Vacation rentals with a kayak in Ocean Pines

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Top-rated kayak rentals in Ocean Pines

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Guest favorite

Home in Ocean City

4.94 out of 5 average rating, 252 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!

Top guest favorite

Tiny home in Ocean View

4.97 out of 5 average rating, 147 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!

Guest favorite

Home in Ocean City

4.96 out of 5 average rating, 102 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.

Guest favorite

Guest suite in Ocean Pines

4.95 out of 5 average rating, 376 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!

Guest favorite

Home in Millsboro

5 out of 5 average rating, 10 reviews

Bayfront Oasis Vacation Rental

Waterfront panoramic views with a crabbing dock and boat slip. 4 bedrooms (full/twin bunkbeds, 2 twin beds + full bath, queen bed + full bath, king bed + full bath, and sleeper sofa in living room); up to 14 guests. Additional features include ½ bath, sunroom, living room, kitchen, laundry room (washer/dryer), and gaming room. Outdoor space with dining table, outdoor kitchen, firepit, gazebo, cornhole. Resort amenities; swimming pool, bikes, playground, pickleball, dog park, marina, store.

Top guest favorite

Home in Selbyville

4.98 out of 5 average rating, 40 reviews

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.

Top guest favorite

Home in Berlin

5 out of 5 average rating, 102 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!

Guest favorite

Townhouse in Bethany Beach

4.9 out of 5 average rating, 104 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 Bethany Beach

4.95 out of 5 average rating, 19 reviews

Beautiful Bethany Beach Retreat - Minutes to Beach

There's space for the whole family in this open and airy canal-front home, a nature oasis only minutes from the beach. Launch the provided kayak from the private dock to explore the Salt Pond and watch for local wildlife. Enjoy stunning views from three tiers of furnished decks, including a lovely screened porch where you can lounge on the outdoor sectional overlooking the canal. No need to pack the beach chairs as you will find ample chairs along with carts and coolers.

Guest favorite

Home in Bethany Beach

5 out of 5 average rating, 42 reviews

5 BR Waterfront Home - walk to beach

Recently updated 5 bedroom waterfront home with views from every room and a massive new deck to enjoy the summer sunset. Located at the end of a quiet street (Tingle Ave) with water on the back and side of the house and walking distance to downtown Bethany Beach. 100+ feet of water frontage with 3 decks and a private dock to launch kayaks. Kayaks / stand-up paddle boards and bikes included! * Fully stocked house with linens and bath towels included *

Top guest favorite

Home in Ocean Pines

4.99 out of 5 average rating, 121 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

Guest favorite

Home in Bethany Beach

4.87 out of 5 average rating, 47 reviews

Waterfront, SUPs, Yaks, & Bikes! Walk 2 the Beach

Beautiful Bayfront Home w/Private Pier & deep water for SUP & Kayak excursions, boating, Fishing & Crabbing! Plus, short walk to the ocean... Discounts Available! Complimentary! 2 SUPs 2 Kayaks 2 Bikes 6 Beach Chairs 1 Beach Cart 1 Beach Umbrella 2 Boogie Boards 3 Beach Parking Passes Free Parking on Property Private Garage to store your belongings Private Patio Bar w/music & frig This will save you big bucks on rental equipment!