Holiday rentals with a pool in Ocean Pines

Gone Coastal *Pool* Bayside with view* Top Floor

Welcome to Gone Coastal! Relax in this beautiful 2BR/2BA getaway featuring: 🛏 1 King (Master) | 1 Twin-over-Full Bunk | 1 Sleeper Sofa 🏊‍♂️ Outdoor Community Pools – Lap & Family Pool (Directly Across!) 🔑 Keyless, Contactless Check-in 🌅 Spacious Deck – Outdoor Dining + Bay & Pool Views 📺 Smart TVs + YouTube TV 🛒 1-Minute to Grocery Store 🍽 Fully Equipped Kitchen 📍 Prime Location – 120th St, Heron Harbor 🚗 Ample Free Onsite Parking A perfect retreat for families & beach lovers! 🌊☀️

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!

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, >3 guests may apply.

Coastal Oasis in Ocean Pines

Coastal sanctuary is a private mother-in-law suite with a private entrance, just 15 minutes from Ocean City MD. 2 bedrooms, spa like bath, family room, w/sleeper sofa, kitchenette overlooking a marsh and bay. You will have the entire floor. 1000 sq feet. Daily visitors include deer, heron, birds and duck. Follow the deer path and use our stand-up paddle boards and/or Kayaks. Assateague wild ponies and Ocean City boardwalk are an close by. Berlin voted the coolest small town in America.

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!

Ocean Pines Fun – Arcade, Pools & Near O.C. Beach

Escape to a serene family retreat in Ocean Pines, MD! Our peaceful home offers the best of both worlds—quiet wooded relaxation with access to seasonal community pools and amenities, plus proximity to Ocean City beaches (less than 10 miles), Golf Club (2 miles), historic Berlin, and Assateague’s wild horses. Perfect for family getaways, with an arcade system, trails, playgrounds, restaurants, and more nearby. Book your stay today and follow us on IG @OceanPinesVacation for more!

Ocean Pines, Waterfront Oasis

"Endless Summer" is on the canal at Moonshell Dr. Located on the St Martins River, North of the Rt 90 bridge in Ocean Pines. Centrally located, close to downtown Ocean City, MD, "the boardwalk", bustling West OC and historic Berlin, MD. Explore Assateauge Island, Del. beaches all minutes' drive in the amenity filled [pools, golf, pickle ball, tennis, trails and parks] OP community. Linens, cleaning team and beach club parking included. Must be 25 or older or military service.

Ocean Pines 3BR 2BA Canal Front Home with Sunroom

Welcome to Qwack House where you can watch the ducks on the canal right out back of the home. Beautiful updated waterfront home in Ocean Pines with 3BR and 2BA. Bring your boat & dock it out back. Huge deck to enjoy the water views. BBQ Grill and fully stocked home makes this a great place to vacation with family & friends. Ocean Pines Community is amenity rich with pools, golf course, play areas and just a short drive to the Ocean City beach - this home has it all! Pet friendly.

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*