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

4.93 out of 5 average rating, 125 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

Home in Adamstown

4.95 out of 5 average rating, 147 reviews

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

Limited Summer Days left* 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/Pool additional cost. Follow us on Insta for more videos. Book your favorite Gamekeeper's Hut next door for larger parties.

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)

Guest favourite

An expansive outdoor area showcases a private in-ground pool surrounded by paved flooring. The home features a two-story design with several balconies and patios overlooking the pool, adding to the inviting outdoor space perfect for relaxation and entertaining.

Guesthouse in Frederick

5 out of 5 average rating, 6 reviews

The Luxe Lounge & warm welcome

Welcome to your private getaway, this beautifully designed guest house offers a peaceful retreat with a private in-ground pool, spacious outdoor entertaining areas.modern interiors. Inside, you’ll find cozy, stylish furnishings and thoughtful touches that make every stay feel special. Every corner is made for comfort and relaxation. Located in a quiet area, minutes from shops and dining, this home blends convenience and comfort ideal for families or weekend trips, unforgettable stay begins

Top Guest favourite

Guesthouse in Potomac

5 out of 5 average rating, 18 reviews

Serenity Cottage of Potomac

Welcome to Serenity Cottage-a retreat on just under 3 acres of whimsical landscaped grounds, the added bonuses being the pool and tennis court. Our cottage affords you an amazing balance of tranquility and convenience, designed to make you feel at home. Whether you're planning a sightseeing visit, a business stay, or a memorable family retreat, Serenity Cottage will be an experience that exceeds all expectations. Every detail has been crafted to envelop you in comfort, peace, and warmth.

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.

Guesthouse 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

Apartment 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.

Guesthouse in Highland

4.98 out of 5 average rating, 306 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

The custom-built home is showcased from the back, featuring multiple peaked dormer windows and a spacious wraparound deck. Surrounding trees display autumn foliage, enhancing the serene setting. Colorful kayaks are visible underneath the deck, suggesting outdoor recreational opportunities.

Cabin in Frederick

4.94 out of 5 average rating, 34 reviews

Exceptional Custom-Built Post & Beam Home

Escape to this stunning custom-built home on 3 private acres in the Urbana area of Frederick, MD. With 3,664 sq. ft. of space, this retreat offers modern comfort and rustic charm. Relax in the inground pool, hot tub, or outdoor shower, or take in the views from the wraparound deck. Perfect for families, groups, or couples, this peaceful getaway is ideal for unwinding and exploring nearby attractions. Located 2 minutes from Worthington Golf Course and 15 minutes from Downtown Fredrick.

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.

Apartment in Reston

4.9 out of 5 average rating, 67 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

Apartment in Gaithersburg

4.81 out of 5 average rating, 16 reviews

Heart of RIO

Welcom to a stylish and comfortable home away from home in Gaithersburg's premier RIO Washingtonian Center area! The unit blends comfort, convenience, and a touch of luxury-perfect for families, business travelers, or getaways. Suburbia DC,commuter friendly. Fully equipped kitchen. Living room with sectional reclining sofas, smart TV, & WiFi. Fully size beds and full baths. Walk to RIO Lakefront, Downtown Crown. Near Shady Grove Metro, 1-270 and MD 200(ICC).