Vacation rentals with a kayak near Ocean City Beach

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Top-rated kayak rentals near Ocean City Beach

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Guest favorite

Two kayaks are positioned on the grassy shore, ready for use on the calm waterway. Bright paddles rest on each kayak, with the inviting waterfront location featuring docks and homes in the background. A propane grill is nearby, adding to the outdoor leisure atmosphere.

Home in Ocean City

4.94 out of 5 average rating, 251 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!

Top guest favorite

A cozy outdoor space is illuminated by string lights, enhancing a welcoming atmosphere. Comfortable seating is arranged around a sandy area bordered by greenery. Decorative elements, such as a hanging basket and patterned rug, complement the rustic charm of the setting.

Tiny home in Ocean View

4.97 out of 5 average rating, 147 reviews

The Bohemian Rhapsody

*Carefully/thoroughly read all descriptions,click photos,read captions BEFORE inquiring to book* Enjoy a rustic "glamping" experience in 2 Bohemian themed sheds-the Grateful Shed & Surf Shack...less than 5 miles from beautiful Bethany Beach, DE!Private driveway/entrance, outdoor bathhouse w/space available to set up tents.We can host up to 8 humans (upon approval) & 2 canine kids.Electric,Wifi,fire pit,sandyard,outdoor grill.Close to area beaches, boardwalks, restaurants & more! No cleaningfees!

Guest favorite

A vibrant green kayak rests on a wooden dock, which extends over calm water. The dock is lined with poles and residential homes are visible in the background, along with a clear sky dotted with wispy clouds.

Home in Ocean City

4.96 out of 5 average rating, 101 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.

Guest favorite

A serene waterway is observed, flanked by neatly maintained banks and a wooden dock. Boats are visible at the dock, while charming homes and trees line the opposite shore, reflecting a peaceful community atmosphere.

Guest suite in Ocean Pines

4.95 out of 5 average rating, 375 reviews

Stunning private waterfront suite

Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City. Park in the driveway and step into your own private escape!

Guest favorite

A wooden dock extends along the calm water, flanked by manicured grass and several shrubs. The serene waterfront is framed by a clear blue sky, showcasing the peaceful connection between nature and the property.

Home in Millsboro

5 out of 5 average rating, 10 reviews

Bayfront Oasis Vacation Rental

Waterfront panoramic views with a crabbing dock and boat slip. 4 bedrooms (full/twin bunkbeds, 2 twin beds + full bath, queen bed + full bath, king bed + full bath, and sleeper sofa in living room); up to 14 guests. Additional features include ½ bath, sunroom, living room, kitchen, laundry room (washer/dryer), and gaming room. Outdoor space with dining table, outdoor kitchen, firepit, gazebo, cornhole. Resort amenities; swimming pool, bikes, playground, pickleball, dog park, marina, store.

Guest favorite

A vibrant yellow kayak is positioned on a wheeled cart in a grassy area. Behind it, a shed with a star emblem displays a weathered blue and gray exterior. The scene is framed by lush greenery, offering a serene outdoor setting.

Cottage in Lewes

4.85 out of 5 average rating, 112 reviews

'Cottage by the bay', sleeps 8 near Rehoboth beach

This bayside getaway is a beautiful 'A' frame style cottage and is located along the Rehoboth bay with direct access to the water. The cottage is within the gated community of Angola by the Bay. About a block away from the front door is one of the three private crabbing/fishing docks, kayak launch and marina! Enjoy walking or biking along the water and trails throughout the community. The large pool is always a favorite too! Baywood greens golf is nearby also! Enjoy the beautiful sunsets!

Top guest favorite

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

5 out of 5 average rating, 102 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!

Guest favorite

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.

Townhouse in Bethany Beach

4.9 out of 5 average rating, 103 reviews

Beach Pebble Square, 1 BLOCK TO BEACH!

Spacious, cozy, townhome one short block from beach! Open floor plan with cathedral ceiling in living room and full renovations throughout make this home fresh and ready for guests! The bedrooms are simple and well appointed. 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, a full bed, and extra seating!

Guest favorite

Home in Lewes

4.98 out of 5 average rating, 42 reviews

Salty Beach Love Family Home

*** 5-day and 7-day discounts. This comfortable family vacation let is perfect for walking and biking safely on the quiet streets and wooded and waterfront nature trails. Bring your kayaks or launch your boat at the neighborhood ramp for an excursion down Herring Creek to the Rehoboth Bay. A community center with a salt-water pool (ten passes included) is a short walk away on a wooded path. From the property, a short drive delivers you to the beaches, restaurants, and shopping.

Superhost

A private dock extends over calm waters, surrounded by tall grasses and trees. The view showcases the serene canal, leading to a grassy area in the background, offering a natural setting for relaxation and exploration.

Home in Bethany Beach

4.95 out of 5 average rating, 19 reviews

Beautiful Bethany Beach Retreat - Minutes to Beach

There's space for the whole family in this open and airy canal-front home, a nature oasis only minutes from the beach. Launch the provided kayak from the private dock to explore the Salt Pond and watch for local wildlife. Enjoy stunning views from three tiers of furnished decks, including a lovely screened porch where you can lounge on the outdoor sectional overlooking the canal. No need to pack the beach chairs as you will find ample chairs along with carts and coolers.

Top guest favorite

Home in Ocean Pines

4.99 out of 5 average rating, 120 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

Guest favorite

Home in Bethany Beach

4.87 out of 5 average rating, 47 reviews

Waterfront, SUPs, Yaks, & Bikes! Walk 2 the Beach

Beautiful Bayfront Home w/Private Pier & deep water for SUP & Kayak excursions, boating, Fishing & Crabbing! Plus, short walk to the ocean... Discounts Available! Complimentary! 2 SUPs 2 Kayaks 2 Bikes 6 Beach Chairs 1 Beach Cart 1 Beach Umbrella 2 Boogie Boards 3 Beach Parking Passes Free Parking on Property Private Garage to store your belongings Private Patio Bar w/music & frig This will save you big bucks on rental equipment!