Search Vacation Homes in Hollywood

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 184 Vacation Homes in Hollywood with updated reviews, rates, and availability.

Discover the charm of Colonial Beach

Discover the charm of Colonial Beach

10.0 out of 10, Exceptional, (3)
"I was in the area for one night for business and had my young granddaughter with me. The room was very comfortable and well furnished. Lots of apps available on the TV. Location is close to plenty of restaurants and the beach. The continental breakfast was very nicely set and had lots of variety. I plan on coming back NOT for business just so I can enjoy another stay. Highly recommend."
The price is SAR 781
SAR 965 total
includes taxes & fees
26 Nov - 27 Nov
Discover the charm of Colonial Beach
Historic charm with modern amenities

Historic charm with modern amenities

2.0 star property
10.0 out of 10, Exceptional, (2)
"The room we stayed in had a separate bedroom, living room and bathroom. Oversized refrigerator was handy. Will definitely stay here again."
The price is SAR 946
SAR 1,081 total
includes taxes & fees
26 Nov - 27 Nov
Historic charm with modern amenities
Inviting and Serene Home on Monroe Bay Creek
View from back deck looking onto the private dock and creek

Inviting and Serene Home on Monroe Bay Creek

10.0 out of 10, Exceptional, (62)
"Absolutely lovely property. Everything is modern and clean. Beautiful nautical decor. On the water with lots of room and space. We loved it so much, we plan to use it again!!!"
Inviting and Serene Home on Monroe Bay Creek
Belle of the Chesapeake Bay
Beach

Belle of the Chesapeake Bay

9.6 out of 10, Exceptional, (9)
"This was a great place to stay in a quiet neighborhood, a short drive from Calvert Cliffs State Park. Plenty of space for four adults. We could have stayed longer and would not hesitate to book again."
Belle of the Chesapeake Bay
Waterfront with spectacular view, close to restaurants and bars
Exterior

Waterfront with spectacular view, close to restaurants and bars

10.0 out of 10, Exceptional, (29)
"Would definitely stay again"
Waterfront with spectacular view, close to restaurants and bars
Waterfront Scotland Beach Retreat w/ Private Beach
Ridge Vacation Rental | 4BR | 4.5BA | 3,000 Sq Ft | 5 Steps Required to Access

Waterfront Scotland Beach Retreat w/ Private Beach

10.0 out of 10, Exceptional, (41)
"The house is lovely and very comfortable for our group of 8 friends. We would highly recommend!"
Waterfront Scotland Beach Retreat w/ Private Beach
WATERFRONT!!! The River's Roost on The Patuxent River
Property grounds

WATERFRONT!!! The River's Roost on The Patuxent River

10.0 out of 10, Exceptional, (18)
"This house is absolutely fabulous! Very spacious, stocked with necessary supplies and many amenities. Beautiful property and views of the water, sunrises and sunsets. We especially liked all the wonderful decks, kitchen on the bottom level, many bathrooms, and comfortable furnishings. John and Christina were excellent host. They responded immediately to any concerns or questions. They were easy to communicate with during the check-in and check-out process. I would definitely love to...
WATERFRONT!!! The River's Roost on The Patuxent River
Colonial Beach Cottage, 7 minutes walk to beach!
Large front deck with lights and private fenced yard

Colonial Beach Cottage, 7 minutes walk to beach!

9.6 out of 10, Exceptional, (22)
" "
Colonial Beach Cottage, 7 minutes walk to beach!
Secluded waterfront house to relax or enjoy water activities from private pier
backyard and pier

Secluded waterfront house to relax or enjoy water activities from private pier

9.8 out of 10, Exceptional, (25)
"Overall very pleased. Seemed like a lot of money for the property but I guess that’s what waterfront cost. House was very clean and well equipped. Loved the mini-splits in each room. The only reason I gave “cleanliness” four stars is because the outside trash can had a bunch of trash the smelled horrible and the recycling container also had trash in it. Michelle was great and very responsive. There’s a great market on the island but very few dining options and no fine dining. Very cozy...
Secluded waterfront house to relax or enjoy water activities from private pier
Riverside House w/ Kayaks, Piano & Fireplace
California Vacation Rental | 5BR | 2.5BA | 2,300 Sq Ft | Stairs Required

Riverside House w/ Kayaks, Piano & Fireplace

9.0 out of 10, Wonderful, (11)
"This house is well-maintained and my business associates enjoy staying here. We will book this house every time it comes available."
Riverside House w/ Kayaks, Piano & Fireplace
Blue Heron Retreat on the Water
Private dock for kayaking , swimming , boating , fishing, and even crabbing

Blue Heron Retreat on the Water

10.0 out of 10, Exceptional, (10)
"The place was as described. Great communication and check in. All professional."
Blue Heron Retreat on the Water
The Schultz Estate
Exterior

The Schultz Estate

8.8 out of 10, Excellent, (14)
"What a wonderful stay we had! The house was so comfortable with plenty of space for everyone to relax and enjoy each other's company. We enjoyed the brisk mornings on the porch and the gorgeous sunsets in the evenings. Very comfortable beds and linens. The scenery and landscape in the area are breathtaking. Every turn provided another incredible view of the water. Fishing Creek is close to so many beautiful, quaint towns along the Chesapeake Bay. Highly recommend!"
The Schultz Estate
Waterfront Relaxing Getaway
Property grounds

Waterfront Relaxing Getaway

9.8 out of 10, Exceptional, (18)
"Nice house, beautiful waterfront property, great host. No complaints whatsoever, highly recommend. "
Waterfront Relaxing Getaway
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Exterior

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (39)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Exterior

**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

10.0 out of 10, Exceptional, (182)
"We had a very relaxing weekend celebrating my 60th birthday. Ray was such a terrific host. Everything about the property and the owner was spectacular!!"
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Waterfront House with Dock, Kayaks, & Sailboat!
California Vacation Rental | 4BR | 2BA | 2,500 Sq Ft | Step-Free Access

Waterfront House with Dock, Kayaks, & Sailboat!

9.0 out of 10, Wonderful, (30)
"We stayed for a motorcross race (son was racing). We didnt do much at the house. Its nestled back in a quiet point on the water. Easy commute to and from to the grocery/simple shopping stores. Starbucks right down the street for you coffee lovers. The interior decor is simple and antique."
Waterfront House with Dock, Kayaks, & Sailboat!
Mid-Century Modern and Marvelous on the Bay
Property grounds

Mid-Century Modern and Marvelous on the Bay

10.0 out of 10, Exceptional, (70)
"The house was amazing! From the moment the front door opened it was a visual feast. The views are incredible, it's quiet, private and very relaxing. There were personal elements reflecting the current and original owners which we found very interesting and the attention to detail throughout was superb! Everything was incredibly well stocked with a multitude of extras. "
Mid-Century Modern and Marvelous on the Bay
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Lusby Vacation Rental | 4BR | 3BA | 1,872 Sq Ft | Stairs Required

Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

9.8 out of 10, Exceptional, (11)
"Would stay again. Steps down to the water are a challenge"
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Private 9 acre Family Retreat on the Chesapeake Bay
Front of house

Private 9 acre Family Retreat on the Chesapeake Bay

10.0 out of 10, Exceptional, (8)
"Incredible sunset views, very nice location to relax, play games on the deck and enjoy time together with friends. A beautiful quiet setting."
Private 9 acre Family Retreat on the Chesapeake Bay
Stunning secluded Luxury waterfront cottage with private deep water pier!
Exterior

Stunning secluded Luxury waterfront cottage with private deep water pier!

10.0 out of 10, Exceptional, (72)
"Great location. Spacious and clean. Easy checking in and communicate with owner."
Stunning secluded Luxury waterfront cottage with private deep water pier!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Hollywood
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Hollywood

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Property grounds

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

9.8 out of 10, Exceptional, (124)
"We chose to celebrate our 10th wedding anniversary here for a quiet weekend away with our dog. The house provided everything we needed and the owners were great to deal with. Highly recommend!! "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
Outdoor dining

Blue Heron Cottage is cozy & convenient. Renovated March 2023!

10.0 out of 10, Exceptional, (38)
"Heather and Ed are superb hosts. The home was very clean, well stocked and in the perfect location! "
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
Soul Oasis - home on the Chesapeake Bay
Exterior

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (17)
"Beautiful and quiet in the fall. A great place for relaxing. Clean, great communication. End of the street with views of the bay. "
The price is SAR 563
SAR 1,178 total
includes taxes & fees
26 Nov - 27 Nov
Soul Oasis - home on the Chesapeake Bay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.