Airbnb your place

House holiday rentals in Hollywood

Find and book unique houses on Airbnb

Quick stats about house rentals in Hollywood

  • Total holiday rentals

    Explore 30 holiday rentals in Hollywood

  • Nightly prices starting at

    Hollywood holiday rentals start at $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,780 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Hollywood holiday rentals include wifi 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!

Top-rated house rentals in Hollywood

Guests agree: these houses are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
Top guest favourite
A serene dock extends over calm waters, surrounded by lush greenery. A small orange kayak is secured nearby. In the background, a custom waterfront home is nestled among tall trees, providing a natural and tranquil setting.
Home in Mechanicsville

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

Custom waterfront home with everything you need to relax and recharge. Two levels of decks offer amazing views of the changing tides on Cat Creek. Soak in the hot tub and watch the eagles soar by, or head down to the dock for crabbing, fishing, and kayaking during high tide. Located in historic Southern Maryland, this quiet, hidden estuary makes for a unique getaway with great amenities. Fast WiFi for work, game room for fun, and a fenced-in yard for dogs. 1 hour from DC but feels worlds away.

5.0 out of 5 average rating, 105 reviews
Top guest favourite
Four black Adirondack chairs are arranged on a lush green lawn, facing the calm waters of Chesapeake Bay. Gentle waves reflect the bright blue sky, offering a serene view. Small bushes line the edge of the property, providing a natural border.
Home in Lusby

Waterfront with sweeping bay view & private beach

Year-round private beach oasis on Chesapeake Bay! Perfect Fall & Winter Escape. An hour from DC beltway & world away. Recharge & relax to the sound of waves & sailboats. Spacious & fully renovated, with modern features, ample outdoor terraces. Enjoy long walks, nature spotting (bald eagles, rays, dolphins), shark tooth collecting. Kayaks provided! Short drive to Solomons Island, and local amenities: restaurants, bars, store, national parks & vineyards. No parties or events. Only relaxing.

4.97 out of 5 average rating, 113 reviews
Top guest favourite
An aerial view captures the waterfront home surrounded by lush greenery with a private dock visible by the water. The neatly maintained property features landscaped lawns and nearby homes, illustrating a serene setting alongside Neale Sound.
Home in Cobb Island

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

Immaculately maintained 4-bedroom waterfront home + home gym on Cobb Island with water views from every window! Four beach cruiser bikes & private dock w/ 4 kayaks, to enjoy the peaceful Neale Sound. Hot tub + private deck off of the kitchen. Wall of windows inside the home, flooded w/ natural sunlight. Views of the sound & the river side of the island. 3 BR are large (2 King beds/1 Queen), w/ their own BA (1 BR w/ BA is on 1st floor, no stairs). Smart TV's in 3 BR's. Great entertaining space!

4.99 out of 5 average rating, 140 reviews
Top guest favourite
A collection of various fossilized shark teeth is displayed on an orange background. The teeth are of different sizes and shapes, showcasing both small and large specimens, with some exhibiting intricate details. The vibrant color of the background contrasts with the dark tones of the teeth.
Home in Lusby

Soul Oasis - home on the Chesapeake Bay

Listen to the waves of the Chesapeake Bay from the trex deck. There are 2 private community beaches in the neighborhood where you can find fossils and sharks teeth. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer around the house! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.

4.95 out of 5 average rating, 143 reviews
Top guest favourite
The exterior of a single-story beach house is visible, featuring white siding and landscaped areas. A stone pathway leads to a cozy outdoor seating area with light cushions. Lush greenery and mature trees are present, contributing to a serene atmosphere.
Home in Lusby

Cove Point Cottage with Chesapeake Bay views

Welcome to our beach house, just a block from the Cove Point Beach on the Chesapeake Bay. Start your beach day by grabbing the beach wagon from the shed, loading it up with beach chairs, towels, and your cooler. A short stroll takes you to the beach, where you can spend the day searching for shark teeth and shells or swimming in the bay's refreshing waters. After a day in the sun, rinse off in our outdoor shower. Our shady patio provides the perfect spot to relax and enjoy the evening breeze.

4.98 out of 5 average rating, 256 reviews
Top guest favourite
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

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.

5.0 out of 5 average rating, 139 reviews
Top guest favourite
A bright and open living space features large windows that provide views of the river. A long dining table is accompanied by upholstered chairs. A modern kitchen counter with stools is visible, along with a chandelier overhead and a cozy fireplace on one side.
Home in St. Leonard

Blue Pearl-Luxury estate with private dock/jacuzzi

The Blue Pearl is a luxurious river front estate with a private pier to catch crabs, fish and kayak. Soak in the outdoor jacuzzi and enjoy the river life. Three bedrooms with three full bath en-suites and over 2800 square feet of luxury accommodations await you. Office has Queen sleeper sofa. Pull up to your private boat dock, catch blue crabs with the provided traps, toast s’mores in the firepit while sitting in your Adirondack chairs. Enjoy two decks to view the sunrises and sunsets.

4.97 out of 5 average rating, 105 reviews
Top guest favourite
Home in Cobb Island

*Solitude At Sunset*

YOUR WATERFRONT OASIS AWAITS! If you are looking for a true getaway, look no further. Tucked away on a small, peaceful island, this hidden gem is uniquely surrounded by 3 bodies of water: The Potomac River, the Wicomico River, and Neale Sound. This quiet island oasis offers the perfect place to step away from the busy world! This cottage is incredibly special to us. For four generations, it has been a sanctuary for our family-filled with love, laughter, and countless memories.

4.97 out of 5 average rating, 102 reviews
Top guest favourite
A private dock extends into the calm water, featuring a wooden platform and seating areas. A vibrant blue paddleboard rests on the grassy shoreline, while an in-ground trampoline is seen nearby. The scene is framed by trees under a clear blue sky.
Home in Montross

Waterfront home, private dock

Relax right next to the water in this tranquil Montross getaway. Fish, crab, kayak, paddleboard, or just sit on the swing and watch dolphins, eagles, herons, and stingrays from your private dock. Dine outdoors on the spacious deck, spend some some quality family time with an in-ground trampoline, tree swing, cornhole, bocce ball, spikeball, and a unique custom-built treehouse. Or just stay inside, relax, and enjoy the views, with an indoor electric fireplace and jacuzzi bathtub.

4.97 out of 5 average rating, 108 reviews
Top guest favourite
An exterior view of the home showcases a light grey facade with a gentle slope roof surrounded by trees. A gravel driveway leads to the entrance, while a calm waterway with a boat dock is visible in the background.
Home in Hollywood

Waterfront Home: Osprey Getaway

Welcome to The Osprey Getaway! This spacious home is the perfect destination for families seeking a relaxing retreat. Our home is not far from Solomon’s Island, Patuxent River Naval Air Station, St. Mary’s College of Maryland, and historic Leonardtown. Here you'll find an open floor plan and plenty of space to unwind and take in your surroundings. Enjoy the peace and quiet of Cuckold Creek and the beauty of our newly renovated home. We can't wait to share our home with you!

4.99 out of 5 average rating, 106 reviews
Guest favourite
The exterior of a spacious six-bedroom home is showcased, featuring a symmetrical façade with a blend of brick and siding. Large black-framed windows reflect a clear blue sky and white clouds, enhancing the inviting appearance of the property.
Home in St. Leonard

Large home w/ 6 Bedrooms, 7 Bathrooms, & Game Room

The Mackall House is a spacious fully-remodeled six bedroom home with two primary suites, five full baths, and two half baths! There are two full kitchens, a huge common area, and a large room downstairs with a pool table, foosball table and a shuffleboard table. There is deck off of the living room that overlooks the large backyard. This is the perfect place for up to 15 guests to comfortably stay! No parties or events are allowed at this time.

4.93 out of 5 average rating, 109 reviews
Top guest favourite
A spacious open-concept living area features large windows offering unobstructed views of the water and sunset. A comfortable sectional sofa is positioned near the windows, with a dining table visible in the background. Natural light fills the space, enhancing the tranquil setting.
Home in Leonardtown

Water's Edge Cottage | Luxury Retreat

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”).

4.99 out of 5 average rating, 139 reviews

Popular amenities for house rentals in Hollywood

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favourite
Home in Montross

Waterfront, 3 Beaches, Dock + Kayaks, Potomac

4.98 out of 5 average rating, 158 reviews
Guest favourite
Home in Lexington Park

Serenity Bay-PrivPool-HotTub-AskAbout2NightStays!

4.93 out of 5 average rating, 104 reviews
Superhost
Home in Waldorf

*Brand New | Modern Farmhouse | Lux 4 BR | Near DC

4.83 out of 5 average rating, 119 reviews
Guest favourite
An aerial view of the house showcases a spacious deck with comfortable seating, surrounded by a railing. A dock extends into the water, equipped with a covered boat lift. Lush greenery borders the property, providing a serene backdrop.
Home in Montross

Coastal Waterfront Escape + Hot Tub & Kayaks

4.96 out of 5 average rating, 106 reviews
Superhost
A well-maintained dock extends over clear water, providing access to a private beach area lined with sand. The surroundings feature trees and several nearby structures, enhancing the outdoor space. The scene is set beneath a blue sky with scattered clouds.
Home in Hague

Year-Round Heated Indoor Pool & Beach Sleeps 16

4.92 out of 5 average rating, 106 reviews
Superhost
A private beach area is depicted with soft, sandy ground, featuring two beach chairs under a blue umbrella. Calm waters extend to the horizon, complemented by a wooden dock and a distant view of the opposite shore under a clear, blue sky.
Home in Montross

The Glebe

4.92 out of 5 average rating, 232 reviews
Top guest favourite
An aerial view captures a spacious home set on a wooded parcel adjacent to a serene body of water. The exterior features a large swimming pool surrounded by decking, with a manicured lawn and tall trees creating a natural boundary.
Home in Cambridge

Gorgeous, Waterfront Home Is Perfect for Families!

4.96 out of 5 average rating, 140 reviews
Guest favourite
An aerial view captures the single-story home situated on a private peninsula, surrounded by water. Lush green lawns and trees frame the property, while a dock extends into the bay. A pool is visible in the backyard, adding to the outdoor amenities.
Home in Abell

New, Waterfront Home w/ Island on St. Clements Bay

5.0 out of 5 average rating, 28 reviews

Weekly house rentals

Top guest favourite
A wooden dock extends into calm waters, showcasing a boat moored at the end. The serene surface reflects the pastel colors of the sky during dusk. Wooden posts line the edges of the dock, enhancing the tranquil setting.
Home in Newburg

The River House, a Wicomico Beach Retreat

4.91 out of 5 average rating, 128 reviews
Top guest favourite
A sunset view is revealed over the Chesapeake Bay, with warm colors reflecting on the water. Wooden deck furniture is positioned to enjoy the scenery, framed by tall trees along the shoreline. Gentle waves are visible in the foreground, enhancing the serene atmosphere.
Home in Lusby

Waterfront Home on the Chesapeake Bay-Pvt Beach

4.95 out of 5 average rating, 186 reviews
Top guest favourite
A scenic view of a sunset over the water, with a silhouette of a person kayaking. Adjacent, a cozy seating area is set up around a fire pit, surrounded by trees. In the foreground, a table with wine and glasses is shaded by a red umbrella, beside a hot tub.
Home in Dameron

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

4.99 out of 5 average rating, 142 reviews
Top guest favourite
The exterior of the house showcases multiple large windows that invite natural light, with a spacious porch area featuring white outdoor chairs. Colorful flower planters enhance the surroundings, providing a serene setting among greenery.
Home in St. Leonard

Cozy Cottage on the Chesapeake Bay

4.92 out of 5 average rating, 199 reviews
Guest favourite
The lake house is surrounded by vibrant autumn foliage, showcasing a two-story structure with a spacious deck. Large windows allow natural light to brighten the interior. The inviting outdoor space features a neatly landscaped yard, providing a serene view of the surrounding woods.
Home in Lusby

Spacious Lake House at the Chesapeake Bay

4.92 out of 5 average rating, 106 reviews
Top guest favourite
A covered deck area features a large black dining table surrounded by striped chairs. A ceiling fan is present above. Scenic views of the water and shoreline are framed by tall trees, creating a serene outdoor dining space.
Home in Cambridge

Sunset Breezes - quiet waterfront retreat

4.99 out of 5 average rating, 224 reviews
Guest favourite
A bright living area is illuminated by large windows, providing a view of the surrounding greenery. A comfortable sectional sofa is arranged around a centerpiece coffee table, while a small pool table sits nearby. Natural light enhances the airy atmosphere of the room.
Home in Lusby

SoMD Waffle House 1.5 acres of cozy coastal living

4.91 out of 5 average rating, 119 reviews
Top guest favourite
A close-up of a colorful hydrangea plant with pink and yellow blossoms is featured in the foreground. The ranch-style home, with a well-maintained gray exterior, is visible in the background, surrounded by lush greenery.
Home in Ridge

Wits End Retreat-Relaxing Beautiful 3 Bedroom home

4.95 out of 5 average rating, 130 reviews

Private house rentals

Superhost
A grassy area is showcased alongside the water, featuring a stacked rack displaying kayaks in vibrant colors. Nearby, there are picnic tables, and in the background, a private pier is visible among lush greenery and calm waters.
Home in California

Patuxents Paradise | Waterfront Getaway -Sleeps 10

4.66 out of 5 average rating, 61 reviews
Guest favourite
Home in Leonardtown

Anne & Fred's Leonardtown Home W/ Arcade room!

4.9 out of 5 average rating, 29 reviews
Guest favourite
Home in Leonardtown

The Primary House

5.0 out of 5 average rating, 7 reviews
Guest favourite
A lush green lawn extends towards Breton Bay, bordered by trees and flowering plants. The calm water reflects the sky, with a red gazebo visible in the distance. Gentle hills create a serene backdrop, inviting relaxation and outdoor activities.
Home in Leonardtown

Abells Wharf Cottage - Natural Splendor Getaway

4.93 out of 5 average rating, 46 reviews
Guest favourite
An aerial view captures a spacious home with a modern Cape Cod style, featuring multiple outdoor decks furnished with umbrellas and seating. A well-maintained garden surrounds the property, enhancing the natural beauty and providing a secluded, inviting area for relaxation.
Home in Mechanicsville

Private, Lakefront Oasis- Lavinia by the Lake

4.96 out of 5 average rating, 76 reviews
Top guest favourite
A charming, two-story yellow house is framed by a white picket fence and a gravel driveway. The house features a metal roof, large windows, and a welcoming front porch with two entry lamps. Lush greenery surrounds the home, enhancing the inviting exterior.
Home in Solomons

Solomons Yellow House - Waterfront

4.98 out of 5 average rating, 58 reviews
Guest favourite
The exterior of a two-story home is presented, featuring a wrap-around screened porch. Lush green lawns surround the house, with trees in the background. The serene waterfront is visible behind the property, reflecting a clear blue sky with scattered clouds.
Home in Lusby

Down the Country

4.91 out of 5 average rating, 22 reviews
Guest favourite
Adirondack chairs are arranged around a fire pit on a grassy area by the water. A private pier with a boat is visible in the background, surrounded by trees and calm water, creating a serene outdoor setting perfect for relaxation.
Home in Lusby

Waterfront, pier, fire pit, crabbing, fishing

4.97 out of 5 average rating, 33 reviews