Family-friendly vacation rentals in Hollywood

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Hollywood

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

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Top guest favorite
A serene sunset over the Patuxent River, with warm hues reflecting on the water. Boats are anchored near a private pier, and a bridge spans the horizon. Fencing and grassy areas frame the scene, adding to the tranquil coastal atmosphere.
Apartment in California
4.93 out of 5 average rating, 238 reviews

Our Little Piece of Heaven

Our 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.

Guest favorite
The vintage A-frame home is nestled amongst trees, featuring a deck with a canopy in the foreground. A stone path leads to the entrance, where large windows allow for ample natural light. The surrounding landscape is adorned with greenery and decorative plants.
Cabin in Lusby
4.91 out of 5 average rating, 234 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 2 bed 1 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 crabs --

Top guest favorite
The sun is seen shining through the branches of a tree, casting rays of light over a calm river. The water reflects the sunlight, creating a sparkling effect. A wooden pier extends into the water, surrounded by lush greenery.
Tiny home in Saint Inigoes
4.98 out of 5 average rating, 380 reviews

Historic St.Mary's City at the Lazy Bear Cottage

Inquire first on pets, there is a 50 lb. weight limit total, can be split up between 2 small dogs or 1 at 50lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

Top guest favorite
The exterior of a two-story house is showcased, featuring light blue siding and white railings. A grassy area is visible in front, with four gray Adirondack chairs arranged around a circular fire pit on a stone patio. The sun casts a warm glow over the scene.
Home in Solomons
5 out of 5 average rating, 116 reviews

The Little House on Back Creek

Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

Top guest favorite
Two light blue Adirondack chairs are positioned on a wooden dock, facing a calm river. The sun sets over the water, casting a warm glow across the surface and creating a serene atmosphere. A weathered wooden table is placed nearby, enhancing the inviting scene.
Guest suite in Lusby
4.98 out of 5 average rating, 367 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is Solomon’s island. This is a safe space for all🥰

Guest favorite
A charming cottage sits at the water's edge, surrounded by lush greenery. A wooden staircase leads down from an elevated deck to the sandy beach. Two blue chairs are positioned on the deck, inviting relaxation as the sun sets in the background.
Cottage in Leonardtown
4.96 out of 5 average rating, 234 reviews

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Guest favorite
A serene waterfront view captures a glamping bungalow with a wooden pier, surrounded by lush trees. The calm water reflects the clear blue sky and the warm colors of the cabins. A boat is visible nearby, emphasizing the tranquil outdoor setting.
Tiny home in Hollywood
4.77 out of 5 average rating, 105 reviews

Charming Rustic Boathouse right on the Water!

Welcome to the Boathouse!! By offering kayaks, swimming, crabbing/fishing opportunity, a beautiful ambiance for drinks and dinner straight on the water and having almost any water adventure right at your fingertips, this glamping (glamour-camping) bungalow on the water is perfect for just about anyone with an adventurous nature-loving spirit! We encourage you to eat what you catch! And even bring your own boat and stay in one of our boat slips! Minutes from Solomons Island by Boat or Car!

Top guest favorite
An open living space features a vibrant wall art piece and comfortable seating, including a recliner and a sofa. A dining area with four chairs is visible, along with a well-equipped kitchen. Light-colored cabinetry complements the neutral tile flooring, creating a welcoming environment.
Apartment in Lexington Park
4.97 out of 5 average rating, 138 reviews

Serene setting great location surrounded by woods

The one-bedroom apartment will sleep 2 adults and 1 child under 18. In a serene setting with woods, a fish pond, and a comfortable patio. Separate code lock entrance. Well-equipped kitchen. Free WiFi, two TVs with Netflix and Amazon Prime. There is also a cedar sauna. Parking is on the property. Apartment situated near shops, restaurants, St. Mary's College and the Patuxent River Naval Air Station. 15 minutes from Chesapeake Bay, 1 hour to DC beltway. French and German also spoken.

Top guest favorite
A bright sun porch features a round glass dining table surrounded by four light-colored chairs. Large windows provide views of the waterfront, allowing natural light to fill the space. A cozy seating area is visible in the background, offering a serene atmosphere.
Home in Leonardtown
5 out of 5 average rating, 143 reviews

White Point Cottage -- Quiet Waterfront Getaway

Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. More on IG @whitepointcottage, and be sure to visit our sister property, Water's Edge Cottage.

Top guest favorite
A serene view of the St. Mary's River is framed by a white awning. Calm waters reflect the clear blue sky and a single sailboat is visible in the distance. Lush greenery lines the far shore, enhancing the peaceful atmosphere.
Apartment in Lexington Park
5 out of 5 average rating, 396 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Top guest favorite
A welcoming cottage exterior features a covered porch with seating, light fixtures, and colorful plantings. A walkway made of stone leads to the entrance, and the surrounding landscape is highlighted by well-maintained grass and nearby neighboring homes.
Cottage in California
4.97 out of 5 average rating, 260 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has an open floor plan that 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 featuring live concerts by top name bands.

Top guest favorite
Cottage in Hague
4.98 out of 5 average rating, 182 reviews

Waterfront Cottage on the Potomac River

Embark on a journey to the serenity of nature and the gentle lullaby of the Potomac River at the cottage. Escape the hustle and let the timeless embrace of water and tranquility rejuvenate your mind and soul. The private sandy beach (no public access) is steps away and awaits your footprints. Delight in the serene surroundings of the Northern Neck countryside. Two hours from DC, Richmond and Maryland.

Popular amenities for Hollywood family-friendly rentals

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Quick stats about vacation rentals that are family-friendly in Hollywood

  • Total vacation rentals

    Explore 30 vacation rentals in Hollywood

  • Nightly prices starting at

    Hollywood vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 1,690 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Hollywood vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Hollywood rentals

  • 4.9 Average rating

    Hollywood stays are highly rated by guests—averaging 4.9 out of 5!