Holiday rentals with a kayak in Ocean City

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!

Outdoor spaces · Location · TV

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, propane 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.

Outdoor spaces · Location · Amenities

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.

Value · Location · Condition

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.

Location · Value · Walkability

The Bayside • Entire House+Yard+Kayaks •Walk2Beach

🏖️ Quick walk to the beach 🌊 🏠 Spacious entire house + full yard 🛋️ 2 Living Rooms, 3 Bedrooms, 2 Bath, 7 beds 🍽️ Full Kitchen + charcoal grill 📍 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 coffee & sunsets🌅 🧺 High capacity washer/dryer in unfinished area of home 🛏️ New memory foam mattresses & provided linens. Book your memories today! 🛶 2 Kayaks

Value · Location · Condition

Spacious waterfront home & boat access!

Waterfront getaway, easy beach access (0.3 mile walk), pool, restaurants, and more. Linens & towels included! Bring your boat! Pier tie up available. Spacious 3 bedroom + bonus room with sleeping arrangements for 10(8 beds). This well-maintained home is close to dining, shopping, NorthsidePark & all the fun activities Ocean City has to offer. Beach chairs, toys, kayaks & paddleboard available. Fireworks from Northside Park can be viewed every Sunday summer night - right from the driveway!

Outdoor spaces · Location · Decor

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.

Outdoor spaces · Location · Access

Hot Tub & Pool Table Waterfront Home | 4King Beds

Yes- Linens are included! (Bed sheets & bath towels) New pool table & jacuzzi!! Experience the ultimate Ocean City getaway this year, with unbelievable water views from every room & a private two-story wrap-around balcony. Enjoy 4 comfy king beds. The home is perfect for groups seeking relaxation & home away from home. Only 4.2 miles from the Ocean City Boardwalk! What else is included? Bonfire pit Parking area Shampoo-Conditioner-Body Wash Soaps Laundry Detergent Kayak Beach chairs

Value · Outdoor spaces · Hot tub

Waterfront Haven: Moments from the Beach!

LINENS and TOWELS PROVIDED + PREMIUM AMENITIES INCLUDED - NO ADDITIONAL COST! Welcome to FENWICK BAY VISTA! Enjoy a relaxing stay in this stunning waterfront luxury townhouse on the Little Assawoman Bay, with ample water views and only 10 minutes from the beach! This airy 2500 sq. ft., 3-level, 3-bedroom, 3.5-bath home sleeps 8 and boasts incredible views of the bay. Nestled in a boutique resort community, you’ll enjoy a bayside pool, gym, sport courts, kayaking, and plenty more!

Location · Outdoor spaces · Cleanliness

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.

Outdoor spaces · Value · Parking

Stunning Bayview Home with Own Private Pool

This home can be occupied by a max of 12 adults with a total of 15 including children. Come relax in this gorgeous bay view single-family home in the lovely Caine's Woods neighborhood of Ocean City, adjacent to Fenwick Island. Imagine lazy days spent on the beach followed by a dip in the pool outside the kitchen door! GUESTS USE POOL AT THEIR OWN RISK! The pool is open from May 1- September 30. Obviously we can’t have it open during cold temperatures!

Location · Outdoor spaces · Pets

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

Value · Outdoor spaces · Bathroom