
Holiday rentals with a pool in Silver Spring
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Silver Spring
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Charming 3BR Rowhouse in Shaw/Bloomingdale
Light-filled, historic Victorian rowhouse. Comfortable and stylish with solar electricity. Original hardwood floors and woodwork, renovated kitchen and bathrooms, laundry, private backyard w/grill and firepit or stock tank pool. Centrally located between Bloomingdale, Shaw & downtown, less than a mile to two Metro stations—NoMa-Galludet U/NY Avenue (Red line) & Shaw/Howard U (Green & Yellow lines)—and a mile to Amtrak at Union Station. Easy access to Convention Center, US Capitol and the Mall.

Luxury 4 Bedroom - Pool/HotTub/Fire Pit
*PLEASE READ OUR LISTING AND HOUSE RULES IN, PRIOR TO BOOKING OUR HOME. SEASONAL POOL/ HOT TUB DATES* Welcome to your beautiful and spacious home away from home! Featuring 4 beautifully decorated bedrooms and 2.5 bathrooms, each designed with comfort and style in mind. Relax in our spacious living areas, take a plunge in the pool & hot tub or lounge by the fire pit in the huge backyard! Experience luxury and comfort in our beautiful home and make unforgettable memories with your loved ones!

Patuxent River View
🏡Stay at this peaceful, amenity‑rich guest house near North Beach, Chesapeake Beach, and Herrington Harbour, with quick access to Washington, DC, Baltimore, and Annapolis. Enjoy a fully stocked kitchen, coffee, fast WiFi, a seasonal pool, and a shaded gazebo designed for comfort and convenience. Perfect for wedding weekends, family visits, work trips, and quiet coastal getaways, this cozy home base makes it easy to relax, cook, stream, and recharge between festivities and exploring the area.

Luxury Living at National Harbor
Spacious Condo in the Heart of National Harbor! Experience comfort and convenience in this stylish one-bedroom apartment with a den, which can be converted into a second bedroom (Air mattress queen size) upon request. Located in the vibrant National Harbor, this condo offers an open-concept design and is surrounded by an exciting mix of restaurants, bars, shops, and entertainment options for all ages. This is your perfect home base for exploring Washington, D.C. and its surroundings.

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.

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.

Beautiful 2BR/1BA Renovated Condo near DC
Beautifully updated 2-bedroom, 1-bath condo located in West Springfield. Step inside from your private patio into a sun-filled living room flooded with natural light, thanks to floor-to-ceiling sliding glass doors that offer easy access to scenic views and the patio. Rows of recessed lighting brighten the freshly painted interior, while sliding door closets in the dining room provide ample storage space. The condo also features newly updated flooring for a sleek, modern look!

Kone Oasis- hot tub, pool, theater/game rm.
Have fun and relax! Near every amenity. Huge Pool w/multiple cabanas, hot tub, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room, 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. Now offering RV for additional cost to add additonal sleeping space. Basement apt so there is some movement noise. 20 mins to DC & National Harbor

Sojourn | VA Square | 2 BR
North Arlington VA Apartments come with the features you expect and want, and even some you’ve always dreamed of, at Virginia Square Towers. We have an eye for luxury, comfort, and practicality, and our amenities reflect that. Enjoy your private space in your furnished two bedroom without worrying about bothering your neighbors or being bothered with excessive sound when you have a home that’s built with noise-reducing walls and floor-to-ceiling windows.

1bed Apt downtown silver spring
Enjoy a beautifully furnished one-bedroom apartment just 10 minutes from DC. Features include a cozy living room with TV and Wi-Fi, a full-sized kitchen, in-unit laundry, and a bedroom with a queen-size memory foam bed. The spacious bathroom has a tub and fresh towels. Indoor plants enhance the ambiance. Located in vibrant downtown Silver Spring, with easy access to shops, restaurants, and bars. Book your stay today for comfort and convenience!

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.

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!
Popular amenities for Silver Spring rentals with a pool
House rentals with a pool

3 bedroom near DC w/pool, large yard, & driveway

Spacious 3Br 2Ba | w/Pool Table Near DC

Nature Zen *Metro Walk *Visit DC *Relaxing Lakes

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

Modern Stays w/ Hot Tub and Pool

Large Home with Private Pool, Gym, Sauna, 7 Bedroo

5BD no. Nat'l Harbor, MD, DC & VA w/yard Oasis

The Bowie Pool House- Your Home Away from Home
Apartment rentals with a pool

Stylish 1BR Condo in Vibrant National Harbor, MD

Modern Elegant apt in Tysons, VA – Easy DC Access

Lovely 1-Bedroom Condo with Pool and City View

Wyndham National Harbor | 3BR/2BA King Bed Suite

DC Views/Walk to Metro jr 1 bedroom

Quiet Condo Near Alexandria ~ Ideal for long stays

Club Wyndham National Harbor, 2 BR Deluxe

Wyndham National Harbor | 2BR/2BA King Bed Suite
Other holiday rentals with a pool

Stylish1BR, FREE Parking, Pool,Gym,Wifi

National Harbor ~ 3Br/2Ba ~ DC!

Nestled Boutique APT Downtown

Luxury 2BR/2BA | Stunning DC City Views + Balcony

Cozy & Calm Cabin

Luxurious Retreat Prime Location

Spacious/Unique in Heart of DC Designer Rowhome

LUXURY RESORT at National Harbor -1 BEDROOM DELUXE
When is the best time to visit Silver Spring?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $152 SGD | $156 SGD | $161 SGD | $152 SGD | $152 SGD | $164 SGD | $155 SGD | $152 SGD | $149 SGD | $147 SGD | $146 SGD | $149 SGD |
| Avg. temp | 3°C | 4°C | 9°C | 15°C | 20°C | 25°C | 27°C | 26°C | 22°C | 16°C | 10°C | 5°C |
Quick stats about holiday rentals with a pool in Silver Spring

Total holiday rentals
Explore 30 holiday rentals in Silver Spring

Nightly prices starting at
Silver Spring holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 590 verified reviews to help you choose

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Silver Spring holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Silver Spring rentals

4.6 Average rating
Silver Spring stays receive an average rating of 4.6 out of 5 from guests
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- Rentals with pools Montgomery County
- Rentals with pools Maryland
- Rentals with pools United States
- Georgetown University
- Walter E Washington Convention Center
- National Mall
- Nationals Park
- M&T Bank Stadium
- The White House
- District Wharf
- Baltimore Convention Center
- National Museum of Natural History
- Capital One Arena
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- Stone Tower Winery
- Arlington National Cemetery
- Howard University
- Sandy Point State Park
- Washington Monument
- Georgetown Waterfront Park
- Patterson Park
- National Harbor
- Cunningham Falls State Park
- Johns Hopkins University
- Smithsonian American Art Museum
- CFG Bank Arena




