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

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

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

Luxury 4 Bedroom - Pool/HotTub/Fire Pit
*PLEASE READ OUR LISTING AND HOUSE RULES IN, PRIOR TO BOOKING OUR HOME. SEASONAL POOL/ HOT TUB DATES* Welcome to your beautiful and spacious home away from home! Featuring 4 beautifully decorated bedrooms and 2.5 bathrooms, each designed with comfort and style in mind. Relax in our spacious living areas, take a plunge in the pool & hot tub or lounge by the fire pit in the huge backyard! Experience luxury and comfort in our beautiful home and make unforgettable memories with your loved ones!

Annapolis Waterfront Condo - Unit #: A-203
Cozy, comfortable condo. Great views - 2nd flr. Fireplace 1 bed/bath condo, sleeps 4 max, covered, water front deck, reserved parking! .5 mile walk to dwnt Annapolis and the Naval Academy, 1.9mi to the Navy stadium. Book NOW for the Summer! Easy access to Spring/Fall boatshows. 12 stairs, no elevator. Pool Memorial to Labor Day: MWTh 4pm-8 Tues: Closed FSS and 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

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 (weather permitting) and adjacent walking trails.

Annapolis Garden Suite
Welcome! We’re tucked away on a forested residential street, roughly a 7 minute drive from restaurants, coffee shops and all that Annapolis has to offer. 15m from the coast, 30m from Baltimore and 35m from DC. Tl;dr: this is a private ground-level guest suite with 3 beds, 2 bedrooms, 1 desk (optional standing desk), 1 kitchen with oven, dishwasher + Nespresso/pour over, 2 tvs, laundry room with washer/dryer, fast wifi, a pool, patio and a forest view. We live on the top floor.

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.

Cozy 1-Bedroom Retreat Near Annapolis, Sleeps 4
This fully updated suite is designed for comfort and convenience. Enjoy a king bed and a LoveSac sofa that converts into a queen bed, perfect for 2-4 guests. The suite includes a private en-suite bathroom, high-speed internet, a fully furnished kitchen, and a coffee bar to make you feel right at home. Located just 4 miles from Annapolis, you're close to all the best spots. Whether you’re here to relax or explore, this suite has everything you need!

1st Floor Condo in Annapolis
This newly renovated, 1st floor studio is perfectly located just across Spa Creek from historic Annapolis in Eastport. Within easy walking distance of restaurants (3 min), Main Street/City Dock (10 min) & USNA's Gate 1 entrance (14 min), our studio includes a full kitchen, high-speed wifi, free onsite parking lot, a secure building entrance, dock and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

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.

5 BEDR, Inground Pool+Billiard Table, Close To D.C
Enjoy the comfort of this fully remodeled, beautifully decorated single family home. This home is located within minutes of National Harbor Waterfront, MGM, Tanger outlets, many restaurants and shops, and only 20 minutes from Washington DC and 20 minutes away from DCA - Ronald Reagan Washington National Airport. The home is built on half an acre of land, with a brand new in-ground pool in the backyard for enjoyment in the summer months.

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, a basketball hoop, beach access, a canoe, a gas grill, a steam shower, and an outdoor redwood infrared barrel sauna.
Popular amenities for Upper Marlboro rentals with a pool
House rentals with a pool

Palisades Retreat

Cozy 1-Bedroom Basement Apt in Gated community

Nature Zen *Metro Walk *Visit DC *Relaxing Lakes

Charming Family & Fido Oasis|Sleeps 8|4 Bedroom

Entire Beach House with Pool and Hot Tub

Large Home with Pool & 7 bedrooms; sleeps 21

5BD no. Nat'l Harbor, MD, DC & VA w/yard Oasis

Tranquility on Tilghman Island – Wide Water Views
Condo rentals with a pool

Stylish 1BR Condo in Vibrant National Harbor, MD

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

National Harbor your D.C. Vacation Springboard.1br

Silver Spring DT LuxePad 2BR, DC Metro, Pool, Gym

Cozy Annapolis Condo

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

Club Wyndham National Harbor, 2 BR Deluxe

Prime Location Waterfront Eastport Condo w Parking
Other holiday rentals with a pool

Luxury 2BR/2BA | Stunning DC City Views + Balcony

Stylish Studio Steps to Tysons Metro - Queen Bed

Cozy 1 BD Apt in Downtown McLean- Balcony/Parking

Luxury BWI/Hanover 3-Level With Bonus Living Space

Cherry Blossom Base of Operations!

One bedroom apartment in Tysons.

Capitol Hill 1BR | WorkSpace Gym | Lounge | Metro

Mclean View | Steps from Tysons Corner & Galleria
Quick stats about holiday rentals with a pool in Upper Marlboro

Nightly prices starting at
Upper Marlboro holiday rentals start at $84 AUD per night before taxes and fees

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Upper Marlboro rentals

4.8 Average rating
Upper Marlboro stays are highly rated by guests—averaging 4.8 out of 5!
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- Walter E Washington Convention Center
- Georgetown University
- National Mall
- M&T Bank Stadium
- Nationals Park
- The White House
- District Wharf
- Capital One Arena
- National Museum of Natural History
- Baltimore Convention Center
- Oriole Park at Camden Yards
- Hampden
- National Museum of African American History and Culture
- Arlington National Cemetery
- Sandy Point State Park
- Washington Monument
- Georgetown Waterfront Park
- Patterson Park
- National Harbor
- Smithsonian American Art Museum
- Great Falls Park
- Six Flags America
- The Pentagon
- Lincoln Park




