Vacation rentals with a pool in Louisa County

4.74 out of 5 average rating, 19 reviews

Lakefront Lake Anna, Pool, Hot Tub, Dock

Your backyard opens directly to Lake Anna. From the main deck, the trees part and the cove appears—quiet water, private dock, a seasonally heated pool, a separate year-round hot tub, and a boathouse that feels like your own waterfront clubhouse. Inside, you’ll find a chef’s kitchen, multiple lounge spaces, a dedicated theater, karaoke room, full game floor, kids’ treehouse loft, office/den, and beautifully styled bedrooms (plus an optional 2-bedroom guest house above the carriage garage). This h

The outdoor area features a large pool surrounded by sun loungers and shaded seating. Bright umbrellas provide respite from the sun. A blue house with a spacious deck is visible in the background, along with a storage shed and landscaped grassy areas.

4.91 out of 5 average rating, 56 reviews

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.

5.0 out of 5 average rating, 74 reviews

A swimming pool is prominently featured, with clear blue water reflecting the sky. Surrounding the pool are stone tiles, offering ample space for relaxation. In the background, playground equipment and a basketball hoop are visible, set against a natural landscape of trees and open fields.

Farm stay in Bumpass

Farm Stay: Vineyard, Animals, Heated Pool

Welcome to Orchid Hollow, our family farm and vineyard in the Virginia Piedmont. The carriage house awaits at the end of winding country roads and a long gravel drive. Start your day with coffee on the deck overlooking the vineyard as horses graze below. Spend the afternoon by the heated pool, or grab a fishing pole and head to our 5-acre lake for fishing, canoeing, or a pedal boat. End the day with wine by the lakeside bonfire as the sun sets and kids run free or swim in the color-lit pool.

Superhost

5.0 out of 5 average rating, 5 reviews

Lakefront | Pool, Hot Tub, Dock, Foosball, Peloton

Lakefront retreat on 2.7 wooded acres, stunning lake views, resort-style amenities perfect for family getaways. • Private POOL & HOT TUB overlooking lake • Dock: Adirondack chairs, paddleboards, water mat & fishing rods • Deck: Gas grill, fire pit & outdoor dining • 1/4-mile hiking trail through woods • Gym: Peloton & weights • Gameroom: pool table, foosball & darts • EV Charger • Lawn space for cornhole & outdoor fun • Expansive deck w/ peaceful view & wooded surroundings • Happy dog fee $179

Guesthouse in Gordonsville

The exterior of La Petite Maison showcases a charming guest house with a large screened porch, surrounded by vibrant flower beds. A turquoise umbrella shades a lounge chair next to the seasonal in-ground pool, providing a relaxing outdoor space.

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.

4.9 out of 5 average rating, 195 reviews

4.95 out of 5 average rating, 21 reviews

Discounted Holiday Getaway Perfect For Families

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.

4.99 out of 5 average rating, 147 reviews

The exterior of the converted barn and silo is softly illuminated by string lights at dusk. A serene pond, framed by smooth stones, reflects the warm glow of light. The porch invites relaxation with its spacious seating and rustic charm, creating a peaceful outdoor setting.

Barn in Louisa

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.

5.0 out of 5 average rating, 14 reviews

Home in Bumpass

Southern-Style Waterfront on Lake Anna's Pvt Side

Escape from your day-to-day at Wine Down - your private-side waterfront Lake Anna, Virginia, retreat on over 9 acres. The custom-built home - completed in late 2017 - evokes Southern charm and hospitality, and it features water views from nearly every bedroom in the home. With two master suites (one upstairs and one on the lower-level), a kids' bunk room, two additional bedrooms, and an oversized playroom/guest room, Wine Down is the perfect vacation rental home for groups and families.

4.95 out of 5 average rating, 78 reviews

A serene house sits on a sprawling lawn, with a wrap-around porch featuring wooden railings. A rainbow arcs over the roof, adding a colorful element to the sky. Gravel pathways lead to the entrance, framed by lush greenery in the background.

Home in Louisa

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!)

The exterior of a spacious two-story home is set against a backdrop of lush greenery. A welcoming porch with white railings is visible, framed by well-maintained landscaping. A gravel driveway leads up to the house, and the property features a mix of trees and shrubs for a serene environment.

5.0 out of 5 average rating, 18 reviews

Nature’s Nook at Lake Anna

Welcome to your perfect Lake Anna family retreat! This spacious home sleeps 10 across 5 cozy bedrooms and 4 bathrooms, offering plenty of room for everyone. Enjoy the private boat dock for lake adventures, relax in a cozy backyard, or take a short walk to the beach. The dedicated workspace is ideal for remote work, while the large deck and backyard are perfect for outdoor activities. This home is ideal for boating, swimming, and unwinding in a peaceful, family-friendly getaway

4.75 out of 5 average rating, 8 reviews

Yurt in Gordonsville

Shenandoah 2BR Yurt on delightful Resort w/amen.

Located on over 1,000 acres of rolling hillside 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. Try our 2-BR luxury yurt stay which includes four-poster beds w/plush linens, flat-screen TVs, elegant bathrooms and fully-equipped kitchens, all with central heat and air, large deck area w/ summer kitchen.