Vacation rentals with a patio in Saint Leonard

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Top-rated patio rentals in Saint Leonard

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Guest favorite

Cabin in Lusby

4.94 out of 5 average rating, 146 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a two bed, one bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish and catch crab --

Jul 20 – 27

R6,167 ZAR per night

Guest favorite

Home in Saint Leonard

4.94 out of 5 average rating, 36 reviews

Cottage on the Bay

Relax with the whole family at this peaceful place to stay. This beach cottage is in walking distance or a short drive to three private beaches in our community. We provide a parking pass to two of the beaches (one has no parking available). Please click each photo for a description. Updated 8/28/2023: to include a 3 person Hot Springs Jacuzzi, this is a shared amenity. 1 hour from DC/Joint Base Andrews /Annapolis. 45 minutes from Waldorf. 15 minutes from Solomons Island and Prince Frederick

Dec 30 – Jan 6

R3,594 ZAR per night

Guest favorite

Home in Lusby

4.99 out of 5 average rating, 114 reviews

Coastal Oasis On The Chesapeake, King Bd sleeps 12

Coastal Oasis On The Chesapeake (PARTY & 4•20 FREE zone) is where you come to: RELAX, DECOMPRESS and RE-CHARGE! You'll experience all the tranquility & majestic beauty of PEACEFUL living on the Chesapeake Bay. You'll awaken to breathtaking & alluring sunrises while also being surrounded by nature's wooded bliss of starry nights. Located 4 miles from Solomon's Island. Contact host for pre-approval of pets, pet fee applies. Unregistered: guests/pets & smoking including marijuana will incur fines!

Oct 23 – 30

R10,027 ZAR per night

Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 118 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silverwater is a lesson in quiet luxury, compelling architecture, unimaginable views and endless comforts. Original fine art and luxe bedding envelope you in a modern, light-filled space. Outside you will be treated to an expansive waterfront lawn that is great for games and afternoon sun. Rest on modern lounges or watch the sunset on your private waterfront bluestone patio tucked into the sea grass. As a guest favorite, your fabulous getaway is here—just read the reviews!

Feb 3 – 10

R8,132 ZAR per night

Guest favorite

Home in Saint Leonard

4.93 out of 5 average rating, 41 reviews

Hickory House on the Chesapeake Bay!

Welcome to Hickory House on the Bay! Charming 2 bedroom, 1 bath cottage overlooking the Bay within walking distance of two community beaches as well as a beach car pass. Relax, enjoy the water view, sounds and breezes. Explore this charming and tranquil community, Long Beach by the Bay. Enjoy all that Southern Maryland offers from this centrally located home - Hiking in Calvert Cliffs, kayaking, fishing, boating, exploring local vineyards, dinner in Solomon’s, visiting Historic St Mary’s.

Mar 1 – 8

R3,937 ZAR per night

Guest favorite

Home in Saint Leonard

4.97 out of 5 average rating, 39 reviews

Blue Pearl-Luxury estate with private dock/jacuzzi

The Blue Pearl is a luxurious river front estate with a private pier to catch crabs, fish and kayak. Soak in the outdoor jacuzzi and enjoy the river life. Three bedrooms with three full bath en-suites and over 2800 square feet of luxury accommodations await you. Office has Queen sleeper sofa. Pull up to your private boat dock, catch blue crabs with the provided traps, toast s’mores in the firepit while sitting in your Adirondack chairs. Enjoy two decks to view the sunrises and sunsets.

Nov 15 – 22

R8,066 ZAR per night

Guest favorite

Apartment in Broomes Island

5.0 out of 5 average rating, 25 reviews

Beautiful waterfront apartment in Broomes Island

Create a lifetime of memories at La Puesta de Sol! Located above Len’s Marina on Broomes Island, you will wake up in your private space, overlooking the beautiful Patuxent River! Enjoy the large deck, sipping a cold beverage, listening to music, watching for herons, swans and osprey or maybe just reading your favorite book! Lounge at the beach, explore in the kayak, or maybe you would rather rent bikes to tour the island! There are hiking trails within 15 mins, and so much more to do!

Apr 23 – 30

R4,399 ZAR per night

Guest favorite

Cabin in Colonial Beach

4.97 out of 5 average rating, 105 reviews

Spring Perfect, Water Front A-frame on Winery

This serene cabin is on the Ingleside Vineyard's property. Have a glass or two of wine and walk around the vineyards and then retreat to your own private a-frame cabin oasis. A beautiful view of the Roxsbury Estate where abundant wildlife can be viewed all around the property and the pond is stocked and ready to be fished. Within driving distance to wineries, Stratford Hall, George Washington & James Monroe's birthplace, Westmoreland State Park, and the beach town of Colonial Beach.

Dec 14 – 21

R2,585 ZAR per night

Guest favorite

Home in Port Republic

5.0 out of 5 average rating, 13 reviews

"HighTideTranquility" Beach wBBQ

Welcome to "High Tide Tranquility" , newly decorated coastal inspired 3 bedroom 2 bath. The main level boosts a Queen Master Bedroom with en suite bathroom, Living room, Kitchen, and Sunroom (Den and Dining room). The spiral staircase leads the way to a game room with ping-pong, Queen Bedroom, Bunk room, Bathroom, and Laundry room. Take a stroll to the private community beach that is only a couple of blocks away with access to the beach, pavilion, playground, basketball, and BBQ.

Aug 11 – 18

R5,726 ZAR per night

Guest favorite

Home in Lusby

4.92 out of 5 average rating, 38 reviews

Soul Oasis - home on the Chesapeake Bay

You can hear the waves of the Chesapeake Bay from the new trex deck. The beach is a short walk away where you can find fossils and sharks teeth and see plenty of nature. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.

Nov 1 – 8

R2,973 ZAR per night

Guest favorite

Home in Leonardtown

4.95 out of 5 average rating, 43 reviews

Old Bay Inn

Part of an adorable beach front community, the Old Bay Inn is a charming rambler styled home located just 6 miles from downtown Leonardtown and 3 miles from Newtowne Neck State Park. Old Bay Inn is a perfect stay when visiting local family or escaping fast-paced city life. Its convenient access to Breton Bay Golf Club, Historic St. Mary’s City, and Patuxent River Naval Air Station makes a great stay for early tee times or honorary celebrations.

May 13 – 20

R2,078 ZAR per night

Guest favorite

Guesthouse in Annapolis

4.99 out of 5 average rating, 108 reviews

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

Sep 25 – Oct 2

R7,330 ZAR per night