Holiday rentals with a kayak near Ocean City Beach

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, 279 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, 56 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.

Apartment 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.

4.8 out of 5 average rating, 46 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, 130 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, 100 reviews

Spacious waterfront home & boat access!

Waterfront getaway with easy access to the beach (0.3 mile walk), pool, restaurants, and more. Linens & towels included! Bring your boat! Pier tie up available. Spacious 4 bedroom home with sleeping arrangements for 10. 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. A fireworks show at Northside Park can be viewed every Sunday summer night - right from the driveway!

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!

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, 65 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.

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.

4.9 out of 5 average rating, 40 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!

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.

4.89 out of 5 average rating, 45 reviews

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, 138 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.

Popular amenities for rentals with a kayak near Ocean City Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.97 out of 5 average rating, 35 reviews

An elevated beach house stands gracefully by the canal, with a spacious upper deck visible under a colorful twilight sky. Lush trees frame the property, while a wooden dock provides direct access to the water, creating a serene and inviting coastal atmosphere.

Home in Ocean View

Waterfront Retreat | Kayaks, Deck, Mins to Beach

4.96 out of 5 average rating, 81 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!

5 out of 5 average rating, 19 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

5 out of 5 average rating, 15 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

4.97 out of 5 average rating, 70 reviews

Hot Tub & Pool Table Waterfront Home | 4King Beds

5 out of 5 average rating, 62 reviews

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.

Home in Bethany Beach

Coastal Cottage! Walk to Beach!

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 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.

4.93 out of 5 average rating, 27 reviews

Pet Friendly Bayside HotTub Grill Bikes Kayaks

Cottage rentals with a kayak

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

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

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, 12 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

Apartment in North Ocean City

The exterior of the Marylander Condominium building showcases a three-story structure with balconies, offering coastal views. Clear skies and the ocean are visible in the background. A sign indicates the condo number and highlights a Superhost. A parking area is nearby, emphasizing convenience.

5 out of 5 average rating, 72 reviews

Steps To Beach. Ocean View. Indoor Pool/GameRoom.

4.95 out of 5 average rating, 39 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

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!

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.

5 out of 5 average rating, 12 reviews

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

4.92 out of 5 average rating, 26 reviews

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.

Home in Ocean View

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

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.

4.94 out of 5 average rating, 54 reviews

New Waterfront House, Bay & Boardwalk!

A multi-level townhouse features a light-colored façade with multiple balconies and gabled roofs. Green shrubbery lines the front, complementing the welcoming aesthetic. Each unit has distinctly separated entrances, and the walkways are clearly defined, providing access to the main building.