Fitness-friendly holiday rentals in Ocean Pines

Lux Estate Mins to OCMD! GameRoom-FirePit-BBQ-Gym

Escape to The Manor at Brooklyn Meadows, a luxury 6-bedroom retreat on a 40-acre equestrian estate. This home is perfect for family vacations and group trips, featuring a private pool, game room, fire pit, BBQ and home gym - all surrounded by rolling horse pastures & peaceful country views. 🛍️ 7 min to Berlin – “America’s Coolest Small Town” 🌊 10 min to Ocean City beaches & golf courses 🐴 15 min to Assateague Island & its wild horses Stay with us & experience the best of MD's Eastern Shore!

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.

Charming Getaway Golf Simulator

4 bedrooms plus a Bonus room and bunkroom with 3.5 Bathrooms Escape to our cozy rental in Berlin, Maryland, just minutes from the charming downtown of "America’s Coolest Small Town." Perfect for families, friends, or golf enthusiasts, this home offers relaxation and fun in one unique package. Golf Simulator: Enjoy a state-of-the-art indoor golf experience, rain or shine. Located near Ocean City beaches, Assateague Island, award-winning golf courses, and downtown Berlin. Book your stay today!

Updated Mid- Town Condo at Ocean City Beach!

Choose your own adventure at this updated bayside space. Short walk to multiple restaurants, mini golf, stores and of course the beach! This comes with 2 free parking spots, pool/hot tub access (for the building) fitness room and a bay view from the balcony. We have a cleaning service between guests to ensure things will be fresh and tidy! We've provided some welcome kit items listed below so you don't have to bring much as well as appliances for your every need. Superhost 6x running.

Bayside Family Oasis - Perfect for Large Families

Welcome to your coastal getaway in Bayside Resort, less than a 5-minute walk to the Sunridge Pool and fitness center. Set along the 17th hole of a Jack Nicklaus golf course, this spacious 5-bedroom home sleeps up to 12 guests and is ideal for families, golf trips, and group getaways. Inside, enjoy an open-concept layout with a fully equipped kitchen, dining area, and fireplace, perfect for relaxing after the beach or pool. Step outside to unwind on the patio with golf course views.

OceanfrontStudio-Slps4-Pool-Pickleball-HBOMax-Dis+

Absolutely stunning studio condo in the iconic Golden Sands! Private balcony offers amazing direct ocean views, and overlooks the building's sun deck. Updated kitchen with stainless steel appliances. Murphy bed & sofa bed allows the unit to sleep 4 comfortably. Includes HBOMAX, Disney+, and electric fireplace. Stylish bathroom with toilet and shower conveniently separated from sink. Building offers restaurants, pools, game rooms, and more! Golden Sands has a $75 registration fee.

OceanPinesFamilyBeachRetreat~JettdTub~KingBed~Golf

Immediate removal of stress at the front door. Being nestled in a marina’s serene waterfront & nature park is good for the soul. Relax in a jetted tub after a sun filled day & an al fresco meal on a back porch with charming outdoor dining. An open concept main level features large windows & comfortable seating through the entire property. 2 full bathrooms upstairs & a king sized bed provide maximum comfort & outdoor living on 2 balconies. Additional fees for pools, pets may apply.

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

Sea Watch Condo's is an ideal family location with tons of amenities. The until is a recently updated 3 bedroom 2 bathroom condo that sleeps 6 people in 2 queen beds, 2 twin beds . The unit is ocean front with a large oceanfront balcony. The amenities Include, basketball court, tennis courts, playground, arcade, movie theater, billiard room, indoor pool and outdoor pool as well as a restaurant. The condo has 24 hour security and plenty of parking. Pools closed in off season

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.

‘Dockside Retreat’ -pool, minutes to OC/beaches

Escape to Dockside Retreat in Bayville Shores, a private community on the scenic Little Assawoman Bay. Start your mornings with beautiful views, unwind with community amenities, or head out for adventure. Splash at Thunder Lagoon, race at Viking Go-Karts, or shop and dine by the coast. Beaches are just minutes away—Fenwick Island (2.5 mi), State Line (2.7 mi), Bethany (4.5 mi), and Ocean City (6.1 mi). The perfect blend of relaxation and fun awaits!

Pineapple Bay ~ Private Pier + Sunsets

Luxury 4BR bayfront townhouse in Ocean City, MD. Enjoy stunning sunsets from the private deck, fish or catch Maryland blue crabs from your private pier, and unwind in beautifully designed spaces. King beds for every couple, custom bunks for kids, plus a full arcade game room, premium ping pong, fitness room, and hidden Harry Potter room. Just minutes from the beach in a private bayside location. Your unforgettable waterfront escape awaits.