Fitness-friendly vacation rentals in Ocean Pines

Amazing Large 4 Bedroom West OC Town House, Pool!

Recently refreshed with new carpet, fresh paint, and updated furniture, this spacious three‑level West Ocean City townhome is perfect for extended families, multiple couples, or groups of friends. With high ceilings, hardwood floors, generous room sizes, and multiple living areas, up to 14 guests can relax comfortably with plenty of space to spread out. Enjoy a fully equipped kitchen, private laundry, free Wi‑Fi, HD TVs in every bedroom, and furnished outdoor decks for coffee or adult beverage

Large Townhouse In GlenRiddle Community #102

GlenRiddle is a luxury town home that features 4 bedroom, 3.5 baths with over 2800 ft.~ of living space. Features include hardwood floors, crown molding, 9 foot ceilings, granite countertops, high end kitchen cabinets, fireplace, and one car garage. Tastefully decorated and ready to enjoy for summer. Guests will have access to the community pool and fitness center. Glen Riddle offers two 18 hole championship golf courses with a Ruth's Chris steakhouse onsite. ***Worcester County License #2017

Salty Sunrise

Welcome!! Come relax in a large quiet townhouse. West OC has a laid back harborside feel, but yet just minutes to the boardwalk, great beaches and loads of fun. You'll have the entire place to yourself, 3 bedrooms, 2 full bathrooms on the 2nd floor and half bath on 1st floor. Full working kitchen and large dining room table. Full access to the indoor and outdoor pools, weight room, playground and tennis/ basketball courts. Enjoy sitting on one of the two back decks, grill out and chill.

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.

Spacious Bayside 2 BR Condo at Sunset Bay

This amazing spacious Condo is located in Midtown OC, right next to Alley Oops for evening duckpin bowling and arcade games! A short walk to Seacrets Bar & Grill, Distillery and The Hideaway! Amazing sunset vibes next door at Mackys. 4 Tommy Bahama Beach chairs, Beach Umbrella, towels, a collapsible cooler & toys are provided. Perfect getaway for a family, group of friends or couples vacation! ***Bed Linens and Towels ARE provided, and beds will be made prior to arrival :)

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

Beachfront 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 a breathtaking view of the beach and ocean.

Cozy Coastal Cottage Ocean Pines

New Paint and Floors! Escape to a fun-filled getaway in this cozy coastal cottage nestled in the Ocean Pines community. Soak in beautiful morning views while inside the screened-in porch. Find top-notch amenities that Ocean Pines is known for: indoor and outdoor pools, golf, fine dining and much more. Minutes to Ocean City beaches, the local casino and only a short drive to the Assateague Island National park. Now under owner management. Contact for previous reviews.

2-Bedroom Oceanfront – Pool, Xbox, Pickleball, Gym, Wi-Fi

Wake up to panoramic ocean views at Blue Wave, a newly renovated 2BR/1.5BA oceanfront condo in the premier Golden Sands Resort! Sleeps 6 with king bed, queen bed, and queen sleeper sofa. Enjoy your private balcony, indoor & outdoor pools, private beach, fitness center, game rooms, tennis, pickleball, and seasonal tiki bar. Relax with a Smart TV + Xbox Series S with Gamepass! Steps to the beach, close to Northside Park, great restaurants, and the Ocean City Boardwalk!

‘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!

21st Floor Carousel - 2 BR Oceanfront & Bay View

NEW!! Welcome to our direct oceanfront 2 bedroom & 2 bath unit at the Carousel! Bringing the comfort of your home to the beach! Bring the whole family for lots of fun memories! We strive to take care of this condo to ensure you have a relaxing, comfortable, and clean stay! Our condo includes 2 DOUBLE SIZED balconies! An oceanfront balcony and a bay view balcony! You can enjoy both the sunrise and sunset!

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.