House holiday rentals in Maryland Beach

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.

4.94 out of 5 average rating, 279 reviews

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 community pool is showcased, featuring a spacious deck and surrounded by a secure white fence. The water is clear, reflecting the blue sky above. Nearby, three multi-story buildings provide a backdrop, characterized by a variety of exterior colors and balconies.

5 out of 5 average rating, 21 reviews

Beach House on the MD-DE Border of Ocean City!

☀️ The community pool will be OPEN till Sept 15! Make the most of the sunny days while they last! 🏖️ This spacious home is the perfect destination for your next vacation. With its prime location just across the street from the beach, you'll have easy access to the sun, sand, and surf Whether you're looking to enjoy a day of sun and sand, explore the local cuisine, or shop till you drop, our location's easy bus access makes it a breeze to navigate Ocean City and experience all of its offerings

A modern two-story house is presented with a large porch featuring a circular window. The front yard includes gravel landscaping with small shrubs and pink flowers. A driveway accommodates off-street parking, and a lamppost stands near the entrance.

4.96 out of 5 average rating, 74 reviews

Steinenbronn by the sea. Bay view.

Ideal for a family getaway, this newly furnished home in Montego Bay is waiting for you! Experience the quiet family friendly neighborhood while comfortably staying close to the beach, restaurants, bars, shopping centers, parks and more. Between Memorial Day and Labor Day enjoy access to community pools, tennis courts, mini golf, fishing pier, walking/jogging/biking at no additional cost. 15% Discount on weekly bookings! Due to our insurance policy, we do not rent to guests under the age of 25.

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, 130 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.

4.84 out of 5 average rating, 32 reviews

2 BR Ocean Front Condo w/Pool, Expansive Views

Your family will be close to everything when you stay at this beautiful condo located right on the beach with expansive balcony views of both ocean and bay. With the best amenities around, this year-round rental is equipped with an enormous indoor pool, basketball and tennis courts, shuffleboard, saunas, gym, library, sun deck, & game room with arcades, claw machines, billiards, and air hockey tables. This 2-bedroom unit comfortably sleeps 6 which makes it ideal for families or couples alike.

5 out of 5 average rating, 52 reviews

New waterfront home on bay, quick walk to beach

Fresh remodeled beach house! Large outdoor canal front, fully fenced large back yard, quick walk to the beach. Well located, friendly residential neighborhood Located on quiet street with red light, quick walk to Gold Coast Mall, Green Turtle and Movie Theater. 3 bed/3 bath with multi-purpose bonus room with queen sleeper- use as a 4th bedroom / gaming room for kids/ office / 2nd family room for TV. All new TV's, appliances, and decor creates a modern experience in a classic beach house

A spacious living area is furnished with two dark leather sofas, providing ample seating. A ceiling fan enhances airflow. The open layout connects to a dining area featuring wooden chairs, while the kitchen is visible in the background, showcasing modern appliances and cabinetry.

4.94 out of 5 average rating, 236 reviews

Right behind Alley Oops & Crab Bag. Walk to beach

Look no further! With Alley OOps in the backyard and a 5-minute walk to the beach, pool, tennis, and shopping, the fun is endless. This 3 bedroom, 2 bathroom house has high-end furniture, fast wifi, 4 flat screens and 2 free parking spots with street parking when available. Our Community offers all of these amenities included in your rental and free putt-putt too! Enjoy our natural wood-burning fireplace and large porch to take in the sunset through the trees. We do not rent to under 25.

Two large windows frame the expansive ocean view, providing natural light to the living space. The scene features sandy beach dunes leading towards the water, where the calm blue ocean meets the clear sky.

4.9 out of 5 average rating, 142 reviews

Closest condo to the beach in OC! Dog Friendly!

Perfect getaway to the ocean in this updated, stylish home. Elevated ocean-front, with stunning views from every room and two private balconies. Amazing location - walk to great restaurants and still enjoy a private-feeling beach with lifeguard stand just steps away. No need to 'pack' for the beach -the house is just steps away. Enjoy coffee at the granite island overlooking the beach! There is a set of stairs up to the condo, and another set of stairs up to the main bedroom.

5 out of 5 average rating, 12 reviews

A charming house with a light blue exterior is surrounded by lush greenery. A spacious deck features potted plants and outdoor seating. Colorful Adirondack chairs in red and blue are placed around a small fire pit on a patterned stone patio, inviting relaxation.

Home in Ocean Pines

Cozy beach home away from home!

Welcome! Come enjoy a cozy experience at this centrally located home in the desired Ocean Pines Community! This home is near the playground and allows access to the on-site golf course, five pools (including indoor pool!) tennis courts, and marina for a small fee. Fun in the sun awaits 15 minutes away in downtown Ocean City, where you can stroll the boardwalk, lounge on the sand, or hit the amusement park. Plenty of restaurants, grocery stores and shopping within 15 minutes.

A bright, sunny exterior view of a beachfront condo building, featuring a two-story structure with several balconies overlooking the ocean. A sandy beach with yellow poles marking the property line is visible in the foreground, complemented by a clear blue sky.

4.98 out of 5 average rating, 41 reviews

Oceanfront 3BDRM 2BTH Condo just steps to beach

The Sand Castle: DIRECT OCEANFRONT 3BDRM 2BATH (sleeps 7) in desirable North Ocean City, Maryland location with breathtakingly beautiful dune and ocean views. First floor convenience with direct beach access, just a few sandy steps to the beach and walkable to several attractions, shops, grocery stores and dining options. This uptown location is a quiet, family friendly, less crowded area of the island. Northside Park and Northside Playground is directly across the street.

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, Delaware

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.

An outdoor deck offers a panoramic view of the sandy beach and the ocean. A dining table with white chairs is positioned under a blue umbrella, with two bright yellow chairs nearby. Ocean waves gently lap at the shore, highlighted by a clear blue sky.