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Holiday rentals with a kayak in Ocean City

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Quick stats about holiday rentals with a kayak in Ocean City

  • Total holiday rentals

    Explore 50 holiday rentals in Ocean City

  • Nightly prices starting at

    Ocean City holiday rentals start at $289 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,220 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Ocean City holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Ocean City rentals

  • 4.9 Average rating

    Ocean City stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated Accommodation with a Kayak in Ocean City

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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Guest favourite
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.
Home in Ocean City
4.94 out of 5 average rating, 286 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!

Outdoor spacesValueDecor

Guest favourite
Home in Ocean City
4.86 out of 5 average rating, 72 reviews

The Chesapeake House

Indulge in the ultimate beach getaway at The Chesapeake House, a newly remodeled 6-bedroom haven in Ocean City. Perfect for large families! Nestled on the serene canal, it offers aquatic adventures with kayaks and paddle boards. Enjoy evenings on the patio, propane grilling under bistro lights. Close to dining hotspots like Liquid Assets, Bull on the Beach, Lombardi's, and Kirby's. A mere stroll away from the beach, this retreat promises relaxation and recreation for your perfect coastal escape.

ValueOutdoor spacesLayout

Top Guest favourite
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.
Home in Ocean City
4.85 out of 5 average rating, 60 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.

ValueOutdoor spacesParking

Top Guest favourite
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.
Home in Ocean City
4.93 out of 5 average rating, 148 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.

ValueOutdoor spacesCleanliness

Top Guest favourite
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
5 out of 5 average rating, 24 reviews

Dog friendly| community pool | gym| kayak| bayside

Welcome to your ultimate family beach escape! Nestled near Fenwick Island this 3 BDR 2 BTH home offers everything you need for a memorable vacation. Unwind with cocktails at the tiki bar, toast marshmallows around the fire pit, or make a splash in the refreshing pool. Stay in shape at the on-site gym, ensuring your fitness routine doesn't miss a beat. With its prime location just moments from the beach and an array of amenities this bayside retreat promises an unforgettable vacation experience.

LocationValueLaundry

Superhost
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.
Home in Ocean City
4.79 out of 5 average rating, 63 reviews

The Bayside • Entire House+Yard+Kayaks •Walk2Beach

🏖️ Quick walk to the beach 🌊 🏠 Spacious entire house + full yard 🛋️ 2 Living Rooms, 3 Bedrooms, 2 Bath, 7 beds 🍽️ Full Kitchen + charcoal grill 📍 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 coffee & sunsets🌅 🧺 High capacity washer/dryer in unfinished area of home 🛏️ New memory foam mattresses & provided linens. Book your memories today! 🛶 2 Kayaks

LocationValueIndoor spaces

Top Guest favourite
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.
Home in Ocean City
4.95 out of 5 average rating, 107 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!

Outdoor spacesLocationCheck-in

Top Guest favourite
A waterfront home is surrounded by green lawns and trees, featuring multiple outdoor seating areas. The spacious deck overlooks the water and is equipped with a gas grill. A dock is visible, allowing for easy access to the bay.
Home in Ocean Pines
5 out of 5 average rating, 63 reviews

Waterfront w/Dock, Rooftop Terrace & 2 Kings

Enjoy stunning views from every room in this bayside beauty located in the peaceful Ocean Pines community just 9 miles from the beach and OC boardwalk. Designer finishes throughout, you'll find everything you need to enjoy a family or small group getaway. *We do not allow smoking or pets. *Saturday check-in with a 7 night minimum stay requirement from July-August. *We are located in a quiet, residential neighborhood. Please consider this when booking. *We do not supply sheets and towels.

Outdoor spacesLocationLayout

Guest favourite
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.
Townhouse in Ocean City
4.95 out of 5 average rating, 63 reviews

New Waterfront House, Bay & Boardwalk!

*Location* Welcome to our beautiful beach house! Location, Location!! WALKING distance to restaurants, bars, convenience stores, shops, Joly Rogers amusement Park, BOARDWALK and BEACH. Located on 25th St on the bayside, our WATERFRONT house has three balconies with a relaxing view of the water and bay. With patio furniture on all three balconies, you can relax, watch the sunrise/sunset and enjoy the bay breeze. Enjoy a dip in the community pool. Your experience will be unforgettable!

LocationOutdoor spacesCheckout

Top Guest favourite
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.
Home in Ocean City
4.95 out of 5 average rating, 75 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.

Outdoor spacesLocationHiking

Guest favourite
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.
Home in Ocean City
4.98 out of 5 average rating, 159 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! GUESTS USE POOL AT THEIR OWN RISK! The pool is open from May 1- September 30. Obviously we can’t have it open during cold temperatures!

LocationValueAccuracy

Top Guest favourite
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
4.91 out of 5 average rating, 56 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

Outdoor spacesLocationComfort

Popular amenities for Ocean City kayak rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Holiday House Rentals with a Kayak

Top Guest favourite
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
4.96 out of 5 average rating, 47 reviews

Salty Serenity

ValueLocationNearby

Guest favourite
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
4.97 out of 5 average rating, 86 reviews

Private pool, waterfront, kayaks, bikes, firepits!

LocationOutdoor spacesBathroom

Guest favourite
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
4.97 out of 5 average rating, 39 reviews

Cozy Beach Escape Mallard Lakes Resort Amenities

Outdoor spacesValueLong stay

Guest favourite
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
4.97 out of 5 average rating, 30 reviews

Waterfront Home

Outdoor spacesLocationNearby

Guest favourite
The exterior of a two-story home features a combination of gray siding and stone accents. Large windows allow natural light to fill the interior, and a welcoming front porch leads to the main entrance. A neatly manicured lawn sits in front of the property.
Home in Berlin
4.92 out of 5 average rating, 25 reviews

Spacious, luxury, 5BD. Perfect for Families!

ValueOutdoor spacesDecor

Top Guest favourite
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.
Home in Ocean View
4.93 out of 5 average rating, 70 reviews

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

Outdoor spacesLocationBeach

Top Guest favourite
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
5 out of 5 average rating, 85 reviews

Coastal Cottage! Walk to Beach!

Outdoor spacesLocationBackyard

Top Guest favourite
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
4.97 out of 5 average rating, 76 reviews

Coastal Oasis in Ocean Pines

ValueLocationWi-Fi

Other holiday rentals with a kayak

Top Guest favourite
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.
Townhouse in Sussex County
4.96 out of 5 average rating, 67 reviews

Waterfront Haven: Moments from the Beach!

LocationOutdoor spacesSleep quality

Top Guest favourite
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
5 out of 5 average rating, 21 reviews

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

LocationOutdoor spacesAmenities

Guest favourite
Townhouse in Ocean City
4.92 out of 5 average rating, 12 reviews

Modern Canalfront Condo with Pool

LocationBarbecueAccess

Top Guest favourite
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.
Home in Ocean View
5 out of 5 average rating, 43 reviews

Ocean View Paradise w/Hot Tub & Free Massages!

ValueLocationWi-Fi

Superhost
Condo in Ocean City
5 out of 5 average rating, 4 reviews

Pyramid 2D Oceanfront with Heated Pool

LocationCheckoutAccuracy

Top Guest favourite
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.
Home in Ocean View
4.95 out of 5 average rating, 41 reviews

6BR/4.5 BA/Pool next door to Home/ Guest Favorite

Outdoor spacesValueCleanliness

Top Guest favourite
A sunroom offers expansive views of a creek, showcasing sliding glass doors that allow natural light. Comfortable seating with orange cushions is arranged around a small table. A ceiling fan hangs above, and a television is mounted on the wall, creating a welcoming space.
Apartment in Selbyville
5 out of 5 average rating, 39 reviews

Creek Suite

LocationOutdoor spacesView

Top Guest favourite
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
4.98 out of 5 average rating, 63 reviews

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

LocationDecorAccuracy

When is the best time to visit Ocean City?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$375 NZD$358 NZD$409 NZD$443 NZD$518 NZD$627 NZD$1,040 NZD$819 NZD$567 NZD$468 NZD$479 NZD$431 NZD
Avg. temp3°C4°C7°C13°C18°C23°C26°C24°C21°C15°C9°C5°C

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