House in Maryland
10 guests · 5 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
Rooms
Bedroom 1
1 King
Bedroom 2
1 King
Bedroom 3
1 Queen
Bedroom 4
1 Queen
Bedroom 5
2 Singles
About this house rental
Escape to this spacious, family-friendly home located on a peninsula on St. Jerome Creek. Close to Chesapeake Bay and boasting a 270-degree panoramic view of the water, enjoy 900 ft of waterfront delight. Outside, you can indulge in wildlife viewing, with ospreys and eagles nesting nearby. Fish, crab, or swim from the 1,200+ square foot pier. Also for your enjoyment, be sure to utilize the provided 50 x 20 pool, bikes, paddleboard, and large, 8-person hot tub.
-- THE PROPERTY --
Inside your waterfront escape, discover a gourmet kitchen with ample gleaming countertops, high-end appliances, and a copper farmhouse sink. Your family will adore relaxing and unwinding in the adjacent living room with ample seating, along with a large screen TV. Also on this main level, you will find a designated office space, the first of the main bedrooms, along with another bedroom and a full bathroom.
The primary bedroom is an oasis that features another work desk, easy outdoor access, and a luxury en-suite bathroom. Indulge in a bubble bath when you dip into the impressive soaking tub or equally beautiful walk-in shower. Dual sinks and a large walk-in closet round out the excellent amenities this space provides.
Upstairs, take in the view of the fabulous Chesapeake Bay from the large A-frame window. The kids will love this space for their weekend morning cartoons and board game nights.
End the evenings with a dip in the pool or watch the sunset from the hot tub. Gather around the firepit to roast s'mores as you reminisce on the sweet memories you've made thus far and those to come.
-- THE LOCATION --
-- REST EASY WITH US --
Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.
-- ADDITIONAL DETAILS --
- Unwind on Maryland’s western shore, close to famed parks, wineries, and historic sites- 5 miles to Point Lookout State Park- 8 miles to Historic St. Mary’s City & Elms Beach Park- 23 miles to Leonardtown restaurants & shops- 24 miles to Piney Point Lighthouse Museum & Park, Piney Point Landing- 78 miles to Ronald Reagan Washington National Airport
-- POLICIES --
- No smoking- No pets allowed- No events, parties, or large gatherings- Additional fees and taxes may apply- Photo ID may be required upon check-in- Quiet hours are from 10:00 PM to 8:00 AM
ADDITIONAL INFORMATION- Guests need to supply their own wood for the indoor and outdoor fireplaces- Your safety matters. The property features 3 exterior security cameras on the exterior of the house. All cameras are outward facing and do not look into interior spaces, and record sound and video when activated by motion
Amenities
Free WiFi/internet
Air conditioning
Non-smoking
TV
Heating
Wheelchair accessible
Coffee/tea maker
Spa
Kitchen
Kitchenette
Balcony/Terrace
Private pool access
Private beach access
Dishwasher
Kitchenware
Garden
Fireplace
Waterfront
Water view
Shower
Bath or shower
Bathtub
Outdoor Cooking
Family friendly
Outdoor dining area
Towels
Linens
Fan
Dining table
Desk
Accessible by stairs only
Hairdryer
Carbon monoxide detector
Map of Maryland
Ratings and reviews
10 / 10Outstanding·Dec 2025
The water views and the pool
10 / 10Outstanding·Dec 2025
I just want to say that the house we stayed in this past weekend was absolutely wonderful! Out of all the places I’ve ever rented, this one is by far my favorite. Anyone looking to book it can do so without hesitation—you’ll enjoy every bit of it. The house is spotless, very comfortable, and simply amazing in every way. I highly recommend it!
10 / 10Outstanding·Dec 2025
This home was gorgeous--the water views were spectacular--incredible birds flying by-herons/eagles/egrets/kingfisher/blue birds--pool/hot tub/outdoor chess. Kids fished (we brought rods based on previous review--the dock was awesome) biking on quiet street. Full stocked kitchen and great hosts. Can't wait to go back!!!!!!!!!
10 / 10Outstanding·Dec 2025
Pleasure Point was a wonderful getaway for our family. It is the perfect mix of seclusion and luxury. The views are magnificent, the pool is amazing, the kitchen has everything you need along with top notch appliances, and the beds are comfortable. What more could you ask for? We appreciated all the small touches and had everything we needed for a wonderful and relaxing vacation. Property was clean and host was responsive. Would love to return again soon!
$$$$
Top rated by guests
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