Holiday rentals with a pool in Ocean Pines

Newly built bright and airy guest suite!!!!

FREE oceanfront parking pass with bookings. 2 PERSON MAX. 2nd floor private suite with parking, patio/firepit, and self check-in private entry. We are located just minutes from the Ocean City beaches, quaint small town of Berlin, Ocean Downs Casino, Assateague, Windmill Creek Winery, restaurants, and outlets. Enjoy neighborhood amenities such as a waterfront Yacht Club with restaurant and live music (seasonal), golf, farm market, playgrounds, 5 pools/fee, (no pool on property) racquet club.

Family · Value · Checkout

Ocean Pines-OCMD Bliss at the Beach- Sat. to Sat.

Welcome to Bliss at the Beach, our charming 3br, 2ba home nestled in the desirable, beloved Ocean Pines community. Loved for its safe, quaint, family friendly neighborhoods. Find yourself less than 15 minutes away from the beautiful beaches and vibrant shopping, dining and boardwalk district of Ocean City. Enjoy the ease of the prepaid parking at the Ocean Pines Beach club on 49th street, just unload the family and walk on the beach!! Summer months Bliss is a 7-night minimum to guests 25+older

Location · Family · Parks

Water view at Ocean Pines Yacht Club Condo

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

Value · Location · Parking

Camelot

HIGHEST RATED HOUSE IN OCEAN PINES! CHECK OUT OUR AMAZING GUEST REVIEWS :) Jumpstart your ultimate beach getaway at this impressive 3-bedroom, 2-bathroom retreat house! Complete with amenity-packed living spaces with vaulted ceilings and a serene location, you’ll never hunger for entertainment at this family friendly home. Grill out on the patio, roast marshmallows by the fire pit, tee off at a nearby golf course, or enjoy some retail therapy at Outlets Ocean City! A short drive to the beach!

Family · Location · Outdoor spaces

Waterfront w/Dock, Rooftop Terrace & 2 Kings

Enjoy stunning views from every room in this bayside beauty located in the peaceful Ocean Pines community just 9 miles from the beach and OC boardwalk. Designer finishes throughout, you'll find everything you need to enjoy a family or small group getaway. *We do not allow smoking or pets. *Saturday check-in with a 7 night minimum stay requirement from July-August. *We are located in a quiet, residential neighborhood. Please consider this when booking. *We do not supply sheets and towels.

Family · Location · Barbecue

Cabin in the Pines I Luxury Touches + EV Charging

Welcome to Cabin in the Pines, a secluded coastal getaway in Ocean Pines! Just minutes from Ocean City beaches, dining, and entertainment. This family-friendly home features 3 bedrooms (1 king, 2 queens + trundle), a dedicated office area, spa-like bathrooms, surround-sound entertainment, and a fully equipped kitchen with all major appliances and cookware. Enjoy EV charging, a fenced yard, towels & linens provided, and our Beach Box with everything needed for a perfect family beach day!

Location · Family · Outdoor spaces

Peace in the Pines- 3BD, 2BA w/ Beach Club Pass

Nestled in the quiet Sherwood Forest neighborhood of Ocean Pines, this 3-bedroom home is central to Ocean City, Berlin, Assateague Island, and local amenities. Each bedroom features a queen bed, and the home is pet-friendly for dogs under 30 lbs. Enjoy a fully stocked kitchen, a relaxing screened-in porch and easy access to nearby walking trails. Conveniently located near great restaurants with a washer and dryer for your convenience. Perfect for a peaceful and comfortable getaway!

Location · Family · Getting around

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.

Location · Value · Nearby

Cozy beach home away from home!

Welcome! Come enjoy a cozy experience at this centrally located home in the desired Ocean Pines Community! This home is near the playground and allows access to the on-site golf course, five pools (including indoor pool!) tennis courts, and marina for a small fee. Fun in the sun awaits 15 minutes away in downtown Ocean City, where you can stroll the boardwalk, lounge on the sand, or hit the amusement park. Plenty of restaurants, grocery stores and shopping within 15 minutes.

Family · Value · View

Peaceful Beach Cottage - Sanitized & WiFi!

Fully renovated clean, sanitized, quaint house in a quiet neighborhood minutes from the beach/ocean! Community offers many amenities such as pools, restaurants, playgrounds, etc. Have peace and quiet while only being minutes from the beach and main OC drag. Very close to the casino! Voted "#1 Safest Neighborhood in Maryland!" *June-August we only accept 7 day rentals with a Saturday check in* *Memorial & Labor Day weekends have 3 night minimum with Fri check in*

Family · Value · Outdoor spaces

Nautical at 82 Newport l private dock & waterfront

Experience this spacious waterfront home featuring 6 bedrooms and 3.5 bathrooms, including 2 master suites. Enjoy a game room, hot tub, and two expansive outdoor areas perfect for sunset views. Recently updated and meticulously maintained, this home offers a clean, inviting atmosphere for your getaway. Ideal for families or groups seeking relaxation and fun by the water! A local manager is here to ensure everything goes smoothly. Driveway parking for 4 vehicles.

Family · Location · Sleep quality

Tortuga Cottage: Your All- Season Getaway

This is an escape to reacquaint with family, nature, and your best self. Come home from the beach just a few miles away to enjoy the gas fire place, outdoor fire pit, and hot tub on chilly nights, fenced in back yard. Take advantage of the parks indoor outdoor pools golf yacht club, just moments from the cottage. Dogs are part of our family, and we are happy to consider canine guests on a case by case basis. Please see policies for breeds.

Value · Location · Beach