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, 278 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!

5 out of 5 average rating, 72 reviews

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.

Apartment in Ocean City

TOP 1% Premiere Condo VIEWS/Indoor Pool/Game Room

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

4.98 out of 5 average rating, 56 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.

Apartment in Ocean City

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

Awesome newly renovated 1 BR 1 bath Condo in Midtown OC perfect for family vacations! Best sunset views in town! Just 1 block from beach with private parking behind building. Full kitchen, Washer/Dryer in unit. Lots of extras! Beach cart, beach chairs, umbrella, boogey boards, toys, cooler, etc. So much to do all within walking distance. Great breakfast place on the corner, Famous restaurants, bike rentals, bowling, kayaking, shopping, ice cream, mini golf, & more! Check us out! Ask about kayaks

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, 46 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.

Townhouse in Bethany Beach

A prominent sign labeled 'Beach Pebble Square' stands in the foreground, leading to a cluster of multi-story townhomes. The building features multiple balconies and a light-colored exterior, set against a clear blue sky, highlighting the peaceful atmosphere of the area.

4.87 out of 5 average rating, 116 reviews

Beach Pebble Square, 1 BLOCK TO BEACH!

Spacious, cozy, townhome one short block from beach! Fully renovated throughout! Open kitchen, dining room, and cathedral ceiling living room. The main level has a cute/private efficiency called "The Captains Quarters". Upstairs, the king bedroom suite has a private deck, private bathroom, and double closets with a Smart TV. The second bedroom has a queen bed, bunk beds w/a trundle and a shared bathroom. The loft is cozy and cool, with two trundle daybeds and a full bed. Loft is best for kids*

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, 126 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 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.

4.96 out of 5 average rating, 79 reviews

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! Max of 8 adults. No parties. No Pets. Renters must sign a Rental Agreement & provide $250 refundable damage deposit. Pool open April-Sept 30th, NOT heated. 5% local room tax will be collected after booking.

The exterior view captures a two-story house situated by the waterfront, surrounded by expansive wetlands and serene ponds. The vibrant green landscape contrasts with the blue water, providing a picturesque backdrop for relaxation. Nearby, the distant skyline is faintly visible.

4.97 out of 5 average rating, 67 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

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.

5 out of 5 average rating, 115 reviews

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!

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.

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

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, 136 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

Popular amenities for kayak rentals in Ocean City

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

4.97 out of 5 average rating, 33 reviews

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.

Home in Ocean View

Waterfront Retreat | Kayaks, Deck, Mins to Beach

5 out of 5 average rating, 19 reviews

Waterfront Home

5 out of 5 average rating, 29 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, 15 reviews

Home in Selbyville

Family + Pet-Friendly Home Near Fenwick Island

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

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 pair of teal Adirondack chairs sits on a wooden dock overlooking calm water. Decorative pillows add a touch of comfort. Boat slips are visible in the background, with a soft reflection on the water's surface as the sun sets behind scattered clouds.

4.95 out of 5 average rating, 39 reviews

Cottage on the water

Other holiday rentals with a kayak

A bright living area features a large sectional sofa and a coffee table with decorative items. A flat-screen television is mounted on the wall, while a wall art piece depicting a beach scene adds color. Sliding glass doors invite natural light and overlook the porch.

4.85 out of 5 average rating, 13 reviews

Sunny Bayside Escape

4.98 out of 5 average rating, 58 reviews

An aerial view of a waterfront home showcases the expansive property with lush green landscaping. The house is positioned near a tranquil waterway, surrounded by other residences, emphasizing its peaceful location. The image captures the proximity to the private dock and expansive outdoor spaces.

Home in Bethany Beach

5 BR Waterfront Home - walk to beach

5 out of 5 average rating, 37 reviews

A spacious outdoor pool is surrounded by lounge chairs and tall trees, providing a refreshing escape. Bright blue umbrellas offer shade, enhancing the inviting atmosphere. The clear water reflects the sunlight, creating a peaceful setting for relaxation and leisure.

Townhouse in Millville

Tranquil and Spacious Retreat near Bethany Beach

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

Superhost

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

4.65 out of 5 average rating, 89 reviews

Maxbeachaus - Chic House with Pool Table in Garage

4.93 out of 5 average rating, 14 reviews

An aerial view of a large pool area reveals multiple swimming pools surrounded by lounge chairs and shaded cabanas. The community center is visible nearby, featuring a green roof. Lush greenery and well-maintained grounds enhance the leisure space, ideal for relaxation.

Home in Selbyville

Bayside - Fenwick|10 min to beach| Amenity Rich

4.94 out of 5 average rating, 36 reviews

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.

Home in Bethany Beach

Bethany Beach Classic