Family-friendly vacation rentals in Saint Leonard

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Top-rated family-friendly rentals in Saint Leonard

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Church Creek

4.78 out of 5 average rating, 161 reviews

Waterview cottage on Chesapeake Bay

(The crabs will be running soon, it getting warmer. Great view of the Chesapeake Bay. The Access to the Bay through canal behind the house. Private beach just five minute kayak ride from the house. Bring your own kayaks or rental them from Blackwater Adventures ask for Matt . There floating dock for a kayak launch. Now easy for you to get in and out of your kayak. New picnic table on porch that seat 6 people and two new beds. Two crab traps set for you and also a holding pen on the property.

Nov 26 – Dec 3

R3,330 ZAR per night

Guest favorite

Cottage in Leonardtown

4.93 out of 5 average rating, 194 reviews

Potomac River Freedom Cottage

Welcome to the Freedom Cottage! We hope you will have a wonderful relaxing stay. Guest access will be provided via a keycode which will be emailed prior to arrival, spare key hanging inside. Guests will have access to the entire house and grounds (front and rear yard, stretching down to the beach/water). I won't be there for check-in/out but guests are encouraged to call/text during their stay if any questions arise. **Off-season long term rentals available, please contact me to discuss.

Sep 14 – 21

R4,007 ZAR per night

Guest favorite

Cottage in California

4.97 out of 5 average rating, 195 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has been completely remodeled. The open floor plan allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum and St. Leonard Volunteer Fire Department featuring live concerts by top name bands.

Mar 1 – 8

R1,684 ZAR per night

Guest favorite

Apartment in Lexington Park

4.97 out of 5 average rating, 511 reviews

Historic St. Mary's City, MD

1,000 square foot two-bedroom, one bath waterfront apartment features separate entrance and a screened-in porch overlooking the St. Mary’s River. Property has a large dock and a small private beach. Jellyfish, crabs, and oysters make swimming challenging, although many swim off the dock in the deeper water. No Diving! Dogs are welcome. We just ask that they be on a leash. The apartment is attached to part of the house where we reside, although it is sealed off and nothing is shared.

Jan 25 – Feb 1

R2,150 ZAR per night

Guest favorite

Home in Arlington

4.97 out of 5 average rating, 396 reviews

Insights AirBNB

Beautiful apartment in basement of house. New construction. Private entrance with keypad (no check-in required). Large bedroom w/king size bed & separate den w/futon (playpen & toddler mattress available). Full kitchen & living room. Full size washer/dryer. Off street (driveway) parking. No smoking. Convenient location in safe, friendly Arlington. Easy transit options to Washington, DC. Walk to several bus stops, 1-2 miles to 3 Metro stops, 10 minute drive to downtown (outside rush hour).

Oct 11 – 18

R1,901 ZAR per night

Guest favorite

Home in Lusby

4.94 out of 5 average rating, 157 reviews

Waterfront Home on the Chesapeake Bay-Pvt Beach

A commanding view of the Chesapeake Bay. Enjoy walking the beach to Calvert Cliffs, bike to parks, art and cultural events. Enjoy the private beach with plenty of fine sand and gentle waves, great for teaching little one's water skills, playing with your canine companion or fishing/crabbing off the beach. You’ll love this waterfront hideaway because of the location, views, and the ambiance. My place is suburb for couples, solo adventurers, business travelers, families, and canine friends.

Jan 3 – 10

R7,447 ZAR per night

Guest favorite

Home in St. Leonard

4.91 out of 5 average rating, 162 reviews

Cozy Cottage on the Chesapeake Bay

Tranquility supreme. Sit on the terrace and gaze at the Chesapeake Bay. Sandy beach -- just 50 steps from front door; quiet residential area; nearby antiquing & fishing; Only 75 min. from DC. Finish your book or just replenish your spirit. Enjoy. Oh, one more thing — looking for the perfect place for a retreat for your small DC team? Strategic planning will be even more creative and enjoyable when you have the Chesapeake Bay as your muse. Note: This property is for non-smokers.

Oct 24 – 31

R4,436 ZAR per night

Guest favorite

Guest suite in Upper Marlboro

4.95 out of 5 average rating, 104 reviews

Private Apartment on a Horse Farm

My place is convenient to Joint Base Andrews (20 minutes), Washington DC and Annapolis MD (both are about 40 minutes by car) but you’ll love my place because of the outdoor space and the peace and quiet. For Equestrians, we are within 10 minutes of the Prince George's Equestrian Center as well. My place is good for couples, solo adventurers, families (with kids), and well-behaved pets. With a full-sized kitchen, this apartment is a great home away from home.

Jul 19 – 26

R1,816 ZAR per night

Superhost

Home in Cambridge

4.89 out of 5 average rating, 111 reviews

Dorothy's Chesapeake Delight

810 Seabreeze Rd is a quiet cozy retreat located on Brooks Creek off the little Choptank river directly across from the ragged point county boat ramp and dock. Guests are welcome to bring their boat. The house's private dock is just a quarter mile from the public marina. This house is the perfect place for boating, kayaking, paddle boarding, fishing, swimming, crabbing or just relaxing watching the sunset over the historic little Choptank river.

Oct 19 – 26

R2,806 ZAR per night

Guest favorite

Apartment in Solomons

4.99 out of 5 average rating, 226 reviews

Island Breeze Solomons

Cute studio apartment on charming Solomons Island. Walking distance to restaurants, live music, boat and kayak rentals. The kitchen has a full sized refrigerator, microwave, toaster, two burner hot plate and coffee maker. We provide all bedding and bath towels for two people. Enjoy your coffee ( provided) or wine on the deck in the fenced in side yard. One well-behaved pet is welcome. Please make sure you pay the pet fee.

Nov 7 – 14

R3,425 ZAR per night

Guest favorite

Home in Lusby

5.0 out of 5 average rating, 111 reviews

Historic Rousby Hall, Waterfront, Patuxent River

*Summer is a 1-week minimum, Friday-Friday* Rousby Hall is located on the Patuxent River, outside of Solomons Island with a view of the river's opening to the Chesapeake Bay. The 16-acre property is adjacent to our very private conservation area that borders our 300 foot private beach. The year-round property has a pier, in-ground pool (May-October) with amazing river views.

Jun 27 – Jul 4

R16,719 ZAR per night

Guest favorite

Cottage in Broomes Island

4.9 out of 5 average rating, 122 reviews

Gorgeous Waterfront Home!

Gorgeous waterfront property with all new furnishings and amenities! Feel free to bring your fishing rod, kayak or paddle board. Water access is just steps away. Bring your bicycle, it's a peaceful and scenic area with a marina & convenience store close by. Please note we DO NOT allow pets or more than 4 guest total. We also do not allow outside visitors or parties.

Apr 21 – 28

R4,183 ZAR per night