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Vacation rentals in Leonardtown

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Top-rated vacation rentals in Leonardtown

Guests agree: these stays are highly rated for location, cleanliness, and more.

Our Little Piece of Heaven
SUPERHOST
Entire apartment · 2 guests · 1 bed · 1 bath

Our Little Piece of HeavenOur cozy studio apartment sets on the Patuxent River. With the perfect views of Myrtle Beach, Point Patient and Thomas Johnson Bridge. Relax watching the boats and birds or take a walk along the water for a lovely neighborhood to stroll for 2.5 miles. Your favorite moments may be when you wake to see the sun rise and again to see the orange sky set. Just over the bridge from the popular Solomon's Island which is full of fabulous restaurants, boat rentals, charter fishing and summer concerts.

Sandy Beach on Breton Bay with Beach
SUPERHOST
Entire house · 6 guests · 4 beds · 1 bath

Sandy Beach on Breton Bay with BeachAmazing waterviews, small sandy beach Fish or Crab from sea wall and beachside patio. Quiet serene location, partially privacy fenced, 7 miles from Leonardtown town center. Historic St Clements Island is within view, kayak to the state park on provided kayaks! Enjoy nature while relaxing in the beautifully designed outdoor space, where bald eagles and blue herons are common sightings. Large screen WiFi TV with cable & premium channels., Great amenities here!!! Well mannered pets welcome :)

Waterfront✦Private Dock✦Incredible Views &Sunsets✦
SUPERHOST
Entire house · 6 guests · 4 beds · 1 bath

Waterfront✦Private Dock✦Incredible Views &Sunsets✦Our dreamy waterfront getaway is the perfect spot to enjoy some rest and relaxation. Located directly on the waterfront of Breton Bay our home offers a scenic deck, screened in porch and private dock, that all feature breathtaking views that just can't be beat! Recently renovated, our 3 bedroom 1 bath home sleeps up to six guests. Our location offers serene privacy, but still within 10 minutes of Leonardtown's restaurants and shops. AC, High speed WiFi, and cable are all included in your stay

Vacation rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Leonardtown vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Leonardtown

SUPERHOST
  1. Entire house
  2. Lexington Park
Horseshoe Point - Waterfront - St. Marys River
SUPERHOST
  1. Private room
  2. Leonardtown
Home away from home
SUPERHOST
  1. Tiny house
  2. Saint Inigoes
Historic St.Mary's City at the Lazy Bear Cottage
SUPERHOST
  1. Tiny house
  2. Solomons
Private cabana on a pier!
  1. Entire guesthouse
  2. Bushwood
Little House by the water
SUPERHOST
  1. Entire house
  2. Lusby
Cove Point Cottage 1 block from Chesapeake Bay
SUPERHOST
  1. Entire cottage
  2. Leonardtown
Breton Breeze
SUPERHOST
  1. Entire cottage
  2. Lusby
Gettin to the point. ( Cove Point Beach)
SUPERHOST
  1. Entire house
  2. Park Hall
Charming 1930s Farmhouse on Scenic Farm
SUPERHOST
  1. Entire guest suite
  2. Leonardtown
Happy Guesthouse! Located waterfront
SUPERHOST
  1. Entire apartment
  2. Lexington Park
Adorable Waterfront Apartment Weekend Getaway
SUPERHOST
  1. Entire loft
  2. Lusby
Beaches, Hiking, Vineyards, Sunset, Fossil Hunting

Nearby destinations