Vacation rentals with a kayak in Ocean City

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, 257 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!

4.98 out of 5 average rating, 55 reviews

A modern kitchen is visible, featuring a stainless steel refrigerator and a spacious countertop. Colorful bar stools surround a kitchen island. A cozy armchair with a decorative pillow complements the warm-toned walls and natural light from the windows, enhancing the open living area.

Condo in Ocean City

GREAT LOCATION! Remodeled 1BR condo w/ Bay View!

Awesome newly renovated 1 BR 1 bath Condo in Midtown OC perfect for family vacations! Best sunset views in town! Just 1 block from beach with private parking behind building. Full kitchen, Washer/Dryer in unit. Lots of extras! Beach cart, beach chairs, umbrella, boogey boards, toys, cooler, etc. So much to do all within walking distance. Great breakfast place on the corner, Famous restaurants, bike rentals, bowling, kayaking, shopping, ice cream, mini golf, & more! Check us out! Ask about kayaks

Colorful armchairs with a fish pattern provide comfortable seating by large windows that offer views of the water and surrounding nature. A small green side table stands between the chairs, adorned with a vase of flowers.

4.83 out of 5 average rating, 40 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, 113 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 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, 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 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.

4.95 out of 5 average rating, 389 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, 77 reviews

A cozy seating area is positioned on the waterfront, featuring plush cushions and decorative pillows. Two lanterns with candles add ambiance. Lush greenery and a clear sky are visible in the background, enhancing the serene view of the water.

Home in Berlin

Private pool, waterfront, kayaks, bikes, firepits!

The Golden Quarter Farm is 150-acre waterfront, nature preserve, centrally located 5 miles from Assateague Island and its wild ponies, small town charm of Berlin, and OC Boardwalk. With a pool, kayaks, SUP, hiking trails, bikes, and birding, there's little reason to leave the property! Max of 8 adults. No parties. No Pets. Renters must sign a Rental Agreement & provide $250 refundable damage deposit. Pool open April-Sept 30th, NOT heated. 5% local room tax will be collected after booking.

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, 165 reviews

A cozy outdoor space is illuminated by string lights, enhancing a welcoming atmosphere. Comfortable seating is arranged around a sandy area bordered by greenery. Decorative elements, such as a hanging basket and patterned rug, complement the rustic charm of the setting.

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 8 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, 30 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!

4.99 out of 5 average rating, 129 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

An outdoor deck features a stylish seating area with a sofa and a coffee table, complemented by an umbrella providing shade. A dining table is visible, suitable for gatherings. The view includes a calm canal with houses along the opposite shore.