Vacation rentals with a kayak in Ocean City Beach

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Top-rated kayak rentals in Ocean City Beach

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Guest favorite

Home in Ocean City

4.94 out of 5 average rating, 220 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!

Jan 22 – 29

G$20,951 GYD per night

Guest favorite

Guest suite in Ocean Pines

4.95 out of 5 average rating, 354 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!

Sep 13 – 20

G$33,789 GYD per night

Guest favorite

Tiny home in Ocean View

4.97 out of 5 average rating, 116 reviews

The Bohemian Rhapsody

*Carefully & thoroughly read entire descriptions & click on photos & read captions!* 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 bath house w/space available to set up tents. We can host up to 6 humans (upon approval) & 2 canine kids. Electric,Wifi,fire pit,beachyard,outdoor grill. Close to area beaches, boardwalks, restaurants & more! No extra fees!

Mar 30 – Apr 6

G$24,895 GYD per night

Guest favorite

Townhouse in Ocean City

5.0 out of 5 average rating, 27 reviews

Edgewater View

Even in (especially in) the fall!! What a great place for a retreat, (small)family getaway, quiet space for alone time, couples time or girls/guys weekend. This special place is in the hub of downtown Ocean City, making it easy to plan your visit; 3 walking blocks to the boardwalk, beach, restaurants and entertainment. Unbelievable sunsets! Sit on the deck which is literally on top of the water and watch all the action or enjoy the peaceful sunsets and early morning wildlife activity.

Jan 17 – 24

G$46,014 GYD per night

Guest favorite

Home in Ocean City

4.98 out of 5 average rating, 109 reviews

Stunning Bayview Home with Own Private Pool

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 right outside the kitchen door! THE POOL IS CLOSED FOR THE 2023 SEASON & WILL RE-OPEN AROUND MAY 1st 2024! Planning to use the pool in chillier months? Keep in mind that the heater does not equal hot tub! It will still be just a slightly less cold pool on those chilly days!

Apr 6 – 13

G$194,169 GYD per night

Guest favorite

Townhouse in Ocean City

5.0 out of 5 average rating, 59 reviews

Escape to the Bay - Relaxing Waterfront Location!

Come enjoy the amazing sunrises at our relaxing retreat on the Bay! The water is just steps from the back patio at this recently updated and beautifully decorated townhouse. Watch the wildlife and boats pass by as you relax in our sunroom or get on the water in our 2-person kayak. Fenwick Island and Ocean City beaches are only a 1-2 miles away, so this is truly a great place for enjoying all the Delaware and Maryland shore has to offer. ***ALL LINENS AND TOWELS INCLUDED****

Jan 5 – 12

G$47,899 GYD per night

Guest favorite

Apartment in Ocean City

5.0 out of 5 average rating, 7 reviews

Sunsets on 17

Embrace coastal living in our Ocean City condo, boasting a private deck with tranquil canal views. Steps away from the bay, this charming retreat offers easy access to sandy beaches, the bustling boardwalk, and vibrant nightlife. Savor dockside sunsets, indulge in local cuisine, or explore nearby attractions. Equipped with convenient driveway and street parking, it's the perfect spot for your beach getaway. Experience a unique blend of relaxation and adventure in Ocean City!

Nov 5 – 12

G$37,308 GYD per night

Guest favorite

Apartment in Frankford

4.98 out of 5 average rating, 123 reviews

Cozy Cottage Getaway

Enjoy this newly remolded 1 bedroom apartment tucked away on 2+ acres 3 miles from Bethany beach. Close to Rehobeth beach for outlet tax free shopping or Ocean City MD just 13 miles. You’ll be minutes away from lots of restaurants, stores, mini golf, arcade, night life etc. Property includes a 1/4 mile walking/running trail, fire pit and basket ball court. This is the perfect place to escape away from the busy Beach life but close enough to enjoy everything fully.

Oct 20 – 27

G$30,871 GYD per night

Guest favorite

Apartment in Selbyville

4.96 out of 5 average rating, 231 reviews

Dirickson Creek Suite Waterfront

Premium Property SPOIL YOURSELF in this Lovely 5 Star One bedroom apartment 6 miles to the Beach LR fireplace, king bed , kitchenette ,snacks fresh ground gourmet coffee, Fabulous sun room awesome views Private entrance , Creek front patio with fire pit & Tiki Bar Free kayaks and standup paddle boards to explore the Creek. beach chairs and umbrella for your use. The kitchenette has a two burner portable stovetop. Tv in Bdr and sunroom NO PETS

Jul 28 – Aug 4

G$59,277 GYD per night

Guest favorite

Condo in Ocean City

4.97 out of 5 average rating, 32 reviews

GREAT LOCATION! Remodeled 1BR condo w/ Bay View!

Awesome Remodeled 1 BR Condo in Midtown OC perfect for family vacations! Best sunset views in town! Just 1 block from beach with private parking. Full kitchen, Washer/Dryer in unit. Lots of extras! Beach cart, beach chairs, umbrella, boogey boards, toys, cooler, etc. So much to do all within walking distance. Great breakfast place on the corner, Famous restaurants, bike rentals, bowling, kayaking, shopping, ice cream, mini golf, & more! Check us out!

Aug 26 – Sep 2

G$50,473 GYD per night

Guest favorite

Home in Lewes

4.98 out of 5 average rating, 157 reviews

Beautiful Waterfront Home-Private, Clean, Relaxing

A beautiful and peaceful get-away all year round! Bright and sunny 3 bed/2 bath waterfront home with wrap-around deck. Fully stocked, community pool, walking trails, kayaks and more! Visit Rehoboth or Lewes Beaches (10 miles away), Cape Henlopen and tax-free outlet shopping (6 miles away)! Great for families, water lovers, and bird lovers! Sunday to Sunday weekly rentals *only* from Memorial Day to Labor Day.

Sep 22 – 29

G$56,657 GYD per night

Guest favorite

Home in Ocean City

4.97 out of 5 average rating, 31 reviews

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!

Dec 7 – 14

G$78,721 GYD per night