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, 287 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!

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, 150 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.

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.

4.85 out of 5 average rating, 62 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.

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.

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, 108 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!

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.

4.79 out of 5 average rating, 66 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

4.98 out of 5 average rating, 80 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

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, 161 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!

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.

4.92 out of 5 average rating, 59 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, 146 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

4.94 out of 5 average rating, 16 reviews

Modern Canalfront Condo with Pool

Escape to our fully renovated 2BR/2.5BA waterfront condo in Ocean City! Perfect for families, this stylish retreat features stunning canal views, two patios, and a dock for fishing. Enjoy a modern kitchen, cozy fireplace, and a dedicated workspace. Located just a 5-minute walk from the beach, local dining, and shops. Comfortably sleeps your group with a sleeper sofa for extra guests.

4.98 out of 5 average rating, 116 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 2 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 kayak rentals near Ocean City Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.97 out of 5 average rating, 86 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!

5.0 out of 5 average rating, 67 reviews

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

Waterfront w/Dock, Rooftop Terrace & 2 Kings

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.

4.95 out of 5 average rating, 76 reviews

Tranquil Water View! Kayaks & SUP Boards Included!

5.0 out of 5 average rating, 90 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!

5.0 out of 5 average rating, 24 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

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, 91 reviews

Spacious Waterfront Home; Walk to the Beach & more

4.97 out of 5 average rating, 30 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

4.83 out of 5 average rating, 24 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

Other holiday rentals with a kayak

4.98 out of 5 average rating, 63 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.

Condo in Ocean City

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

5.0 out of 5 average rating, 6 reviews

Condo in Ocean City

Pyramid 2D Oceanfront with Heated Pool

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.

5.0 out of 5 average rating, 22 reviews

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

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.

4.95 out of 5 average rating, 66 reviews

New Waterfront House, Bay & Boardwalk!

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.

Waterfront Haven: Moments from the Beach!

4.96 out of 5 average rating, 69 reviews

A serene view of marshland and water under a pastel sky reflects soft pink and blue hues. The calm water is bordered by grass and stretches towards distant houses, creating a tranquil coastal landscape.

4.8 out of 5 average rating, 30 reviews

Bayfront, sunset view, 3 decks, dock + boat slip

4.89 out of 5 average rating, 9 reviews

Apartment in Ocean City

Bayfront Condo w/ Pool & Scenic Views - HS104