Vacation rentals with a pool in Lake Anna

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Lake Anna

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Apartment in Madison

4.9 out of 5 average rating, 229 reviews

The Studio at Dark Run Retreat

Quiet studio on a secluded 5 acres only 3 miles from town. Kick back and relax by the pool in the warmer months, or in the hot tub in the cooler months. Small trails lead to the creek running along the property, maybe you'll even catch a glimpse of the deer or turkey that wander thru...we've even seen a lil bear once! There is an apartment above the studio, so we ask that you be mindful of those guests if occupied. *The studio got a make-over! As of 10/6/20, we will no longer be hosting pets*

Jul 14 – 21

$71 per night

Guest favorite

Guesthouse in Gordonsville

4.91 out of 5 average rating, 171 reviews

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.

Jul 28 – Aug 4

$125 per night

Guest favorite

Guesthouse in Charlottesville

5.0 out of 5 average rating, 110 reviews

Hidden Gem near town and Monticello with a pool

We call this our hidden gem because it's not too far from town, wineries, UVA, Monticello and more that Charlottesville has to offer, but yet it's far enough away from the hustle and bustle. The renowned Clifton Inn, a popular destination wedding venue is less that 1/4 mile away. Thomas Jefferson's Monticello is a 7 minute drive. The campus of UVA is a 15 minute drive. We call this our studio loft because it has the feel of a mountain cabin. The views are gorgeous and the setting is peaceful.

Mar 17 – 24

$185 per night

Guest favorite

Apartment in Ruckersville

4.98 out of 5 average rating, 115 reviews

Historic Estate: The Carriage House Near C'ville

One of the Historic Southern sporting Estates has been a 5* destination for the past five years for overnight stays, weddings, and events. We would be delighted to welcome you to the Carriage House, Pool House, or The Cottage. (Listed separately) Located on a 550-acre estate with 9+ miles of woodland trails with spectacular views of the Blue Ridge Mountains. Work or relax with our High-Speed Internet, two tournament pickleball courts, saltwater pool, or swim in our natural spring-fed lake.

Nov 14 – 21

$180 per night

Guest favorite

Home in Boston

4.97 out of 5 average rating, 117 reviews

Peacefield - Blue Ridge views near Culpeper

Welcome to the Peacefield! This retreat is nestled in the rolling foothills of the Blue Ridge Mountains in the shadow of Old Rag, overlooking Hazel River Farm (160 acres). The spacious estate is perfect for escaping the city. There are many options for relaxing with a deck, hot tub, pool (summer only), home theater, and an open kitchen connecting the dining and family rooms. The beauty of the estate includes walking trails, glimpses of sheep, and local art (watercolor and photography).

May 30 – Jun 6

$405 per night

Guest favorite

Home in Robertson

4.92 out of 5 average rating, 182 reviews

One Of A Kind Home in VA Wine Country on 50 acres

Welcome to Lumusa Lodge. Leave your cares behind as you turn onto the windy road that leads you to this beautiful 50-acre retreat. We are proud to share our home and hope your time here is rejuvenating. Designed/built by a Hollywood actor and situated in wine country, this home is an hour from Dulles, 45 minutes from Charlottesville & 15 minutes from Culpeper. We have an adjacent farmhouse if you need additional space. Great venue for weddings, bachelorettes, and other special events.

Feb 26 – Mar 5

$584 per night

Guest favorite

Farm stay in Bumpass

5.0 out of 5 average rating, 36 reviews

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!

Oct 26 – Nov 2

$306 per night

Guest favorite

Home in Mineral

5.0 out of 5 average rating, 10 reviews

Secluded Lakefront | Private Pool | Dock | Hot Tub

**Discover Ultimate Luxury at LesLee at the Lake: a Deep Water Lakefront Haven with Private Inground Pool, Hot Tub, and Dock** Nestled on the public side of Lake Anna, this picturesque 2.63-acre secluded property offers stunning waterfront views, a boat house for easy water access, and a lakefront fire pit. Our expansive and luxurious 9,000 sq. ft. home with game room, spacious kitchen, and movie theater, is ideal for an unforgettable escape and perfect for accommodating large groups.

Mar 3 – 10

$845 per night

Guest favorite

Cabin in Culpeper

4.97 out of 5 average rating, 159 reviews

Comfortable and unique 1790's log cabin

Recently restored 1790's log cabin with modern amenities on a 30 acre horse farm. Secluded wooded setting with pond view, less than 1,000 feet from main house and only 5 miles from downtown Culpeper with it's fine dining and quaint shops. Take a short drive to scenic Shenandoah hiking & biking trails, local vineyards and distilleries, Civil War sites, Commonwealth Equestrian Park, stroll around the farm or just unwind on the front porch or in front of the wood stove with a good book.

Jul 8 – 15

$120 per night

Guest favorite

Guesthouse in Troy

4.99 out of 5 average rating, 116 reviews

Beaver Pond Farm - Near Charlottesville

Relax at this unique and tranquil getaway. Sit on the screened in porch and enjoy the sights and sounds of nature while you enjoy a beverage. Take a walk on miles of trails that are adjacent to the property. Visit the Downtown Mall, Monticello, a Winery, a Brewery, or UVA (20 min). Enjoy a dip in the pool (JUN-AUG) or relax by the firepit - perhaps joined by the horses for cocktails. Feel like staying in - SmartTVs and Gig-speed Internet await. Easy checkout. No cleaning fee.

Dec 14 – 21

$127 per night

Guest favorite

Cabin in Gordonsville

4.87 out of 5 average rating, 306 reviews

18th Century Charming Bungalow# 127 pool & wifi

Escape & unwind from city life on a beautiful historic, 250 acre estate 20 minutes from Charlottesville! Our historic bungalow comfortably fits 2-4 people and is perfect for those who just want to take a step back in history and enjoy the wonder nature has to offer! For outings we are only 20 min away from Jefferson's "Monticello" & 35 min from James Madison " Montpelier". Play golf 5 min away at Spring Creek Golf. Treat yourself to an onsite certified massage wellness therapist.

Aug 26 – Sep 2

$120 per night

Guest favorite

Guesthouse in Mineral

5.0 out of 5 average rating, 61 reviews

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 and taking in the views. After a gradual slope, the backyard levels out providing a perfect spot for spreading a blanket or enjoying backyard games adjacent to the private dock. This property is attached to the main house, but you will have your own entrance and private experience.

Jan 16 – 23

$273 per night