Holiday rentals with a pool in Lake Anna

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

Lakefront retreat on 2.7 wooded acres, stunning lake views, and resort-style amenities creates perfect 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 • Lawn space for cornhole & outdoor fun • Expansive deck w/ peaceful lake view & wooded surroundings • Happy dog fee $179

Family · Outdoor spaces · Cleanliness

Lakefront Getaway | Close to DC | Near Winery

This Lake House features a delightful open floor plan and modern design with direct access to water from the backyard. Perfect for swimming, fishing and enjoying sunsets. Included: Awesome work-from-home setup with dual monitors, universal docking station, keyboard and mouse, so you can spend as much time out of the office as possible. The community offers a number of amenities including a pool, beaches, golfing and more! If none of those strike your fancy, our favorite winery is 5 min away.

Location · Family · Long stay

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.

Location · Family · Kitchen

Beach, Hot Tub, Arcade, Golf, Pub: The Lucky Duck!

Unforgettable retreat with partial lake view, luxurious 7-person Jacuzzi, custom pub featuring a retro 4-player arcade with 7,500+ games and trackball, cozy woodstove, and delightful surprises! Ideal for epic family vacations, The Lucky Duck in the exclusive gated Lake of the Woods offers year-round fun—two lakes, eight pristine beaches, two pools, a golf course, an equestrian center, and scenic parks with fitness trails await! Come experience lakeside fun and relaxation! #TheLuckyDuckLOW

Location · Family · Hospitality

Lakefront at Turtle Cove

Enjoy the lake life in a peaceful quiet cove on the gorgeous large lake within Lake of the Woods. When not enjoying the newly renovated home with a vaulted ceiling great room, huge screened porch, and a desk and flat screen TV in each room, you can swim, float, kayak, or paddleboard in the quiet, secluded cove, or enjoy the 9 beaches or 2 community pools. Catch fish off the dock in one of the best fishing coves on the lake, and then warm up at night by the fire pit . Great for families.

Location · Family · Layout

Bellemount, circa 1850, horse farm with pool

Farm house on working horse farm. Originally built circa 1850, the house was most recently renovated in 2023. The farm is home to around 20 horses and two tractors. The family that runs the farm has been here since 1980. Kings Dominion Theme Park - 17 miles Meadow Event Park/State Fair - 20 miles Lake Anna Pleasants Landing - 12 miles Town of Ashland - 21 miles Downtown Richmond - 33 miles 15 min from I-95 Across the street we have a 3B/2b as well. Inquire for more information.

Location · Family · Checkout

Lakefront Luxury Villa w/ Infinity Pool, Swim Spa

"Lake Anna Luxury" is a one-of-a-kind, ultra-modern lakefront villa with gorgeous sunset views over the lake. The exterior boasts a heated infinity pool, a massive 15 person swim spa (hot year round), a private beach, dock, and kayaks. Inside, you'll love the soaring industrial ceilings with walls of glass and modern finishes. With 8 bedrooms (7 masters), the villa sleeps 20 comfortably. Plus, pet friendly! Managed by Chris at New School Hosting- see my profile for more reviews.

Location · Family · Backyard

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

Location · Family · Comfort

Lakefront Access | Hour from DC | Kayaks Provided

Welcome to Lakeside Serenity, located in the Locust Grove gated community of Lake of the Woods. This charming residence, situated in a quiet cove, features a spacious backyard with direct lake access perfect for swimming, fishing, kayaking, or lounging lakeside. Enjoy the convenience of an on-site grill for delightful barbecues and dine al fresco in our outdoor seating area overlooking the lake. This home is a haven for anyone looking for a peaceful getaway!

Family · Location · Pets

Lakefront Lake Anna, Boat Dock, Deck Views

Halcyon Blue is a luxury lakefront escape on Lake Anna’s exclusive Private Side, designed for elevated comfort, connection, and calm. This 7-bedroom, 3-level retreat features gourmet kitchens, a private dock and beach, kayaks, paddleboard, fire pits, hot tub, and gym. Enjoy lake views from expansive decks, a game room with arcades and PlayStation, and serene screened-in porches. Ideal for families, groups, or anyone seeking a peaceful, unforgettable getaway.

Family · Location · Condition

Panorama Shores

Take a break and unwind at this peaceful expansive oasis. This lake front retreat boasts more lake access than you can imagine. Your own, pool, tennis court and huge yard to create memories with your friends and family. All linens provided including a set of outdoor towels for your use. The kitchen has been newly expanded and completely upgraded with 3 ovens, 2 islands and 2 sinks. This property was formerly listed as Anna Breeze. Now managed privately.

Family · Location · Accuracy

Lakefront Escape | Private Pool + Dock Access

Immerse yourself in lakeside luxury at our serene waterfront retreat, located in the premier Rock Island Landing community on the private side of Lake Anna. Built in 2024, this spacious home features an open-concept design with three separate living areas, perfect for families and groups. Enjoy exclusive amenities, including a private boat dock, hot tub, fire pit, and a brand-new private waterfront pool for the ultimate lake getaway.

Family · Beach · Decor