
Holiday rentals with a pool in Upper Marlboro
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Top-rated rentals with a pool in Upper Marlboro
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House rentals with a pool

Cozy 4BR Retreat with Heated Pool Near MGM & DC!
We really enjoyed our stay here and felt right at home. The house looked just like the pictures and was very cozy. Luam even reached out during our stay to ensure everything was going well. If we’re ever in the area again we would definitely return.

Bay Breeze Retreat
Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.

Harpers Ferry Farmhouse, Heated Year Round Pool
This was such a wonderful home! As other reviewers said, lots of room for a big group to spread out. We had 8 guests. (6 adults and two kids) We explored Harpers Ferry and enjoyed hiking the Maryland Heights Trail. We felt absolutely comfortable hanging at this serene house for our mornings and evenings. Cooked most of our meals, played billiards, sang karaoke, and enjoyed the plunge pool. We had an epic round of hide and go seek. Great interior design and lots of space to spread out for quiet time, and many perfect reading nooks. Thanks Leigh, for being so responsive and friendly!

Gorgeous, waterfront home - Perfect for Families.
Clare and Chris could not be nicer and easier to work with. My family/friends have been getting together since 1994 and have been to many great Airbnb's and VRBO's. My group could not stop telling me how great of a week we had. The primary features that were import to us which the house scored big are as follows: It has a dock (we arrived via boat), The kitchen is big, laid out for many "Cooks", The kitchen was open to the dining room table, The dining room table is open to the sitting areas, The pool was clean and inviting, The fire pit with seasoned firewood was a big hit for our group, All the beds were comfortable, The bedrooms were large and comfortable, The baths were clean, modern & large and The location to "What to do in Cambridge" is only 7-10 miles away. We made prearrangements: Richardson Maritime Museum to have a guided tour with David Williams on Friday and Spocott Windmill with George Radcliff. Both of these tours were fascinating. Our weekend was 5-Stars.

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit
Our family had such a great time staying at MJ's place last year that we came back again this summer. As before, we all loved the view, pool, firepit, grilling on the deck, and walking down to the neighborhood beach. The house was very clean and the kitchen was well-stocked. All the beds were comfortable, and all bedrooms had well-functioning blinds/shades, which is really helpful when putting younger kids to bed. The lower level bathroom had been renovated since our last stay which was a great bonus. We are looking forward to returning next summer!

Cosy 4-Bedroom House Close To DC
Perfect stay for a large group! Lots of rooms! Lots of beds! 3.5 baths is clutch!!!! And affordable!!!! Also, the water pressure was amazing! We’ll have to come back when we can use the pool! Thanks so much!

Waterfront Farmhouse Meets Modern Luxury
Beautiful house! Clean, well maintained, and exactly as described. The host was easy to communicate with and very responsive throughout our stay. The space felt comfortable and welcoming, and everything we needed was thoughtfully provided. We had a great experience and would definitely love to come back!

Historic Peace and Plenty Farm: Pool House
Duane and Matt were absolutely wonderful hosts! They helped make our quick weekend getaway truly unforgettable. Every amenity at the property was thoughtfully provided, and our daughters enjoyed every bit of it. Even while traveling internationally, Duane remained incredibly attentive and responsive, going above and beyond to ensure our stay was perfect. One of the highlights for our girls was getting to meet a baby sheep—such a thoughtful and special touch! They were especially taken with little Pinky Pie and are still talking about her. Thank you again, Duane, for sharing your beautiful property and creating such a memorable experience for our family!
Condo rentals with a pool

Rooftop bay and river views
Our stay was great. The location was perfect for us with the beach and shops just a short walk from the house. The rooftop patio was really nice in the evenings. Several of our guests enjoyed the pool area as well. We would definitely stay at this house in the future.

Charming Annapolis Waterfront Condo
Great host, great location. Walkable to great restaurants as right over the bridge from Main Street Annapolis. The pool is literally right in front of the apartment overlooking the water and the boats going by. The place is not huge but location, location, location.

Cozy Annapolis Condo
This was an awesome stay! If you have infants their place is a must as it is easily baby proofed and has so many accessible items!

Lovely 1-bedroom condo w/ 2 parking spots near DC
I definitely loved this home soooo spotless felt right at home. You might hear people walking here and there BUT it’s not an all the time thing, other than that it’s so peaceful. Kitchen is beautiful and has all the spices you kinda need if you wanna cook, bed was sooooooo comfortable and the living room was so inviting. It’s close to food spots banks grocery stores, etc. I’m definitely booking again.

Wyndham National Harbor ツ 3 Bedroom Deluxe!
Very nice place to stay near Gaylord convention center. Super clean condo. All the essentials are there. Lots to do at the resort as well as nearby walking distance. Having a baby in the group we did quite a bit of laundry. A laundry room was on our floor with two washers and four dryers and free of charge. We barely passed anyone on the seventh floor. We would def stay here again.

Club Wyndham National Harbor, 2 BR Deluxe
Where do I start? This was the most perfect place to stay. From the ease of the check-in process to the amenities offered, this was the best AirBNB experience ever. The room looks even better than in the pictures for starters. It was the perfect amount of space for all 6 of my family members. The amenities offered for the kiddos were a game room, pool, and there were activities for all ages hosted by the resort most evenings. Any kind of restaurant you could think of was within walking distance & some even offered a 10-20% discount for staying in the area. The rooms were clean upon arrival. I had 2 issues during my stay and they were resolved within 5-10 minutes of me texting the provided number. Unheard of. Every staff member we encountered was friendly and helpful. The concierge service even helped us planned our Washington DC activities for the day. I cannot rant and rave enough about this accommodation. Don’t hesitate to book. Do it now!

DTSS LuxePad 2B2B w/ Rooftop Pool + DC View Lounge
Trip went very well worth every penny. Owner was very helpful answered whenever we called to help with check in gave us no problems about playing music on their Alexa or living room tv. Would get again for another trip.

Luxurious Suite King/Queen Beds in North Bethesda
We enjoyed a comfortable 7 night stay with our daughter, son-in law and 2 years old granddaughter who traveled from Oslo, Norway. Oleg is very kind and responsive, the best host we have ever encountered. After we requested some bedding for crib, he ordered them right away and sent us a nice little blanket and a small pillow for our granddaughter in the next morning! He even let us to keep the bedding! The apartment is clean and neat and has all the conveniences needed. It is in a great location, convenient walk to metro, above WholeFoods and other nice restaurants/Starbucks and CVS. We highly recommend the apartment to those who plan to stay in the North Bethesda area.
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- Nationals Park
- The White House
- National Mall
- Georgetown University
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- District Wharf
- Smithsonian National Museum of Natural History
- Hampden
- M&T Bank Stadium
- Sandy Point State Park
- Georgetown Waterfront Park
- Patterson Park
- Arlington National Cemetery
- Washington Monument
- Great Falls Park
- National Air and Space Museum
- National Harbor
- Smithsonian American Art Museum
- Lincoln Park
- Maryland Renaissance Festival
- Meridian Hill Park
- Caves Valley Golf Club
- Robert Trent Jones Golf Club