
Vacation rentals with outdoor seating in Hollywood
Find and book unique outdoor seating rentals on Airbnb
Top-rated outdoor seating rentals in Hollywood
Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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 --

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.

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.

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🥰

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.

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

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!

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. Be sure to visit our sister property, Water's Edge Cottage.

Chic Loft | Rest and Relax l Private Beach Access
Outage worker welcome: 1 guest. orefer night sleeper as we will come and go thru garage during the day and the dog will bark..We cant guarantee quiet daytime sleeping conditions Relax in a chic, private loft just 5 minutes from Chesapeake beaches and 10 minutes from Solomons Island & Calvert Cliffs. Enjoy our private, above-garage hideaway with private beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home.

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 outdoor seating rentals
House rentals with outdoor seating

Osprey's roost: Spring and summer 2025

3N+ PROMO-Waterfront w/Gamerm, Firepit, Dog+EV OK

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

The Glebe

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

Waterfront with sweeping bay view & private beach

Sunset Breezes - quiet waterfront retreat

Beach Please! River cottage w/private beach & dock
Apartment rentals with outdoor seating

Pop's Place

Magnolia Hideaway - Apt in town

Peninsula Pad

Sandy Feet Retreat - Beachfront

Historic St. Mary's City, MD

Sail Away To - Beachfront Views & Private Balcony

Gilly’s Getaway!

Sonny's Hideaway at the Beach! Walkable Downtown
Other vacation rentals with outdoor seating

Waterfront Home: Osprey Getaway

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

Hickory House on the Chesapeake Bay!

The Little Blue Cottage

Exclusive Waterfront Getaway

Barnyard Retreat

Shewell’s Cottage by the Shore

Cottage on the Creek
When is the best time to visit Hollywood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$46,029 GYD | G$42,472 GYD | G$48,749 GYD | G$53,352 GYD | G$57,536 GYD | G$53,979 GYD | G$56,490 GYD | G$56,699 GYD | G$54,607 GYD | G$56,281 GYD | G$56,490 GYD | G$56,281 GYD |
| Avg. temp | 3°C | 4°C | 8°C | 14°C | 19°C | 24°C | 26°C | 25°C | 22°C | 16°C | 10°C | 5°C |
Quick stats about vacation rentals with outdoor seating in Hollywood

Total vacation rentals
Explore 20 vacation rentals in Hollywood

Nightly prices starting at
Hollywood vacation rentals start at G$12,553 GYD per night before taxes and fees

Verified guest reviews
Over 1,690 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 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!
Destinations to explore
- House rentals Hollywood
- Rentals with a patio Hollywood
- Rentals with a fireplace Hollywood
- Family-friendly rentals Hollywood
- Rentals with a fire pit Hollywood
- Rentals with a washer and dryer Hollywood
- Waterfront rentals Hollywood
- Rentals with outdoor seating St. Mary's County
- Rentals with outdoor seating Maryland
- Rentals with outdoor seating United States
- Walter E Washington Convention Center
- Georgetown University
- National Mall
- Nationals Park
- The White House
- District Wharf
- Capital One Arena
- National Museum of Natural History
- National Museum of African American History and Culture
- Arlington National Cemetery
- Sandy Point State Park
- Washington Monument
- Georgetown Waterfront Park
- National Harbor
- Smithsonian American Art Museum
- Six Flags America
- The Pentagon
- Lincoln Park
- Library of Congress
- Smithsonian National Air and Space Museum
- The Anthem
- Quiet Waters Park
- Meridian Hill Park
- National Museum of African American History and Culture




