Vacation rentals with a kayak in Ocean City

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, 262 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!

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.

4.8 out of 5 average rating, 44 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.

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, 120 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.

4.94 out of 5 average rating, 34 reviews

The front exterior of the house features a yellow facade with large windows and a welcoming doorway. A wooden deck is accessed by a set of stairs, and outdoor chairs are positioned for seating. Surrounding trees indicate a natural, wooded setting.

Home in Ocean Pines

Salty Serenity

Relax and recharge at our cozy 3 bed/2 bath home in Ocean Pines, a peaceful community near Ocean City, MD. Enjoy bikes, kayaks, and a fire pit in the large backyard, or use the pools, marina, yacht club, and golf course in the neighborhood. Beach parking at the Ocean Pines Beach Club in Ocean City is included. You can explore the boardwalk, casino, outlets, and the many nearby restaurants. Or, visit Berlin, or see the wild horses at Assateague Island. Come experience all the area has to offer!

4.96 out of 5 average rating, 27 reviews

An aerial view of a well-appointed beach club showcases a spacious outdoor pool surrounded by lounge chairs and umbrellas. A tennis and pickleball court is visible, along with a serene pond nearby. The surrounding landscape features neatly arranged homes and lush greenery.

Townhouse in Ocean View

OceanViewBeachClub-minutes from Bethany Beach/Golf

Enjoy this spacious, 3br 2ba 1,300 sq ft NEW condo with 12ft ceilings 1.5 miles to Bethany Beach, a 5 min drive or a 10 min bike ride. Minutes from Bear Trap Dunes Golf Course and boardwalk This condo is part of the highly sought after Ocean View Beach Club, the first new construction beach club in Ocean View as you drive from Bethany beach. OVBC offers an amazing large outdoor pool- great for kids! Plus sauna, steam room, fitness center, billiards, basketball/pickleball court and more

4.96 out of 5 average rating, 79 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, 115 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!

4.95 out of 5 average rating, 73 reviews

A bayfront view is presented from a spacious balcony, with clear waters reflecting the sky. A collection of homes lines the opposite shore, providing a charming neighborhood backdrop. The scene is completed by wispy clouds under a bright blue sky.

Townhouse in Ocean City

Gorgeous Bayfront Grill Kayaks Dock Views

Book 3 nights, get 1 night FREE stays thru March 10. inquire before booking This is a Ocbeachfrontrentals ,com premier property 24/7 SUPPORT LINEN & TOWELS PROVIDED Direct bayfront 3bd 2.5 ba w/ huge balcony over looking bay and gorgeous sunsets. 2 FREE ASSIGNED PARKING SPOTS. Large outdoor patio area with furniture. Enjoy fishing off the pier or stroll along the boards. Quiet area with plenty of local attractions and restaurants nearby!

4.99 out of 5 average rating, 133 reviews

A charming house with large windows is situated by the water, framed by lush greenery. A wooden dock leads from the house to the water's edge, surrounded by tall grass. Soft evening light highlights the structure, creating a serene ambiance.

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

A vibrant pot of red flowers is positioned in the foreground, with a wooden deck leading to a clear blue pool in the background. The pool area features a white fence and steps, surrounded by greenery and a cloudy sky above.

4.98 out of 5 average rating, 152 reviews

Stunning Bayview Home with Own Private Pool

This home can be occupied by a max of 12 adults with a total of 15 including children. Come relax in this gorgeous bay view single-family home in the lovely Caine's Woods neighborhood of Ocean City, adjacent to Fenwick Island. Imagine lazy days spent on the beach followed by a dip in the pool outside the kitchen door! The pool is open from May 1- September 30. Obviously we can’t have it open during cold temperatures!

4.98 out of 5 average rating, 110 reviews

The townhouse complex features multiple levels with private decks overlooking the water. A wooden dock extends from the property, with two floating docks situated nearby. Lush greenery surrounds the area, adding to the natural setting along the waterfront.

Townhouse in Ocean View

Waterfront Bethany Marina Escape

Exquisite Waterfront Property offering 3 impressive levels of living in this 2 bed, 3.5 bath townhouse. Located in the private community of Bethany Marina overlooking the Indian River Bay. This home has 3 large decks where you can enjoy panoramic views of the bay and amazing sunsets. We are approximately a 10 min drive from downtown Bethany Beach or the Delaware National Seashore.

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.

4.94 out of 5 average rating, 63 reviews

Tranquil Water View! Kayaks & SUP Boards Included!

Welcome to LIVIN ON BEACH TIME! Enjoy this Cozy Peaceful Retreat this year! Our updated home has all you need for a great time! Loaded with all amenities you need to make your stay comfy & fun. Our deck overlooks the gorgeous canal. Enjoy stunning sunsets . We have everything on hand for happy outings at the beach or fun on the water. RELAX... You're at the Beach!

Popular amenities for Ocean City kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.89 out of 5 average rating, 19 reviews

A three-story residential home is presented, featuring a combination of gray siding and stone accents. Black shutters frame the windows, and two separate entrances can be seen on the façade. The well-maintained lawn enhances the overall curb appeal.

Home in Berlin

4 BR/3.5 Bath w/Community Pool, Hot Tub, Gym

A spacious dining area features a wooden table surrounded by chairs, complemented by a comfortable sofa nearby. Natural light filters through the black-outlined windows, highlighting the inviting interior design and providing a relaxed atmosphere for meals and gatherings.

4.87 out of 5 average rating, 30 reviews

Marina Retreat | Relaxing Balconies & Pool

A modern kitchen features a spacious island with four black bar stools positioned around it. White cabinetry is paired with stainless steel appliances, including a refrigerator and microwave. Natural light is provided by recessed lighting and a large window, creating a bright, inviting cooking space.

5 out of 5 average rating, 12 reviews

Ocean View Paradise w/Hot Tub & Free Massages!

A two-story gray house stands along the water's edge, featuring a wrap-around balcony on the upper level. Several outdoor chairs are arranged on the lower deck, and a white fence outlines the property, providing an inviting view of the canal and surrounding area.

5 out of 5 average rating, 43 reviews

5 Bedroom Canal Front home- 3 min walk to beach

A cozy family room is presented with a large flat-screen TV mounted above a stone fireplace, featuring comfortable seating options, including a spacious sofa and a futon. Vibrant arcade games are visible against the textured wall, enhancing the entertainment options.

5 out of 5 average rating, 54 reviews

Coastal Cottage! Walk to Beach!

A modern bathroom features a spacious white jetted tub with black accents, positioned near a window. Soft lighting is provided by three fixtures above a marble countertop with dual sinks, while the floor is laid with light-colored hexagonal tiles.

4.92 out of 5 average rating, 63 reviews

SPACIOUS 3BR 2.25BA 5 BEDS - 2 Miles to sand

4.97 out of 5 average rating, 69 reviews

A welcoming approach to a spacious home is depicted, framed by tall trees reaching towards a bright blue sky. A neatly paved driveway guides the eye towards the house, with manicured lawns and colorful foliage adding to the inviting landscape.

Home in Ocean Pines

Coastal Oasis in Ocean Pines

A bright living room showcases a spacious sectional sofa with warm, earthy tones. Two armchairs complement the seating area. A medium-sized television, featuring a beach scene, is positioned on a wooden entertainment unit, with a rug adding texture to the light-hued flooring.

4.91 out of 5 average rating, 35 reviews

Entire House+Walk2Beach• 3 bdrm + 2 Living Rms

Cottage rentals with a kayak

4.85 out of 5 average rating, 120 reviews

A welcoming entrance to Angola by the Bay is captured at sunset, featuring a large, well-lit sign with the community's name. Soft hues of orange and purple fill the sky, and the surroundings include neatly landscaped greenery and a paved road leading into the community.

Cottage in Lewes

'Cottage by the bay', sleeps 8 near Rehoboth beach

A light green cottage features a screened porch with red seating and a charcoal grill. White lounge chairs are positioned on the deck, which is surrounded by colorful flowerbeds and lush greenery, creating an inviting outdoor space for relaxation.

Cottage in Millsboro

4.48 out of 5 average rating, 25 reviews

Deck & Indian River Bay Views: Coastal Cottage

4.81 out of 5 average rating, 37 reviews

A cozy living area is highlighted by a comfortable striped sofa facing a light coffee table. A soft yellow armchair sits nearby, accompanied by a lamp. Sunlight filters through the large windows adorned with fabric valances, creating a bright and inviting space.

Cottage in Ocean Pines

Ocean Pines Beach House in the Woods

Superhost

A fully remodeled kitchen features a large island with seating for six. Stainless steel appliances are positioned alongside quartz countertops. A ceiling fan provides airflow, and colorful wall accents add warmth. Natural light streams through the window, illuminating the modern design.

Cottage in Lewes

4.67 out of 5 average rating, 6 reviews

Lewes beach family cottage

4.99 out of 5 average rating, 203 reviews

A spacious kitchen with a large central island is featured, complemented by white cabinetry and stainless steel appliances. Natural light fills the room through the window, illuminating the dining area with a wooden table and blue chairs nearby, creating an inviting space for gatherings.

Cottage in Lewes

Ebb & Flow Beach House - Lewes Bay Beach Retreat

4.89 out of 5 average rating, 53 reviews

The image showcases a vibrant coastal street scene with people walking and enjoying a beach day. A family wades in gentle waves, while a picturesque cottage stands nearby under evening light. The surrounding area features outdoor dining spaces and inviting accommodations, presenting a welcoming atmosphere.

Cottage in Bethany Beach

Perfect Family Vacation at Bethany Beach Cottages!

A bright and open suite layout features a spacious bed, a kitchenette with modern appliances, and a small dining area. Natural light highlights the sleek design, while the wood-style flooring adds warmth to the space.

Private room in Rehoboth

4.63 out of 5 average rating, 8 reviews

Beach Suite 2 King Beds Pet Friendly Canalside Inn

A light grey cottage is shown with a welcoming front porch and white railings. Large windows allow natural light to fill the space, while landscaped flower beds add color at the base. A gravel driveway leads to the entrance, framed by greenery.

Cottage in Ocean Pines

4.78 out of 5 average rating, 18 reviews

Breezy Ocean Pines Cottage w/ Patio & Pool Access!

Other vacation rentals with a kayak

An aerial view of a waterfront home showcases the expansive property with lush green landscaping. The house is positioned near a tranquil waterway, surrounded by other residences, emphasizing its peaceful location. The image captures the proximity to the private dock and expansive outdoor spaces.

4.98 out of 5 average rating, 53 reviews

5 BR Waterfront Home - walk to beach

5 out of 5 average rating, 12 reviews

The exterior of a two-story townhome is depicted, featuring a symmetrical facade with dual peaked roofs. Large windows provide natural light, while well-maintained shrubs flank the entrance. A set of steps leads to the front door, which is framed by a covered porch.

Townhouse in Ocean City

The Salt Life at 94th St. Ocean City, MD

Two white Adirondack chairs are positioned on a top deck, offering views of a canal. A small side table is nearby, accompanied by a potted green plant. The scene is framed by a railing, with other houses visible in the background.

4.97 out of 5 average rating, 58 reviews

Newly Updated S. Bethany Canal Front/Walk to Beach

A tranquil view of the Assawoman Canal, showcasing water reflecting the vibrant greens of surrounding trees. The landscape features leaning branches that create an archway over the water, enhancing the serene environment. Soft ripples disrupt the stillness, adding to the peaceful ambiance.

4.92 out of 5 average rating, 26 reviews

Canal-front, pet friendly, 2 mi to Beach + Kayaks!

The waterfront home is illuminated at night, showcasing large windows that reflect soft light onto the water. A wraparound deck can be seen, with outdoor seating and decorative plants. The surrounding canal creates a serene setting, enhancing the peaceful ambiance of the location.

4.91 out of 5 average rating, 11 reviews

The Flying Dutchman Waterfront 420 Friendly

Superhost

The living room features a large sectional couch with decorative pillows, a coffee table in front, and a wall-mounted flatscreen TV. Light wooden flooring complements the grey walls adorned with framed artwork. A ceiling fan hangs above, enhancing comfort in the space.

Townhouse in Ocean City

4.65 out of 5 average rating, 89 reviews

Maxbeachaus - Chic House with Pool Table in Garage

The bayfront home is shown with a vibrant blue exterior. A spacious deck featuring blue lounge chairs overlooks the water. Two kayaks are positioned on the dock, while a landscaped area with green grass is visible in the foreground.