Vacation rentals with a kayak in Ocean City

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.

4.95 out of 5 average rating, 255 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!

4.97 out of 5 average rating, 152 reviews

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

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!

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.

4.83 out of 5 average rating, 29 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.

4.94 out of 5 average rating, 104 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 suite in Ocean Pines

A cozy living area features a white couch and two accent chairs with a leaf pattern. A glass coffee table sits on a woven area rug. Large sliding doors provide a view of the outdoor patio, framed by greenery and water, enhancing the space's natural light.

4.95 out of 5 average rating, 377 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!

4.96 out of 5 average rating, 74 reviews

Two kayaks, one green and one red, rest against a tree near the water's edge. The grassy area features a stone path leading to a wooden pier, with trees providing shade in the background.

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! 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.

5 out of 5 average rating, 105 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!

A welcoming entrance features a set of wooden steps leading to a covered porch. Colorful flowers in vibrant hues surround the entryway, complemented by green foliage and shrubs. Bright light filters through the branches of trees overhead, creating a serene and inviting atmosphere.

4.97 out of 5 average rating, 32 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.

Two kayaks, one yellow and one red, rest beside a calm waterway. Lush green grasses line the bank, with a wide expanse of sky filled with soft clouds overhead. The scene conveys a peaceful outdoor setting, ideal for leisurely exploration.

4.94 out of 5 average rating, 16 reviews

Entire House+Yard+Kayaks •Walk2Beach• 2 Living Rms

🏖️ Quick walk to the beach 🌊 🏠 Entire house + full yard 🍽️ Full Kitchen + charcoal grill 🛋️ 2 Living Rooms, 3 Bedrooms, 2 Bath, 7 beds 🛶 Kayaks 📍 Centrally-located, walking distance to top rated Bayside Skillet & Ropewalk Restaurant, the bay & more 👯Plenty of space for the whole family- breakfast bar, dining table, plus front porch table to enjoy dinner sunsets🌅 🧺 High capacity washer/dryer in home 🛏️ New memory foam mattresses & provided linens. Book your memories today

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.

4.89 out of 5 average rating, 106 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!

4.96 out of 5 average rating, 26 reviews

A scenic view of the Assawoman Bay is captured, showcasing calm waters under a blue sky adorned with clouds. A white railing frames the image, guiding the eye towards a distant dock extending into the bay.

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, 125 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

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

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Luxurious estates for the ultimate escape

Bungalows

Intimate homes. inviting architecture

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.

5 out of 5 average rating, 22 reviews

Salty Serenity

CoraRating, 5 stars2 weeks ago

Dan and Heather's place was quite lovely with all the amenities of home. The kitchen was stocked with miscellaneous items one may sometimes forget to pack. The instruction manual was quite useful as well as having access to WiFi, the Ocean Pines Beach Club, etc. If you enjoy a rustic outdoor fire pit area, you'll be in for a treat. The Ocean Pines vibe is memorable, peaceful and continually pulls me back for more! The listing for this home is accurate and my husband and I would love to come back again in the future.

The image shows a balcony view overlooking a marina filled with boats. The calm water reflects the fluffy clouds above, and nearby buildings are visible along the shoreline. Green grass frames the balcony area, creating a serene outdoor space.

4.85 out of 5 average rating, 20 reviews

Marina Retreat | Relaxing Balconies & Pool

JonRating, 5 stars1 month ago

All around great place to stay! We felt right at home! Perfect layout and tons of space! Views from the back deck are amazing! Very walkable to anything you would need and easy 1.2 mile walk across the bridge to the boardwalk and beach! Would certainly stay again!!

5 out of 5 average rating, 6 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!

LanRating, 5 stars2 weeks ago

This was one of the best rentals our family has ever stayed in—beautiful, clean, comfortable, great location, and thoughtfully stocked with everything we could possibly need! We especially loved the hot tub, massage chair, and ALL the games (e.g. arcade, air hockey, skeeball, foosball, basketball) that kept everyone entertained. We got great use of the pool and gym at the clubhouse, which also conveniently offered a shuttle to the beach. The beach gear made our days on the sand easy and fun, and the kayaks were a fantastic bonus. Host communication was excellent- extensive instructions and information including local recommendations. We’re already hoping to return next year. Thanks, Joe and Jen!

5 out of 5 average rating, 7 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

RyanRating, 5 stars1 week ago

Serena was great to deal with and communicated effectively with us. Unfortunately, the weekend was rainy weather, but the neighborhood amenities were able to keep our young children entertained. The neighborhood is very friendly and all the neighbors were pleasant. We look forward to staying here again in the future.

Top guest favorite

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

5 out of 5 average rating, 34 reviews

Coastal Cottage! Walk to Beach!

JosephRating, 5 stars1 week ago

My family and I had an amazing time at the Coastal Cottage! Between the awesome sound system and the heated pool, we almost didn’t want to leave the house to check out the local bars and restaurants! Steve is an incredible host. Super friendly and made the whole check in and check out process very easy. The only thing I wish were different is that we booked a couple more days! I highly recommend this place and know for certain that we will be looking at the available dates for our future trips back to Bethany Beach!

Top guest favorite

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.

4.98 out of 5 average rating, 52 reviews

Coastal Oasis in Ocean Pines

TerryRating, 5 stars3 days ago

Very pleased with our choice. Sandra and her husband were very responsive. Would love to book again

4.95 out of 5 average rating, 21 reviews

Peaceful, pet and family-friendly beach retreat

JasonRating, 5 stars1 month ago

My first time staying at an Airbnb so wasn’t sure what to expect. Sara’s place exceeded all expectations. Always quick to respond when i had questions. Would not hesitate to book again.

An open living space is showcased with warm wood flooring that leads to a cozy seating area featuring a leather sofa adorned with colorful cushions. Natural light floods through sliding doors that offer access to outdoor views. A staircase leads to the upper level.

4.93 out of 5 average rating, 28 reviews

Waterfront Oasis

KayceeRating, 5 stars1 month ago

we loved staying here! it was the perfect quiet place for our group to enjoy our short weekend!

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Cottage rentals with a kayak

4.84 out of 5 average rating, 114 reviews

A charming 'A' frame cottage features a blue exterior and a front deck covered by a vibrant red umbrella. Lush green grass surrounds the home, with decorative plants and shrubs enhancing the landscape. The inviting entrance is framed by a white railing, suggesting a welcoming atmosphere.

Cottage in Lewes

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

ChrisRating, 5 stars2 weeks ago

Needed a clean, quiet place for a long weekend for a local wedding. Very few options willing to accomodate us. The property and Tim were wonderful

4.9 out of 5 average rating, 52 reviews

The exterior of a two-story house features a modern design with a blue and white color scheme. Large windows allow natural light to fill the interior. A staircase leads to an inviting porch with white railings, while the surrounding landscape includes grass and shrubs.

Cottage in Milton

Sandcastle directly ON the beach

ChrisRating, 5 stars2 months ago

Awesome location with modern amenities and all the things you need for a laid back family beach vacation. Our fur babies loved it almost as much as we did!

A light green cottage features a screened porch with red seating and a charcoal grill. White lounge chairs are positioned on the deck, which is surrounded by colorful flowerbeds and lush greenery, creating an inviting outdoor space for relaxation.

Cottage in Millsboro

4.48 out of 5 average rating, 23 reviews

Deck & Indian River Bay Views: Coastal Cottage

JessicaRating, 5 stars12 months ago

Our stay was perfect! We had a wedding to go to while down there and everything was no more than 30 minutes from us. Cindy and Dave were fantastic and friendly. They made us feel right at home. The house was in the perfect location and made us feel right at home. Would recommend this place to everyone.

The exterior of a charming house is surrounded by lush greenery. A covered front porch features white railings and a welcoming entry. An American flag hangs beside the door, with multiple windows adorned by green shutters, enhancing the inviting feel of the home.

Cottage in Ocean Pines

4.81 out of 5 average rating, 31 reviews

Ocean Pines Beach House in the Woods

MorganRating, 5 stars10 months ago

Enjoyed my stay here, the home was cozy and clean. I would stay again!

Top guest favorite

A spacious kitchen with a large central island is featured, complemented by white cabinetry and stainless steel appliances. Natural light fills the room through the window, illuminating the dining area with a wooden table and blue chairs nearby, creating an inviting space for gatherings.

Cottage in Lewes

4.99 out of 5 average rating, 189 reviews

Ebb & Flow Beach House - Lewes Bay Beach Retreat

AlexandraRating, 5 stars1 week ago

This was our second time staying at Frank and Dayle's. Their place is perfectly located, just a few minutes walk to the beach or to the shops and restaurants in town. The bike trail and tennis courts are also close by. The house was clean, welcoming, and comfortable for our family of four, including parents and two young adults. Our son was able to work remotely and found the enclosed porch provided a perfect work space. WiFi was also excellent. Frank and Dayle are responsive and helpful hosts. Our family have stayed in close to two dozen Airbnbs and I would rank Ebb and Flow beach house as one of the best!