Holiday rentals with a pool in High Point

Cool Off @ The Cave • Peaceful Adult Oasis

Tucked away in the peaceful Sedgefield PGA community of Greensboro, The Cave is a 2-bedroom, 1-bath poolside guest suite designed for relaxation & comfort. This serene grown-up getaway boasts luxury amenities including exclusive use of our private seasonal (summer) pool, indoor & outdoor theaters, Brunswick pool table, bar/ kitchenette, & more. Enjoy personalized service & a prime location—just minutes from top dining, shopping, golf courses, entertainment venues, sports arenas, & universities.

Family · Location · Check-in

Private 4BR w/ Heated Pool, Hot Tub & Fire Pit

Welcome to Oak Hollow Estates, a sought-after lakeside neighborhood in High Point, NC. This spacious 3,000+ sq ft home has 4 bedrooms, 5 beds, a saltwater pool(heat avail for fee Mar-Oct only)+year-round hot tub, fire pit, and foosball table. Fully equipped kitchen, home office & printer, high-speed wifi (500+Mbps). Fenced backyard, 4 free parking spaces. Minutes from Oak Hollow Lake, HPU, and the Furniture Market. GSO airport just 19 min away Sleeps 12max. Dog-friendly. Washer/dryer in-home

Family · Location · Kitchen

Cozy King Blue H2O Staycation , Pool & Hot Tub

Quiet secluded STAYCATION w/ Fully Fenced Back Yard for the PUPS. We have a hot tub for year round use and a Stock Tank Pool (Closed until 5/23/25) . A fire pit to unwind. Back yard BBQ with a built in bar top table and a cozy Sectional to enjoy the outdoors. Inside we have an amazing plush King size mattress to take all stress away. Full kitchen * Hot tub - I will do my best to have it available at all times unless there is a mechanical issue. (No refunds if hot tub is not available)

Value · Location · Hiking

Cozy and Convenient - Entire Townhome w/view!

This immaculate and cozy three (3) bedroom townhome is fully furnished and has everything you need for a comfortable stay. It is located in High Point, NC only 1 mile from the Palladium shopping center with many great restaurants, shopping, and a movie theater. The home is situated in the back of the development and is very quiet and peaceful. Near PTI airport, High Point University, Guilford Tech, and close to the Furniture Market. Fast internet, ideal remote workspace! You'll love it!

Location · Family · Decor

Sanctuary – 1bedroom & 1bathroom

My modern and convenient condo located in the heart of Winston-Salem’s shopping district will provide you with a 1 bedroom & bathroom space. The condo is professionally furnished and cleaned to provide a 5 star experience. Basic appliances provided (microwave, kitchen appliances, washer & dryer, dishwasher, Keurig). Very spacious with patio furniture for extra relaxation! You can also enjoy the community pool and gym. This space is NOT shared. Guests have the entire space to themselves.

Family · Location · Biking

Grey Sapphire Hideaway - 2BR/2BA w/ Arcade

Nestled along a leafy tree-lined street in a quiet neighborhood is this stylish property with all the modern comforts of home and an inviting community pool waiting for you to enjoy. Inside this modern hideaway, you’ll find plush sofas, a warm fireplace, a gourmet kitchen, king and queen bedrooms and a bright sunroom filled with a Pac-Man arcade & an air hockey table. Centrally located only minutes from Hanes Mall, Downtown Winston Salem, Medical Centers, shops, restaurants, and more!

Location · Value · Condition

Historic Street House/Hot Tub

3 min. drive to Furniture Market, Hospital, Truist Point Baseball Stadium, Children’s Museum. High Point University, Carolina Core Soccer 1 mile away. Uptowne shops, Restaurants, Breweries, Alex's House Diner, Toms Place, Sweet Ol Bill's, Historic JH Adams Inn less than a mile away. Weekend Live Music, Greenway/Pickleball Courts. Joy Bar coffee 2 blocks away. Farmers Market. Library, Krispy Kreme, Relaxing front porch or ping pong inside! Hot Tub. 10 foot plunge pool. Backyard chickens!

Location · Family · Outdoor spaces

Modern, Relaxing, Peaceful home near Mkt and HPU

Stay at this luxurious house located in a beautiful sub-division in High Point! Self-Check in is available and the host will be available to assist with any potential issues. House is located: 15 miles from PTI Airport 5 miles from High Point Furniture Market 4 miles from High Point University 11 miles from Winston Salem State 24 miles from Wake Forest University 14 miles from downtown GSO/UNCG/NC A&T 2 miles from I-74 which connects to I-40 and I-85 35 miles from Pilot Mountain

Family · Value · Sleep quality

3BR Condo w/ Pool Near HPU & Market + Desk

Enjoy modern comfort and convenience in this newly renovated 3 bedroom, 2 bath Condo near Downtown High Point and HPU.Fully equipped kitchen,free parking, High speed Wi-Fi, computer desk,free Netflix, pool access starting in may, and in-unit laundry with washer and dryer, this space is perfect for families, couples, or businesses travelers looking to relax and explore everything High Point has to offer. Ring doorbell cameras located outside for security purposes and compliance.

Location · Value · Hospitality

Townhouse near the Airport

Welcome to my home! Ideally located just 5 minutes away from the PTI airport, this home boasts a convenient main level primary bedroom with Spacious Living Room and Kitchen. Upstairs, you'll discover a cozy and inviting loft, a second bedroom, and a bathroom. The home also includes a well-equipped kitchen, perfect for cooking your own meals or eating taking out. The living room features a cozy fireplace and Apple TV for your entertainment. I look forward to hosting you!

Family · Location · Amenities

Comfy townhouse near airport and dining!

Your family will be close to everything when you stay at this centrally-located townhouse. Just minutes from the airport and shopping plazas, with plenty of dining and entertainment options within a short drive! Easy access to multiple highways makes this a convenient stay to get to Greensboro, High Point, or Winston Salem. We offer high speed internet with wifi, a seasonal outdoor pool, and free parking in front of unit. A perfect stay for those on business or vacation!

Value · Family · Indoor spaces

5 Min to High Point Market | Sleeps 8 | Near HPU

Escape to Arden Place Retreat, an elegantly relaxed home in a quiet, family-friendly neighborhood just minutes from downtown High Point and 20 minutes from Greensboro. Enjoy a private in-ground pool with ample lounge space, a gourmet kitchen with dining for 10, 3 bedrooms with a total of 4 beds, and bonus pop up bed, spacious baths, a cozy game area, and full laundry. Light-filled and welcoming, it’s the perfect luxury family retreat for making lasting memories.

Family · Comfort · Indoor spaces