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, 268 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!

The exterior of a charming home features a spacious front porch with white railings, inviting seating, and seasonal planters. A neatly manicured lawn extends from the sidewalk, complemented by a tree nearby. The house sits under a partly cloudy sky, enhancing its welcoming appearance.

4.94 out of 5 average rating, 47 reviews

Pet Friendly -Spacious Coastal Cape-Explore WestOC

WEST OC VIBING!! Bring the whole family -INCLUDING ALL YOUR FUR BABIES- CAR SHOW- BIKE WEEK,OCEANS CALLING HOT SPOT, AVOID DELAYS IN BUS TRANSPORTATION & CATCH BOAT TAXI - 1 BLOCK AWAY!2 large driveways & garage can hold many vehicles! 4 Bedrooms - 2 up (2 full beds ea) full bath. Main flr has HUGE Ensuite & 2nd bed with bath! Great for fishing groups, golfers, multi families! Walk to Harborside, PUBLIC BOAT RAMP, & MANY MORE! Patio with TV, hot tub & fenced yard. Great outdoor entertaining!

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, 45 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, 122 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 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.

5 out of 5 average rating, 21 reviews

Ocean View Paradise w/Hot Tub & Free Massages!

Our special place is close to everything for your DE beach visit! Make memories at our unique, updated Sharp Ocean View Paradise. Free access to a zero gravity, full body massage chair as you relax. Short discount to Bethany Beach and pools, gym, sports court and beach club community access. Enjoy a private hot tub, full range of games & arcade systems for your family sleeping up to 14. Enjoy grilling, large outdoor dining & access to full range of kayaks for canal access near our backyard!

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 out of 5 average rating, 57 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.

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!

4.9 out of 5 average rating, 50 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, 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.

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, 64 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, 39 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!

The bright living room features large windows overlooking the river, allowing natural light to fill the space. Comfortable seating arrangements are present, with patterned sofas and a wooden coffee table at the center. A television stands beside a cozy fireplace, enhancing the inviting ambiance.

5 out of 5 average rating, 9 reviews

Riverside Retreat- 3 Story/Direct Waterfront

This spacious three-story residence features 4 bedrooms and 2.5 bathrooms, including a king bedroom with an en-suite bath & balcony. Enjoy an open kitchen, dining area, and a stunning living room with river views. The backyard offers a private "beach" with Adirondack chairs and picnic tables. Just 20 minutes from Ocean City’s shopping, dining, and beaches. Perfect for family fun and relaxation! A local manager is here to ensure everything goes smoothly

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, 89 reviews

2500 sqft home. Walk to beach, pool, restaurants

Sleeps 13 (8 adults maximum). Our spacious waterfront home is one of the best secrets in Ocean City and perfect for the multi-generational families. Walk to the beach, pools, restaurants and more. Kids love fishing and crabbing off the dock. Bring your own boat or kayak. We have a fully stocked kitchen and amenities to ensure that you feel right at home. You will not be disappointed with booking our home for your family vacation in OCMD.

Popular amenities for Ocean City kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

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.

4.95 out of 5 average rating, 39 reviews

Salty Serenity

5 out of 5 average rating, 9 reviews

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.

Home in Bethany Beach

Bethany Beach New Castle 4BR 2BA Canal Front Home

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.

4.97 out of 5 average rating, 31 reviews

Waterfront Retreat with Kayaks, Deck, Views!

4.96 out of 5 average rating, 79 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, 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

Family + Pet-Friendly Home Near Fenwick Island

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.

4.94 out of 5 average rating, 33 reviews

5BR/4.5 BA/Pool Next to House/ 1.5 miles to beach

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, 69 reviews

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.

4.91 out of 5 average rating, 23 reviews

Pet Friendly Bayside Grill Bikes Kayaks

Other vacation rentals with a kayak

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.

4.92 out of 5 average rating, 26 reviews

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

4.93 out of 5 average rating, 54 reviews

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.

Home in Bethany Beach

Georgo Family Beach House

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

5 out of 5 average rating, 44 reviews

A two-story gray house stands along the water's edge, featuring a wrap-around balcony on the upper level. Several outdoor chairs are arranged on the lower deck, and a white fence outlines the property, providing an inviting view of the canal and surrounding area.

Home in Bethany Beach

5 Bedroom Canal Front home- 3 min walk to beach

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.

4.92 out of 5 average rating, 63 reviews

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

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

4.69 out of 5 average rating, 16 reviews

A living room area features a dark gray sofa and a compact coffee table, complemented by an orange accent chair. A large window allows natural light and offers views of the canal. A television is placed on a wooden console, and lamps provide additional illumination.

Apartment in Ocean City

Bayfront uptown OC, 3 BR, Sleeps 9