Location

Dates

Guests

Vacation rentals in Ocean Pines, Maryland, United States

Offshore Tails

2 bedrooms·2 baths

Ocean Pines • Maryland

4.92(24 reviews)

$1,114.84 USD total for 3 nights

May 12 – 15, 2027

Happy Ours on Sunset Island

Happy Ours on Sunset Island

Happy Ours on Sunset Island

Covered porch off of living room

Covered porch off of living room (bayside)

Happy Ours on Sunset Island

5 bedrooms·4½ baths

Ocean City • Maryland

5(12 reviews)

$4,663.68 USD $4,530.32 USD total for 7 nights

Jun 6 – 13, 2027

Beach Get Away

2 bedrooms·1 bath

Ocean City • Maryland

5(1 review)

$706.00 USD total for 3 nights

Dec 21 – 24, 2026

Master Bedroom with a king bed and private bathroom

Master Bathroom

San Remo 210B

2 bedrooms·2 baths

Ocean City • Maryland

$784.00 USD total for 3 nights

Oct 25 – 28, 2026

Wight Bay Unit 245

Wight Bay Unit 245

Wight Bay Unit 245

Wight Bay Unit 245

Wight Bay Unit 245

Wight Bay Unit 245

2 bedrooms·2 baths

Ocean City • Maryland

4.89(204 reviews)

$350/ night(excl. fees & taxes)

Sunset View

3 bedrooms·2½ baths

Ocean City • Maryland

$1,400.00 USD total for 3 nights

Oct 23 – 26, 2026

Sunset Terrace

3 bedrooms·2 baths

Ocean City • Maryland

4.95(19 reviews)

$1,088.91 USD total for 3 nights

Oct 25 – 28, 2026

Bayfront Sunsets, Renovated Coastal Retreat image 1

Bayfront Sunsets, Renovated Coastal Retreat image 2

Bayfront Sunsets, Renovated Coastal Retreat image 3

Bayfront Sunsets, Renovated Coastal Retreat image 4

Bayfront Sunsets, Renovated Coastal Retreat image 5

Bayfront Sunsets, Renovated Coastal Retreat

2 bedrooms·2 baths

Ocean City • Maryland

5(3 reviews)

$1,625.00 USD total for 3 nights

Oct 23 – 26, 2026

Living Area w/ Cozy Fireplace & Big Screen LCD TV

Living Room w/ Queen Sleeper

Living Area w/ Queen Sleeper Featuring an Air Dream Mattress

Kitchen Area w/ Granite Counter Tops & Stainless Steel Appliances

Makai Unit #411

2 bedrooms·2 baths

Ocean City • Maryland

4.93(137 reviews)

$444.00 USD total for 3 nights

Oct 25 – 28, 2026

Sunset Overlook

Sunset Overlook

Sunset Overlook

Sunset Overlook

Sunset Overlook

Sunset Overlook

3 bedrooms·2 baths

Ocean City • Maryland

$1,126.65 USD total for 3 nights

Oct 23 – 26, 2026

Makai Condominiums

Areal photo of the Makai

Dining Area Table set for Six

Makai Unit #314

2 bedrooms·2 baths

Ocean City • Maryland

4.96(187 reviews)

$444.00 USD total for 3 nights

Nov 1 – 4, 2026

Constellation House North 105

2 bedrooms·2 baths

Ocean City • Maryland

5(2 reviews)

$1,202.40 USD total for 3 nights

Oct 23 – 26, 2026

Worcester House 401 | 1 BR | 1.5BA | 634 Sq Ft | Elevator Access | Open Corner Balcony / Patio | Private Entrance

Living Room | Queen Sleeper Sofa with Upgraded 5" Thick Gel Memory Foam Mattress (No Coils)

Kitchen | Cooking Basics | Keurig Coffee Maker | Drip Coffee Pot | Dishwasher | Glass-Top Stove with Oven | Built-In Microwave | Under-Cabinet Lighting | Granite Countertops | Refrigerator with Top Freezer | Fully Equipped Kitchen

Bedroom | Queen Bed | 12-Inch Medium-Firm Mattress with Eggshell Memory Foam | USB Charging Ports Embedded in Lamps

Full Bath | Bath Towels, Toilet Paper and Hand Soap Provided | Other Personal Toiletries Not Provided

BeachBox III • Unreal Views • Oceanfront Balcony • Couple's Getaway • Worcester House 401

1 bedroom·1½ baths

Ocean City • Maryland

5(78 reviews)

$543.68 USD total for 3 nights

Oct 23 – 26, 2026

Private balcony with sunrise ocean views over the dunes

The Ocean City beach at 51st Street in front of Worcester House

Cozy coastal living room with private balcony and beautiful ocean views

A moonlit night over the Atlantic Ocean

Bright coastal-style bedroom with natural light and calming decor

BeachBox VI • Direct Oceanfront • Walk to Seacrets • Couple's Dream • Worcester House 203

1 bedroom·1½ baths

Ocean City • Maryland

5(6 reviews)

$412.91 USD total for 3 nights

Oct 26 – 29, 2026

Living room complete with queen-sized sleeper sofa, TV, entertainment center, side chair, eating nook with table and chairs for two.

Living room with beachy decor and queen sleeper sofa.

Living room view facing the patio.

Dining area with table for two plus four barstools at kitchen counter.

We provide dish and dishwasher soap and starter paper towels.

33rd St, Near Attractions, Pool, 1st Fl, King Bed

1 bedroom·1 bath

Ocean City • Maryland

$587.32 USD total for 3 nights

Oct 23 – 26, 2026

Sun deck overlooking the bay

Jacuzzi in Master Bath

Seas the Day

3 bedrooms·3 baths

Ocean City • Maryland

5(17 reviews)

$2,292.00 USD $2,244.96 USD total for 7 nights

Oct 23 – 30, 2026

Welcome to Surf's Edge

Path to the beach

Welcome to Surf's Edge

Enjoy the views!

Ocean Front room (Queen)

Surf's Edge - Ocean front with stunning views

2 bedrooms·2 baths

Ocean City • Maryland

5(57 reviews)

$922.14 USD total for 3 nights

Oct 28 – 31, 2026

Stylish retreat steps to beach with all amenities!

Bright and beautiful kitchen!

Dining room table and view of second set of patio doors

Living room with doors to the deck.

Stylish retreat steps to beach with all amenities!

2 bedrooms·2 baths

Ocean City • Maryland

5(3 reviews)

$150 – $450/ night(excl. fees & taxes)

East Winds 202 | 1BR | 1.5BA | 601 Sq Ft | Private Entrance | Stairs Required for Initial Check-In (2nd Floor) | Elevator Available After Check-In

Property Interior | Elevator Access Once Inside | Ocean Views

Kitchen | Cooking Basics

Bedroom | Queen Bed

BeachBox I • Oceanfront Balcony • Sunrise Views • Couple's Retreat • East Winds 202

1 bedroom·1½ baths

Ocean City • Maryland

5(50 reviews)

$482.14 USD total for 3 nights

Oct 23 – 26, 2026

East Winds 502 | 1BR | 1.5BA | 601 Sq Ft | Private Entrance | Stairs Required for Initial Check-In (5th Floor) | Elevator Available After Check-In

Coastal-chic condo with bright open layout, modern kitchen & comfy seating

Fully equipped coastal kitchen with stainless appliances, quartz countertops, and glass-tiled backsplash | Dishwasher | Glass-Top Stove w/ Oven | Built-In Microwave | Refrigerator w/ Top Freezer

Sunny bedroom with 2 full/double beds, Smart TV, A/C, and beachy decor

Full bathroom w/ vessel sink, porthole mirror & butcher block vanity | Bath Towels, Toilet Paper and Hand Soap Provided | Other Personal Toiletries Not Provided

BeachBox V • 5th-Floor Oceanfront • Expansive View • Beachfront Bliss • East Winds 502

1 bedroom·1½ baths

Ocean City • Maryland

5(32 reviews)

$494.96 USD total for 3 nights

Oct 23 – 26, 2026

NEW LISTING SPECIAL 20% OFF Your Ocean City getaway -just steps from the sand.

NEW LISTING SPECIAL 20% OFF Your Ocean City getaway -just steps from the sand.

NEW LISTING SPECIAL 20% OFF Your Ocean City getaway -just steps from the sand.

Step into comfort at OC Oasis — our bright, beach-inspired living room features plush couches, a large smart TV, and plenty of space to unwind after a day exploring Ocean City.

The dining area at OC Oasis blends coastal style with comfort — featuring a bright open layout that flows seamlessly from the kitchen to the living room.

NEW LISTING SPECIAL 20% OFF Your Ocean City getaway -just steps from the sand.

2 bedrooms·2 baths

Ocean City • Maryland

$913.37 USD total for 3 nights

Oct 23 – 26, 2026

Great views. Walk out and your practically stepping in the sand.

Open entertainment area. Complete with two power chaise lounge chairs that recline.

Fantastic Ocean view, newly renovated

Fantastic Ocean view, newly renovated

New sectional. Power reclining chaise lounges. Pull out Full bed

Fantastic Ocean view, newly renovated

1 bedroom·1 bath

Ocean City • Maryland

$386.00 USD total for 3 nights

Oct 23 – 26, 2026

Fantastic Ocean Block Condo with Ro

Fantastic Ocean Block Condo with Ro

Fantastic Ocean Block Condo with Ro

Fantastic Ocean Block Condo with Ro

Fantastic Ocean Block Condo with Ro

Fantastic Ocean Block Condo with Ro

2 bedrooms·1 bath

Ocean City • Maryland

5(16 reviews)

$1,877.01 USD total for 3 nights

May 20 – 23, 2027

Bahia Vista II

3 bedrooms·2 baths

Ocean City • Maryland

4.95(21 reviews)

$1,800.00 USD total for 3 nights

Oct 23 – 26, 2026