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

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 Downtown DC & 6Flags.

Newly renovated private guest's suite with parking
Completely remodeled lower level guest suite, accommodates up to 4 guests. Features a private entrance and parking on premises for 1 car. Walk or bike to Veterans Park and Occoquan Bay National Wildlife Refuge. Conveniently located 12 minutes away from Quantico Marine Corp Base and Historic Occoquan attractions & restaurants. 30 minutes from Washigton DC, Old Town Alexandria and National Harbor, MD. Come enjoy this bright and quiet private stay. *Please note this is a NO SMOKING environment. *

3+N PROMO Waterfront + Gameroom | Dogs + EV OK
*Ask about our 3+ Night promotions* ☀️ Waterfront 🛶 Kayak/Paddleboard 👨🍳 Gas griddle ⛱️ 3 Community Beaches 🔥 Fire pit 🐶 Dogs OK 🎯 Gameroom ⚡️EV Outlet 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 Relax - Star Gaze - Kayaks/Paddleboard - Hike - Fish - Swim - Beach & more! Book your getaway today or ❤️ us for next time!

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!

Peaceful 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, high speed 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, Starbucks, and Restaurants. Less than 2 miles from Spa World. And 10 min drive to King Spa.

La Casita on Harris Creek, St. Michaels
Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

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.

The Little Gypsy BoHome
Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower, an outdoor redwood panoramic barrel sauna and a redwood cold plunge!

T&T’s Comfy Artists’ Retreat BnB
You’ll love this private walk-out basement of a family home for its incredibly comfy queen bed, big screen UHDTV w/Netflix, great bath/shower, WiFi, separate bedroom, well lit living room w/breakfast nook (fridge, microwave, coffee, tea), yard w/trampoline, playground, and tennis. Enjoy 1300sf near Potomac Mills Outlets, 6-min walk to free DC commute, I-95 HOV lanes to DC (1/2hr, 23 miles), kayaking, golf, and museums. Great for singles and families with kids.

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.

Amazon HQ-Luxurious DMV-WiFi-Cozy Suite-DC Airport
Revel in a stylish experience at this bold, bright - modern "Cozy Mustard" studio apartment. Experience the audacious ambiance of opulence and comfort the "Cozy Mustard" delivers. It is centrally located in the heart of Crystal City. Adjacent to Amazon Headquarters, and just minutes away from downtown D.C. Traveling professionals taking care of business or tourists exploring the city for leisure, the "Cozy Mustard" is the place for you.

Peaceful Haven: nature & charming town
Do you want to get away from it all, change your surroundings and recharge yourself mentally and physically? Welcome to Peaceful Haven. Shops and restaurants of the lovely historic Village of Irvington are only a couple of minutes away. Hike just outside your door or in nearby parks, ride bikes around the meadows or to town, hang outside and listen to the birds, or just sink into the comfy couch to enjoy a movie on our large TV screen.
Popular amenities for Southern Maryland rentals with a pool
House rentals with a pool

Come for the Holidays to Gorgeous, Waterfront Home

Nature Zen *Metro Walk *Visit DC *Relaxing Lakes

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

Spacious and private waterfront, sleeps 10

Stay&Play:Games, Pool, FirePit, Beach & Boardwalk!

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

Luxury 4 Bedroom - Pool/HotTub/Fire Pit

Magical wooded cottage pool +priv hottub walk2town
Condo rentals with a pool

Wyndham National Harbor ツ 2 Bedroom Deluxe

Rooftop bay and river views

Charming Annapolis Waterfront Condo

Cozy Annapolis Condo

Club Wyndham National Harbor, 2 BR Deluxe

Lovely 2-bedroom condo with pool and gym

Luxury Living at National Harbor

Met Park 2BR•Playground•Costco•5 min to DC/Metro
Other holiday rentals with a pool

King Size Bed - Reston Metro Apt

Luxury Farmette -Private & Secluded-1hr to DC

National Harbor 1BR Deluxe w/Jetted Tub & Kitchen

Sandy Feet Retreat - Beachfront

32-Acre Farm, Pool • Hot Tub • Holiday Lights

Sail Away To - Beachfront Views & Private Balcony

The Beached Whale

Cozy 1BR1BA Suite with Private Entry Near GMU & DC
Destinations to explore
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- Rentals with a kayak Southern Maryland
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- Bed and breakfasts Southern Maryland
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- Rentals with pools United States
- Nationals Park
- Georgetown University
- National Mall
- The White House
- District Wharf
- Smithsonian National Museum of Natural History
- National Museum of African American History and Culture
- Arlington National Cemetery
- Sandy Point State Park
- National Harbor
- Georgetown Waterfront Park
- Washington Monument
- Great Falls Park
- Six Flags America
- The Pentagon
- Smithsonian American Art Museum
- Lincoln Park
- Library of Congress
- Piney Point Beach
- North Beach Boardwalk/Beach
- Quiet Waters Park
- Ragged Point Beach
- Breezy Point Beach & Campground
- Meridian Hill Park




