Holiday houses in Oyster Pond

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Top-rated holiday rentals in Oyster Pond

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Top Guest favourite
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
4.94 out of 5 average rating, 277 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!

Guest favourite
A cozy living area features a striped sofa paired with two accent chairs. A round table with a potted plant is centered on a light rug. Large sliding doors provide an unobstructed view of the ocean and access to the private balcony.
Condo in Ocean City
4.94 out of 5 average rating, 82 reviews

Oceanfront Oasis: Sunrise Balcony, Pool and Beach!

Wake up to breathtaking sunrises from Cara Mar Condominiums Studio’s full balcony, relax in comfort on a full size Murphy bed with Tempur -Pedic mattress or a queen size sofa bed. Enjoy a full kitchen, bath, high speed internet , NFL SUNDAY TICKET AND RED ZONE ! HBO MAX! Disney and You Tube TV,. Elevator access , private beach entrance, pool, and free parking. Coin operated laundry on-site Just a 2 minute walk to the beach, Star Bucks , dining , beach night life , FISHING jet ski bowling !

Guest favourite
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.
Home in Ocean City
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

Top Guest favourite
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.
Home in Ocean City
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.

Top Guest favourite
A cozy living area features a white couch and two accent chairs with a leaf pattern. A glass coffee table sits on a woven area rug. Large sliding doors provide a view of the outdoor patio, framed by greenery and water, enhancing the space's natural light.
Guest suite in Ocean Pines
4.95 out of 5 average rating, 395 reviews

Stunning private waterfront suite

Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City. Park in the driveway and step into your own private escape!

Top Guest favourite
An open living area is presented with large windows, offering expansive ocean views. Comfortable seating includes a dark blue sofa, while a dining table for four is seen nearby. A textured area rug and light wood flooring contribute to a relaxed coastal ambiance.
Condo in Ocean City
4.99 out of 5 average rating, 137 reviews

Direct Oceanfront Condo with Expansive Ocean Views

Welcome to our second home! You will appreciate the relaxing ocean views! This updated 2 bd/2 ba oceanfront condo feels like you are sitting on top of the beach. The condo hosts plenty of space for enjoying the expansive, direct ocean and beach views. Cook gourmet meals in the well appointed kitchen with granite counter tops. Enjoy the den as either a third bedroom or as a private oasis. We allow full or mini weeks, with check in and check out on either Thursday or Sunday in the summer.

Guest favourite
The exterior of a single-story home is presented, featuring a light gray facade with dark shutters. A two-car garage is visible on the left, while a welcoming front porch offers seating. Well-maintained landscaping with green shrubs frames the entrance, completing the inviting curb appeal.
Home in Clarksville
5 out of 5 average rating, 5 reviews

Gorgeous Home at Ocean View Beach Club

Your vacation awaits. This gorgeous 3-bedroom, 2 -bath, single-story home in the sort after resort of Ocean View Beach Club awaits. Relax with your family and friends in this home built for entertainment in a community with so many amenities, you will struggle to decide what to do. Nestled just minutes from Bethany Beach and area restaurants, Ocean View Beach Club has it all. Large outdoor pool, fitness center, vibrant clubhouse, library, shuttle service to downtown Bethany, need I say more?

Top Guest favourite
The exterior of a charming cottage is surrounded by green grass and trees. The wooden shingle siding complements the white trim around the windows and doors. A pathway leads to the entrance, and an American flag is displayed on the front porch, hinting at a welcoming atmosphere.
Cottage in Ocean View
4.9 out of 5 average rating, 263 reviews

Basil Cottage at Good Earth, near Bethany Beach

Welcome to the "Basil Cottage" at Good Earth. The cottage is the perfect size for a family, with 2 bedrooms (1 queen bed, and 2 single beds) a kitchen, and a living area. You'll be staying on our 10-acre property, 4.7 miles from Bethany Beach. Convenient amenities include an on-site restaurant, market, theater, and ample parking. Our AIRBNB "Village" includes 2 tiny houses, a lofted apartment, two cottages, a "glamper", and 4 tent sites. Staying at Good Earth is more than just a beach trip.

Top Guest favourite
The exterior of a charming boutique home is displayed, featuring a welcoming front porch with white railings. Lush greenery surrounds the house, and two hanging planters add a touch of nature. A pebble pathway leads up to the entrance, creating an inviting atmosphere.
Cottage in Selbyville
4.96 out of 5 average rating, 84 reviews

The Cove Cottage, West Fenwick

Enjoy a stylish experience at our centrally-located boutique home! Music Lover? Walk to Freeman Stage for the summer concert series! Avid golfer? Steps away from the Bayside Resort Golf Club. Here to unwind? Happy hour by the bay any day! Want a little exercise? Stand up paddle board and bike rentals minutes away! Need convenience? Dash to local amenities! Beach goer? A quick jaunt to the best of the DE beaches! Foodie? Take a short excursion to fine dining on the shoreline!

Top Guest favourite
A private balcony features a high table with two chairs, providing an unobstructed view of the ocean and beach below. The scene is enhanced by the bright blue sky and gentle waves, creating an inviting spot for enjoying morning coffee.
Condo in Ocean City
4.99 out of 5 average rating, 151 reviews

Beautiful Renovated Ocean Front Condo 1b/1.5ba

Beautiful renovated ocean front condo. Get ready to relax in comfort and style! This large 836 sqft one 1b/1.5ba offers breath taking views of the ocean. You will be just steps away from the sand in one of the closest buildings to the beach. Enjoy your coffee or a different sunrise each day from your private balcony off the living room. Updated patio furniture with a cozy bench and high table with 2 chairs that bring a spectacular, completely unobstructed view of the beach and ocean.

Guest favourite
Home in Ocean Pines
5 out of 5 average rating, 13 reviews

Fabulous Waterfront Getaway with Sunsets & Eagles

Welcome! Take a front row seat and watch an exquisite sunset while the quiet waters of Manklin Creek slowly become like glass. You will be mesmerized by the beautiful and serene waterfront and all the wildlife around you. Amenities include the fabulous sunroom and gourmet kitchen, all flowing to the large screen porch set up for outside dining; entertainment center with ice maker, beverage frig and separate wine frig. Awesome first floor master suite. See the pics and book your week!

Guest favourite
A comfortable living area features a sectional sofa facing a small coffee table, surrounded by bright curtains. A large mirror and decorative wall accents enhance the space. Natural light fills the room, highlighting the wood-look flooring and blue area rug beneath the seating arrangement.
Condo in Ocean City
4.93 out of 5 average rating, 213 reviews

Coastal and Bright Oceanfront Condo

Relax and find your inner peace at our oceanfront condo. Enjoy breathtaking unobstructed ocean views from the private balcony. Wake up to a beautiful sunrise each morning and enjoy a peaceful moon-lit view in the evening. Our condo is filled with coastal and bright decor sure to make you feel right at home. Located in North Ocean City, you will find plenty of shops and restaurants within walking distance. Park your car, bury your feet in the sand, and forget about your worries.

Popular amenities for Oyster Pond holiday rentals

  1. Airbnb
  2. United States
  3. Maryland
  4. Worcester County
  5. Oyster Pond