Family-friendly holiday rentals in Saint Leonard

Dazzling day/night water views,1st class amemities

TREAT YOURSELF! YOU DESERVE THE VERY BEST! HUGE DISCOUNTS FOR WEEK AND MONTH LONG STAYS! Treat yourself to the good life while in Annapolis! Gorgeous 14yr. old custom designed & furnished 1470sq.ft. waterfront apartment, 9ft. ceilings, fantastic water views day & night! Private pier, firepit and 40ft. waterfront covered patio for guests use. Guest parking for 4 cars. Few minutes to US Naval Academy, Annapolis Harbor, restaurants, shopping. Pet-friendly, must be cleared with host. *see below*

Bay Breeze Retreat

Incredible private luxury retreat on the eastern Chesapeake Bay. Complete with every amenity- saltwater pool, firepit, multiple Smart TVs, sleeps 10 in comfort, premium memory foam mattresses in every room, fast Wi-Fi, 100' pier, huge front yard. Unbelievable views!!! Extensively renovated. Please note that no parties or disturbances will be tolerated. We require that guests respect our neighbors and serene community at all times. We explicitly do not allow bachelor or bachelorette parties.

Perfect Bay and Beach Getaway one hour from DC!

Our waterfront home with sweeping views of the Chesapeake Bay is close to beaches, the Flag Harbor Marina, Solomon's Island, Flag Pond Nature Preserve and Calvert Cliffs State Park. You’ll love the spectacular sunrises/sunsets over the Bay, diving ospreys and eagles, and exploring the bay by kayak, canoe, or paddle board. Our house is great for families (with kids), groups, and well-mannered dogs. New in 2023: we will be replaced the upstairs HVAC system, baby proofing, and fall 2023 paint

Enchanted! 1BR Apt near DCA in quiet neighborhood

Full accomodations and amenneties with plenty of space. Books, Movies and Games are available for rainy days. Curl up by the fireplace on cool nights. Although the listing says "not suitable for kids 2-12" I leave that decision up to you. It is not childproof for younger children so I don't want to be responsible for your child's safety, however kids are welcome. An infant would be fine but you will have provide the bed and bedding and take care of safeguarding.

SM’s Premier Rental Heated Pool opens 4/11/2025

Harbor Hideaway's in- town location and now featuring a PRIVATE POOL is a rare find. Steps away from everything that SM's has to offer. HH is a 1940’s - 1 1/2 story cottage loaded with thoughtful amenities. Airy and appointed with modern/ comfortable furnishings, resort quality linens, a well stocked kitchen; this 2 bdrm /2 B cottage is sure to please! Perfect for 1 to 2 couples, girls' wknds, small family, or anyone just in need of a relaxing getaway.

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise

Gift yourself this private, secluded second floor Flat & Solarium Bedroom. Best hideaway to rest, bond, restore, create, or work. A breezy, country-like setting provides space to escape the city hustle! Nearby scenic drives & groceries, or venture to Annapolis TJ/WF or historic walks. Fully relax with pier, kayaks, swings, fire pit, starry nights, sun-drenched loungers, cozy up with books/movies & luxuriate in the deep soaking tub or European shower.

MODERN HOME NEAR CAPITOL HILL ✩✩✩✩✩ Walk to METRO subway

♢ 2 blocks to the nearest Metro subway station ♢ 8-minutes by car to downtown Washington DC ♢ HDTV + Roku TV in living room & Master bedroom ♢ Amazon's Alexa at your service on the Echo ♢ High-speed Wi-Fi ♢ Kid- and family-friendly rental Relax in style in this lovely DC home, located just minutes from Capitol Hill and the must-see H St. Corridor in the Hill East community, and just a short metro ride from the museums.

Spacious Family Retreat in Tranquil Neighborhood

Our home is one of the largest homes in the neighborhood. It is beautifully decorated for your enjoyment. Our large family room will make you feel like you are at home. House is 2,700 sq ft. The house is a close 2.5 miles from the well-known National Zoo. Also, 0.7 miles to the METRO station that has a direct route to the National Mall - a perfect tourist destination.

Cozy chic apartment in lovely Mt. Pleasant

Cozy, well appointed apartment on tree-lined street in historic neighborhood, close to everything. Private entrance off street, shaded patio in back, sharing tranquil backyard w/host family residence above. This unoccupied apartment is delightful alternative to hotel, w/all amenities. Easy walks to Zoo, Rock Creek Park, and Metro.