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Vacation rentals with a pool in Leesburg

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Leesburg

  • Nightly prices starting at

    Leesburg vacation rentals start at €43 per night before taxes and fees

  • Verified guest reviews

    Over 100 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Leesburg rentals

  • 4.9 Average rating

    Leesburg stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated rentals with a pool in Leesburg

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

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Top guest favorite
A tranquil pool area is surrounded by lush greenery and vibrant flowers. The charming cottage, featuring a welcoming porch, is visible in the background under a bright blue sky. The clear water of the pool reflects the sunlight, inviting relaxation.
Cottage in Hamilton

*Cottage @ Firefly Cellars* VA Wine Country escape

The Cottage at Firefly Cellars is a private, tranquil escape on the tasting room property. Come enjoy the private pool (in summer months), walk the property with a glass of wine, enjoy views of the neighboring horses, hop to local wineries, or just sit back and enjoy all the cottage has to offer. The cottage is meticulously maintained, beautifully designed, and you will feel at home the moment you walk through the doors. Perfect for a couple, or an individual looking to escape from busy life!

4.95 out of 5 average rating, 426 reviews
Top guest favorite
A horse stands peacefully in a lush green pasture, surrounded by a black wooden fence. In the background, a well-maintained barn with a cupola is visible, complemented by a clear blue sky and scattered clouds.
Farm stay in Purcellville

The Hunt Box @ Tally Yo Farm

Residence above 5-stall horse barn. Two bedroom house with 2 bath, Juliette balcony, vaulted ceilings, fully appointed kitchen, laundry. Traditional English equestrian decor, with horse shows & fox hunts close by. Pool open 5/15-10/15. Extra guests $55/night. Pet fee $35 each. Please advise through Airbnb. Lovely antiques, equestrian art & decor, warm rugs. On site also~AirBnb: www.airbnb.com/rooms/826639006057875355?guests=1&adults=1&s=67&unique_share_id=4cdf4b76-3173-498a-9287-5ab54a38b4ee

4.98 out of 5 average rating, 241 reviews
Top guest favorite
An outdoor seating area is set in a grassy space, featuring weathered chairs arranged around a stone fire pit. A wooden picnic table is visible, surrounded by lush greenery and trees. The backdrop reveals a scenic view of the rolling hills under a partly cloudy sky.
Cabin in Bluemont

Rustic Blue Ridge Cabins

Quaint Rustic Cabin nested at the top of the Blue Ridge Mountains w/detached 150 ft² bedroom Cabin, located in the heart of Western Loudoun Wine Country. Sitting on 1/3rd acre with access to wooded a trail leads to 5 small cold springs. Amenities 4 person hot tub, beautiful view of the Loudoun Valley, Wifi, Loft bedroom with a loft ladder, hiking along the Appalachian Trail, Shenandoah River, with restaurants, breweries, distilleries and wineries close by! These are rustic not luxurious Cabins

4.99 out of 5 average rating, 635 reviews
Top guest favorite
A well-maintained sign for Tonka Farm is positioned at the entrance along a gravel driveway. Lush green grass surrounds a neatly trimmed shrub. Black wooden fencing lines the pathway, leading to a serene and inviting country setting.
Farm stay in Middleburg

Retreat to horse country!

Enjoy your visit while staying in a private country setting complete with a swimming pool and gardens creating a resort like feel. This beautiful family farm includes an English style apartment with large windows, gas fireplace, 1.5 bathrooms, 1 large bedroom with king size bed. An open concept living space, access to the pool a large & outdoor seating and dinning. Minutes to vineyards, Salamander, Goodstone, Upperville and Shadow Creek in Purcellville! Please read “other details” for pet info😊

4.97 out of 5 average rating, 102 reviews
Top guest favorite
Farm stay in Bluemont

The Cottage at Nestled Inn

Nestled into the Blue Ridge mountains, practically walking distance from Bear Chase Brewery, Twin Oaks Tavern Winery & The Applachian Trail, our home offers you poolside views of our garden, hottub views of the stars, backyard views of our free range chickens & front yard views of our two horses as well as onsite massage therapy, cats & dogs. While being tucked away, we are still just 10minutes from Purcellville or Berryville & 30minutes from Leesburg, Middleburg, Winchester or Harper's Ferry.

5.0 out of 5 average rating, 115 reviews
Top guest favorite
A spacious solarium features large windows allowing plenty of natural light to fill the room, with views of the surrounding greenery. A comfortable seating area is arranged with a mix of sofas and chairs, complemented by various plants adding a touch of nature. The heated concrete floor enhances comfort in this inviting gathering space.
Home in Knoxville

An Escape Bordering National Park land 1 mi to C&O

Relax in this serene setting with a hot tub overlooking Harpers Ferry National Park Land. Enjoy evening fires, the pool, screened-in porch, a book in the solarium or go hiking/tubing nearby. We hope our home (Harpers Getaway) provides a tranquil backdrop to immerse you in nature and lower your stress level so you can reconnect with those you love! It is located only 1 mile from the C&O towpath & Potomac River, 2 miles (by foot) from historic Harpers Ferry w/ breweries, wineries galore nearby.

5.0 out of 5 average rating, 109 reviews
Top guest favorite
A spacious pool area features a heated in-ground pool and spa surrounded by lounge chairs. A well-maintained lawn and shaded seating areas complement the outdoor space, while a house is visible in the background, nestled among the trees.
Home in Marshall

Clean 5BR w Heated Pool, Spa - Horse, Wine Country

Escape the city to this spacious 5BR / 3.5BA home with a heated pool and spa on 8 acres in the heart of Northern Virginia's Horse and Wine country. The house is professionally designed for large groups of adults and kids for family vacations, reunions, and retreats. 2 miles from the one-stop-light town of Marshall with nationally recognized restaurants, bakeries. And in the heart of Virginia's Horse & Wine country - 7 wineries, equestrian facilities/shows, and state park within 15 minutes.

4.94 out of 5 average rating, 147 reviews
Top guest favorite
A charming outdoor seating area features red wooden chairs and a fire pit, surrounded by lush greenery and pavers. The Cottage, with its welcoming facade and gray metal roof, is visible in the background, offering a cozy retreat in a natural setting.
Cottage in Bluemont

Cottage on Horse Farm: Wineries/Breweries, Horses!

**Pool open May 1- Sept 29 ** PRIVATE 3 hours pool time daily. Plus private patio, grill and fire pit! Horses outside every window! The Cottage is located on a 230 acre horse farm. Red Gate Farm is a full-service, upscale equestrian farm, containing the Cottage, original farm house and 50 horses & ponies. Convenient to Middleburg and Purcellville, you are surrounded by mountains, wineries, breweries, and hiking, with horses right at your doorstep. All in the beautiful town of Bluemont.

4.95 out of 5 average rating, 288 reviews
Guest favorite
A spacious outdoor area features a large in-ground pool surrounded by a patio. Lounge chairs in a bright blue color are arranged along the edge. A picnic area with tables and chairs is also visible, along with a children's play area nearby.
Home in Lovettsville

COZY3500sf Private-10acres Pool-PickleBall-Hot Tub

Immerse yourself in tranquility and laid-back luxury in our expansive home adorned with 6 cozy furnished bedrooms. Hemingway Retreat is nestled with 10 acres of spectacular farmland, with awe-inspiring vistas of horses grazing peacefully a picture-perfect escape from your routine life. With amenities such as fire pits, enjoyable hot tub, & tennis courts, indulge in a variety of recreational activities. Experience the fusion of comfort & exciting adventures at every corner of our property.

4.87 out of 5 average rating, 142 reviews
Guest favorite
A modern living room features two gray sofas with blue accent pillows, positioned around a light wooden coffee table. Natural light enters through the large windows, revealing a scenic view. A small plant adorns the table, while subtle greenery decorates the corners.
Apartment in Reston

King Size Bed w/ Home Office

Welcome to Reston! This brand-new apartment boasts a grocery store on site (Wegmans), 10 minute walk to Reston Metro Station and modern luxuries for you to enjoy. The state-of-the-art kitchen has cookware, bakeware, flatware, and everything you need to kick off your culinary creations. The 4K Roku smart TV is waiting for you to catch up on all your shows. Laundry in unit for your convenience. Wifi, utilities, and linens are all included with your stay. We look forward to hosting you!

4.83 out of 5 average rating, 102 reviews
Guest favorite
The exterior of the farmhouse is showcased at dusk, highlighting the blend of historic and modern architecture. A stone path leads to the welcoming entry, framed by glowing flower pots. The wraparound porch features multiple illuminated windows, reflecting a cozy and inviting ambiance.
Home in Harpers Ferry

Historic Farmhouse | Heated Plunge Pool, Billiards

Named a 2025 Silver Winner for Best Vacation Rental by WV Living magazine, this 1800s farmhouse is full of character and designed for comfort. The highlight is a heated saltwater plunge pool, open year-round, plus outdoor gathering spaces for summer and 3 fireplaces for cozy fall and winter stays. Guests rave about the incredibly comfortable beds! The Harpers Ferry area is a delight in every season, offering hiking, history, shopping, dining, river adventures, wineries and breweries.

4.96 out of 5 average rating, 219 reviews
Guest favorite
A wooden deck extends from the cabin, surrounded by lush green trees. A striped awning provides shade over a picnic table, creating a space for outdoor dining or relaxation. The natural ambiance enhances the secluded feel of the property.
Cabin in Keedysville

Quiet Antietam Cabin

This quiet cabin is located between Boonsboro and Sharpsburg in Keedysville, MD. It is surrounded by tall oaks and pines. A wide path leads to Antietam Creek, popular for fishing, kayaking, and tubing. 45-min drive to Whitetail Ski Resort (30 miles); 1-hr to Gettysburg, PA; Close to Antietam Battlefield, Shepherdstown, Harpers Ferry, Hagerstown, Frederick, Washington, D.C., C&O canal bike trail and Appalachian Trail. Minimum age to rent is 25 yrs. Families with children are welcome.

4.82 out of 5 average rating, 129 reviews

Popular amenities for Leesburg rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
Home in Front Royal

Windy Knoll Adventure | River Front | Hot Tub!

4.81 out of 5 average rating, 170 reviews
Guest favorite
A landscaped backyard features a patio table with an orange umbrella and four chairs. Sunlight filters through the trees, illuminating the area. A path leads to a wooded setting, with autumn leaves scattered on the ground, creating a serene atmosphere.
Home in Reston

Nature Zen *Metro Walk *Visit DC *Relaxing Lakes

4.91 out of 5 average rating, 141 reviews
Guest favorite
Home in Fort Washington

Inground Pool | Hot Tub | Sauna | Theme Room

4.89 out of 5 average rating, 229 reviews
Guest favorite
Home in Fort Washington

5BD nr Nat’l Harbor, MD, DC & VA w/yard Oasis

4.92 out of 5 average rating, 102 reviews
Top guest favorite
Home in Harpers Ferry

3BR Chalet | Sauna · Plunge · Hot Tub | Views

4.97 out of 5 average rating, 64 reviews
Guest favorite
An aerial view of a two-story farmhouse surrounded by lush greenery, showcasing a private fenced outdoor area with a pool. A small outbuilding is visible in the background, alongside a tree with purple foliage.
Home in Purcellville

Shiloh

4.95 out of 5 average rating, 41 reviews
Guest favorite
The exterior of a two-story wooden home is surrounded by lush greenery and vibrant shrubs. A swimming pool with a unique shape is visible in the foreground, accompanied by lounge chairs and an umbrella. The tranquil setting is enhanced by the soft blue sky above.
Home in Waterford

Sunny Cabin Getaway | Pets Welcome | Near Wineries

4.95 out of 5 average rating, 22 reviews
Guest favorite
Home in Bluemont

Red Rooster Cottage with hot tub and seasonal pool

4.95 out of 5 average rating, 38 reviews

Condo rentals with a pool

Superhost
A welcoming living room features a gray sofa adorned with colorful throw pillows, flanked by two yellow armchairs. A light wood coffee table sits atop a textured area rug, with a serene wall art piece above. Natural light is provided by nearby windows.
Condo in West Springfield

Beautiful 2BR/1BA Renovated Condo near DC

4.85 out of 5 average rating, 267 reviews
Top guest favorite
Condo in National Harbor

Luxury Condo • In the heart of National Harbor

4.91 out of 5 average rating, 199 reviews
Guest favorite
Condo in Tysons Corner

Modern Elegant apt in Tysons, VA – Easy DC Access

4.95 out of 5 average rating, 20 reviews
Guest favorite
A well-maintained outdoor swimming pool is surrounded by lounge chairs under shaded pergolas. The backdrop features a modern, multi-story building with large windows, providing a blend of comfort and leisure in a vibrant setting.
Condo in National Harbor

Club Wyndham National Harbor, 2 BR Deluxe

5.0 out of 5 average rating, 22 reviews
Superhost
Condo in Alexandria

Sleeps 8 | Summer Pool · Near DC & Old Town

4.85 out of 5 average rating, 61 reviews
Guest favorite
A large resort building features multiple floors with a mix of brick and smooth facade. The pool area is visible below, surrounded by lounge chairs and shaded seating. Landscaping elements, including trees and shrubs, enhance the outdoor ambiance, with the street and waterfront visible in the background.
Condo in National Harbor

Wyndham National Harbor | 1BR/1BA King Bed Suite

5.0 out of 5 average rating, 32 reviews
Guest favorite
A serene outdoor pool area features a hot tub and lounge chairs positioned under a pergola. Water cascades gently from a nearby fountain, while the backdrop consists of a multi-story building with large windows.
Condo in National Harbor

Wyndham National Harbor | 3BR/2BA King Bed Suite

4.97 out of 5 average rating, 37 reviews
Guest favorite
A modern resort building is showcased, featuring multiple floors with a mixture of glass and brick façades. An outdoor pool area is visible in the foreground, surrounded by lounge chairs. The surrounding streets and sidewalks indicate a vibrant urban setting.
Condo in National Harbor

Wyndham National Harbor- 2 bdrm condo

4.86 out of 5 average rating, 28 reviews

Other vacation rentals with a pool

Top guest favorite
A spacious living area features plush seating in elegant patterns, arranged around a round coffee table. Decorative lamps provide soft lighting, while rich red wallpaper and floral accents contribute to a warm atmosphere. A flat-screen TV is mounted on the wall, complemented by tasteful decor.
Guesthouse in Frederick

Romantic Getaway-Heated Spa - Seasonal Pool!

4.98 out of 5 average rating, 206 reviews
Guest favorite
A living area is highlighted by a deep green accent wall and a flat-screen television mounted above a decorative rug. A comfortable sofa with throw pillows sits adjacent to a small dining table with a chair. A potted plant adds a touch of greenery to the space.
Townhouse in Fairfax Station

Cozy Private Entry 1BR1BA Suite Close to GMU & DC

4.9 out of 5 average rating, 111 reviews
Top guest favorite
A gravel area features several rustic wooden chairs arranged around a stone fire pit, with a gentle fire burning. Soft string lights illuminate the space, enhancing the cozy atmosphere. The exterior of the cabin is visible in the background, surrounded by trees.
Cabin in Hedgesville

Modern Cabin: Hot Tub, Arcade, FirePit, Pets+Pool

4.95 out of 5 average rating, 188 reviews
Top guest favorite
A warm interior features a spacious bed dressed in a rich, burgundy coverlet, complemented by wooden wall panels and exposed beams. A cozy seating area is provided next to the bed, with light streaming in from a window adorned with wooden shutters.
Cabin in Delaplane

Herb Cottage-Elegant Cabin plus Optional Farm Tour

5.0 out of 5 average rating, 156 reviews
Top guest favorite
The cabin exterior is surrounded by trees, creating a natural setting. A welcoming porch features seating and leads into the interior. Large windows allow natural light to illuminate the space, while a gravel pathway connects the home to the surrounding area.
Cottage in Harpers Ferry

Harper's Ferry Tree House/ hot tub / nature/ trees

4.95 out of 5 average rating, 234 reviews
Top guest favorite
A clear saltwater pool is surrounded by a wooden fence, with a spacious deck area nearby. The pool's surface reflects the sky, and lush green grass borders the surrounding area. A modern building is visible in the background, set against a cloudy sky.
Guesthouse in Midland

Modern Farm Stay

4.97 out of 5 average rating, 259 reviews
Guest favorite
The cabin features a contemporary A-frame design with large windows that reflect surrounding trees. A spacious deck wraps around the structure, providing outdoor seating options. Natural light streams through the windows, inviting a connection with the outdoors.
Cabin in Hedgesville

Bear Pines Retreat ~ Game Room ~ Screened Porch

4.93 out of 5 average rating, 318 reviews
Top guest favorite
A spacious bed is centered in a softly lit room, featuring a rustic wooden frame and decorative pillows. A muted blue throw is casually draped over the footboard. Two bedside tables with lamps are positioned on either side, and a framed artwork of a cow adorns the wall above.
Guesthouse in Middletown

Luxe Cottage, Pool, & Breakfast on MD Horse Farm

5.0 out of 5 average rating, 164 reviews

Destinations to explore