Vacation rentals with a pool in Glen Burnie

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Glen Burnie

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Rental unit in Stevensville

4.98 out of 5 average rating, 272 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 favorite

Home

4.85 out of 5 average rating, 135 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

Relax at this large 7-bedroom spacious top-quality home that is ideal for large gatherings where all can be together in one place. All will be comfortable in large open areas both inside (4,125 sq ft, tall ceilings) & outside (1 acre). Enjoy a huge first-class kitchen with all the granite countertop space, cooking & serving supplies you will ever need. Enjoy the large fenced-in backyard with pool, grill, & fire pit. Ideal for family events, quiet getaways, sports teams, & business meetings

Guest favorite

Guest suite in Arnold

4.9 out of 5 average rating, 115 reviews

Cozy Comfort - only 7.5 Miles to Annapolis & USNA

Close to historic Annapolis, our cozy first floor guest apartment of our home in a quiet large single family home neighborhood. 'The Oasis' is private and spacious with 2-bedrooms, a living room, mini sit-in kitchen, bathroom, and laundry room. Close to waterfront restaurants, B & A trail, Sandy Point Public Beach and Park, festivals, shopping, bowling, miniature golf, wineries and more. Our guests are welcome to enjoy some time relaxing in our wooded backyard with gazebo and patio areas.

Guest favorite

Guesthouse

4.97 out of 5 average rating, 143 reviews

Poolside Paradise in Monrovia, Maryland.

Enjoy your stay in this fabulous pool house located in a quiet neighborhood. Relax poolside during the day and enjoy the outdoor bar and kitchen for cocktails at sunset. Breathtaking views all around. Just 50 minutes from Baltimore and Washington DC and 10 minutes to historic downtown Frederick. Private entrance to backyard with a large green space on the backside of the pool house. We consider ourselves a couples retreat and don’t host gatherings. We look forward to hosting you soon:)

Guest favorite

Guest suite

4.94 out of 5 average rating, 500 reviews

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.

Guest favorite

Cottage in Saint Michaels

4.97 out of 5 average rating, 157 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 favorite

Guest suite

4.95 out of 5 average rating, 115 reviews

Patterson Park Penthouse with Rooftop Deck!

Located overlooking the lovely Patterson Park and close to Canton & Fells Point this is a great spot for a Baltimore visit! This large and newly renovated Baltimore rowhouse less than 10 min from the Inner Harbor, Johns Hopkins main campus, Bayview, Fells Point, Canton. We invite you to stay in a lovely private apartment oasis on the top floor of the row house that has stunning views of the park and access to a balcony and large rooftop deck for lounging or dining.

Guest favorite

Guesthouse

4.98 out of 5 average rating, 277 reviews

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 and adjacent walking trails.

Guest favorite

Condo in Annapolis

4.96 out of 5 average rating, 251 reviews

Annapolis Waterfront Condo - Unit #: A-203

BOOK NOW FOR SUMMER 2025! SPRING and FALL BOAT SHOW AVAILABILITY! Free reserved parking! Walk to show in minutes! Great views - 2nd flr. condo (12 stairs, no elevator.) Pool hours are fixed: Mon: 4pm-8 Tues: Closed Wed: 4-8 Thurs: 4-8 Fri: 3-8 Sat/Sun/Holidays: 12pm-8 The pool is one of the best places to be on a hot summer day. If hours are unacceptable, pls select another location. 15 min. walk to downtown Annapolis/USNA. MULTIPLE Free parking options.

Guest favorite

Guesthouse

5 out of 5 average rating, 250 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 favorite

Guest suite in Arnold

4.94 out of 5 average rating, 151 reviews

Coastal Comfort Suite Near Annapolis, Hottub, EV

Yes, the hot tub IS open! 24/7/365 :-) Ideal for a couple's retreat, this king suite guest room has a massive bedroom with a seating area, mounted TV, and coffee bar with microwave/mini-fridge. An ensuite bathroom provides a luxurious shower with dual shower heads and a spacious closet. The pool and hot tub are seasonal. Please don’t hesitate to reach out with any questions, concerns, or expectations so that we can address them prior to your stay.

Guest favorite

Home in Tracys Landing

4.99 out of 5 average rating, 194 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.