Holiday rentals with a kayak in Ocean Pines

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Top-rated rentals with kayak in Ocean Pines

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Superhost

Home in Ocean City

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!

Superhost

Tiny home in Ocean View

4.97 out of 5 average rating, 152 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!

Superhost

Home in Ocean City

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.

Superhost

Home in Ocean Pines

5 out of 5 average rating, 22 reviews

Salty Serenity

Relax and recharge at our cozy 3 bed/2 bath home in Ocean Pines, a peaceful community near Ocean City, MD. Enjoy bikes, kayaks, and a fire pit in the large backyard, or use the pools, marina, yacht club, and golf course in the neighborhood. Beach parking at the Ocean Pines Beach Club in Ocean City is included. You can explore the boardwalk, casino, outlets, and the many nearby restaurants. Or, visit Berlin, or see the wild horses at Assateague Island. Come experience all the area has to offer!

Superhost

Guest suite in Ocean Pines

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!

Superhost

Home in Ocean Pines

4.93 out of 5 average rating, 28 reviews

Cottage on the water

We are located right off of Route 90 and minutes to the beach. Ocean Pines is filled with amenities. We have a public access yacht club and golf course are close to the town of Berlin for dining and a visit to the famous Burley Oak Brewery. The family will enjoy Ocean City for fun at Jolly Rogers or the Boardwalk for the rides. West Ocean city has the famous Orange Crush at the Harborside restaurant and don't forget Assateague Island and the horses. We are also 2 miles from the local winery.

Superhost

Home in Ocean Pines

5 out of 5 average rating, 47 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.

Superhost

Home in Ocean Pines

4.95 out of 5 average rating, 21 reviews

Peaceful, pet and family-friendly beach retreat

Escape the busy and hurried life in our Ocean Pines home. Nestled among the trees, enjoy your coffee peacefully, sitting on the wrap-around deck. Unwind in our open and bright family room with lots of natural light and huge windows. Equipped with fast WI-FI and lots of other essentials, we know your stay will be easy and relaxing. It's stocked with everything you need for a family vacation-games, puzzles, books, grilling supplies, kids supplies (pack-n-play, bibs, booster chair), and more!

Superhost

Home in Ocean Pines

4.98 out of 5 average rating, 52 reviews

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.

Superhost

Home in Berlin

5 out of 5 average rating, 105 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!

Superhost

Townhouse in Bethany Beach

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!

Superhost

Home in Ocean Pines

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