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, 284 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.

4.82 out of 5 average rating, 51 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.

4.94 out of 5 average rating, 140 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.

A spacious living area features comfortable seating arrangements, including a large sectional sofa and recliners. A flat-screen television is positioned on an entertainment unit, and ample natural light is provided by multiple windows and a sliding door leading to the sunroom. Wooden flooring enhances the open atmosphere.

4.95 out of 5 average rating, 102 reviews

Spacious waterfront home & boat access!

Waterfront getaway, easy beach access (0.3 mile walk), pool, restaurants, and more. Linens & towels included! Bring your boat! Pier tie up available. Spacious 3 bedroom + bonus room with sleeping arrangements for 10(8 beds). This well-maintained home is close to dining, shopping, NorthsidePark & all the fun activities Ocean City has to offer. Beach chairs, toys, kayaks & paddleboard available. Fireworks from Northside Park can be viewed every Sunday summer night - right from the driveway!

4.97 out of 5 average rating, 74 reviews

Hot Tub & Pool Table Waterfront Home | 4King Beds

Yes- Linens are included! (Bed sheets & bath towels) New pool table & jacuzzi!! Experience the ultimate Ocean City getaway this year, with unbelievable water views from every room & a private two-story wrap-around balcony. Enjoy 4 comfy king beds. The home is perfect for groups seeking relaxation & home away from home. Only 4.2 miles from the Ocean City Boardwalk! What else is included? Bonfire pit Parking area Shampoo-Conditioner-Body Wash Soaps Laundry Detergent Kayak Beach chairs

4.97 out of 5 average rating, 31 reviews

A screened-in room features a comfortable sectional sofa adorned with pillows, alongside a glass-topped table. Two high-backed chairs are positioned at a small table, with a view of a serene landscape and sunset reflected in the glass doors.

Home in Selbyville

Cozy Beach Escape Mallard Lakes Resort Amenities

Located in the peaceful Mallard Lakes community just minutes from Fenwick Island, Ocean City, and Delaware Beach. This relaxing coastal retreat in Mallard Lakes combines resort-style amenities with the comfort of home — perfect for family vacations, couples getaways, beach weekends, and remote work stays. Why Guests Love Staying Here Less than 3 miles to the beach 2 pools + tennis courts Family-friendly layout Dedicated workspace + fast Wi-Fi Self check-in Outdoor shower after beach days

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.

4.89 out of 5 average rating, 47 reviews

Entire House+Walk2Beach• 3 bdrm + 2 Living Rms

🏖️ Quick walk to the beach 🌊 🏠 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 unfinished area of home 🛏️ New memory foam mattresses & provided linens. Book your memories today!

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, 69 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! BECAUSE THIS IS A SEASONAL LISTING, MAY 23 - SEPT 7 2025, REQUIRE CHECKIN/CHECKOUTS ON SATURDAYS AND SUNDAYS ONLY.

4.89 out of 5 average rating, 47 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

5 out of 5 average rating, 115 reviews

A wooden dock extends over calm water, surrounded by tall trees. A pair of Adirondack chairs provide a peaceful spot to enjoy morning sunlight filtering through leaves, creating a serene atmosphere perfect for relaxation.

Home in Newark

Secluded Waterfront · Kayaks, Firepit, Beach 15mi

Casa Blue Heron is a 2,254 ft² (209 m²) custom waterfront home with a private dock, firepit, and water views throughout - nestled on a tidal inlet connected to Chincoteague Bay - and near Assateague, Berlin, Ocean City, Snow Hill, and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature… Wish I had booked an extra day!" Add us to your wish list by clicking the ❤️ in the upper-right corner.

4.99 out of 5 average rating, 141 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 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.

4.88 out of 5 average rating, 33 reviews

Pet Friendly Bayside HotTub Grill Bikes Kayaks

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.

Popular amenities for kayak rentals in Ocean City

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.89 out of 5 average rating, 64 reviews

The Chesapeake House

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.

4.93 out of 5 average rating, 27 reviews

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

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, 40 reviews

Ocean View Paradise w/Hot Tub & Free Massages!

5 out of 5 average rating, 17 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

Dog friendly| community pool | gym| kayak| bayside

5 out of 5 average rating, 24 reviews

A serene exterior view of the property is displayed, featuring a charming white and grey home with a covered porch. Lush green bushes and trees frame the house, while a paved pathway leads to the entrance, accentuated by decorative elements in the landscaped garden.

Home in Berlin

Waterfront Home

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, 71 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

An outdoor area features a circular fire pit surrounded by four black and yellow Adirondack chairs. A sandy playground with a slide and climbing structure is visible nearby, along with a white picket fence and lush greenery in the background.

4.71 out of 5 average rating, 14 reviews

Nature at the Beach

Cottage rentals with a kayak

4.82 out of 5 average rating, 38 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

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

4.79 out of 5 average rating, 19 reviews

Patio, Pool Access! Coastal Ocean Pines Cottage

4.89 out of 5 average rating, 53 reviews

A cottage-style, two-story home is depicted with a light-colored exterior and pink shutters. The raised structure features a spacious deck with a railing. Sunlight filters through the trees, creating a warm ambiance around the property, which is surrounded by a white picket fence.

Cottage in Bethany Beach

Perfect Family Vacation. Summer is available !

5 out of 5 average rating, 13 reviews

The elevated home features a white exterior with blue shutters and an American flag hanging from the front porch. A gravel driveway accommodates parking beneath the house. Lush landscaping includes flowering trees and green grass surrounding the property.

Cottage in Sussex County

Cozy Beach Cottage Escape! Dog Friendly!

Other holiday rentals with a kayak

4.95 out of 5 average rating, 43 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

4.93 out of 5 average rating, 54 reviews

The exterior of the vacation home is shown, featuring a sturdy deck elevated above lush grass. A wooden dock extends into a calm canal, surrounded by trees and other houses. A clear blue sky with scattered clouds frames the scene, creating a serene waterfront atmosphere.

Home in Bethany Beach

Georgo Family Beach House

5 out of 5 average rating, 38 reviews

A spacious outdoor pool is surrounded by lounge chairs and tall trees, providing a refreshing escape. Bright blue umbrellas offer shade, enhancing the inviting atmosphere. The clear water reflects the sunlight, creating a peaceful setting for relaxation and leisure.

Townhouse in Millville

Tranquil and Spacious Retreat near Bethany Beach

Superhost

Home in Selbyville

5 out of 5 average rating, 4 reviews

La Danza del Sol, Keenwik on the Bay

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

6BR/4.5 BA/Pool Next to House/ 1.5 miles to beach