Holiday 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, 45 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, 121 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.

The living room features a comfortable arrangement of teal sofas and decorative pillows, centered around a coffee table. A smart TV is mounted on the wall, with a cozy fireplace nearby. Natural light enters through multiple windows, enhancing the inviting space.

5 out of 5 average rating, 9 reviews

Sunset Bay at Traders Cove

Sunset Bay at Traders Cove invites you to experience a perfect blend of luxury and comfort in Ocean City, MD. This spacious 4-bedroom, 2.5-bath waterfront condo offers stunning bayfront views, breathtaking sunsets, and a prime location just a 5-minute walk to the beach. Enjoy quick access to vibrant nightlife, restaurants, and attractions like the Ocean City Boardwalk and Jolly Roger Amusement Park. With a 50-foot deck, sunroom, and private balcony, this retreat is ideal for relaxation and fun!

4.96 out of 5 average rating, 28 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!

Superhost

A bayfront home is depicted with a large deck featuring a wooden railing and an American flag. A private boat dock is visible alongside the home, accommodating several boats. Nearby properties are shown, with lush greenery and open spaces enhancing the waterfront view.

4.9 out of 5 average rating, 21 reviews

Pet Friendly Bayside Grill Bikes Kayaks

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 Perfect Family Friendly Beach House! This 4bd/2ba waterfront home sleeps 11 guest comfortably! Soak up the sun & grill for your family and friends on the large furnished patio overlooking the water! Just a one block walk from the beach and walkable to many favorite local restaurants and attractions.

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!

Welcome to the Cottage at Saltwater Pines, a newly-remodeled 3-bedroom family home, walking distance to the beach and just blocks from downtown Bethany and the boardwalk. With a stylish interior, comfy beds, whole-house state-of-the-art audio system, and heated covered pool, your getaway promises a memorable stay. Explore the pristine shores, vibrant boardwalk, and outdoor activities nearby. Book now for a coastal retreat filled with relaxation and fun!

4.89 out of 5 average rating, 45 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

The waterfront home is presented with a two-story gray exterior, accented by a white railing on the deck. Three Adirondack chairs are positioned on the deck, overlooking the water. Neighboring houses are visible on either side, demonstrating the serene community atmosphere.

4.96 out of 5 average rating, 89 reviews

2500 sqft home. Walk to beach, pool, restaurants

Sleeps 13 (8 adults maximum). Our spacious waterfront home is one of the best secrets in Ocean City and perfect for the multi-generational families. Walk to the beach, pools, restaurants and more. Kids love fishing and crabbing off the dock. Bring your own boat or kayak. We have a fully stocked kitchen and amenities to ensure that you feel right at home. You will not be disappointed with booking our home for your family vacation in OCMD.

4.99 out of 5 average rating, 134 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

Popular amenities for Ocean City kayak rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.94 out of 5 average rating, 36 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

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, 14 reviews

Ocean View Paradise w/Hot Tub & Free Massages!

5 out of 5 average rating, 14 reviews

A large, inviting pool area features clear blue water surrounded by lounge chairs and umbrellas. The pool is equipped for swimming laps, with marked lanes. A spacious building with numerous windows provides a welcoming atmosphere adjacent to the pool.

Home in Selbyville

Family + Pet-Friendly Home Near Fenwick Island

A coastal-inspired three-story home is presented with a welcoming façade. The exterior features light grey and white siding, a covered front porch with railings, and an expansive set of stairs leading to the entrance. The two-car garage is positioned below. Lush greenery is visible on the property.

4.94 out of 5 average rating, 33 reviews

5BR/4.5 BA/Pool Next to House/ 1.5 miles 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

The exterior of a charming home features a spacious front porch with white railings, inviting seating, and seasonal planters. A neatly manicured lawn extends from the sidewalk, complemented by a tree nearby. The house sits under a partly cloudy sky, enhancing its welcoming appearance.

4.94 out of 5 average rating, 47 reviews

Pet Friendly -Spacious Coastal Cape-Explore WestOC

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

4.89 out of 5 average rating, 9 reviews

A newly constructed beach home is shown with a light-colored exterior and multiple balconies. The lawn features well-maintained grass and landscaped areas, with paths leading to the entrance. Nearby houses exhibit a similar modern architectural style, enhancing the neighborhood's charm.

Home in Selbyville

Bayside Resort Beach Home

Cottages 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

4.92 out of 5 average rating, 61 reviews

The exterior of a two-story house features a modern design with a blue and white color scheme. Large windows allow natural light to fill the interior. A staircase leads to an inviting porch with white railings, while the surrounding landscape includes grass and shrubs.

Cottage in Milton

Sandcastle directly ON the 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

Other holiday rentals with a kayak

Townhouse in Sussex County

A serene view of the Little Assawoman Bay is showcased at sunset, with soft pastel colors reflecting off the water. Marshland and grasses frame the landscape, and charming homes line the opposite shore, creating a tranquil atmosphere.

4.95 out of 5 average rating, 61 reviews

Waterfront Haven: Moments from the Beach!

A wooden deck leads to a paved outdoor area with lounge chairs, overlooking a calm canal. A large blue umbrella provides shade. Nearby, grassy patches complement the seating arrangement, while residential homes are visible across the water, creating a serene ambiance.

5 out of 5 average rating, 9 reviews

Bethany Beach New Castle 4BR 2BA Canal Front Home

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!

5 out of 5 average rating, 37 reviews

Townhouse in Millville

Tranquil and Spacious Retreat near Bethany Beach

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

4.57 out of 5 average rating, 14 reviews

Waterfront Bethany Beach home w/ private access

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.