
Family-friendly holiday 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.

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.

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 --

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🥰

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.

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!

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.

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.

Stunning Sunsets on Breton Bay, Seaside apartment
Charming efficiency apartment decorated with a coastal theme overlooks Breton Bay. Use of pier for hanging out... or crabbing and fishing. Apartment is in the second floor of detached garage on the premises of a private home. Beautiful serene surroundings 5 min. from downtown Leonardtown with shopping, restaurants and events. Area offers historical sites, wonderful parks, a large Mennonite and Amish community, great restaurants and friendly people! 25 minutes from Solomons Island.

Walk to famous Tiki Bar on Solomons Island!
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. We also have a boat slip across the street that you can rent

Chic Loft Retreat | Private Beach & Near Solomons
STAY IN or ADVENTURE OUT Relax in a chic, private loft just 5 minutes from Chesapeake beaches and 10 minutes from Solomons & Calvert Cliffs. Enjoy your own private above-garage hideaway with private beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home. Our open-concept space, has a bedroom area, bathroom, workspace, living room & kitchen. SMOKE FREE SCENT FREE PET FREE PEANUT FREE We offer an Air Purifier and use only all natural cleaning products.

Little House by the water
Serenity - Privacy - Beauty - This little house by the water has it all. New Sealy queen size mattress, well equipped kitchen, Cuisinart coffee maker, full oven, glass topped stove, new refrigerator, and fully screened porch with water view. Perfect for 1 or 2 adults looking to get off the grid and recharge. In St. Mary's County,MD, just 90 minutes south of Washington DC. However, the space is small and it is really a studio apartment as I think the pictures make evident.

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.
Popular amenities for Hollywood family-friendly rentals
Family-friendly home rentals with a hot tub

Horseshoe Point - Waterfront - St. Marys River

Cozy Cottage, Winter Promo, Hot Tub, BlockToBeach

Peace Point - Waterfront, Secluded, Home w/hot tub

Waterfront, Dog-friendly, Hot Tub, Peleton

Waterfront 4-BR home w/ hot tub & charging station

Lakefront/Dock, Woods, 3 Beaches, Kayaks, Hot tub

Beach Please! River cottage w/private beach & dock

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade
Family- and pet-friendly home rentals

Frolic Fields: A Woodsy 14 Acre Homestead w/ Sheep

Loft in Montross

Dorothy's Chesapeake Delight

Historic St. Mary's City, MD

Old World Cottage/Fabulous Sunsets/Polite Pets OK

Nature's Rest in Church Creek

Perfect spot for a Vacay!

Gettin to the point. ( Cove Point Beach)
Family-friendly home rentals with a pool

10/15-18 OPEN Waterfront | Gameroom+Kayak+Firepit

Starboard on McKeil Point, w/heated pool & hot tub

The Glebe

Come for Water Fowl, Hunting-Big, Beautiful Home!

Spacious and private waterfront, sleeps 10

Shewell’s Basement Studio at Long Beach

The Potomac House: 13 acre riverfront property

Patuxent River View
Quick stats about holiday rentals that are family-friendly in Hollywood
Total rentals
30 properties
Nightly prices starting at
$52 SGD before taxes and fees
Total number of reviews
1.6K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
Destinations to explore
- Rentals with a firepit Hollywood
- House rentals Hollywood
- Rentals with a fireplace Hollywood
- Rentals with a washing machine and dryer Hollywood
- Rentals with a patio Hollywood
- Rentals with outdoor seating Hollywood
- Waterfront rentals Hollywood
- Family-friendly rentals Maryland
- Family-friendly rentals United States
- Nationals Park
- The White House
- National Mall
- Georgetown University
- District Wharf
- Smithsonian National Museum of Natural History
- National Museum of African American History and Culture
- Sandy Point State Park
- Arlington National Cemetery
- Georgetown Waterfront Park
- National Harbor
- Washington Monument
- Six Flags America
- The Pentagon
- Smithsonian American Art Museum
- Library of Congress
- Lincoln Park
- Breezy Point Beach & Campground
- Piney Point Beach
- American African Museum
- Quiet Waters Park
- Meridian Hill Park
- Ragged Point Beach
- Chesapeake Beach Water Park