Holiday rentals with a pool in Louisa County

18th Century Charming Bungalow #127 Pool & Spa

Escape & unwind from city life on a beautiful historic, 250 acre estate 20 minutes from Charlottesville! Our historic bungalow is perfect for those who want to take a step back in history and enjoy the wonder nature has to offer! Steep stairs access the upstairs bedroom, 2 can sleep downstairs. We are only 20 min away from Jefferson's "Monticello" & from James Madison's " Montpelier". Treat yourself to an onsite certified massage with a wellness therapist.Please book online at Spagreensprings.

NEW 4BR Lake Anna with Pool, Beach, Patio, Hot Tub

Owl's Nest is the ultimate Lake Anna retreat, a newly built modern farmhouse in The Waters community. It combines cozy woodland charm with a prime location near the community beach. Perfect for families, couples, or groups, it features a boat slip, huge patio with 7-person hot tub, grill, and a fire pit, and a backyard playhouse with swings. The home offers high-end details, and all 4 bedrooms have attached bathrooms. Community amenities like a pool* and pickleball courts provide year-round fun.

LakefrontPool WaterSlide Sauna Dock HotTub Peloton

Lake Anna Lakefront: Private pool, 50-foot water slide, barrel sauna, Peloton, kayaks, ping-pong/pool table, game room... Gather 'round fire pit under starlit sky. Relax in the sauna or soak in a secluded hot tub, both overlooking the lake. No steps to primary bedroom on 1st floor. Private Dock: 3 kayaks, floats Game Room: foosball, air hockey, hoops, arcade Sleeps 12 in 5BR+loft: K, K, K, Q, Q, 2x bunk (twin/full) 3-Car Garage w/EV charger (standard/Tesla) $150 Dog fee, $150/day pool heating

Blue House and a Pool

Relax at Lake Anna with friends and family at your own pool, hot tub and dock. Blue house boasts numerous spaces for entertaining and private chill time. House features 4 bedrooms, 3 large couches and 3 full bathrooms. The gourmet kitchen is fully stocked and ready for a home cooked meal after a full day on the lake. Tim's at Lake Anna is a short car ride or boat ride to enjoy a meal and cocktail. The Cove and Lake Anna Plaza at the 208 bridge are close by including boat and jet ski rentals.

2BR Del Cabin Shenandoah Resort with resort amenities

Located on over 1,000 acres of rolling hillside and lush pasture lands that encompass a scenic 60-acre lake, Shenandoah Crossing® is the perfect place to stay for those who love the outdoors. The resort combines an old country estate and horse farm with acres of wilderness in a pristine area that lies just beyond the Shenandoah Valley. Rustic elegance of a 2-bedroom cabin featuring full kitchens and baths, fireplaces, master bedrooms, balconies and porches, and separate dining and living areas.

3 Acre 5BR Resort: private pool, hot tub boat dock

Gather your loved ones at a secluded 5BR lakehouse on 3 lush acres at Lake Anna. Dive into the new heated Salt-Water Infinity pool & hilltop lake view hot tub, soothe muscles in the sauna, or spark friendly rivalries in the game room and volleyball court. Cook up joy in the fully stocked kitchen and unwind by the fire under crystal clear starry skies. Serene water views, fireside chats, and room for every adventure, this is where cherished memories are made—your ultimate private escape awaits!

Family-Friendly Retreat w/Pool Tennis Beach Access

Welcome to Always On Lake Time! We are your destination for relaxation and unforgettable family fun at Lake Anna. Our retreat offers access to the lake from the comforts of The Waters at Lake Anna, a private, resort-like community. Enjoy mornings sipping coffee on the front porch, afternoons by the community pool and beach, and evenings playing tennis. Fish from the community docks or launch your boat. We also have a game room, two kayaks, two paddle boards, and life vests for your enjoyment.

La Petite Maison at Hedgeapple Hollow

La Petite Maison (our guest house) is the perfect place to simply get away from the hustle and bustle and relax! Sit in the private screen porch and watch the sun melt into the mountains. Deer, hummingbirds, bluebirds, and the occasional turkey like to hang out on the 8 acres of the property, perfect for any wildlife lover. Enjoy the fenced in common area featuring a seasonal in-ground pool. Conveniently situated near award-winning wineries, Montpelier, and historic downtown Gordonsville.

Unique OASIS - Silo Barn - Swim Pond- 5 Miles Trai

4 unique rentals available (click our profile)! Unwind at this Central VA Country Paradise! Stay in a converted Barn & Silo w/ private natural swim pond and waterfall tucked into the woods on 140 Acres! Your own Oasis awaits, step out on your porch for coffee/drinks with the farm animals. Take a hike around the Lake on the 5+ miles of trails before cooling off in the pond while you gaze up at the stars. Sheep, Dwarf Fainting goats(next to silo 10' away), Chickens, Ducks, Bunnies, & Turkeys.

Poplar Cove - Lake Anna (Private Side)

Poplar Cove is a 2-bed 2-bath waterfront property with beautiful views. We are situated in a spacious cove; great spot for safely swimming, kayaking, floating or just sitting on the dock or one of the many patios. The backyard levels out at the bottom providing a perfect spot for spreading a blanket or enjoying backyard games adjacent to the private dock. This property is a downstairs walkout that is attached to the main house; but you will have your own entrance and private experience.

Tranquil Lakefront Farm Oasis: Heated Pool

Welcome to the charming 2BR 1Bath oasis on the magical 25-acre farm tucked back off a long gravel road. Escape the big-city crowds, take in the breathtaking views, and enjoy the tranquil and friendly ambiance where kids play, and the animals roam. Here's a glimpse of our fantastic offer: ✔ 2 Comfy BRs ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Outdoors (Pool, Games, Playground, Dining, Lounges, BBQ) ✔ Lake (Dock, Paddleboat, Canoe) ✔ Wi-Fi ✔ Smart TVs ✔ Parking See more below!

Venson’s Getaway!

Venson’s Getaway is a beautiful house that was recently remodeled into a comfortable and cozy getaway. The house sits on 30 acres of peaceful and private land, and in its immediate surroundings it has a nice patio with a fire pit and three grills, and a beautiful heated swimming pool that was also recently finished. The area is surrounded by nature, including a creek that runs through the property! It is also located 30 minutes away from Charlottesville (famous Monticello's location!)