
Vacation rentals with a pool in Maryland
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Top-rated rentals with a pool in Maryland
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Maryland rentals with a pool
House rentals with a pool

Mins to Annapolis from Waterfront home Pool, Pier
House owners were extremely responsive and informative. House was well stocked , and a great location and view made the stay even better.

4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acr
Judy's place was amazing. The pool was clean, the kitchen amendities were great, and the movie theater room had confortable seats and its surround sound was intense. There is even a really nice park 100 yards away from the property with a basketball court and a sand volleyball court which was a nice surprise. Judy made everything about staying here very easy and was quick to respond to all questions. Would love to stay here again.

Sophia’s victorian
Perfect place for our stay in Germantown. Very cozy and the kitchen was fully stocked with cookware. Plenty of rooms for everyone to have their own space and also the family room was big enough for everyone to hang out together.

The Bury Oasis: Pool◈Hot Tub◈Master Suite◈PingPong
The Oasis was perfect for our needs . We will definitely book it again in the future!

Modern Bay Dream
Rick was very supportive and his communication was superb. Great host with a beautiful cozy home. 5 star all across the board.

Large Home with Pool & 7 bedrooms; sleeps 21
The house was roomy and accommodated our large group. Really enjoyed the Bible verses on the walls.

Luxury Home with Pool for 20
This was a great place for our family of 13 to stay during the weekend of our niece's wedding in Baltimore. The home has plenty of large common areas, dining space, and super comfortable beds - even the queen-size bunk beds on the lower level had high-end mattresses. The kitchen is well-equipped. We had 4 additional family members drop in for dinner on our last night there, and it was no problem preparing food for, and serving, 17 people. Everyone was happy with this choice for our accommodations.

5 BEDR, Inground Pool+Billiard Table, Close To D.C
It was simply amazing. Daniel was a fantastic host. The house was incredible. Spacious, beautiful and peaceful felt just like home. The family and I enjoyed every inch of it. Family vacation home for every trip we take to DC.
Condo rentals with a pool

Bayside Boaters' Paradise | Pool | Family Fun
Beautiful view on the bay. Ally was very thorough & communicative throughout the process. Only thing that is kind of a bummer is that linens are not included. But other than that, I highly recommend Ally's condo.

Ocean Front 802 Midtown Oasis Pool & Parking
I enjoyed staying at this location. The view once you enter the condo is fantastic. Access to the beach and to other ocean city restaurants are great very walkable or very very short drive . The building is undergoing some kind of construction so when you walk into the building it’s clearly being worked on and is a bit dusty but once you get in the condo everything melts away. The condo also comes with some beach chairs and umbrellas.

2BR Waterfront | 1st Floor | Patio | Pool | W/D
Jacquelyn was amazing! She responded to messages very quickly and was super helpful and accommodating. She was also very kind. Her check in and check out instructions were very clear and easy to follow. The space was beautiful and located in the perfect spot. Will definitely be going back!

Ocean View Condo W/ Indoor and Outdoor Pool
We’ve stayed at Seawatch for many years so we’re already familiar with the great location. The condo was exactly as described and was a great place for our family. Would definitely book again.

Time N Tide Condo - 2 BR w/Pool, Boardwalk/Beach
The Time-n-Tide condo was great! Very well furnished, great decor, excellent amenities and great location. We felt very relaxed and comfortable during our stay, super cozy. Tina & Daryl we're very helpful with information and responsive to any questions we had. We hope to stay here again - great choice and value.

OC's Only Private Resort
Great place in a great spot! We enjoyed quiet mornings on the porch and being able to walk to nearby shops and restaurants with ease.

Paradise At Sunset Island In OC
We love staying at Sunset Island. This is the first time in a condo and it was perfect!

Family Friendly Two BR OCMD Condo Bay Side
It was a great place with lots of space! Diane even had a helpful manual with local stores, restaurants, hospitals, and pharmacies around the area. Very easy check in and check out process.
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