Pit, Near Downtown & Golf

5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip

5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip
Pinehurst
9.6 out of 10, Exceptional, (15)
"Great golf stay"
United States
Patrick K.
The price is NZ$548
includes taxes & fees
30 Dec - 31 Dec
5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip

Beautiful 1 Bed Condo on Pinehurst Course No.5!

Beautiful 1 Bed Condo on Pinehurst Course No.5!
Pinehurst
9.0 out of 10, Wonderful, (17)
"This property was perfect for our last minute trip to the Pinehurst area. Easy parking and great communication for easy access at check in time. We will definitely stay here again if it is available on our next trip."
United States
Michael
The price is NZ$335
includes taxes & fees
30 Dec - 31 Dec
Beautiful 1 Bed Condo on Pinehurst Course No.5!

NEW LISTING! Pinehurst Tee Time Retreat

NEW LISTING! Pinehurst Tee Time Retreat
Pinehurst
9.8 out of 10, Exceptional, (6)
"Great location !!Great condo !!"
United States
Eric Z.
The price is NZ$591
includes taxes & fees
6 Jan - 7 Jan 2026
NEW LISTING! Pinehurst Tee Time Retreat

The Perfect Lie in Pinehurst! A golfer's paradise!

The Perfect Lie in Pinehurst! A golfer's paradise!
Pinehurst
9.8 out of 10, Exceptional, (60)
"Great location, very comfortable beds, very clean. "
United States
kristine r.
The price is NZ$467
includes taxes & fees
12 Jan - 13 Jan 2026
The Perfect Lie in Pinehurst! A golfer's paradise!

Mulligan Manor- 0.2 mile walk to Vitos Ristorante and Pizzeria and many others!

Mulligan Manor- 0.2 mile walk to Vitos Ristorante and Pizzeria and many others!
2.0 star property
Southern Pines
9.8 out of 10, Exceptional, (9)
"Very nice place. A short walk from downtown. Comfortable beds and ice cold A/C"
United States
Joshua R.
The price is NZ$562
includes taxes & fees
3 Jan - 4 Jan 2026
Mulligan Manor- 0.2 mile walk to Vitos Ristorante and Pizzeria and many others!

The Downtown Pines Hideaway - Walkable to Downtown Southern Pines!

The Downtown Pines Hideaway - Walkable to Downtown Southern Pines!
Southern Pines
10.0 out of 10, Exceptional, (9)
"Walkable to downtown and perfect weekend getaway location!"
United States
Scott B.
The price is NZ$509
includes taxes & fees
4 Jan - 5 Jan 2026
The Downtown Pines Hideaway - Walkable to Downtown Southern Pines!

The Quail House - Marvelous 3-bedroom house - Modern luxury on Pinehurst #3

The Quail House - Marvelous 3-bedroom house - Modern luxury on Pinehurst #3
Pinehurst
10.0 out of 10, Exceptional, (1)
"This is a one level home that is beautifully updated inside. It was an open floor plan with one bedroom and in-suite bath on the opposite end of house from two bedrooms and bath on other end of house. It has lots of windows with a view of the golf course in the back. A back porch with rocking chairs and a screen porch with rockers as well. Wonderful stay!"
United States
Pam R.
The price is NZ$688
includes taxes & fees
12 Jan - 13 Jan 2026
The Quail House - Marvelous 3-bedroom house - Modern luxury on Pinehurst #3

Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse

Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse
Pinehurst
9.8 out of 10, Exceptional, (36)
"Great! Nice host and place"
United States
Tim K.
The price is NZ$352
includes taxes & fees
4 Jan - 5 Jan 2026
Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Five Points Hotel Reviews

Find out more about Five Points

Everything you need to know about Five Points holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Five Points holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Five Points holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Five Points holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Five Points. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Five Points holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Five Points holiday rentals we have selected for you start as low as NZ$250 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Five Points rentals

At Expedia, we put the best Five Points holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Five Points rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Five Points holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Five Points. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Five Points?

Yes, there are holiday rentals close to the most popular sights in Five Points, or you can select a more secluded option if you're looking for a relaxing stay. Five Points is known for its golf courses.

What are some of the best holiday rentals that Five Points has to offer?

Pool-Sleeps 20-Stylish- 5 mins to downtown Southern Pines- Close to Pinehurst: This holiday home rental outside of Five Points offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What can I see and do in Five Points?

While you're exploring the area, Lake Rim Park and Beaver Creek are a couple of picturesque spots to get outside and enjoy nature. Carolina Horse Park and Deercroft Golf Course are other places to visit while you're in town.

What are holiday rentals like in Five Points?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Five Points. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family gatherings.