Fitness-friendly vacation rentals in Assateague Island

Come enjoy Summer on Smith Island at the HH Ranch

Relax in this 1910 era Smith Island home. Has one large upstairs bedroom with second twin bed separate from main bedroom. Comfortable family room with seating for 5. Updated enclosed patio is ideal in the summer. Large kitchen fully stocked to cook your meals. New front deck. Large bathroom with dual rainhead shower. Easy access to the water. Bikes and SUP available in the shed. Kayaks are covered outside by shed. Island is only accessible by boat. Enjoy the tranquility of this unique place.

2BRCapri: Indoor Pool, Game Room, Massage Chair

ALL THE COMFORTS OF HOME AT THE BEACH! BRAND NEW RENOVATED BATHROOMS! -ALL LINENS INCLUDED -Comfortable electric-reclining sofas -65-in smart Roku TV with soundbar. -Massage chair in master bedroom -Balcony & Dining Area w/ Ocean +Bay Views -In-unit W/D -Many conventional & USB Outlets -Arcade level features b-ball hoop, pool tables, ping-pong, shuffleboard, air-hockey -Outdoor tennis court -Large heated indoor pools -can swim full laps -Sauna and Gym -Board games in unit -Fast Wifi

Home Away From Home

Bring the whole family to this spacious home in a community with year-round resort amenities and water access in the OC area. You’ll enjoy completed amenities while being less than 5 miles from Downtown OC where you can enjoy the boardwalk and just 6 miles from Assateague Island, known for its wild horses and beautiful beaches. Nearby Berlin offers charming streets full of shops and restaurants. OCMD is a known destination for golf vacations, just minutes from several highly-rated golf courses.

2 BR Ocean Front Condo w/Pool, Expansive Views

Your family will be close to everything when you stay at this beautiful condo located right on the beach with expansive balcony views of both ocean and bay. With the best amenities around, this year-round rental is equipped with an enormous indoor pool, basketball and tennis courts, shuffleboard, saunas, gym, library, sun deck, & game room with arcades, claw machines, billiards, and air hockey tables. This 2-bedroom unit comfortably sleeps 6 which makes it ideal for families or couples alike.

Bright, Updated Condo, Pool, Convention Center

Makai 206 is a bright and modern 2‑bed, 2‑bath condo in Midtown Ocean City—just a short walk to the beach, the convention center, and great local dining. Perfect for families or small groups, the condo sleeps up to 5 guests comfortably. Close to beach and Great for events located at the convention center next door. What You’ll Enjoy • Private balcony for morning coffee or evening relaxation • Fully equipped kitchen • In‑unit washer and dryer • High‑speed Wi‑Fi and smart TVs • Indoor pool

Love Above the Waves-OceanView/Rooftop Heated Pool

🥂 Complimentary bottle of champagne on arrival, endless ocean views, private balcony, golden sunrises, rooftop heated pool, and direct beach access set the stage for a dream vacation. Celebrate your love from the 15th floor of Love Above the Waves - a romantic heaven for birthdays, anniversaries, engagements, and special escapes for two. Inside, the open layout allows the Atlantic to become the centerpiece of your stay, whether you're relaxing indoors or stepping out onto the balcony.

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

Sunset Bay Villas 219 waterfront condo

Amazing views- Welcome Bird Watchers, Nature and Beach Lovers! Designer condo with direct views of the Intracoastal Waterway Chincoteague Channel and Wallops Long term rental from October-May with government per diem per person and special offers for long term occupancy. Max. occupancy per Chincoteague town fire code is 8. This includes adults, children (2 and older) and infants (children under two). Government ID issued required to be shown on or before check in date.

Oceanfront 2 Bed/1.5 Bath, Balcony, Pools, Lounge

Wake up to breathtaking ocean views at Driftwood, a beautifully remodeled 2BR/1.5BA oceanfront condo in the amenity-rich Golden Sands Resort! Sleeps 6 with 2 queen beds + queen sleeper sofa. Enjoy your private balcony, indoor & outdoor pools, private beach, fitness center, game rooms, tennis, pickleball, volleyball, huge sun deck, and seasonal tiki bar. Steps to the sand and close to Northside Park, top restaurants, and the iconic Ocean City Boardwalk!

Serene Family Getaway | OC & Assateague Adventures

Coastal fun awaits! This 3BR, 2.5BA townhome in The Landings at Bayside is minutes from Ocean City, Assateague, and downtown Berlin. Enjoy pools, a playground, sports courts, crabbing pier, and kayak launch. Bikes, beach gear, and surf spots nearby—plus local favorites like Sinepuxent Brewery and the Assateague Island Surf Shop. Perfect for families, friends, and adventure seekers! EV charger in garage.

Eagles Nest- (Water View)

Home built in 2023. Local beach. Relax at this unique and tranquil getaway. Beautiful sunsets, water view, 3 decks, kids area, outdoor patio & pergola, outdoor Shower Feed and watch deer from back deck. Close walking distance to carnival grounds and pony auction. The house list occupancy of 5, however, there is a futon on bottom floor that sleeps 2 more comfortably.

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

This is a Ocbeachfrontrentals .com premier property 24/7 SUPPORT LINEN & TOWELS PROVIDED 8TH FLOOR PENTHOUSE! This stunning top floor 3 b 2.5 ba unit is the ULTIMATE friends & family beach trip, located in a premier building in Ocean City. Enjoy the ocean breeze and stunning views from over 150 square ft of private balcony. Wake up to ocean views from every room!