Vacation 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, 283 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!

Condo 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.

STEPS 2 BEACH! Ocean/bay/sunrise/sunset views from balcony! SO close to so much fun when you stay at this centrally-located condo in quieter area of OCMD. All within WALKING DISTANCE: BEACH, Northside PARK w/pier overlooking BAY, mini golf, restaurants/fast food, grocery/beer/liquor/wine store. INDOOR POOL. GAME/arcade ROOM: ping pong/air hockey/games of chance. Sun deck/patio w/dining tables. Concierge service/manager on site. Linens/towels provided. Stacked Washer/Dryer in condo. TOILETRIES

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.

4.81 out of 5 average rating, 48 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, 133 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.

5 out of 5 average rating, 16 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.

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, 101 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, 57 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

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.

4.97 out of 5 average rating, 70 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

Coastal sanctuary is a private mother-in-law suite with a private entrance, just 15 minutes from Ocean City MD. 2 bedrooms, spa like bath, family room, w/sleeper sofa, kitchenette overlooking a marsh and bay. You will have the entire floor. 1000 sq feet. Daily visitors include deer, heron, birds and duck. Follow the deer path and use our stand-up paddle boards and/or Kayaks. Assateague wild ponies and Ocean City boardwalk are an close by. Berlin voted the coolest small town in America.

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, 68 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, 45 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

4.99 out of 5 average rating, 139 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

4.92 out of 5 average rating, 24 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

Take it easy at this unique and tranquil getaway. Great views of the creek. Large deck with dining table and relaxing chairs. Your own bbq grill. And a private little beachy area on the water. Queen bed. Flat screen tv custom bath with shower. Keurig coffee and fresh beans. We have laying hens on the property so we should have some fresh eggs for you

Popular amenities for Ocean City kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.96 out of 5 average rating, 83 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!

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!

5 out of 5 average rating, 34 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!

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

4.94 out of 5 average rating, 33 reviews

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

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

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.

5 out of 5 average rating, 67 reviews

Coastal Cottage! Walk to Beach!

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.

4.9 out of 5 average rating, 30 reviews

Pet Friendly Bayside HotTub Grill Bikes Kayaks

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.

4.8 out of 5 average rating, 10 reviews

Nature at the Beach

Other vacation rentals with a kayak

A wooden deck leads to a paved outdoor area with lounge chairs, overlooking a calm canal. A large blue umbrella provides shade. Nearby, grassy patches complement the seating arrangement, while residential homes are visible across the water, creating a serene ambiance.

5 out of 5 average rating, 11 reviews

Waterfront Oasis with Private Dock

4.98 out of 5 average rating, 60 reviews

Waterfront Retreat | Dock, Kayaks, Walk to Beach

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.

4.93 out of 5 average rating, 54 reviews

Georgo Family Beach House

5 out of 5 average rating, 3 reviews

Home in Selbyville

The Sun Dance, Keenwik on the Bay

4.65 out of 5 average rating, 89 reviews

The living room features a large sectional couch with decorative pillows, a coffee table in front, and a wall-mounted flatscreen TV. Light wooden flooring complements the grey walls adorned with framed artwork. A ceiling fan hangs above, enhancing comfort in the space.

Townhouse in Ocean City

Maxbeachaus - Chic House with Pool Table in Garage

The bayfront home is shown with a vibrant blue exterior. A spacious deck featuring blue lounge chairs overlooks the water. Two kayaks are positioned on the dock, while a landscaped area with green grass is visible in the foreground.

4.89 out of 5 average rating, 53 reviews

2 Master Suites, Bayfront, SUPS-YAKS, walk 2 Ocean

Apartment in Bethany Beach

A light-filled living area is shown, featuring a spacious couch, two armchairs with decorative pillows, and a coffee table. A wall-mounted TV is visible, along with a Murphy bed seamlessly integrated into the cabinetry. Glass doors open to a serene outdoor space.

4.57 out of 5 average rating, 63 reviews

Bethany waterfront apt w/ private veranda sleeps 4

A two-story beach house is surrounded by greenery, elevated on pillars above the ground. The exterior features light-colored siding and multiple windows. A wooden staircase leads to the main entrance, while a gravel area provides parking space beneath the house.