Vacation rentals with a pool in Charles County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Charles County

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

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Top guest favorite

A detailed decorative emblem is presented, featuring a stylized representation of a grand estate along with a flamingo wearing sunglasses. Elements such as palm trees and a drink are included, offering a playful and elegant design. The color scheme is warm, enhancing the inviting aesthetic.

Home in Waldorf

4.91 out of 5 average rating, 43 reviews

*NEW* Huge 5Br Entertainment Retreat, Near DC

(Luxury is good but fun is better) Welcome to your ultimate getaway at our Entertaining and fun 5-bedroom, 3-bathroom home nestled in the heart of Maryland. With 8 beds and 3 different couches to crash at. Perfectly blending elegance with comfort, this stunning retreat offers an unforgettable stay for families, groups, or anyone looking to experience a slice of paradise. *THIS FULLY FURNISHED PROPERTY IS IDEAL FOR COPORATE HOUSING, RELOCATING FAMILIES AND TRAVELING AGENTS; LONGER STAYS WELCOME.

Top guest favorite

A spacious outdoor screened living area is equipped with a comfortable seating arrangement featuring red cushions. A coffee table with a fire feature is centrally located. A ceiling fan provides airflow, and bar seating is positioned nearby, enhancing the outdoor gathering experience.

Home in Colonial Beach

5 out of 5 average rating, 35 reviews

Modern River Relaxation

Welcome to your modern retreat at Colonial Beach. Newly built with sleek design, this single home is perfect for families and friends seeking both relaxation and adventure. Located just a short walk or lively golf cart ride to the beach, this home places you close to the best local dining, breweries, wineries, and attractions. Private hot tub for relaxing, and a huge outdoor screened living space to maximize fun. Community pool open thru mid-Oct and playground just steps away! Pet friendly!

Guest favorite

A comfortable living area features a navy blue sofa adorned with patterned cushions, complemented by a wooden coffee table. Large windows provide a view of the water, while natural light fills the space. A ceiling fan and indoor plants add to the ambiance.

Apartment in Colonial Beach

4.87 out of 5 average rating, 62 reviews

Sail Away - Beachfront & Stunning Balcony Views

Sail Away, CoBe Condo’s brand new, waterfront condo w/ stunning views is now available! Reach out to accommodate more by booking our sister condo, Sail Away To! → Private patio w/ 180° views, perfect for a morning coffee or wine at sunset → Access to pool (owners and guests only) → 1,025 ft² of stylish, cozy space, steps from the water and restaurants → Master suite which looks upon the water → Fully equipped kitchen and living room, smart TVs → Reserved parking space → ❤️ of Colonial Beach

Top guest favorite

The exterior of the house is showcased, featuring a front stone chimney and a welcoming turquoise door. A spacious lawn surrounds the property, with a driveway visible to the right. Trees are seen in the background, highlighting the peaceful neighborhood setting.

Home in Colonial Beach

4.97 out of 5 average rating, 29 reviews

Stay&Play:Games, Pool, FirePit, Beach & Boardwalk!

Escape to our cozy Airbnb, nestled in a peaceful neighborhood with ample parking and thoughtfully designed for up to 10 guests. Enjoy bright living areas with games, a dedicated workspace, and comfortable bedrooms, including two king suites. Step outside to a private backyard oasis with a pool, lounge seating, and dining for six. Just a short walk to the beach, close to dining, shopping, and boardwalk, our home is the perfect mix of relaxation and adventure. Book now for an unforgettable stay!

Superhost

A bright living area features a mustard-yellow sofa adorned with decorative pillows, accompanied by a round dining table set for four. A tall indoor plant adds a touch of greenery, while a sunburst mirror hangs on the wall, reflecting the room's natural light.

Guest suite in Woodbridge

4.89 out of 5 average rating, 308 reviews

Newly renovated private guest's suite with parking

Completely remodeled lower level guest suite, accommodates up to 4 guests. Features a private entrance and parking on premises for 1 car. Walk or bike to Veterans Park and Occoquan Bay National Wildlife Refuge. Conveniently located 12 minutes away from Quantico Marine Corp Base and Historic Occoquan attractions & restaurants. 30 minutes from Washigton DC, Old Town Alexandria and National Harbor, MD. Come enjoy this bright and quiet private stay. *Please note this is a NO SMOKING environment. *

Superhost

A field features a tall windmill set against a backdrop of lush green trees and a rainbow arching across a cloudy sky. The natural landscape demonstrates a picturesque rural setting, with golden grass swaying gently in the breeze.

Farm stay in La Plata

4.94 out of 5 average rating, 34 reviews

Oasis at Charity’s Hope Farm Resort

Enjoy the perfect retreat for families, couples or anyone looking for rest and relaxation among a quiet, breath-taking location. This revived historic farmland is an icon in the area. Located just 30 miles outside of Washington DC, features a grand Victorian home w/ modern amenities. This small “farm resort” features pasture areas with alpacas, mini-cows, horses, chicks, bunnies, barns, a private pond for fishing, beautiful pool, large patio w/ outdoor fireplace, an indoor garden, and more.

Guest favorite

A colorful artwork depicting game pieces and dice is displayed in a black frame on the wall. Below, a clear sign with white script reads, 'This is our happy place,' adding a playful touch to the space.

Home in Waldorf

4.94 out of 5 average rating, 32 reviews

TheFUNHOUSE-POOL Still OPEN‼️5️⃣ BR’s 5 Star Stay

Looking for THE PERFECT Place to kick back, relax or just have some FUN with Family or Friends? This isn’t just a place to say- it’s THE FUN HOUSE and it’s JAM packed with excitement, games and a chance to create lasting memories with those you love. After all the fun, unwind in 1 of the 5 beautifully designed bedrooms. There are 3 King Sized Beds to chose from so the choice of how you chose to luxuriate is totally yours! The IN-GROUND POOL is OFFICIALLY OPEN and awaiting YOUR ARRIVAL!

Guest favorite

A spacious dining area is surrounded by large floor-to-ceiling windows, allowing natural light and views of the outdoors. A long wooden table is accompanied by modern chairs and is adorned with plants, enhancing the inviting atmosphere of the space.

Home in Stafford

4.9 out of 5 average rating, 110 reviews

Stunning Riverfront Home w/ Pool, Hot Tub & Kayaks

This property sits on the edge of a bluff overlooking the Potomac River and boasts stunning views, both from within and around the home, perfect for bird watching (eagles/osprey), fishing or just relaxing and soaking in nature, just minutes from DC! PLEASE READ CAREFULLY: The pool and spa are CLOSED from LABOR DAY through MEMORIAL DAY. The official open season for pool and spa is between Memorial Day and Labor Day, please confirm availability (if requesting) outside of standard season.

Top guest favorite

A light-filled living area features a spacious sectional sofa arranged around a natural fiber rug. Two accent chairs are positioned to invite conversation. A light fixture hangs above, while large windows offer views of the outdoors. A flat-screen TV is mounted on the wall.

Townhouse in Colonial Beach

5 out of 5 average rating, 40 reviews

Potomac Paradise in Colonial Beach, VA

Welcome to Potomac Paradise in the beautiful town of Colonial Beach. This new townhouse is the perfect place for friends and family to relax and unwind. It's within walking distance or a quick golf cart ride to the beach, restaurants, breweries, and local attractions. This 4 Bedroom, 3.5 bath end-unit townhouse has coastal beach vibes and awesome views of the Potomac River from the rooftop deck. It also has a community pool just steps away! It's the perfect spot for making memories!

Guest favorite

The living room features three couches arranged around a glass coffee table, providing ample seating. A television is positioned for viewing, with light streaming through the large windows dressed with curtains. The warm tones of the wooden floors and brick wall create a cozy atmosphere.

Home in Charlotte Hall

4.95 out of 5 average rating, 22 reviews

Cozy Retreat w/ Pool: MIR & DC

Relax in this spacious 4-bedroom, 1-bath home with a private pool (open May 13th - October 1st) perfect for families or groups. The Maryland International Raceway and Budds Creek Motocross Park are only 7 miles away, making this an ideal spot for race fans...and we have plenty of parking for your race trailers or cars. Washington, D.C. is also just a short drive. With a prime location and plenty of space to unwind, this home offers comfort and convenience for your next getaway.

Superhost

A modern, two-story home is set on a gravel path surrounded by lush greenery. The front porch features rocking chairs, while a spacious upper balcony is visible. Natural light beams down, enhancing the inviting exterior design of the property.

Home in King George

4.9 out of 5 average rating, 68 reviews

FxBurg Retreat

Breathtaking. Beautiful. Earthy. Modern. Warm. This newly renovated oasis is the perfect getaway for up to 10 guests! RELAX in one of Three King Sized Beautiful Beds that include beautiful linens and plenty of pillows. This home also offers a queen bed and a trundle bed with two twin mattresses. REJUVENATE in one of three Shower Spas. RECHARGE on the second-story Sun Deck that overlooks the grounds, sitting at one of three picnic tables, or rocking on the front porch.

Guest favorite

An open concept living area features a combination of seating, including two armchairs and a side table. A dining area with a striking blue rug and wooden chairs is visible in the background, alongside a well-lit kitchen area with modern appliances.

Guesthouse in Owings

4.93 out of 5 average rating, 120 reviews

Patuxent River View

🌊 Nestled near North Beach, Herrington Harbor, Herrington on the Bay, and Chesapeake Beach, this serene guest house offers a peaceful escape for travelers of all kinds—whether you’re exploring local sights, reconnecting with nature, visiting family, or just passing through. Guests enjoy thoughtful amenities at no extra cost: a fully stocked kitchen, complimentary coffee and tea, high-speed WiFi, a pool and gazebo, and more comforts to make you feel right at home.