Holiday rentals with a pool in Montgomery County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Montgomery County

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

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Guest favourite

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

4.94 out of 5 average rating, 119 reviews

Nature Zen *Metro Walk *Visit DC *Relaxing Lakes

When you stay here you will experience the comfort of your home and close to various amenities. You can explore nature trails and lakes for a serene retreat. Home is located near Wiehle Reston Metro, providing easy access to D.C and Airports. You will enjoy a fully equipped kitchen with pots, pans, silverware, fridge, microwave, and washer & dryer. Your family will enjoy Gigabit high-speed WIFI for streaming on electronic devices and work quietly from private home office. * Book your stay now! *

Guest favourite

Home in Howard County

5 out of 5 average rating, 9 reviews

The Blissful House

Welcome to The Blissful House, a serene retreat designed for relaxation and convenience. Nestled in Western Howard County. This memorable home with 3 spacious bedrooms & 3 full B. Spacious & stylish home with modern interior touches. Ample parking space for your convenience Prime location – just few minutes away from Turf Valley Resort, restaurants, and Patapsco Valley State park. Easy access to Route 70 & Route 32 for effortless travel. We will be closing the pool at the end of September.

Guest favourite

A welcoming exterior view of the house features a well-maintained lawn and garden. The facade is highlighted by a large bay window and flower boxes beneath, complemented by decorative shutters. A pathway leads to the front door, framed by neatly landscaped greenery.

Home in Rockville

4.92 out of 5 average rating, 64 reviews

Serene House on the Cul de Sac - Lic # STR23-00110

House is located on a quiet cul de sac with friendly neighbors. The house is cozy, clean, very comfortable,great to relax in after a long day of site seeing. The White House is only 15 miles. Also conveniently located to Annapolis, Baltimore, and Northern Virginia. There is plenty of shopping and restaurants nearby. Beautiful hiking trails (Great Falls), walking trails (Rock Creek Park), public parks, skateboarding park, indoor swim pool, tennis courts, volleyball court, racketball (Olney)

Top guest favourite

Home in Adamstown

4.94 out of 5 average rating, 144 reviews

Wizard's Escape | Sleep15+ | 2 Escape Rooms &Pool

Wizards and Humans are invited to experience the magic of Wizard's Escape. A magical home with an escape room twist as you immerse yourself in 2 thrilling themed escape rooms. Perfect for large family gatherings, bachelorette/bachelor/birthdays. Spend hours on our magical scavenger hunt throughout the castle to find the 7 cruxes. Weddings/ Events and Pool rental are an additional cost. Follow us on Insta or Fb for more videos/pics. Book your favorite Gamekeeper's Hut or airbnb next door.

Guest favourite

The pool area features a crystal-clear pool bordered by stone pavers and landscaped greenery. A pool house with large glass doors is visible in the background, accompanied by a defined hot tub and neatly arranged lounge chairs. Surrounding trees and bushes enhance the outdoor setting.

Guest house in Monrovia

4.96 out of 5 average rating, 164 reviews

Poolside Paradise in Monrovia, Maryland.

Enjoy your stay in this fabulous pool house located in a quiet neighborhood. Relax poolside during the day and enjoy the outdoor bar and kitchen for cocktails at sunset. Breathtaking views all around. Just 50 minutes from Baltimore and Washington DC and 10 minutes to historic downtown Frederick. Private entrance to backyard with a large green space on the backside of the pool house. We consider ourselves a couples retreat and don’t host gatherings. We look forward to hosting you soon:)

Guest favourite

Flat in Gaithersburg

4.96 out of 5 average rating, 25 reviews

Luxury Downtown Crown Apt (Close to DC)

This apartment is located in the upscale hub of Rio in Gaithersburg, just 30 minutes outside of DC. The place embodies luxury style elements and sits on the top floor. Large windows in every room capture breathtaking views and allow a plethora of natural light. All building amenities are available to you, from an onsite gym to a seasonal pool to a Billiards table. Our abode sits steps away from regarded restaurants, shopping, Starbucks, and much more! It simply doesn't get any better!

Top guest favourite

A wooden table is set with a bottle of Walnut Crest Cabernet Sauvignon and two etched wine glasses. A red apple rests in a dark, leather-like bowl, with a serene backdrop of green foliage visible through a screened window.

Guest house in Highland

4.98 out of 5 average rating, 303 reviews

Woodland Retreat

Welcome to our private woodland retreat! This stylish and secluded mid-century modern guesthouse is nestled on five acres in horse country in Highland, Maryland. Totally separate from our owners home, our guesthouse combines the serenity, privacy, and safety you crave with all the conveniences of modern life including: a full bath; kitchenette; internet; and a screened porch with access to our beautiful lighted and heated swimming pool (weather permitting) and adjacent walking trails.

Guest favourite

A modern living space is presented, featuring a light-toned hardwood floor and neutral walls. Two accent chairs and a sofa are positioned around a coffee table, with decorative plants adding a touch of nature. Artwork adorns the walls, and soft lighting creates a comfortable ambiance.

Flat in North Bethesda

4.93 out of 5 average rating, 15 reviews

Modern Condo, Walk to Metro

*Newly remodeled condo* Conveniently located near Metro’s Red Line and just steps from Grosvenor Market, this home offers easy access to everything you need. Only 1.5 miles from CVS, Balducci’s, Starbucks, Java Nation, and more. Quick highway access makes getting to Washington D.C., Baltimore, Virginia, and surrounding areas a breeze. Whether you're here for business or a relaxing getaway, you'll love the location and comfort. Please note: no parties or unauthorized guests allowed.

Guest favourite

A bright bedroom features a spacious bed with light-colored bedding. Natural light enters through a large window, illuminating the room. A wooden dresser and a mirror complement the soft, neutral tones, while a floor lamp adds warmth to the inviting space.

Flat in Reston

4.9 out of 5 average rating, 62 reviews

King Size Bed - Reston Metro Apt

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 TV is waiting for you to catch up on all your shows. Laundry in the unit for your convenience. Wifi, utilities, and linens are all included with your stay. We look forward to hosting you!

Guest favourite

The modern kitchen is equipped with stainless steel appliances, including a range hood above a five-burner stove. Light gray cabinetry and a granite countertop create a sleek environment. A door leads to a private outdoor area, with natural light illuminating the space through multiple windows.

Home in Chevy Chase

4.82 out of 5 average rating, 17 reviews

Modern 3 bedroom home filled with art/POOL

This unique place has a style all its own. Filled with Art. Upper level of mid century modern home. 3 bedrooms , 2 bathrooms. Private Swimming pool available mid-May to mid September. Please send me a message for exact dates. Level 2 EV charger in driveway the basement is not included in this listing but we usually will be traveling during the time the house is rented . Please inquire and confirm if we will be home or not. 6 adults over 18 max

Guest favourite

A spacious living area showcases a comfortable sofa arranged near a round coffee table. A dining table with multiple chairs is positioned nearby, and plantation-style shutters allow for natural light. Access to patio doors is provided, enhancing the inviting atmosphere.

Guest suite in Gaithersburg

4.93 out of 5 average rating, 42 reviews

Driveway Parking, No Stairs, Baby Crib

1.7 miles from I-270, 4.7 miles from Germantown Soccerplex, 0.4 miles from Bowling alley, 1 mile from Kaiser Permanente, 4 miles from Shady Grove Hospital and Shady Grove Metro Station, 0.7 miles from the Gaithersburg MVA, 1.2 miles from the shopping center, 3.1 miles from Fitness centers, 3 minute walk from the RideOn bus stop (61, 74, 78), and minutes away from Tech Hub and pharmaceutical companies.

Guest favourite

A modern living area is showcased with a comfortable leather sofa and two accent chairs. A medium-sized coffee table sits in front of the seating, complemented by a flat-screen television mounted on the wall. Large windows allow natural light to enter, providing a view of the outdoor space.

Flat in McLean

5 out of 5 average rating, 12 reviews

Cozy 1 BD Apt in Downtown McLean- Balcony/Parking

Welcome to your modern cozy apartment in the heart of McLean, VA- just minutes from Washington, DC! Ideal for Business Travelers, Solo Guests, or Families. This modern, fully-furnished 1 bed, 1 bath residence offers the perfect blend of comfort and convenience. Enjoy a spacious layout with a full kitchen, outdoor pool, pickle ball court, tennis court, basketball court, gym, sauna and more!