
House vacation rentals in Hollywood, St. Mary's County
Find and book unique houses on Airbnb
Top-rated house rentals in Hollywood, St. Mary's County
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Hollywood, St. Mary's County house rentals
House rentals with a pool

Stunning North Beach Getaway w/ Inground Pool
Patti was an amazing host. She made sure that we had everything we need and she went the extra mile providing toys for our toddler. The house was beautiful. Very peaceful neighbourhood and you can just walk to the beach where you can find nice restaurants and a playground. Perfect getaway for families. And the heated pool is the icing on the cake

Waterfront Paradise with a Private Pool
It was absolutely wonderful staying at Joanne's home. It was very comfortable and loved the outdoor firepit. Very peaceful and lovely home. We would love to come back again for another visit.

Gorgeous, waterfront home. Perfect for Families.
We had the most beautiful Thanksgiving gathering at Casey’s Porch on the bay for an extended family reunion. The house is lovely - spacious, gorgeous and cozy at the same time. The views on the water were amazing. There were plenty of beds and ‘hang out’ spots for our tweens and teens, and 3 private baths for the adult couples were much appreciated. And our hosts could not have been more helpful and friendly. Thank you for giving us this opportunity to make more happy memories together!

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit
The area and view are beautiful and the home's decor is welcoming. The home was very comfortable for our family group and had a VERY well-stocked kitchen. The master bed was VERY comfortable as were the rest of the beds. My husband and I slept well. We all felt at home. MJ was very responsive when I had questions and communicated about the property in clear, concise language. The host provided many outdoor recreation opportunities, which included paddleboards, kayaks, and life jackets. There was a nice sized pool but we were visiting out of season so we did not use it. The exercise room downstairs has a lot of equipment. We all enjoyed our time together. Our family is asking to come back again next year. Thanks for a great stay!

Spacious and private waterfront, sleeps 10
The location for this house is beautiful! We loved the private dock and spacious backyard. We stayed in late March so it was a bit cold some days but we still had a great time using the provided Kayaks and sitting on the dock and watching the beautiful surroundings. The location was perfect to have some s'mores nights around the firepit. The hosts were VERY responsive. The few times I had questions they replied within minutes and were very accomodating with our requests. They were very proactive with instructions and generously mentioned a foldable crib for the infant in our group - although we had our own that we used. The kitchen had all of the dinnerware and cookware that we needed for the meals that we made. The living areas were open and inviting. It was perfect for our group. One thing to watch for is the very steep driveway. It took a few times to get used to. We would definitely stay there again when we visit our family in the area.

Family Friendly: Hot Tub, Grill, Pool & More!
Me and some friends stayed here and we all loved it. More than enough space and so much stuff/activities from movie nights to playing pool to hitting the hot tub and more to do in the house! We would definitely stay here again and the host was great.

Serenity Bay-Relaxing, Spacious House-Private Pool
We thoroughly enjoyed our stay at Serenity Bay! Our host was extremely responsive before and during our visit. This was our third year staying in this home for the Maryland State Swimming Championships. The swimmers and parents enjoyed the comfortable and roomy home.

Historic Rousby Hall, Waterfront, Patuxent River
What a lovely stay! Incredibly charming home with such hospitable hosts. Our group felt comfortable and relaxed. Picturesque environment.
Weekly house rentals

Riverhurst on the Potomac
We had a great stay at Cameron’s home. Even though the weather didn’t cooperate we were able to spend a lot of time on back patio which felt like we were almost outside. Cameron was nice enough to let us check in early. Overall great time and looking forward to next time. Thanks again Cameron.

Waterfront Sunrise Farmhouse near Blackwater NWR
Awesome place to stay with family. Great place to hangout, fish, crab, and catch oysters! Kim is a very responsive and friendly host. I highly recommend!

Waterfront with sweeping bay view & private beach
Perfect place to rest and unwind for couple days. Lovely house with its very own private beach. Great for family fun. I enjoyed the stunning bay view. Being in front of the ocean and the sea breeze. House was clean and comfy. 2 rooms with ocean view. Ample garden space kiddo played around. The upper part of the house is off limits for private use . Only 1 bathroom but okay we were only 3. Loved walking around and exploring Salomon island parks and restaurants. Highly recommend the ruddy duck great food and friendly atmosphere and the island hideaway at Solomon’s. The house water had a sulphur smell making it unpleasant to shower / brush our teeth. Colin was great and communicative the whole time. Loved using one of the kayaks to paddle around the bay. Overall great stay and would come back easily loved the view.

*Brand New | Modern | Lux 4 BR | Huge | 24 m to DC
This place was just like the photos in person the Host Demetria was the best host I have worked with in Airbnb she is very helpful very sweet and very responsive when you reach out my daughter and cousins were very satisfied with her sleepover and she didn't want to leave....This place felt just like home away from home... Nice size bedrooms and the decor was beautiful I am definitely booking again in the future....Thank You again Dee your the best. Loved the entire house.

A Vacation for All, Away From It All
If you are looking for a peaceful escape, you found it. Although this home can be used for large gatherings, it is also the perfect getaway for 2. My husband and I loved watching the water and the natural wildlife. DO NOT MISS THE OPPORTUNITY TO EXPERIENCE THIS HOUSE!

Lovely 5 bedroom home, TVs in all bedrooms.
We had a quick weekend getaway and loved every moment. House was perfect for our group of 10. Beds were comfortable and the fire pit was amazing. The house came with everything we needed along with extras we didn’t even expect. Denise was a wonderful host and we will definitely be back!

Bahia Breeze - Beachfront Cottage
Clean, nicely decorated and cozy. Easy communication and a very nice place to visit for a couple of days. Had everything we needed right at hand.

Magical Bayfrnt Home, Pier, Beach, Fossils, trails
An extraordinary place to rest & recharge. The views, the comfort of the home, and the gorgeous walking trails, through woods & beach are a perfect combination. Everything we needed & then some.
Private house rentals

Welcome to our beach house.
This place is wonderful! Awesome views and wildlife! So quiet you can hear the birds wings flap in the air. Host was very responsive and we Definitely will return.

Radiant 2 bedroom house close to the beach!
This house was amazing. Super clean with lots of amenities. Every detail was thought out to make our stay feel like home. Our kids loved the bunk beds and the UNO and Jenga games. The location was just right, close enough to everything without being right on top of it all. We did not have any issues but when I did reach out to Eboni she responded right away and it was a holiday weekend too. I would definitely recommend this house and looking forward to coming back this summer.

WaterfrontHotTubPvtPierFirePitKayakGrillQuietHouse
Everything was exactly as advertised, plus many extra touches that made our stay great. Would like to come back when the temp is a little warmer, but the hot tub and water access were perfect even for early spring. Thanks Maria!

Waterfront Home, Spectacular View & Private Beach!
I had a wonderful stay at this beautiful house over looking the bay! The views all around the property were absolutely stunning, creating such a peaceful and relaxing atmosphere. I was on a work trip with several coworkers, and the house was incredibly comfortable and spacious —it truly felt like home. The space was clean, safe, and well-maintained, making it the perfect retreat after long workdays. The kitchen was fully stocked with everything needed to prepare a large family meal, which was a huge plus. Most importantly, our host was amazing—she was incredibly kind, attentive, and thoughtful, anticipating our needs before we even had to ask. I would absolutely stay here again and highly recommend this property to anyone looking for a serene and welcoming getaway. Thank you, for such a great experience!

6 Bd 4Ba - Steps to Shops & Shore - Pet Friendly
Are stay included two families that are in-laws and it was 11 of us total and we had an absolute beautiful weekend it was great the house I cannot say enough about how immaculate and perfect it is how accommodating Megan is how she has so many things that are there that she didn't even tell you and listen the amenity section literally you don't need to bring anything with you but yourself in your clothes we will definitely be back here again for another stay as extended family and I couldn't say more about how wonderful the place is

River Front 3 bedroom home with pier and beach.
Our family traveled from South Carolina for a funeral in LaPlata MD (a short drive away from this home). Jane's property was just what we needed to accommodate our family of 6. The house was clean, comfortable and well equip with everything that was needed. The ping pong table in the garage provided much needed entertainment when we had down time. The views were absolutely beautiful and we can not wait to come back. While there we enjoyed crabs at Captain John's crab house a couple of miles away. I would totally recommend this home to anyone that is traveling for business, leisure or just a peaceful, quiet getaway. Thanks Jane for your hospitality and sharing your beautiful home with us.

Waterfront house with private beach and pier
Lovely spot. Beautiful views. Excellent kitchen and living space with really nice bedrooms. Slept six very comfortably. Would definitely return!

Sweet Bamboo
Perfect getaway to acclimate our new 4 legged family member to being away from home and hearing and seeing new sights and sounds. The fenced yard was great to give him some freedom and peace of mind for us. We loved being able to walk to the boardwalk and to restaurants in the evening.
Quick stats about house rentals in Hollywood, St. Mary's County
Total rentals
30 properties
Total number of reviews
1.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Destinations to explore
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Nationals Park
- The White House
- Lincoln Park
- National Mall
- National Museum of African American History and Culture
- Georgetown University
- Sandy Point State Park
- Smithsonian National Museum of Natural History
- Smithsonian American Art Museum
- Washington Monument
- Arlington National Cemetery
- National Harbor
- District Wharf
- Georgetown Waterfront Park
- National Air and Space Museum
- Six Flags America
- American African Museum
- Meridian Hill Park
- Gerry Boyle Park
- Leesylvania State Park
- Quiet Waters Park
- Maryland Renaissance Festival
- Lee's Hill Golfers' Club
- Ragged Point Beach