Vacation rentals with a pool in Southern Maryland

2 BR barn w/ loaded game room and pool available

This custom-built barn features 2 BR and 1 BA. The main level boasts a fully-equipped game area with billiards, shuffleboard table, air hockey, a 60-game arcade machine, a Mortal Kombat machine, a poker table, and two cabinets brimming with card and board games. Three smart TVs adorn the walls. The shared backyard outdoor space includes a hot tub, hammock, outdoor putting green, an adjustable basketball hoop, swings, a grill, horseshoes, a playground, a gazebo area, and a stocked fishing pond.

Chic King 1B Met Park•Costco•Min to DC/Metro/Mall

✨Enjoy a relaxing experience located minutes away from DC, Amazon HQ, and surrounded by popular restaurants and Mall. Our stylish home has a dreamcloud like king-size bed, working space, fast free Wi-Fi, and paid on-site garage parking. With all its amenities along with in-unit laundry for an extended stay, you'll feel right at home, Our home is: ❤ in front of Met park ❤ 2 min walk to Whole Foods ❤ 4 min walk to Metro ❤ 5 min from Reagan National Airport (DCA) ❤ 6 min to National Mall/Museums

Dupont West 4: Charming 1BR

Charming one bedroom apartment in a uniquely Washington, Victorian-era townhouse (circa 1880s) with original character. Original hardwood floors, exposed brick walls, and quality furnishings in a modern rustic style. Enjoy the wonderful adjoining balcony overlooking one of the cutest streets in DC. 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

3+N PROMO-Waterfront w/Gamerm, Firepit, Dog+EV OK

*Ask about our 3+ Night promotion* ☀️ Waterfront 🛶 Kayak/Paddleboard 👨‍🍳 Gas griddle ⛱️ 3 Community Beaches 🔥 Fire pit 🐶 Dogs OK (Max 2) 🎯 Gameroom ⚡️EV Outlet Relax - Star Gaze - Kayaks/Paddleboard - Hike - Fish - Swim - Beach & more! If you're looking to take a break or connect with nature, the Riverside Retreat in Montross, VA offers a peaceful sanctuary that is perfect for families, small groups, & couples Book your getaway today or ❤️ us for next time!

Kone Oasis- hot tub, pool, theater/game rm.

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 DC & National Harbor

Patuxent River View

Stay at this peaceful Chesapeake Bay guest house, perfectly located near North and Chesapeake Beaches and Herrington Harbor, with easy access to Washington, DC, Baltimore, & Annapolis. Enjoy a fully stocked kitchen, coffee and tea, fast WiFi, a seasonal pool, and a shaded gazebo—designed for comfort and convenience. Ideal for weddings, family visits, work trips, and quiet coastal retreats, this cozy home base makes it easy to relax, cook, stream, and recharge between festivities and exploring.

Beach Please! River cottage w/private beach & dock

Come unwind at "Beach, Please!" Our renovated cottage on the river with a private beach and dock is waiting for you! What's there to do? There's boating, fishing, crabbing, bird watching, tanning, and hammock-napping. Need more? Ok, antique shops, breweries, wineries, live music, crab boils and oyster fests. Still need more? Cornhole, can jam, horseshoes, hiking, and swimming and tennis at the community pool. That's not all, so just trust us - you will LOVE your time in Montross, Virginia!

Rosses Chance Guest House

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

Stylish 1BR Apt | Arlington | Pool, Gym

You will love stepping into modern elegance in our thoughtfully designed 1-bedroom apartment unit in downtown Arlington. Your ultimate home away from home awaits, boasting a prime location with all conveniences at your fingertips. Just mins away from top-notch restaurants, bars, entertainment venues, & parks, your perfect getaway is closer than you think! ★ 12 Min to Georgetown Waterfront ★ 10 Min to Pentagon Mall ★ 15 Min to Reagan National Airport ★ 15 Min to Lincoln Memorial

The Glebe

This 3br 2ba home with own private beach is nestled off of the Potomac River and boasts serene and expansive views. Sunbathe on the private beach, cool off in the water, go fishing/crabbing from the dock, or just listen to the waves crash. Whatever it is, you’ll find it absolutely relaxing. Be sure to explore local wineries, breweries, shops and enjoy the community pool and tennis court. It's the perfect getaway house for couples/families or anyone looking for a serene weekend.

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.

Waterfront-View of Bay from your Bed-Steamy Sauna

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.