Holiday rentals with a home theatre in Worcester County

4.94 out of 5 average rating, 266 reviews

A light and airy deck features a rectangular dining table surrounded by aqua-colored chairs. A calm water view is visible beyond the railing, with flags gently waving in the breeze. Soft lighting is provided by string lights overhead, enhancing the inviting atmosphere.

Home in Ocean City

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

A spacious living area features large windows providing ocean views. A light-colored sectional sofa is complemented by throw pillows in various colors. A round accent ottoman and a patterned area rug enhance the space, while a dining table with wooden chairs is positioned nearby.

5 out of 5 average rating, 27 reviews

Beach Front Condo in Ocean City

Relax with your family at the Sea Watch condominiums with spectacular ocean and bay views. Unit 814 has 2 bedrooms, 2 full bathrooms, den and kitchen. Free Wi-Fi and DirecTV, laundry and conveniently located within walking distance to grocery stores, retail shopping, restaurants and coffee shops. Indoor pool (scheduled to open 4/1/25), outdoor pool and toddler pool (seasonal), arcade, playground, movie theater, tennis/pickleball, basketball and volleyball court. Full week rentals June- August.

An open-concept living and dining area features a wooden dining table set for six, complemented by modern chairs. A comfortable seating arrangement with light-colored couches is situated near large windows, offering views of the surrounding area. A mounted TV and decorative elements enhance the space.

4.96 out of 5 average rating, 124 reviews

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

Launch your fabulous beach getaway at amenity-rich Sunset Cove at Sea Watch, part of an oceanfront condo complex offering 3 pools, complimentary movie theater, game room, gym, and much more. Enjoy spectacular ocean and bay views from 2 balconies, smart TVs in every bedroom and living room with provided satellite programming, fully equipped kitchen, comfortable living and bedroom spaces–and that’s just the beginning as your group has a blast at the beach and all of Ocean City’s fun attractions.

4.87 out of 5 average rating, 15 reviews

A spacious outdoor deck features cozy seating arrangements and a coffee table, with ocean views visible beyond. Relaxing chairs are positioned around, while the sparkling coastline and beach access paths are displayed in the background.

Home in Ocean City

NEW!OceanView-Pool-Sundeck-Bike-Theater-Game Room

Welcome to Your Elegant Oceanview Escape Home Experience the perfect blend of upscale comfort and family-friendly amenities in this spacious 5-bedroom retreat designed to host unforgettable getaways. Overlooking the sparkling coastline, steps from the beach, this home sleeps 16+ and offers everything you need to relax, recharge, and reconnect. Highlights • Breathtaking ocean views from multiple decks • Pool and sundeck (Pool closes Sept 29th 2025) • Arcade/game room • Outdoor movie deck!

4.97 out of 5 average rating, 69 reviews

A welcoming approach to a spacious home is depicted, framed by tall trees reaching towards a bright blue sky. A neatly paved driveway guides the eye towards the house, with manicured lawns and colorful foliage adding to the inviting landscape.

Home in Ocean Pines

Coastal Oasis in Ocean Pines

Coastal sanctuary is a private mother-in-law suite with a private entrance, just 15 minutes from Ocean City MD. 2 bedrooms, spa like bath, family room, w/sleeper sofa, kitchenette overlooking a marsh and bay. You will have the entire floor. 1000 sq feet. Daily visitors include deer, heron, birds and duck. Follow the deer path and use our stand-up paddle boards and/or Kayaks. Assateague wild ponies and Ocean City boardwalk are an close by. Berlin voted the coolest small town in America.

A bright living area features blue walls complemented by light-colored furniture. Two sofas are positioned around a centrally placed coffee table, which holds decorative items. Large glass sliding doors open to a balcony, allowing natural light to fill the space.

4.88 out of 5 average rating, 95 reviews

Updated Mid- Town Condo at Ocean City Beach!

Choose your own adventure at this updated bayside space. Short walk to multiple restaurants, mini golf, stores and of course the beach! This comes with 2 free parking spots, pool/hot tub access (for the building) fitness room and a bay view from the balcony. We have a cleaning service between guests to ensure things will be fresh and tidy! We've provided some welcome kit items listed below so you don't have to bring much as well as appliances for your every need. 4 time Superhost!

4.84 out of 5 average rating, 68 reviews

A spacious living area features large windows showcasing a sunset over the water. A modern sectional sofa is positioned elegantly, while a coffee table adds function to the space. Natural light enhances the tranquil ambiance, inviting relaxation and enjoyment of the picturesque views.

Townhouse in Ocean City

Pineapple Bay ~ Serene & Breathtaking Sunsets

Welcome to the stylish 4BR 3.5Bath end-unit townhouse nestled in a serene neighborhood of Ocean City, MD. Escape the big-city crowds and enjoy gorgeous sunsets from the outdoor deck and balcony while still being within short distance of restaurants, shops, beaches, and numerous attractions. ✔ Close to Beach ✔ 4 Comfy BRs ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Outdoor Deck/Balcony ✔ Private Pier ✔ Game Room - Arcades/Ping Pong ✔ Fast Wi-Fi ✔ 2 to 3 Dedicated Car Parking

5 out of 5 average rating, 38 reviews

A charming beach home is shown with light grey shingles and a front porch. An American flag is displayed, and vibrant flowering azaleas are planted in the front yard, accompanied by well-maintained grass. A paved walkway leads to the entrance, with a garage visible on the left.

Home in Ocean City

One-Of-A-Kind, single family home at the beach!

This one-of-a-kind beach home is just what you’ve been looking for! Located in a peaceful community, it’s just blocks from the beach, bay, shopping, dining, and entertainment. Featuring 4 bedrooms, 3 bathrooms, a private main suite with a king bed and fireplace, and sleeping space for 10, it’s perfect for family or guests. Enjoy a covered porch, sunroom, unique indoor balcony, 2-car garage, and parking for 8. Don’t miss this rare opportunity to own your dream coastal retreat!

4.99 out of 5 average rating, 75 reviews

The living area features comfortable seating options arranged around a central area rug, with a fireplace adding warmth. A large television is mounted on the wall opposite, while natural light streams through the windows, which are adorned with blinds.

Villa in Ocean City

Walk to the Beach! Firepit-Grill-Bikes-Fence-N64!

Escape to the Blue House, a pet-friendly retreat just 6-mins to the beach. - Full kitchen and charcoal grill - Coffee bar (k-cups, espresso, coffee grinder, french press, and pour over) - Fully fenced patio with a fire pit and ping pong - Outdoor shower - 5 Bikes - Northside Park - 2 min walk away - N64 - 48W EV charger - Rrecord Palyer Sleep 10 (8 Adults 2 Children) in our 3 bedrooms - 1 king, 1 queen, 1 full over full bunk bed, and full sofa bed. NOT POSTED ON C.LIST

A panoramic view of the ocean is visible, with gentle waves lapping at the sandy beach. Below, an outdoor pool is surrounded by lounge chairs and clear pathways, providing a peaceful atmosphere. Skies are blue, enhancing the serene coastal setting.

4.87 out of 5 average rating, 113 reviews

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

Sea Watch Condo's is an ideal family location with tons of amenities. The until is a recently updated 3 bedroom 2 bathroom condo that sleeps 6 people in 2 queen beds, 2 twin beds . The unit is ocean front with a large oceanfront balcony. The amenities Include, basketball court, tennis courts, playground, arcade, movie theater, billiard room, indoor pool and outdoor pool as well as a restaurant. The condo has 24 hour security and plenty of parking. Pools closed in off season

A courtyard area is showcased, featuring white Adirondack chairs arranged around a central table. Additional blue umbrellas provide shade over several tables. The surrounding building contains multiple balconies, and vibrant landscaping enhances the outdoor ambiance.

4.95 out of 5 average rating, 43 reviews

Orleans Court Bayside great pool and kids pool

This is a very quiet building mostly Owner's. The pool area is great and includes a kiddie pool. We are walking distance to the beach. We don’t supply beach chairs. We also do include sheets and towels not pool towels. We start you off with toilet paper and trash bags you then have to supply after that.. This is a non smoking building and only owners can have pets. Great courtyard where everyone seems to gather. Renters must be at least 22. Freeman stage 10 minutes.

Superhost

A modern living area features large windows providing ample natural light and panoramic ocean views. Comfortable seating includes a blue sofa and an armchair. A wooden coffee table sits in the center, with a television mounted on the wall nearby, enhancing relaxation and entertainment options.