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

4.92 out of 5 average rating, 132 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! *

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Guest favourite

Home in Silver Spring

4.89 out of 5 average rating, 63 reviews

DC/Baltimore Escape | Private Pool & Yard

Whether you're here for a family getaway, a group celebration, or a long weekend reset — this Silver Spring rancher delivers on every front. 4,000 sq ft, private pool, half-acre , and enough space that everyone can spread out without stepping on each other. Inside: 3 bedrooms (King, Queen, Full), 3.5 baths, 2 fireplaces, pool table, 80" TV, modern kitchen with steel appliances, and a dedicated work desk when you need it. Outside: a deck, hammock, and a pool that makes you feel like a vacation.

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Guest favourite

Home in Adamstown

4.94 out of 5 average rating, 154 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.

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Top 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, 170 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:)

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Top guest favourite

Flat in Silver Spring

5 out of 5 average rating, 12 reviews

Penthouse 2BR • Pool • Metro

Welcome to your upscale urban escape in the heart of downtown Silver Spring! This beautifully penthouse offers high-end comfort, sweeping city views, and unbeatable convenience—perfect for business travelers, couples, or small groups seeking style and serenity above the city. Steps from the Metro, making it easy to reach Washington, D.C., and surrounding areas in minutes. Walk to: Trendy cafes, restaurants, bars, and shops The Fillmore Silver Spring, AFI Silver Theatre, and Whole Foods

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Top guest favourite

Serviced apartment in Gaithersburg

4.97 out of 5 average rating, 31 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!

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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, 311 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.

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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, 36 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.

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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, 72 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!

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Guest favourite

Flat in Gaithersburg

4.85 out of 5 average rating, 20 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).

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Superhost

The Great Room features vaulted ceilings and an open layout. A spacious sectional sofa with colorful cushions is arranged around a unique coffee table. A dining area with chairs is visible beside the kitchen, which is equipped with modern appliances and decorative items on the shelves.

Guest suite in Woodbine

4.69 out of 5 average rating, 217 reviews

Treetop Penthouse at Streit Manor

NEWLY REDECORATED! Our 2,500 sf penthouse has its own private parking, entrance, kitchen, full laundry. It has 3 inviting bedrooms and a large 1,000 sq ft bath suite with multi person Jacuzzi. Located 18 miles from Baltimore, 31 miles from the White House. Owners live in separate residences on the site. Fully furnished and well-appointed to ensure an enjoyable stay! NO PARTIES OR GATHERINGS WITHOUT PRIOR APPROVAL. NO SMOKING ALOWED INSIDE THE HOUSE!

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Top guest favourite

Guest house in Potomac

5 out of 5 average rating, 35 reviews

Serenity Cottage | Pool • Tennis • Near DC

Escape to Serenity Cottage, a retreat tucked within lush mature trees and whimsical cottage gardens . Whether you’re visiting Washington, DC, reconnecting with family, or simply looking for a relaxing getaway … you’ll enjoy the comfort of a thoughtfully designed space, and adore the tranquility of nature. Wake up to birdsong, sip your morning coffee on your front porch , and unwind after a day of exploring with one of our many amenities.

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