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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Guest favourite

A bright living area features large windows offering panoramic water views. A wooden dining table accommodates six, while a comfortable seating arrangement includes a blue armchair and a neutral-toned sofa. A ceiling fan is visible above, and decorative coastal artwork adorns the walls.

Apartment in Colonial Beach

Sail Away To - Beachfront Views & Private Balcony

Sail Away To, CoBe Condo’s brand new, waterfront condo w/ stunning views is now available! Reach out to accommodate a group by booking our sister condo, Sail Away! → 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

4.94 out of 5 average rating, 98 reviews

Guest favourite

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

*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.

4.92 out of 5 average rating, 60 reviews

Top guest favourite

A spacious home is set amidst lush greenery, featuring a well-manicured lawn and vibrant plantings. The two-story structure has multiple gabled roofs and a welcoming front entrance. A circular driveway leads to the garage, with trees and a play area visible in the background.

Farm stay in Newburg

Private 32-Acre Retreat- Pool, Hot Tub, & Karaoke

Escape to this private 32-acre retreat, perfect year-round! Relax in the 7-person hot tub or heated saltwater pool & pool house (May 1–Sept 30). Gather by the fire pit, unwind on 2 screened porches, or enjoy the theater, game room with ping pong & poker, and NEW karaoke bar (Sept 1) with mics & JBL speakers! 5BR/6BTH, large TVs, comfy beds, stocked kitchen, fishing pond & grassy play areas. From Nov 1–Jan 31, thousands of holiday lights transform Shady Oak Farm into a magical winter wonderland!

5.0 out of 5 average rating, 44 reviews

Guest favourite

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

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. *

4.9 out of 5 average rating, 349 reviews

Top guest favourite

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

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!

4.96 out of 5 average rating, 50 reviews

Top guest favourite

A spacious rooftop deck is presented, featuring comfortable seating arranged around a fire pit. A patterned area rug adds texture to the wooden surface. Clear views of the sky and surrounding greenery create an inviting atmosphere for relaxation.

Townhouse in Colonial Beach

Rooftop bay and river views

Watch sunrise & sunsets overlooking the Potomac River and Monroe Bay on the rooftop deck. Your new, open, spacious and quiet (end unit) townhome, fully furnished with beach towels, shampoo, everything, you need AND DOG FRIENDLY. Walk to the beach or rent a golf cart and explore. Separate levels with tv's so kids and adults can be on separate floors. Relax by the rooftop fire pit or in the HEATED pool. 2 adjacent parks kids love! Close to the city, but world's apart! $100/dog/stay. No cats.

4.98 out of 5 average rating, 80 reviews

Guest favourite

An aerial view captures the single-story home situated on a private peninsula, surrounded by water. Lush green lawns and trees frame the property, while a dock extends into the bay. A pool is visible in the backyard, adding to the outdoor amenities.

Home in Abell

New, Waterfront Home w/ Island on St. Clements Bay

Wake up to breathtaking panoramic views of St. Clements Bay at this newly renovated 4-bedroom waterfront retreat in Abell, MD. Perched on a private peninsula, the home features a 160-ft dock for crabbing and fishing, bay beaches, an island, pool, hot tub and endless space to relax by the water. Paddle to your own private island to sit on the beach, swim, or explore. With kayaks, crab pots, beach chairs, and a Weber grill included, it's everything you need for the perfect waterfront escape.

5.0 out of 5 average rating, 28 reviews

Guest favourite

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

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.

4.91 out of 5 average rating, 124 reviews

Guest favourite

Home in Mechanicsville

The Southern Maryland (SoMD) Diamond House

A covered front porch with porch swing and multi tier decking in rear over looks a beautiful gunite pool with a slide and a diving board. Depth 3 1/2 ft to 13 foot. Nice big country kitchen. The sliding glass doors from kitchen go to deck over looking pool, nice landscaping, and forest. The master bedroom with a master bath, sliding glass door to deck over looking pool. Full basement patio and pool deck. Has full size bar, full brick hearth fireplace and a full bath. Pool table & Bar.

4.78 out of 5 average rating, 18 reviews

Top guest favourite

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

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!

5.0 out of 5 average rating, 50 reviews

Guest favourite

A spacious house is set amidst a well-maintained landscape featuring green lawns and colorful flower beds. The entrance is framed by trees, with a winding driveway leading up to the front porch. Sunlight filters through the leaves, casting gentle shadows on the ground.

Home in Charlotte Hall

5 acre oasis near Budd's Creek, MIR & DC region.

Your private oasis nestled on 5 sprawling acres in Charlotte Hall, Maryland awaits. This spacious retreat offers the perfect blend of relaxation and entertainment, with the added bonus of easy access to the vibrant capital and a short drive to Budd's Creek and MIR. Sanctuary at the Hall offers a true escape with options for everyone. Whether you're looking to relax by the pool, immerse yourself in nature, experience the excitement of the speedway, or explore the nation's capital.

4.8 out of 5 average rating, 15 reviews

Guest favourite

Farm stay in La Plata

Huge Farmstay w/ Pool, Animals, Pond, & Game Room

Come enjoy the perfect retreat for families, couples or anyone looking for fun, 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 with 6 bedrooms and lots of modern amenities. The grounds feature a petting zoo, clubhouse, barns, a private pond for fishing, a beautiful pool area, a brick courtyard with outdoor fireplace, garden, and more.

4.9 out of 5 average rating, 60 reviews