House holiday rentals in Hollywood
Find and book unique houses on Airbnb
Top-rated house rentals in Hollywood
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Hollywood house rentals
House rentals with a pool
Home in Montross
4.93 out of 5 average rating, 166 reviewsThe Glebe
4–11 Dec
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
15–22 Dec
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
12–19 Jul
Home in Hollywood
4.85 out of 5 average rating, 27 reviewsRiverhouse
16–23 Feb
Home in Montross
5.0 out of 5 average rating, 7 reviewsThat 70's Hive - Retro Retreat w/ Beaches, Pool +
28 May – 4 Jun
Home in California
4.93 out of 5 average rating, 14 reviewsWaterfront home with pier near Solomon's Island
20–27 Oct
Home in Lusby
4.91 out of 5 average rating, 67 reviewsSpacious and private waterfront, sleeps 10
21–28 Nov
Home in Montross
5.0 out of 5 average rating, 48 reviewsWaterfront+Kayaks+Gameroom+Pool+Firepit+EV/Dog OK
23–30 Sep
Weekly house rentals
Home in Heathsville
4.93 out of 5 average rating, 122 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
16–23 Feb
Home in Colonial Beach
4.99 out of 5 average rating, 199 reviewsBeach Blonde Cottage
3–10 Dec
Home in Leonardtown
4.95 out of 5 average rating, 43 reviewsOld Bay Inn
13–20 May
Home in Hollywood
5.0 out of 5 average rating, 40 reviewsWaterfront Home: Osprey Getaway
20–27 Sep
Home in Mechanicsville
5.0 out of 5 average rating, 50 reviewsWaterfront. Spacious. HotTub. Kayaks. DogFriendly.
27 Dec – 3 Jan
Home in Montross
4.85 out of 5 average rating, 34 reviewsThe Haven at King Copsico - Comfortable and Cozy
9–16 Nov
Home in Hague
5.0 out of 5 average rating, 4 reviewsSeahorse Inn
10–17 Apr
Home in Mechanicsville
5.0 out of 5 average rating, 4 reviewsModern luxury waterfront retreat Summer fun!
2–9 Jun
Private house rentals
Home in Hollywood
5.0 out of 5 average rating, 45 reviewsArtist/Healer Zen Waterfront Home
29 Aug – 5 Sep
Home in Solomons
5.0 out of 5 average rating, 30 reviewsBlue Heron Retreat - on the Water
9–16 Sep
Home in Saint Leonard
4.94 out of 5 average rating, 36 reviewsCottage on the Bay
10–17 Dec
Home in Saint Leonard
4.96 out of 5 average rating, 82 reviewsLarge renovated home w/ 6 bedrooms and 2 kitchens!
24–31 Dec
Home in Solomons
4.97 out of 5 average rating, 61 reviewsRoomy 6 bedroom home in the heart of Solomons, MD
23–30 Dec
Home in Leonardtown
5.0 out of 5 average rating, 5 reviewsGarden Getaway
8–15 Jul
Home in Solomons
5.0 out of 5 average rating, 45 reviewsHome with Boat Slip on Solomons Island
4–11 Sep
Home in Leonardtown
4.93 out of 5 average rating, 41 reviewsThe River House: A private waterfront oasis…
18–25 Jul
Quick stats about house rentals in Hollywood
Total rentals
30 properties
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
30 properties include access to Wi-Fi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1K reviews
Destinations to explore
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