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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.

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Barn

4.9 out of 5 average rating, 181 reviews

1 BR barn w/ loaded game room and pool available

This custom-built barn features 1 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.

Guest favourite

Flat

4.98 out of 5 average rating, 273 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Guest favourite

Guest suite

4.89 out of 5 average rating, 272 reviews

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. *

Guest favourite

Cottage

4.98 out of 5 average rating, 130 reviews

Church Creek - waterfront cottage & pool - private

Close to Blackwater NWR and the Harriet Tubman Center, enjoy peaceful days at our secluded waterfront cottage on Church Creek. Great for winter remote work! Our closest neighbor is across a cove. Our estate offers 50 acres of privacy and one of the best waterfront views on the Chesapeake. Enjoy a view from every window and nature all around you. Excellent walking, swimming (in-ground pool-May 3-Oct 1), great birding and bicycling. Launch your kayak from the backyard. Perfect private getaway!

Guest favourite

Home

4.96 out of 5 average rating, 112 reviews

Spend Christmas at Gorgeous, Waterfront Home!

If you were thinking of heading to the Eastern Shore, Casey's Porch is the place to go. Come and see for yourself. Bring your extended Family. Bring your friends. Please note spring mid-week rates! Kayaks and paddle boards and bikes await you at this beautiful home on Hudson Creek. Fish from the dock. Pull crabs from the creek. Walk down quiet country lanes. Sit around the fire pit. So many fun, outdoor things to do. Casey's Porch has it all. *4th Night Free is Winter Special

Guest favourite

Home

4.99 out of 5 average rating, 144 reviews

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!

Guest favourite

Home

4.92 out of 5 average rating, 119 reviews

Indoor pool/spa nestled in Southern Md. woods.

Contemporary all-brick French manor nestled within 16-acres of secluded woodlands. Indoor pool/spa with waterfall inside a stunning, sunlit atrium. Three bedrooms and three bathrooms accommodate 6-8 people. Centrally located near the Chesapeake Bay where quaint towns include restaurants, antiques, sandy beaches and fishing boat rentals. Centrally located for trips in all directions: Washington, D.C. (35 miles); Annapolis (30 miles) Baltimore (50 miles) and Ocean City (139 miles).

Guest favourite

Home

4.94 out of 5 average rating, 191 reviews

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.

Guest favourite

Cottage

4.97 out of 5 average rating, 158 reviews

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.

Guest favourite

Home

4.99 out of 5 average rating, 197 reviews

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!

Guest favourite

Guest house

5 out of 5 average rating, 252 reviews

Waterfront Getaway - View of bay from your bed

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.

Guest favourite

Cottage

5 out of 5 average rating, 100 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

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Popular amenities for Southern Maryland rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home

5 out of 5 average rating, 82 reviews

Waterfront Escape: Gameroom-Firepit-Dogs & EV OK

Guest favourite

Home

4.97 out of 5 average rating, 34 reviews

Perfect Gift•Game Theme•Dock+Boat+King bd+EV Chrgr

Guest favourite

Home

4.96 out of 5 average rating, 83 reviews

Waterfront Dock, Hot Tub, Beach, Pool, Kayaks, SUP

Home

4.81 out of 5 average rating, 155 reviews

Bay Breeze Retreat

Guest favourite

Home

4.99 out of 5 average rating, 80 reviews

Waterfront Farmhouse Meets Modern Luxury

Home

4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

Guest favourite

Home

4.89 out of 5 average rating, 46 reviews

FxBurg Retreat

Guest favourite

Home

4.94 out of 5 average rating, 16 reviews

Family Friendly: Hot Tub, Grill, Pool & More!

Apartment rentals with a pool

Guest favourite

Apartment

4.98 out of 5 average rating, 40 reviews

Rooftop bay and river views

Guest favourite

Apartment

4.88 out of 5 average rating, 8 reviews

Beach Haven - 3BR with River Views

Guest favourite

Apartment

4.81 out of 5 average rating, 27 reviews

Wyndham National Harbor- 1 bdrm

Apartment

4.95 out of 5 average rating, 19 reviews

Beautiful 1 BR Suite at Wyndham National Harbor!

Guest favourite

Apartment

4.91 out of 5 average rating, 116 reviews

Lovely 1-Bedroom Condo with Pool and City View

Apartment

4.75 out of 5 average rating, 4 reviews

The Fountains condo one bedroom 2 level apartment

Guest favourite

Apartment

4.86 out of 5 average rating, 22 reviews

Wyndham National Harbor | 1BR/1BA King Bed Suite

Guest favourite

Apartment

4.86 out of 5 average rating, 22 reviews

Heart of Tysons Corner | Balcony | Spacious | Luxe

Destinations to explore