Vacation rentals with a kayak near Ocean City Beach

Two kayaks are positioned on the grassy shore, ready for use on the calm waterway. Bright paddles rest on each kayak, with the inviting waterfront location featuring docks and homes in the background. A propane grill is nearby, adding to the outdoor leisure atmosphere.

4.94 out of 5 average rating, 258 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!

Superhost

4.78 out of 5 average rating, 41 reviews

The Oliver House

This property boasts breathtaking views of the Ocean City skyline and is nestled in a quiet neighborhood in West Ocean City. Bring your boat, paddle boards, kayaks and firewood for the most incredible vacation. Crabs and clams are plentiful and the kids can enjoy playing in the small beach area while splashing or swimming in the bay. Although you may never want to leave, it's a short drive to Ocean City's beaches and boardwalk, Assateague Island and the quaint must-see town of Berlin, Maryland.

Superhost

A prominent sign labeled 'Beach Pebble Square' stands in the foreground, leading to a cluster of multi-story townhomes. The building features multiple balconies and a light-colored exterior, set against a clear blue sky, highlighting the peaceful atmosphere of the area.

Townhouse in Bethany Beach

4.87 out of 5 average rating, 114 reviews

Beach Pebble Square, 1 BLOCK TO BEACH!

Spacious, cozy, townhome one short block from beach! Fully renovated throughout! Open kitchen, dining room, and cathedral ceiling living room. The main level has a cute/private efficiency called "The Captains Quarters". Upstairs, the king bedroom suite has a private deck, private bathroom, and double closets with a Smart TV. The second bedroom has a queen bed, bunk beds w/a trundle and a shared bathroom. The loft is cozy and cool, with two trundle daybeds and a full bed. Loft is best for kids*

A vibrant green kayak rests on a wooden dock, which extends over calm water. The dock is lined with poles and residential homes are visible in the background, along with a clear sky dotted with wispy clouds.

4.93 out of 5 average rating, 118 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.

Guest suite in Ocean Pines

A serene waterway is observed, flanked by neatly maintained banks and a wooden dock. Boats are visible at the dock, while charming homes and trees line the opposite shore, reflecting a peaceful community atmosphere.

4.95 out of 5 average rating, 390 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!

4.96 out of 5 average rating, 52 reviews

A bright and welcoming living area features comfortable seating, including a green sofa and patterned armchairs. A wall-mounted TV is positioned above a neutral console. Natural light streams through large windows dressed with light curtains, while coastal artwork adds decorative touches to the space.

Townhouse in Ocean City

New Waterfront House, Bay & Boardwalk!

*Location* Welcome to our beautiful beach house! Location, Location!! WALKING distance to restaurants, bars, convenience stores, shops, Joly Rogers amusement Park, BOARDWALK and BEACH. Located on 25th St on the bayside, our WATERFRONT house has three balconies with a relaxing view of the water and bay. With patio furniture on all three balconies, you can relax, watch the sunrise/sunset and enjoy the bay breeze. Enjoy a dip in the community pool. Your experience will be unforgettable!

5 out of 5 average rating, 114 reviews

The exterior of a two-story house is framed by lush greenery and neatly arranged flower beds. A covered front porch with white railings invites guests, while the clean lawn extends towards the street. The sky above showcases a mix of clouds and blue.

Home in Berlin

Stay Salty OC Beach House

Welcome to your ultimate getaway near Assateague State Park & Ocean City! Our spacious retreat sleeps 14 guests and boasts resort-style amenities including pools, a gym, kayaks, and tennis courts. Located just moments from beaches, charming towns, and exciting attractions, you'll have everything you need for an unforgettable vacation. With a fully stocked kitchen, game rooms, cozy reading nooks, puzzles, and a balcony, there's something for everyone. Book now and let the relaxation begin!

4.97 out of 5 average rating, 167 reviews

Tiny home in Ocean View

The Bohemian Rhapsody

*Thoroughly read all descriptions,click photos,read captions BEFORE inquiring to book* Rustic "glamping" in 2 Bohemian themed sheds. Less than 5 miles from Bethany Beach, DE!Private driveway/entrance, outdoor bathhouse w/space available to set up tents.We can host up to 6 humans (upon approval) & 2 canine kids.Electric,Wifi,fire pit,sandyard,outdoor grill.Close to area beaches, boardwalks, restaurants & more! No cleaningfees! Scheduled check in time is between 4:00pm-6:00pm.

Two kayaks, one yellow and one red, rest beside a calm waterway. Lush green grasses line the bank, with a wide expanse of sky filled with soft clouds overhead. The scene conveys a peaceful outdoor setting, ideal for leisurely exploration.

4.9 out of 5 average rating, 31 reviews

Entire House+Walk2Beach• 3 bdrm + 2 Living Rms

🏖️ Quick walk to the beach 🌊 🏠 Very spacious entire house + full yard 🛋️ 2 Living Rooms, 3 Bedrooms, 2 Bath, 7 beds 🍽️ Full Kitchen + charcoal grill 🛶 2 Kayaks 📍 Centrally-located, walking distance to top rated Bayside Skillet & Ropewalk Restaurant, bay and more 👯Plenty of space for everyone to spread out, + front porch table to enjoy dinner sunsets🌅 🧺 High capacity washer/dryer in home 🛏️ New memory foam mattresses & provided linens. Book your memories today!

4.88 out of 5 average rating, 40 reviews

A spacious living area is highlighted by a large sectional couch adorned with decorative pillows. A coffee table with smooth stones is present, and a high-definition television is mounted on the wall. Floor-to-ceiling sliding doors open to a stunning waterfront view.

Townhouse in Ocean City

Ocean 14 - Amazing Waterfront Views & Beach Access

Waterfront Beach Home with large deck with amazing view of the Assawoman Bay and walking distance to the Ocean/Beach, Fagers Island Restaurant & Bar. Linens and towels included. Watch sunsets on community gazebo and dock. Boards games, cards, sunbathing on outdoor couch, Large Yeti Cooler on deck. Chef kitchen. 2 kayaks and 2 SUPs 8 Public lighted Tennis courts (free when pro shop is closed) High Def, Smart TVs High speed internet

4.99 out of 5 average rating, 132 reviews

Home in Ocean Pines

Charming Waterfront Cottage w/2 King Suites + Dock

Newly renovated, sparkling, spacious house with room for seven and waterfront views is waiting for you. Perfect for a single or double family getaway, girls weekend, or quiet retreat. *Please note this is a No Smoking and No Pet Property. **We are located in a quiet, residential neighborhood with lovely neighbors in close proximity. Please consider this when booking. ***We do not supply sheets and towels. Rental License #2162