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, 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!

ValueLocationAccuracy

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, 147 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.

Outdoor spacesValueAccuracy

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, 59 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.

Outdoor spacesValueComfort

4.88 out of 5 average rating, 69 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.

ValueLocationParking

5.0 out of 5 average rating, 23 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

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.

ValueLocationGetting around

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, 106 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!

LocationOutdoor spacesAccuracy

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.

5.0 out of 5 average rating, 62 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 spacesLocationNearby

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, 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 spacesValueGetting around

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.

4.91 out of 5 average rating, 54 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

LocationOutdoor spacesIndoor spaces

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.

4.99 out of 5 average rating, 146 reviews

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

ValueOutdoor spacesWalkability

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!

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! Please note: Max of 8 adults. No parties. No Pets. Renters must sign a Rental Agreement. Pool open May-Sept 30th isn't heated.

LocationOutdoor spacesQuiet

4.97 out of 5 average rating, 29 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

Escape to Jenny's Place, a waterfront retreat in charming Berlin, MD. Just minutes from Ocean City & Assateague Island, this 5-bedroom home comfortably fits your whole crew. Enjoy a private boat slip, a fenced yard with a fire pit, and a fully equipped kitchen. Perfect for family getaways, this peaceful canal-front home offers the best of coastal relaxation and adventure.

Outdoor spacesLocationBackyard

Popular amenities for Ocean City kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.97 out of 5 average rating, 37 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

Outdoor spacesLocationParks

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.

4.78 out of 5 average rating, 60 reviews

Entire House+Walk2Beach• 3 bdrm + 2 Living Rms

ValueLocationBathroom

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.

4.97 out of 5 average rating, 75 reviews

Coastal Oasis in Ocean Pines

ValueLocationQuiet

4.8 out of 5 average rating, 20 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

LocationBarbecueCheckout

5.0 out of 5 average rating, 83 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!

Outdoor spacesLocationIndoor spaces

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

LocationOutdoor spacesCondition

An A-frame structure features large triangular windows inviting ample natural light. A spacious deck extends from the entrance, bordered by wooden railings. Surrounding trees provide a sense of privacy and tranquility. The modern design is complemented by a stone pathway leading to the entrance.

4.91 out of 5 average rating, 33 reviews

Ocean Pines, 2 Kayaks @ beach, RV & Boat parking

LocationValueNearby

5.0 out of 5 average rating, 43 reviews

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

Ocean View Paradise w/Hot Tub & Free Massages!

Outdoor spacesValueSleep quality

Other holiday rentals with a kayak

5.0 out of 5 average rating, 9 reviews

Modern Canalfront Condo with Pool

LocationComfortHospitality

4.98 out of 5 average rating, 62 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!

LocationCheck-inDecor

5.0 out of 5 average rating, 3 reviews

Condo in Ocean City

Pyramid 2D Oceanfront with Heated Pool

LocationAccuracyComfort

4.94 out of 5 average rating, 36 reviews

A spacious deck showcases a set of white Adirondack chairs and a small table, inviting relaxation. The expansive view includes a calm waterway, framed by trees, under a clear blue sky, enhancing the serene atmosphere of the outdoor space.

Apartment in Selbyville

Water Front Apartment

Outdoor spacesLocationQuiet

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.

4.88 out of 5 average rating, 26 reviews

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

LocationOutdoor spacesCondition

5.0 out of 5 average rating, 8 reviews

Apartment in Ocean City

Bayfront Condo w/ Pool & Scenic Views - HS104

LocationHospitalityView

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, 62 reviews

New Waterfront House, Bay & Boardwalk!

ValueLocationDecor