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Five Points Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Five Points vacation rentals

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

Apartment in Pinehurst

Located in # 6 golf community, close to First Health Moore Regional Hospital.
10.0 out of 10, Exceptional, (67)
"Great stay in Pinehurst!"
United States
jb22901
The price is ￥10,138
￥23,793 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Located in # 6 golf community, close to First Health Moore Regional Hospital.
Terrace/patio
Calhoun Clubhouse - 5 Bedroom Split Level Home Near Pinehurst #6 / Firepit 🔥

Vacation Home in Pinehurst

Calhoun Clubhouse - 5 Bedroom Split Level Home Near Pinehurst #6 / Firepit 🔥
2.0 star property
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 ￥22,524
￥79,591 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Calhoun Clubhouse - 5 Bedroom Split Level Home Near Pinehurst #6 / Firepit 🔥
Desk, iron/ironing board, free WiFi, bed sheets
The Lucky Lie - Entire Condo in Pinehurst

Condo in Pinehurst

The Lucky Lie - Entire Condo in 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 ￥13,257
￥36,323 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Lucky Lie - Entire Condo in Pinehurst
Private kitchen
The McCaskill Cottage in the Village of Pinehurst!

Vacation Home in Old Town Pinehurst

The McCaskill Cottage in the Village of 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 ￥13,359
￥42,342 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The McCaskill Cottage in the Village of Pinehurst!
3 bedrooms, WiFi, bed sheets
Gene's Green - Mins from downtown!

Condo in Pinehurst

Gene's Green - Mins from downtown!
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 ￥13,476
￥57,701 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Gene's Green - Mins from downtown!
Fridge, microwave, oven, stovetop
The Cottage at Knollwood Manor

Cottage in West Southern Pines

The Cottage at Knollwood Manor
2.0 star property
9.8 out of 10, Exceptional, (15)
"Love it, was perfect for us. "
United States
Creative Technical Solutions
The price is ￥11,698
￥29,081 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Cottage at Knollwood Manor
Fridge, microwave, oven, stovetop
COMPLETELY REMODELED 3 BDR, 2 Bath, Golf Course View Condo

Condo in Pinehurst

COMPLETELY REMODELED 3 BDR, 2 Bath, Golf Course View Condo
2.0 star property
10.0 out of 10, Exceptional, (16)
"Excellent location and a fabulous property."
United Kingdom
ALAN N.
The price is ￥25,834
￥56,494 total
includes taxes & fees
Dec 31 - Jan 1, 2026
COMPLETELY REMODELED 3 BDR, 2 Bath, Golf Course View Condo
Interior
2BD Pinehurst Golf Condo on Fairway of No. 3. Near Village, Resort & Fair Barn

Condo in Pinehurst

2BD Pinehurst Golf Condo on Fairway of No. 3. Near Village, Resort & Fair Barn
2.0 star property
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 ￥16,470
￥41,527 total
includes taxes & fees
Jan 13 - Jan 14, 2026
2BD Pinehurst Golf Condo on Fairway of No. 3. Near Village, Resort & Fair Barn
Fridge, microwave, oven, stovetop
"Charming 3-Bedroom Home with Private Gym in Prime Neighborhood!"

Vacation Home in Westover

"Charming 3-Bedroom Home with Private Gym in Prime Neighborhood!"
9.0 out of 10, Wonderful, (12)
"I would book again"
United States
Warren J.
The price is ￥11,261
￥44,272 total
includes taxes & fees
Jan 11 - Jan 12, 2026
"Charming 3-Bedroom Home with Private Gym in Prime Neighborhood!"
Interior
Newly Renovated Property.

Condo in Pinehurst

Newly Renovated Property.
10.0 out of 10, Exceptional, (132)
"Great place"
United States
Darron G.
The price is ￥21,056
￥46,882 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Newly Renovated Property.
Fridge, microwave, oven, stovetop
Great golf property - walking distance to Pinehurst Resort

Condo in Pinehurst

Great golf property - walking distance to Pinehurst Resort
10.0 out of 10, Exceptional, (103)
"Nice place great for golf trip"
United States
Eric M.
The price is ￥20,276
￥46,002 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Great golf property - walking distance to Pinehurst Resort
Terrace/patio
Sweet Retreat w/ Fire Pit, Near Downtown & Golf

Vacation Home in Southern Pines

Sweet Retreat w/ Fire Pit, Near Downtown & Golf
2.0 star property
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 ￥30,024
￥68,198 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Sweet Retreat w/ Fire Pit, Near Downtown & Golf
Interior
5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip

Condo in Pinehurst

5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip
9.6 out of 10, Exceptional, (15)
"Great golf stay"
United States
Patrick K.
The price is ￥12,774
￥51,621 total
includes taxes & fees
Jan 4 - Jan 5, 2026
5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip
Interior
Beautiful 1 Bed Condo on Pinehurst Course No.5!

Vacation Home in Pinehurst

Beautiful 1 Bed Condo on Pinehurst Course No.5!
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 ￥10,568
￥32,237 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Beautiful 1 Bed Condo on Pinehurst Course No.5!
Pool
NEW LISTING! Pinehurst Tee Time Retreat

Condo in Pinehurst

NEW LISTING! Pinehurst Tee Time Retreat
9.8 out of 10, Exceptional, (6)
"Great location !!Great condo !!"
United States
Eric Z.
The price is ￥17,755
￥55,026 total
includes taxes & fees
Jan 4 - Jan 5, 2026
NEW LISTING! Pinehurst Tee Time Retreat
Fridge, microwave, oven, stovetop
The Perfect Lie in Pinehurst! A golfer's paradise!

Condo in Pinehurst

The Perfect Lie in Pinehurst! A golfer's paradise!
9.8 out of 10, Exceptional, (60)
"Great location, very comfortable beds, very clean. "
United States
kristine r.
The price is ￥17,469
￥42,476 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Perfect Lie in Pinehurst! A golfer's paradise!
Fridge, microwave, oven, stovetop
Mulligan Manor- 0.2 mile walk to Vitos Ristorante and Pizzeria and many others!

Villa in Southern Pines

Mulligan Manor- 0.2 mile walk to Vitos Ristorante and Pizzeria and many others!
2.0 star property
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 ￥20,471
￥51,548 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Mulligan Manor- 0.2 mile walk to Vitos Ristorante and Pizzeria and many others!
Private kitchen
The Downtown Pines Hideaway - Walkable to Downtown Southern Pines!

Apartment in Southern Pines

The Downtown Pines Hideaway - Walkable to Downtown Southern Pines!
10.0 out of 10, Exceptional, (9)
"Walkable to downtown and perfect weekend getaway location!"
United States
Scott B.
The price is ￥12,634
￥46,353 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Downtown Pines Hideaway - Walkable to Downtown Southern Pines!
Private kitchen
The Quail House - Marvelous 3-bedroom house - Modern luxury on Pinehurst #3

Vacation Home in Pinehurst

The Quail House - Marvelous 3-bedroom house - Modern luxury on Pinehurst #3
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 ￥16,571
￥61,895 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Quail House - Marvelous 3-bedroom house - Modern luxury on Pinehurst #3
Fridge, microwave, oven, stovetop
Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse

Condo in Pinehurst

Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse
9.8 out of 10, Exceptional, (36)
"Great! Nice host and place"
United States
Tim K.
The price is ￥13,257
￥32,078 total
includes taxes & fees
Jan 4 - Jan 5, 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

Comfort Inn Pinehurst - Southern Pines

Comfort Inn Pinehurst - Southern Pines

10/10 Excellent
"Clean. Stress free check in and good breakfast "
Jason 1-night trip
Posted 4 days ago
Comfort Inn Pinehurst - Southern Pines

Find out more about Five Points

Search for holiday rentals in Five Points on Expedia! You can easily find your home rentals, villas, holiday apartments in Five Points using one of the methods below:

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Look no further and take a look at our great range of rental properties in Five Points!

Frequently asked questions

Are there vacation rentals in Five Points?

Yes, we give you a choice of vacation rentals close to popular points of interest in Five Points, or you can select a secluded option if you want a relaxing place to stay. Five Points is known for its golf courses.

What are some of the best vacation rentals in Five Points?

Pool-Sleeps 20-Stylish- 5 mins to downtown Southern Pines- Close to Pinehurst: Visitors like this Five Points vacation home rental. It offers a patio, a selection of games, and a barbecue grill 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 vacation rentals like in Five Points?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Five Points. Vacation rentals provide amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for small groups.