Holiday rentals in Ocean Pines

4.88 out of 5 average rating, 90 reviews

Luxurious Oceanfront Retreat with Amazing Views!

This stunning recently renovated direct Oceanfront condo features a designer king-sized bedroom, a chef's kitchen, a sunny living area with a 65" 4K smart tv, and unobstructed beach and ocean views that can't be beaten! Every detail is designed to give guests a stylish and sophisticated place to relax while offering all of the upscale amenities you'd expect in a luxury vacation rental. Located on the Ocean City Beach with unobstructed Beach and Ocean Views! 13 Min Drive to Ocean City Boardwalk

4.91 out of 5 average rating, 46 reviews

OCMD family vacation rental 2BR, 2BA, Pool.

Top floor end unit with large (private) wrap around balcony giving views of the ocean and bay! (54th street Bayside, 1 block from the beach). This 2 bedroom/2 bath is nicely furnished and can accommodate 8 guests. The kitchen is fully equipped with full sized fridge, microwave, dishwasher, washer/dryer, whirlpool tub, central A/C, cable and wifi. Location is perfect for walking to restaurants, miniature golf, shops and nightlife. Rental includes: pool/Hot tub, fitness center,two parking spots.

4.79 out of 5 average rating, 24 reviews

Home in Ocean City

The Oliver House

This property boasts breathtaking views of the Ocean City skyline and is nestled in a quiet neighborhood in West Ocean City. Bring your boat, paddle boards, kayaks and firewood for the most incredible vacation. Crabs and clams are plentiful and the kids can enjoy playing in the small beach area while splashing or swimming in the bay. Although you may never want to leave, it's a short drive to Ocean City's beaches and boardwalk, Assateague Island and the quaint must-see town of Berlin, Maryland.

5 out of 5 average rating, 10 reviews

Home in Millsboro

Bayfront Oasis Vacation Rental

Waterfront panoramic views with a crabbing dock and boat slip. 4 bedrooms (full/twin bunkbeds, 2 twin beds + full bath, queen bed + full bath, king bed + full bath, and sleeper sofa in living room); up to 14 guests. Additional features include ½ bath, sunroom, living room, kitchen, laundry room (washer/dryer), and gaming room. Outdoor space with dining table, outdoor kitchen, firepit, gazebo, cornhole. Resort amenities; swimming pool, bikes, playground, pickleball, dog park, marina, store.

Top guest favourite

Home in Lewes

5 out of 5 average rating, 27 reviews

Cottage by the Bay

Enjoy what lower, slower Delaware has to offer in this cozy cottage near the bay. This gated family-friendly community offers many activities including pool, kayaking, basketball, pickle ball, and crabbing docks, and is close to beaches, shopping, golf, and dining. This will be your home away from home with 3 bedrooms and 3 full baths, a well-equipped kitchen, and laundry room, all season porch, and a relaxing backyard with a fire pit, bar, dining area, and TV!!! 5 minutes from Baywood Greens!

Townhouse in Bethany Beach

4.93 out of 5 average rating, 109 reviews

Lakefront slps 6; beach, pools, tennis, gym, view!

Lake front in Sea Colony Resort! Walk to beach, pools, tennis/pickleball, putting green, bocce, shuffleboard, fishing ponds, fitness center & more! 24/7 security. Completely renovated. Well equipped kitchen opens to bright, charming living/dining rooms with seating for six. AC, charcoal grill, washer/dryer, wifi, 3 flat screen TV's & 3 queen beds. Beach tram & pool across street. Large deck with great view of lake and fireplace in living room! Professionally cleaned between guests.

4.87 out of 5 average rating, 71 reviews

UNIQUE Bay Front Sanctuary Condo

Gorgeous upscale Bay Front Condo - This is your quiet, secure patrolled dream vacation. You will have a spacious one bedroom, one bath open-concept condo that can sleep 4. Watch the magnificent sunsets from your dining room or private balcony on the beautiful Bay. Fish right from your pier, bring your kayak or enjoy the views from the lovely picnic area. Walk across the street to the famous Ocean City Boardwalk and beach. Enjoy parasailing or jetski without even getting into your car!!

Top guest favourite

Home in Selbyville

4.95 out of 5 average rating, 19 reviews

The Villa at Bayside Resort

Introducing a stunning, professionally decorated vacation rental property nestled in the heart of the prestigious Bayside Resort. Property Features: 4 beautifully-appointed bedrooms, 3.5 baths A spacious loft A sun-soaked living area Sun room, An elegant dining room, perfect for memorable family meals A scenic patio off of a wooded lot, offering a serene outdoor retreat. Bayside Amenities: Golf course 4 pools Fitness center Tennis courts Playground Kayaking Trails Concert Venue

4.81 out of 5 average rating, 104 reviews

*Ocfrt Bldg w/ Views, Pool, Elevator and upgrades*

Memorial to Labor Day- Monday or Friday check in and/or out only. Come stay at a 2bed/2bath condo with tons of appeal. Fantastic ocean views from large balcony, LR and master suite. Sleeps 6 in style. 1 private king, 1 regular queen bed, 1 twin bunk bed and one queen pull out couch. All regular beds upgraded mattresses. Unit has 3 tv’s with Blu-ray and streaming capabilities. We have free and upgraded WIFI. All the amenities needed for the perfect beach vacation! Email required

4.83 out of 5 average rating, 6 reviews

Flat in Ocean City

Aventurra 406| Outdoor Pool| Balcony

This is an Ocean City Vacation Homes property Soak up the sun on the beautiful beaches when you stay in this bright and airy 3 bedroom condo for 8. This stylish condo is located on the fourth floor, so you can easily admire the breathtaking ocean sunrise view and the amazing bayside sunset view. Boasting 2 private parking spaces, a kitchen, and a wraparound balcony, a pool, this is the ultimate beach destination. Please not the cleaning fee includes sheets and towels.

4.9 out of 5 average rating, 49 reviews

Home in Ocean City

Beachy Sunset Island Townhouse!

Located in the heart of Sunset Island, this 4 bed/4.5 bath townhouse is steps away from the clubhouse and bay. Beautifully decorated and suitable for families, this home even includes baby gear and a crib so you don't have to bring anything with you. Relax on Sunset Island's private beaches and never leave the community. Everything is available at your fingertips for an unforgettable stay. With 2,400 square feet of living space, there is room for everyone!