Holiday rentals with a pool in Ocean Pines

4.93 out of 5 average rating, 118 reviews

Home in Ocean City

3 BR Waterfront Home, Minutes to the Beach

Recently updated waterfront house located in the family-friendly Montego Bay community. Enjoy beautiful sunsets on the back deck or hop in one of the kayaks for a paddle around the wide-open canal. Try your hand at crabbing or fishing off the dock to catch your dinner. Within easy walking distance of the beach and Northside Park (about 10 minutes walk to both). Beach chairs, toys, boogie boards, and umbrellas are yours to use for fun in the sand and surf. The dock is available for boat tie-ups.

4.91 out of 5 average rating, 325 reviews

Oceanfront Family Oasis: Pool, Beach & Parking!

CONSTRUCTION NOTICE NOV 24 to MAY 25, noise may be heard Wake up to the ocean sunrise in this modern 2 bedroom, completely renovated, condo. Prime location on 29th street, 2 blocks north of the famous OC Boardwalk, 2 blocks east of OC's premier amusement and water park along with two famous crab house and other restaurants within walking distance. One hassle free off street parking spot, free WIFI, full size washer & dryer, and a beautiful outdoor pool steps from the beach. Enjoy the bay sun

4.97 out of 5 average rating, 187 reviews

Condo in Ocean Pines

Ocean Pines Getaway

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

4.96 out of 5 average rating, 105 reviews

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! 🌊☀️

4.98 out of 5 average rating, 132 reviews

Home in Ocean Pines

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!

4.96 out of 5 average rating, 137 reviews

Home in Ocean Pines

Little house in Berlin, Md.

Our home is located in Ocean Pines, Maryland. Spend the day at the beach, golf, come back and relax on our spacious screened porch. The community has 5 pools, walking trails, Parks, and more. The house is a short drive to Ocean City, Md. (8 Miles) via Rt. 90 or Rt. 50. Assateague Island National Seashore is also just a short drive 12 miles. You can see wild horses, beautiful sunsets, ride bikes, or go to the beach. There are many golf courses within 15 miles of the house all very nice.

5 out of 5 average rating, 114 reviews

Home in Berlin

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!

4.8 out of 5 average rating, 210 reviews

Home in Berlin

Bayside community, near OCMD, great rates

Welcome to MERMAID DREAMS where you can have FUN or just RELAX! We are ONLY 5 miles from OC, MD beaches & Assateague National Park/beaches. Our gated, beautiful community, is bayside, has 2 awesome pools, big splash pool, rec center, a fishing/crabbing pier, pond with paddle boats, 2 playgrounds+ more For kiddos of all ages, we are located right next door to Frontier Town, which has awesome water slides , western shows, mini golf, a rope course, ice cream shop.. short term stay

Guest suite in Ocean Pines

4.99 out of 5 average rating, 132 reviews

Newly built bright and airy guest suite!!!!

FREE oceanfront parking pass with bookings. 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.

4.88 out of 5 average rating, 148 reviews

Oceanfront 2BR Condo w/ Balcony & Pool

Enjoy a relaxing beach escape in this 2-bedroom condo at St. Tropez in Ocean City, MD. Perfect for couples or small families, this unit features a full kitchen, two bathrooms, a private balcony with ocean views, and in-unit laundry. Take advantage of beachfront access, a seasonal outdoor pool, and proximity to the boardwalk, shops, and eateries. With comfortable living spaces and convenient amenities, this seaside retreat offers everything needed for a perfect coastal getaway.

4.96 out of 5 average rating, 271 reviews

Caramar Couples Retreat

This cute little first floor efficiency condo is ocean front for a perfect vacation to the beach. It’s an older building but has been partially renovated and updated. You can get to the beach by a very short walk through a private walkway from the condo building. The view from the private balcony is perfect and relaxing. WiFi provided upon check in- xfinity, Netflix, and internet. Indoor and outdoor dining areas and a full kitchen. Closet and dresser for storage use.