Vacation rentals with a kayak near Ocean City Beach

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 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

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.

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*

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.

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!

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!

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.

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.

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!

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

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