House holiday rentals in Maryland Beach

4.9 out of 5 average rating, 608 reviews

A charming tiny house features wooden shingles and a welcoming front door. It is framed by colorful flowers in a garden, enhancing the outdoor landscape. A sign above the door adds a personal touch, while large windows allow natural light to fill the space.

Home in Ocean View

Tiny House at Good Earth, near Bethany Beach

A custom 165 sq. ft. "Tiny House" located right between our theater and the garden dining area. True to the show "Tiny House Nation".. cool interior with custom woodwork, stairs to a lofted bed. Fully functioning kitchen. Spacious bathroom & shower. We provide TV and internet in the unit. We have 2 on-site restuarants, market, theater, and parking. Our AIRBNB village consists of 2 tiny houses, 2 cottages, tent sites, a loft appartment, and more! Staying at Good Earth is more than a beach trip!

A back deck features a seating area composed of a sofa and ottoman with soft cushions, facing a calm canal. A wooden table is positioned nearby. A red umbrella is closed and stands beside the seating, while a sunset casts gentle hues across the water.

4.93 out of 5 average rating, 121 reviews

3 BR Waterfront Home, Minutes to the Beach

Recently updated waterfront house located in the family-friendly Montego Bay community. Enjoy beautiful sunsets on the back deck or hop in one of the kayaks for a paddle around the wide-open canal. Try your hand at crabbing or fishing off the dock to catch your dinner. Within easy walking distance of the beach and Northside Park (about 10 minutes walk to both). Beach chairs, toys, boogie boards, and umbrellas are yours to use for fun in the sand and surf. The dock is available for boat tie-ups.

A spacious common area is designed with high-end leather sofas and armchairs, arranged around a central coffee table. Bright natural light enters through large windows, highlighting the tasteful decor. A dining area is visible in the background, creating a warm and inviting environment.

4.88 out of 5 average rating, 132 reviews

Upscale House Steps 2 Ocean 3 Balconies Pool Bikes

Book 3 nights, get 1 night FREE stays thru March 10. inquire before booking This is a Ocbeachfrontrentals .com premier property 24/7 SUPPORT LINEN & TOWELS PROVIDED This spacious 3-level beach home is perfect for family & friends. Relax on 3 balconies, hang out poolside, go for a bike ride or walk to the beach. With 5BD/3.5BA, high-end furniture, high-speed WiFi, 6 flat screens, a Weber grill, and a foosball table, there's room for everyone! Must be 25 or older unless accompanied by adult

A spacious living area features two sofas, one in dark leather and the other in a light fabric, arranged around a low wooden coffee table. A flat-screen TV is mounted on a light wall above a stone fireplace, adding a cozy touch to the room.

4.97 out of 5 average rating, 133 reviews

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.

Relax with the family in this comfortable and charming home. There is room for 8 to sleep comfortably. The dining room and breakfast nook offer plenty of seating for all with a spacious kitchen. Our corner lot offers the option for outdoor fun like slip and slide, corn hole, frisbee, and more! Nearby: Beach, Bay, Wildlife sanctuary surrounded by a walking trail, Pool, Tennis, restaurants & Eventful Northside Park! Quiet and peaceful location to make family or romantic memories of a lifetime.

A charming bayside home features a covered porch adorned with twinkle lights, creating a welcoming entry. The exterior showcases light-colored siding, large windows, and landscaped greenery, complemented by playful flamingo decorations on the front lawn.

4.97 out of 5 average rating, 106 reviews

Beach Oasis w/ King Suite + Outdoor Shower & Pool

Looking for a romantic weekend away? Planning a family vacation? Enjoy this entire bayside home in the quiet, coveted neighborhood of Montego Bay. This spacious 3 bed/2 bath retreat has it all!! Enjoy sunsets, steamed crabs, or coffee on the large porch picnic table or relax in the gliders with a cocktail under the twinkle lights! There is 2 car off-street parking & the community offers two public pools, tennis courts, trails, mini golf & is just a short walk to the beach & Northside Park!

4.86 out of 5 average rating, 113 reviews

A modern kitchen is showcased with a dark refrigerator and sleek stainless steel appliances. A central island features a light granite countertop, while decorative shelves display dishware against a vibrant blue wall. Pendant lights illuminate the area, enhancing the functional layout.

Home in Ocean View

Pet Friendly | New EV Charger - New 100’ Fence!

NEW Fence JUST INSTALLED! 7 Hudson is a COMPLETELY renovated, three-bedroom, two full bathroom / family & pet friendly cottage that has everything you need for the perfect getaway. With 55” TV’s in every room. Located less than one mile to the town of Bethany Beach and within walking distance to restaurants, walking trails, parks, and other attractions. There are no CO producing appliances. Hardwired CO monitors on both floors. Thank you for your interest. (King bedroom on 1st & 2nd floor)

4.88 out of 5 average rating, 142 reviews

Beautiful Cottage W/ shared pool & close 2 beach

"Beautifully decorated & completely renovated 3 BR/2 BA/ plus den. The home is 2 blocks from the bay and a 20 min. walk to the beach! Enjoy this entire home in the quiet neighborhood of Montego Bay which boasts 2 pools, tennis courts, a fishing pier, a walking pond, mini golf and Northside Park. The kitchen is fully stocked and the house is kid-friendly. There are 2 parking spaces & off-street parking. Finally, enjoy the sunset on the large deck complete with an area for al fresco dining.

A charming two-story home is framed by lush greenery and features a welcoming front porch with white railings. Skylights adorn the roof, allowing natural light to flood the interior. A spacious driveway provides access to the home while a mailbox stands at the curb.

4.97 out of 5 average rating, 170 reviews

The Laurel House - Large fenced in yard!

Recently renovated 3 bedroom, 2 bath with outside shower. 1625 square foot single family home with fenced-in yard in the Caine Woods section of North Ocean City. 2 Smart TV's, 2 TV'S with Roku, all with Netflix, Comcast, and fast Wi-Fi. Complete kitchen including dishwasher. Two off street parking spaces with ample free street parking in area. Short 5 block walk to the beach. Nearby shops, restaurants, community area, and amusements all in walking distance.

4.85 out of 5 average rating, 198 reviews

The cottage exterior is seen with a large deck featuring white railings and a blue and white striped awning. A set of outdoor furniture is arranged on the deck, and steps lead down to a grassy area. The well-maintained, light-colored siding complements the serene environment.

Home in Fenwick Island

Hall Cottage, Fenwick Island, DE

Charming, updated cottage. Wifi and space to work. Located between Bethany Beach, DE and Ocean City, MD, Fenwick is known as 'The Quiet Resort.' Two blocks to the beach. The cottage is the perfect size for a couple or small family. Sitting on a lovely, quiet block, between the ocean and the bay, the cottage is a quick walk to fine dining, pubs and shopping. The cottage comes with two beach chairs and an umbrella, an outdoor shower, and a beach parking pass.

A charming bungalow features dark blue siding and large front windows, framed by neatly trimmed bushes. A concrete walkway leads to the front door, and a well-maintained lawn surrounds the home. The sky is partly cloudy, adding to the inviting exterior.

4.95 out of 5 average rating, 186 reviews

Pet Friendly SFH w/ fenced yard, 2blocks to BEACH!

PET FRIENDLY with fenced in yard, 2 blocks to the beach! Summer rentals avail. Sunday - Sunday. An 8min walk to the beaches of N. Ocean City! Our home is located in a quiet neighborhood, between the beach & bay! You'll have access to a fenced backyard, full kitchen, smart TV, & WIFI. We expect guests to be courteous to neighbors. Parties & loud music are not permitted. **Not traveling with pets? Check out our ocean side condo near Northside Park!**

4.97 out of 5 average rating, 105 reviews

A cozy living area presents a light brown couch adorned with colorful cushions and a decorative throw. Two accent chairs sit across from the couch, positioned on a patterned area rug. Natural light filters through sheer curtains covering a large window, illuminating the space.

Home in Ocean Pines

Sweet Retreat

Sweet Retreat is conveniently located in Ocean Pines, Maryland. The premiere residential and resort community of Ocean Pines is located eight miles inland from the ocean resort town of Ocean City. Ocean Pines has over 9 miles of waterfront property and 3,000 acres of wooded areas. Community amenities include beaches, a yacht club, golf course, community center, a Beach Club Pool and other community pools. Passes are available at ocean Pines Association.