Holiday rentals with a pool in Silver Spring

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.

Location · Family · Getting around

Historic Row Home Near Conv Center w/ Tank Pool

Historic Victorian row home featuring private backyard w/grill, firepit, and stock tank pool. Solar electricity, original hardwood floors and woodwork, renovated kitchen and bathrooms, and full laundry. Centrally located between Bloomingdale, Shaw & downtown, less than a mile to two Metro stations—NoMa-Gallaudet/NY Avenue (Red line) & Shaw/Howard (Green/Yellow lines)—and a mile to Amtrak at Union Station. Easy access to Convention Center, Capitol, Smithsonian, and the Mall. Happy dog fee $89

Location · Family · Walkability

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)

Location · Family · Indoor spaces

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

Location · Family · Hospitality

Modern Apartment at Ripley

 Upscale modern 1-bedroom apartment at Ripley just steps away from Downtown and Silver Spring Metro offers stylish, comfortable city living in a prime location. The apartment features an open, light-filled layout, a sleek kitchen with stainless-steel appliances, a comfortable bedroom and in-unit laundry adds everyday convenience. Ripley’s luxury amenities include a rooftop pool and Sky Lounge, a fully equipped fitness center, and elegant shared spaces for relaxing or entertainment.

Location · Quiet · Getting around

Spacious - King/King Beds - No Cleaning Fee

Welcome to our spacious two-bedroom unit in a peaceful community within the DC metro area. This inviting space features two comfortable bedrooms with ample closet storage, a roomy living and dining area, a fully stocked kitchen, and a balcony perfect for relaxing with a morning coffee or tea and a good book. Enjoy access to high-speed internet, cable TV, Netflix, and an Apple TV for all your entertainment needs. HVAC centrally controlled, switch to AC mid-April. Portable AC provided.

Value · Location · Checkout

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!

Family · Location · Parking

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

Value · Family · Heating

Cozy Private Entry 1BR1BA Suite Close to GMU & DC

Welcome to your beautiful one-bedroom suite with a modern and cozy interior. This private space features a walkout basement with its own entrance, ensuring privacy and convenience. The suite includes: Bedroom: Comfortable queen-sized bed, large closet Air mattresses: Additional sleeping space if needed. Kitchenette: Fully equipped with essentials . Dining Area Office Desk: Ideal for remote work or study. Updated Bathroom: Includes modern fixtures and amenities. Washer/Dryer

Value · Family · Heating

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.

Value · Location · Air conditioning

Inground Pool | Hot Tub | Sauna | Theme Room

Enjoy the comfort of this fully remodeled, beautifully decorated single family home. Located minutes from National Harbor Waterfront, MGM, Tanger Outlets, restaurants and shops, and just 20 minutes from Washington, DC and DCA Airport. Situated on half an acre, the home features a brand-new in-ground pool for summer enjoyment, plus a private hot tub and indoor infrared sauna for year-round relaxation. Please supervise children and follow posted rules for safety.

Family · Value · Access

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.

Value · Location · EV charging