Vacation rentals with a pool in Chevy Chase

Apartment in Upper Marlboro

A spacious swimming pool is surrounded by lush greenery, with colorful pool floats gently resting on the water's surface. A concrete deck provides access, and a handrail leads into the pool. A large screen for outdoor viewing is positioned nearby.

4.95 out of 5 average rating, 135 reviews

DC Oasis- hot tub, pool, theater/game rm, & more

Have fun and relax at this stylish oasis! Packed w/ amenities. Huge Pool w/multiple cabanas, HOT TUB, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room and outdoor projector too, basketball court, grill, spa/library with sauna and full gym!! 5 comfy beds. Rooms split for privacy. Open kitchen/dining/living room. Cold DeerPark water fountain. Basement apt so there is some movement noise. Updated bath and an outdoor shower. 20 mins from Downtown DC & 6Flags.

4.97 out of 5 average rating, 150 reviews

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

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 suite in Catonsville

A fenced-in pool area is surrounded by lush greenery, with tall plants and trees creating a natural backdrop. The pool features calm blue waters, and a small paved pathway leads toward it. A black chair is positioned near the entrance of the pool gate.

4.94 out of 5 average rating, 527 reviews

Rollingside: Two-Room Guest Suite

Two-room guest suite with private entrance located in picturesque Catonsville, MD on a pre-Colonial road originally used for rolling tobacco to the harbor. Downtown Baltimore is 20 minutes away, BWI airport and Amtrak station 15 minutes, and our street is located on a bus route. Beautiful 3.5 mile walk to historic Ellicott City and an hour from Washington, D.C. Individuals and families with children are welcome, but the Airbnb member renting the property must be over the age of 25.

4.98 out of 5 average rating, 290 reviews

A serene swimming pool is illuminated by soft lighting, surrounded by trees. Lounge chairs are positioned beside the pool, offering a tranquil space for relaxation in the evening ambiance. The mid-century modern guesthouse is partially visible among the foliage, enhancing the secluded atmosphere.

Guesthouse in Highland

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.

Apartment in North Bethesda

A spacious living area features hardwood flooring and large windows with blinds, allowing natural light to enter. A white sofa is positioned near a glass coffee table. A dining table with four black chairs sits in front of the windows, creating an inviting space for meals.

4.91 out of 5 average rating, 77 reviews

Sleek studio with awesome view- 1 block from metro

Our beautiful studio is within walking distance to metro (1 block) and grocery stores (Harris Teeter). It is also located across a brand new iPic Movie Theater and shopping area. You can walk to several restaurants and convenience stores. The studio is very spacious with lots of light. You also have access to the condo fitness area, pool table, and quiet/business common rooms. A pool is available during summer. The place is good for couples, solo adventurers, and business travelers.

4.92 out of 5 average rating, 107 reviews

A light-filled living area features a comfortable sectional sofa adorned with neutral tones and decorative cushions. The circular area rug in soft blue anchors the space, complemented by abstract art pieces on the wall and a modern mirror reflecting natural light.

Condo in Centreville

Peaceful resort- like patio condo

Stylish 1 bedroom condo on ground level with 1 designated parking space directly in front. This home provides a perfect setting for both luxurious and comfortable living. Bright southern exposure, No steps from parking, 2 smart TV, Highspeed internet, queen size bed, the patio opens to private green nature. Plenty of guest parking as well. Long paved walking trail passing by, Walk to Giant, Starbuck, and Restaurants. Less than 2 miles from Spa World. And 10 min drive to King Spa.

Apartment in Downtown Silver Springs

A bright bedroom features large windows with partial city views. A spacious bed covered with soft linens is complemented by subtle accent pillows. A cozy green chair sits in the corner, adding a touch of comfort to the inviting space.

4.75 out of 5 average rating, 36 reviews

Modern 1BR in Silver Spring

Welcome to your home away from home! This modern one-bedroom apartment is located in the heart of downtown Silver Spring, just minutes from Washington, DC. Enjoy contemporary amenities, a comfortable living space, and easy access to dining, shopping, and public transportation. Perfect for solo travelers, couples, or business visitors. Explore the vibrant local scene or take a short trip to the nation’s capital. Make your stay memorable in this cozy and convenient urban retreat!

4.82 out of 5 average rating, 131 reviews

A two-story condo building is set against a twilight sky, with blooming trees framing the entrance. Pathways lined with greenery lead to the front, showcasing a well-maintained exterior and inviting balcony spaces on the upper floor.

Condo in Annandale

Remodeled 1BR/1BA Condo: close to DC with pool!

Spacious and completely remodeled condo at Fairfax Heritage. Newly painted and featuring brand new carpet and vinyl flooring throughout the unit. All-new kitchen including stainless steel appliances, cabinets, quartz countertops, sink, lighting and plumbing fixtures. Remodeled bath. Generously-sized bedroom with double closet. Large private balcony overlooking treed courtyard. Common laundry on lower level, private storage unit. Grilling available in picnic area.

Apartment in Foggy Bottom

A cozy living area is seen featuring a light-colored sofa and two accent chairs. A wooden coffee table holds decorative items, while a large piece of abstract wall art adds visual interest. Soft light filters through two windows, enhancing the neutral color palette.

4.81 out of 5 average rating, 585 reviews

#3 Foggy Bottom/Georgetown Apartment

Stay in a luxury apartment in one of DC’s most walkable neighborhoods, between the West End and Georgetown on Pennsylvania Ave. Walk to the National Mall, Smithsonian museums, historic Georgetown, top restaurants, and nightlife. Renovated in 2016, this stylish space offers modern comforts, plus free access to Balance Gym Foggy Bottom & Capitol Hill. Enjoy waterfront views, scenic parks, and DC’s vibrant culture—all just minutes away!

4.97 out of 5 average rating, 141 reviews

The living area features a flat-screen TV mounted on a white media console. A wooden coffee table occupies the center, surrounded by a textured area rug. A sunroom filled with natural light showcases a desk and panoramic views of the greenery beyond.

Condo in McLean

Luxury 1bd in Heart of Tysons

Located in the heart of Tysons next to shopping, restaurants, and 20 minutes from DC. Luxury 1bed/1bath with an incredible high rise view. Work in the sunroom with expansive views of DC or walk downstairs for a coffee. Everything you need for a relaxing vacation or productive work trip. Includes your own dedicated parking spot underground. Enjoy the multi amenity building by using the gym or the rooftop with a pool.

Townhouse in Dupont Circle

The front bedroom features a queen bed adorned with floral-patterned linens. Two nightstands with vibrant orange lamps flank the bed. A wall art piece depicting a cyclist stands above the headboard, while an exposed brick fireplace is visible on one side.

4.93 out of 5 average rating, 408 reviews

Dupont West 1: Charming 2BR

Large 2BR/1BA apartment in a uniquely Washington, Victorian-era townhouse (circa 1880s) with original character. Hardwood floors, exposed brick walls, and quality furnishings throughout. Private rear patio. Explore DC from a safe neighborhood, steps to everything: restaurants for every taste and price range, art galleries, easy transportation, shops, community pool, and Rock Creek Park. Parking available.

Apartment in Dupont Circle

An expansive rooftop area features a sparkling pool accompanied by comfortable seating arrangements. Clear skies provide a serene backdrop, while lounge chairs invite relaxation. The rooftop setting offers sweeping views of the surrounding cityscape and greenery.

4.94 out of 5 average rating, 156 reviews

Upscale 1Bdrm Apt in Heart of DC

Welcome to our cozy and charming one bedroom, one bathroom apartment in the heart of downtown Washington, DC! You’ll feel right at home in this beautiful space with tons of natural light, 60” 4k TV, a king sized Nectar mattress, and a fully equipped kitchen. Located just steps away from the city's most iconic landmarks, restaurants, and nightlife, our apartment is the perfect home base for your DC adventure!

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Popular amenities for Chevy Chase rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 19 reviews

Home in Temple Hills

Cozy 4BR Retreat with Heated Pool Near MGM & DC!

Home in Northwest Washington

5 out of 5 average rating, 27 reviews

Palisades Retreat

4.95 out of 5 average rating, 21 reviews

A spacious dining area features a large wooden table set for dinner, accompanied by a padded bench and modern chairs. Natural light enters through two windows dressed in sheer curtains, while colorful wall decor adds a touch of vibrancy.

Home in Fort Washington

Spacios 2-Bed Room Near DC /APT

4.93 out of 5 average rating, 98 reviews

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

Nature Zen *Metro Walk *Visit DC *Relaxing Lakes

5 out of 5 average rating, 11 reviews

A cozy living area is present, featuring a light gray armchair and a television on a low stand. A fireplace with a white mantel is integrated into the wall. French doors open to a private outdoor space, allowing natural light to enhance the ambiance.

Home in Georgetown

Georgetown Awesome Townhome 3BR 3.5BA

4.92 out of 5 average rating, 61 reviews

Home in Rockville

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

4.92 out of 5 average rating, 156 reviews

Home in Fort Washington

5 BEDR, Inground Pool+Billiard Table, Close To D.C

4.97 out of 5 average rating, 30 reviews

A clear blue pool invites relaxation, surrounded by a textured patio. The deck slopes gracefully to the rear of the house, where outdoor seating is visible. Lush greenery lines the space, complementing the serene atmosphere. Safety equipment is strategically placed near the pool area.

Home in Annandale

Suburban Paradise: Minutes to DC

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Condo rentals with a pool

4.94 out of 5 average rating, 50 reviews

An outdoor pool area is presented with a spacious pool and a whirlpool spa. Lounge chairs are arranged around the pool, with an elegant waterfall feature flowing into the hot tub. Evening lights illuminate the surroundings, creating a relaxing environment.

Condo in National Harbor

2BDRM, 2BA near MGM, Gaylord, Top Golf & Shopping!

4.81 out of 5 average rating, 16 reviews

A private room features two single beds with light blue bedspreads, positioned on a soft carpet. Each bed is complemented by a bedside table with a lamp. A ceiling fan provides additional comfort, and the walls are adorned with a neutral color, enhancing the tranquil atmosphere.

Condo in Annandale

Clean Condo in Annandale.

4.88 out of 5 average rating, 131 reviews

A community swimming pool is surrounded by lounge chairs and trees, with several tall residential buildings in the background. The clear blue water invites relaxation, while an area for sunbathing is visible nearby, enhancing outdoor leisure options.

Condo in Virginia Square

Lovely 1-Bedroom Condo with Pool and City View

4.86 out of 5 average rating, 14 reviews

A bright living room is furnished with a blue couch and a brown leather sofa. A marble coffee table with an irregular shape rests on a patterned area rug. Large windows allow natural light to fill the space, revealing views of the outside.

Condo in Alexandria

The Fountains condo one bedroom 2 level apartment

Condo in Northwest Washington

A dining area features a round table with a decorative tablecloth, surrounded by six light-colored chairs. A wooden cabinet spans the wall, showcasing shelves for display items. A bowl filled with apples rests at the center of the table, adding a subtle touch of color.

Magnificent fully furnished, parking, Metro

5 out of 5 average rating, 11 reviews

A modern living space is shown with a sleek kitchen in the background. A dark sofa contrasts with a patterned area rug. A wooden coffee table is centered, and a wall-mounted TV is visible. Bar stools are positioned near the kitchen counter.

Condo in NoMa

Veni Vidi Vici DC 1-Bed Lux Apt

4.78 out of 5 average rating, 32 reviews

The exterior of Club Wyndham National Harbor is displayed, showcasing a multi-story building with a warm palette. A swimming pool is visible at the forefront, framed by lounge chairs. An American flag is prominently featured, indicating proximity to the Gaylord Convention Center.

Condo in National Harbor

Wyndham National Harbor ツ 3 Bedroom Deluxe!