Vacation rentals in Oyster Pond

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Top-rated vacation rentals in Oyster Pond

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Guest favorite

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.

Home in Ocean City

4.93 out of 5 average rating, 114 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.

Top guest favorite

A serene waterfront scene is captured at sunset, with vibrant colors reflected in the calm water. A charming building with large windows is illuminated, surrounded by lush trees, and boats are docked along the waterfront, creating a peaceful atmosphere.

Condo in Ocean Pines

4.97 out of 5 average rating, 177 reviews

Ocean Pines Getaway

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

Guest favorite

An open living area is highlighted by large windows that offer views of the bay and pool. A comfortable sectional sofa is positioned adjacent to a smart TV, while a modern dining table for four is visible next to the kitchen. The space features light-colored walls and natural wood flooring.

Condo in Ocean City

4.96 out of 5 average rating, 102 reviews

Gone Coastal *Pool* Bayside with view* Top Floor

Welcome to Gone Coastal! Relax in this beautiful 2BR/2BA getaway featuring: 🛏 1 King (Master) | 1 Twin-over-Full Bunk | 1 Sleeper Sofa 🏊‍♂️ Outdoor Community Pools – Lap & Family Pool (Directly Across!) 🔑 Keyless, Contactless Check-in 🌅 Spacious Deck – Outdoor Dining + Bay & Pool Views 📺 Smart TVs + YouTube TV 🛒 1-Minute to Grocery Store 🍽 Fully Equipped Kitchen 📍 Prime Location – 120th St, Heron Harbor 🚗 Ample Free Onsite Parking A perfect retreat for families & beach lovers! 🌊☀️

Guest favorite

The exterior view of a multi-story beach house is captured under clear skies. The structure features a spacious balcony on the top floor, with multiple windows framed by white siding. A manicured lawn is visible in front, alongside a paved driveway leading to a double garage.

Home in Selbyville

4.96 out of 5 average rating, 27 reviews

Coastal Comfort: 4BR 3BH House Pool & Rooftop Deck

Welcome to your dream beach getaway in Selbyville! Immerse in luxury at our modern 4BR home, where comfort meets elegance. • Stunning rooftop deck with panoramic views • Shared outdoor swimming pool for refreshing dips • Spacious kitchen with a large island, perfect for gatherings • Two master bedrooms, each with private bathrooms • Game room with ping pong & foosball • Much more! Start each day with breathtaking sunrises from the deck. Book now for an unforgettable beachside experience!

Top guest favorite

A modern two-story home is set in a charming community, featuring a covered front porch with railings. A two-car garage is visible, accompanied by a neatly landscaped yard with grass and shrubs. The surrounding homes have varied architectural styles, contributing to the neighborhood's appeal.

Home in Selbyville

5 out of 5 average rating, 29 reviews

Bayside Retreat! Guest Favorite! Golf Cart Incl.

Exceptional, and spacious 5-bedroom, 3 full plus 1 half bath vacation home in West Fenwick's Bayside Resort! An easy bike ride to pools, tennis and fitness facilities. A fantastic place to launch your family's beach adventures, this amazing luxury home features 4 TVs, Central air conditioning, washer and dryer, Gas fireplace, Gas grill, Wireless Internet. Driveway parking. 6 seat golf cart included. Guest passes for amenities available for purchase to pools/gym/aquatic center (not included)

Guest favorite

The kitchen features modern cabinetry and stainless steel appliances. An island with seating for four complements the large dining table that seats eight. Pendant lights hang above, providing ample illumination. Large windows allow natural light to brighten the space.

Home in Ocean City

5 out of 5 average rating, 9 reviews

Shore Thing! • Townhome + Gameroom

Welcome to Shore Thing! Brand new, spacious, luxuriously designed, and close to the beach & restaurants — your perfect escape! This family friendly home features 3 bedrooms with an en-suite bathroom, and two additional sleeping areas. The 5 balconies are ideal for morning coffee, eating crabs or enjoying sunset views. The bonus room is a fun-filled game room by day and a sleeping area by night – complete with shuffleboard, arcade game & board games for fun after the beach or on a rainy day.

Guest favorite

The living area displays a light-filled space with large sliding glass doors that open to an oceanfront balcony. A neutral-colored couch is accompanied by a round wooden dining table. A large mirror and minimalist decor enhance the room's serene atmosphere, with a view of the sea in the background.

Condo in Ocean City

4.92 out of 5 average rating, 827 reviews

Light and Airy Oceanfront Condo with Large Porch

Wake up to the sound of the waves crashing outside your window and finish off your days relaxing on the private balcony as you watch the moon rise over the ocean. Come find your serenity by the sea in our modern oceanfront condo. Located in midtown Ocean City, you can keep your car parked in our dedicated spot and walk to many of the towns best restaurants, bars, and entertainment as well as the Convention Center and Performing Arts Center. Morning beach strolls and evening sips await :)

Superhost

A beach-front balcony features two comfortable lounge chairs and a matching ottoman, all adorned with light green and white striped cushions. A small lamp sits on the floor beside the chairs. A view of the ocean with clear blue skies and a sandy beach is visible in the background.

Condo in Ocean City

4.81 out of 5 average rating, 101 reviews

Lovely beach-front condo with pool and views

Kick back and relax in this calm, stylish space. This one-bedroom condo is the perfect space for 1-2 couples, or a family. You have floor-to-ceiling beach views, plus amazing sunrises and sunsets from the two separate balconies. The kitchen is well equipped to cook every meal, or eat out at Ocean City's many restaurants. Your stay also comes with 4 pool passes for accessing the onsite seasonal outdoor pool (viewable from the unit) and access to the building’s tennis/pickleball courts!

Guest favorite

A bright living area is highlighted by large sliding glass doors that open to a beachfront balcony, featuring seating for two. A comfortable sofa and an armchair with decorative accents are positioned near the window, offering views of the ocean and sky.

Condo in Ocean City

4.85 out of 5 average rating, 211 reviews

Beachfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with a breathtaking view of the beach and ocean.

Guest favorite

A bright living area features a comfortable sectional sofa facing a wall-mounted television. A ceiling fan provides airflow, while natural light enters through sliding glass doors leading to a balcony. A decorative rug and indoor plants enhance the inviting atmosphere of the space.

Condo in Ocean City

4.94 out of 5 average rating, 86 reviews

Two-story condo blocks to beach

Perched up on the top floor with no footsteps coming from above, this lofty, two-story condo will bring comfort and convenience to your next getaway to North Ocean City. This condo sits four blocks west of the beach and one block south of the Maryland-Delaware state line, allowing you excellent access to the Fenwick Island Lighthouse and all sorts of tax-free shopping. Restaurants, bars, and ice cream shops are within walking distance as well.

Guest favorite

The kitchen features a wooden countertop that extends into a two-person eating area with barstools. The refrigerator is adorned with colorful floral magnets, while various kitchen appliances are neatly arranged on the shelves. String lights and greenery create a cheerful ambiance along the ceiling.

Tiny home in Selbyville

4.97 out of 5 average rating, 294 reviews

Destination Location! Farm Animals, Tours, Beaches

✨Scratch tiny house living off your bucket list!✨ Wake up to the cheerful sounds of barnyard animals that surround this unique tiny house escape! The "Garden Hideaway" is thoughtfully curated to inspire joy and help you reconnect with the simpler things in life. Just a few minutes from the beach, this tiny home comfortably sleeps two (2) guests, with an option to add a third (3) for a small fee.

Top guest favorite

An enclosed patio provides a direct view of the ocean, with sandy beach and water visible beyond a railing. Comfortable seating options are arranged with a small table, allowing for relaxation while enjoying the ocean scenery.

Condo in Ocean City

4.98 out of 5 average rating, 230 reviews

Direct Oceanfront close to Northside Park!

Location, location, location! 2 bed, 2 bath direct oceanfront condo, with incredible ocean sunrise views from your private enclosed patio. Master bedroom features unbelievable views of the ocean, glass slider out to the patio & in suite full bath! Walking distance to Northside Park, restaurants & shopping. 2 assigned parking spaces. Elevator or steps - you pick. Washer/dryer in unit.