Holiday rentals with a pool in Highlands

Estate-Like Retreat/ Walk to Town /Hot Tub & Pool

Escape to Meadowstream Lodge—a one-of-a kind mountain retreat on 2.5+ acres. Rare open pasture (perfect for kids & pets), creek, forest, and view of Black Rock Mountain create a true estate feel—yet you can walk to downtown dining, shops, and bars. Relax in the heated pool + hot tub, gather around the fire pit, or unwind on the café-lit deck with fire bowl. Thoughtfully designed interiors. Fully stocked for families, pets, and play. We've carefully planned every detail for an unforgettable stay.

Cozy Cabin • Creek, Trails, Pool, Hot Tub & Gym

Adventure meets comfort! Explore Sylva’s breweries, Dillsboro’s artsy village, Cashiers’ upscale charm, Franklin’s gem mining, and Cherokee’s culture. Hike trails, fish in the creek, zip-line, raft, tube (tubes provided), boat, or go on a trail ride. Easy drive, no steep roads. Enjoy seasonal pool, hot tub, gym, clubhouse, playground, trails, and Casper mattresses. Minutes to Western Carolina University (WCU) & Castle Ladyhawke. Near NOC, Blue Ridge Parkway & Great Smoky Mountains National Park.

Highlands Spacious Cabin w/Hot Tub,games,gym+wifi

Bring the whole family to this stunning, newly updated Highlands retreat! This spacious 5BR + loft home features 3 full & 2 half baths, 3 king bedrooms, and 2 family rooms with large-screen TVs. Enjoy a chef’s kitchen with top-of-the-line appliances, cozy fireplace, fire pit, hot tub, and games including air hockey, ping pong, and Pac-Man arcade.Professionally decorated for comfort and style, with upgraded Starlink Wi-Fi. Just 4 miles from downtown Highlands—your perfect mountain getaway awaits!

Cataloochee Sky *private spring fed pool & hot tub

This VERY RUSTIC, contemporary home designed by Norwegian architect, Bernardo Rostad, is situated at the foot of the Great Smoky Mountains National Park & adjoins the renowned Cataloochee Ranch. Enjoy spectacular sunrises from the east facing windows perched high above the clouds at 4,700 ft elevation w/ 360 degree views of the Smoky Mountains, located on 25 PRIVATE acres. *See "THE SPACE" description below & confirm that you have read prior to booking request. Reply: I have read "THE SPACE".

Treetop Cabin w/ firepit + Mountain Stream

No matter the time of year, adventure always awaits in Sky Valley! With room for the whole family and your four-legged friend, this 3-bedroom, 2-bath cottage has all the amenities to make your time here effortless and unforgettable. Hike, zipline, golf, and sightsee in the beautiful mountains of North Georgia! Enjoy the sound of running water from a mountain runoff stream that flows right through the property! Enjoy resort amenities including pool (seasonal), hot tub, sauna, gym, and tennis.

Beautiful Lake Keowee Condo with great Amenities

"Boasting lake views, a fully equipped kitchen, and resort-style amenities, this 2-bedroom, 2-bath Salem vacation rental condo in Keowee Key will have you experiencing the true meaning of life on the lake. Cool off with a dip in the community's outdoor pool which sits right next to the marina where you can rent a boat for a day out on the water. Tee up a round of golf on the renovated 18-hole course, walk along the trails of Oconee State Park, or catch a football game at Clemson University!"

Stunning Views and Hot Tub, at Beary Cozy Cabin

Welcome to our stunning mountain retreat, at Beary Cozy Cabin! Our home is located on Cowee Mountain in the Great Smoky Mountains, near the charming town of Franklin, NC. Featuring 4 bedrooms, 4 full baths, and 2 half baths, our cabin is the perfect getaway for up to 12 guests. Enjoy our expansive deck with a hot tub and breathtaking mountain views, perfect for seeing the natural fog that gives the Smokies their name. Come experience the area’s beauty and create unforgettable memories!

Wonderful mountain cottage with amazing view!

3 Bedrooms, 2 Baths, Sleeps 6-8 Enjoy phenomenal, long-range mountain and lake views all the way to South Carolina from the expansive windows and covered back deck of this high elevation, one-level, three-bedroom, two-bath home. Open floor plan, stone fireplace, wood flooring, granite countertops, garage, and natural light. Full resort amenities such as golf, tennis, indoor and outdoor pool and hot tubs, lake, waterfalls, weight room, and skiing. Vibrant mountain dining and shopping!

Beautiful Cozy Mountain Retreat

This beautiful space is a large, 1600 sq foot downstairs basement apartment, with a private entrance through the shared garage. It is a quiet peaceful area and is conveniently located nearby unique shopping in Cashiers, as well as beautiful gorgeous hikes, waterfalls. and lakes. An outdoor deck circles the entire length of the apartment and many windows provide a beautiful view of the mountain. At the Wyndham Resort, just down the road is recreational fun for everyone with a pass.

DeerSong Cottage - Private Hot Tub Under the Stars

Welcome to DeerSong Cottage — a brand-new 3-bedroom mountain modern retreat in Highlands, NC, blending clean design with rustic charm. Relax by the fireplace, sip coffee on the deck, or soak in the private hot tub under the stars while enjoying the fresh mountain air. Just 4.5 miles (about 8 minutes) from downtown Highlands, you’ll find local shops, dining, and easy access to waterfalls and trails like Dry Falls, Glen Falls, Sunset Rock, and Whiteside Mountain. @DeerSong_Cottage

Acorn Cottage in Highlands, NC “Fireplace"

Unforgettable adventures and quality time with the loved ones await you, when you book this cozy mountain hollow getaway! Acorn cottage is the perfect mountain retreat located minutes from Main street in Highlands, NC. A fabulous shopping and dining experience awaits! The home is equipped with fiber optic cable to provide a seamless Smart TV or Work streaming experience. Plenty of parking is available. Wood Burning Fireplace on porch! Gas Fireplace in the Living Room.

Keowee Key Luxury Condo - Stunning Views!

Freshly renovated condo at the sought after Tall Ship condos in Keowee Key. This is hands down the best unit the complex has to offer with amazing views. Enjoy grilling out on the patio overlooking the marina, walking on the trail, or relax in the pool which is only a short walk away. This is truly a paradise. Guest boat slip is available at the marina for boats or jet skis. Slip is $50 per day. Recommended to book one month in advance.