Holiday 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*

Sandcastle Haven

Welcome to our 4-bedroom house in Millville!Comfortably hosting 10. Pack light! We provide towels (bathing & beach),linens,and essential toiletries & laundry pods.Seasonal beach shuttle is available too (10am-10pm for 2025)!Gather in our spacious open living area,enjoy outdoor fun in our large backyard and indoor entertainment in our game room,plus books,board games,and DVDs. Our guests enjoy Millville by the Sea's amenities: 3 pools,pickleball,trails,fishing pond,clubhouse grill,and crab shack.

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.

Family + Pet-Friendly Home Near Fenwick Island

Welcome to your ultimate family beach escape! Nestled near Fenwick Island this 3 BDR 2 BTH home offers everything you need for a memorable vacation. Unwind with cocktails at the tiki bar, toast marshmallows around the fire pit, or make a splash in the refreshing pool. Stay in shape at the on-site gym, ensuring your fitness routine doesn't miss a beat. With its prime location just moments from the beach and an array of amenities this bayside retreat promises an unforgettable vacation experience.

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.

Waterfront, Bring your own boat! Huge canal home.

Look no further for your vacation rental at the beach, this house has it all! Extraordinary waterfront coastal home with amazing views of the Assawoman Bay and the Ocean City skyline. With 2 expansive living areas with open floor plans, there is plenty of space for multiple parties to unwind. Relax on the deck or in the yard and enjoy the canal breezes. Cook in the updated kitchen and enjoy panoramic water views! Enjoy the beach in Fenwick Island, DE/Ocean City, MD just over 2 miles away.

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!

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.

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