Vacation Rentals By Owner In Ocean Pines, MD

Open concept floor plan with lots of light and space for all of your guests in beautiful Ocean Pines. The property features a large open living area, screened in porch and patio with firepit and grill. The living room has a full-size sleep sofa to accommodate extra guests. The oversized master bedroom has an ensuite bathroom with a walk-in shower. The front bedroom has a full size bed while the middle bedroom has a queen bed. The kids room feature two twin beds and all of the bedrooms, along with the living room, are equipped with Smart TV's (note: the house does not have cable and linens are not provided). The property is right down from Bainbridge Park which features a stocked fishing pond, playground, and nature trails. Rental includes beach club parking pass for the Ocean Pines Beach Club on 49th Street. Pool passes can be purchased separately for an additional fee as well as passes for other community amenities such as tennis or golf.

Beautiful Beach Cottage in Ocean Pines

Ocean Pines, Maryland, United States

Bed

Bath

Sleeps

$432.49

There is nothing quite like getting your fill of quality time and sweet relaxation here in Ocean Pines, so make yourself at home and spread out in this stunning home-away-from-home. Sitting mere minutes from the heart of town and the calm waters of Isle of Wight Bay, you will have no trouble filling each day with fun activities and memories in no time. Plus, you can easily take advantage of the on-site tennis courts, pickleball courts, fitness center, indoor pool, beach club, three outdoor pools, marina, fishing and crabbing piers, a skate park, and so much more! brWhen you find yourself having a bit of downtime inside, the bright interior of this home will dazzle even the most design-oriented guests. Modern decor, comfortable furnishings, and an open concept layout are just the beginning of how special this escape is. Hop into the full kitchen and prepare anything from a quick snack to munch on during movie nights in the living room to a gourmet meal enjoyed at the accommodating dining table. And, if you want a bit of alone time at the end of an exciting day, the jetted tub in the primary bedroom will be just the place to soak in bliss!

Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in

Ocean Pines, Maryland, United States

Bed

Bath

8

Sleeps

$248.27

Bring the whole family to this great place with lots of room for fun.brbrWelcome to your cozy getaway with stunning water views from every room! This sweet 3-bed, 2 Bath, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City.

Condo

3-bedroom condo in an Ocean Community on a golf course

Ocean Pines, Maryland, United States

Bed

Bath

7

Sleeps

$366.24

What you have been looking for...brbrComing soon to rent, furnished, July, Aug, Sept, & Oct. A memorable, cozy rancher, 3 bedroom, 2 bathroom home at Ocean Pines Community with indoor/outdoor pool, Boating, & aerobics & much more! This is an all season favorite for your family for years to come! Minutes away from Ocean City Beaches and the Outlets. Please research Winter activities as well as Summer fun. Near us is Snow Hill MD, Salisbury, MD, Ocean City MD, Pocomoke River State Park and Nassawango Creek, fishing, hunting & more.brbr 6-10 minutes away from Ocean City Beaches and outlets. Go to the beach and have fun and return to a nice quiet home. You will love the relaxing feeling you get as soon as you step foot into this family friendly, cozy Ocean Pines get away. Continue your vacation outside on the deck complete with table and chairs for early morning coffee or evening meal. Take advantage of all the community has to offer. Plan a family picnic lunch at the park, let the kids run off their energy at one of the many playgrounds, or schedule a tennis or golf outing (fees apply). Ocean Pines offers indoor and outdoor pools (great for all seasons), a Yacht Club with restaurant, bar, marina (offers boat docking and boat ramps), amazing views, tennis courts, parks, swimming, crabbing piers, and so much more.brbrLocation is : 25 minutes to historic Snow HIll Md, Snow Hill is also located minutes from Historic Sotterley, Susannah's Watch B&B, Seabreeze Restaurant and Crab House, and Sandgates Inn Restaurant and Crab House. The perfect location for a full weekend getaway of fun, 6 minutes to Peninsula Regional Medical Center, 12 minutes to Berlin Hospital, 33 minutes to award winning Salisbury Zoological park, 34 minutes to Salisbury University, 32 minutes to shopping and dining at the Centre of Salisbury, 42 minutes to University of Maryland Eastern Shore and just 15 minutes from the world famous Ocean City boardwalk and beach. Enjoy and relax on your vacation… After all... You Deserve it!brbrEffective March 3rd 2021- Ocean Pines will permit Guests to access pools for a per day fee of: $10 per adult, $8 per child (5-17 years old), children 4 and under do not need a pass. Fees are to be paid at the pool directly. Guests are welcome to purchase the Ocean Pines Beach Club Parking Permit from the Ocean Pines Association office directly for $125 per week. Permits must be ordered 7 days or greater prior to check-in. Parking located on 49th street and there is a pool/restaurant there with volleyball, picnic tables and more right on the beach. Outdoor pools are open seasonally. There is an indoor pool open all year with exercise equipment s and aerobics. Very relaxing.br brThis Cozy house is seasonal relaxation Please research Winter activities and Summer funbrbrWinter Activities in Ocean City: brhttps://deyewa.com/things-to-do-ocean-city-maryland-winter/brwww.oceanpines.orgbrbrWinter Activities in Snow Hill:brhttp://www.snowhillmd.gov/winter-in-snow-hill.htmlbrhttps://www.tripadvisor.com › Attractions-g41381-Acti...brbrPlease call for additional assistance.brbrProperty Amenitiesbr- Screened-In Porchbr- Washer & Dryerbr- Central ACbrbrPlease know this property has a maximum occupancy of 7- 10, which includes children and infants.

Cozy Home Minutes From Downtown Ocean City

Ocean Pines, Maryland, United States

Bed

Bath

Sleeps

$350.84

** This property allows 1 dog at a daily rate of $25.00 per day.brbrEnjoy the cool breezes under the covered porch, grilling on the deck or try your hand at fishing in the back yard. You'll feel like you are on a lakefront property! This home is beautifully decorated and shows pride of ownership. You'll love the open floor plan while still having a second living area and loft to get away. The well-stocked kitchen is ready for your culinary creations and there is wi-fi for those of you who must stay connected. brbrThe community of Ocean Pines is conveniently located to Ocean City, Assateague Island, historic Berlin and Salisbury. It is the perfect location for families with sporting events in Salisbury, looking to enjoy the numerous local golf courses or wanting to be strategically located for all the area has to offer. The community has 5 swimming pools, an 18-hole golf course, several lakes, tennis courts, basketball courts, walking trails, parks with playgrounds, boat launches and plenty of fishing. There are plenty of nearby activities for the family to enjoy, such as fantastic restaurants, miniature golf, go-carts and a water park to name a few. For the adults, there is plenty of outlets for shopping and the Ocean Downs Casino is a short drive away. Don't forget to plan a night watching the harness races! brbrTHINGS TO KNOW:br* Contactless check-in process. No waiting in line for a key.br* Home has a private driveway that will fit 2 vehicles.br* This is a non-smoking/ non-vaping unit.br* Sorry, no pets are allowed.br* Ocean Pines community pools require a daily entry fee which is not included in the rental. br* This unit does not rent to graduating seniors or to parents renting on behalf of graduating seniors. Sorry, no exceptions. All individuals in a non-family group must be a minimum of 25. The minimum age for groups increases to 30 on holiday weekends. br* The pier is not available for docking boats, jet skis, etc.br* One dog allowed at $25/ per daybr* This unit includes bed linens, towel sets, hotel quality bathmats and kitchen hand towels.br* We provide a welcome packet which includes toilet paper and 1 roll of paper towels, dish washing liquid, and dishwasher pods.br* No extra stop at a separate office location required. Guests will receive complete check-in information via email prior to arrival.br* TV's can be a combo of cable and/or streaming. TV viewing options are chosen by the property owner.br* The sleep total of 7 is the maximum occupancy allowed, including children and infants.brbr**To our guests** We do not advertise on Craig's List or other classified ad sites

Enjoy Beautiful Views From This 3 BR 2 BA Home on Quiet Canal in Ocean Pines.

Ocean Pines, Maryland, United States

Bed

Bath

Sleeps

$308.77

Quiet and Private Spacious home, our guest have the privacy of a full kitchen, three large bedrooms, a large living room with a fire place as well as an outdoor patio perfect for Cookouts or Smores.brbrThis secluded home is only 10 minutes away from the Beach and is a perfect Family Get-Away from Home!brbrWe are very accommodating host so if you have any questions about pricing, dates and availabilities or amenities please contact us at any time.brThe spacebrAll space of home is to guest.brGuest accessbrAll space of home are for guest.brOther things to notebrThe house also comes with Snacks for guest, Washer and Dryer as well as full access to Cable and WIFI.

Luxe Homey Get-Away Beach Cove

Ocean Pines, Maryland, United States

Bed

Bath

8

Sleeps

$399.96

5 Bedroom Home in Ocean PinesbrbrBeautifully nestled on a wooded lot, this spacious and fully renovated two-story, five-bedroom, three-full-bath single-family home comfortably sleeps up to eight guests. Thoughtfully updated in 2021, the home features fully renovated bathrooms with all-new plumbing, tubs/showers, and vanities. The modern kitchen is a chef’s dream, while the cozy fireplace in the living area adds warmth and charm. Convenient main-level bedrooms offer easy accessibility. Outdoors, enjoy the beautifully furnished screened-in porch and a patio dining area—ideal for relaxing and taking in the peaceful, wooded surroundings. A range of amenities include free parking, central A/C, and Wi-Fi. Guests also have optional access to four community pools and the Ocean Pines Beach Club located on 49th Street in Ocean City.brbrThings to know: br* Trash Collection days are Monday and Thursday. Trash cans need to be at the end of the driveway Sunday and Wednesday nights. br* This home is No Smoking - in the house or in the screened in porch; No Pets, No Parties. br* Indoor pool is open year 'round. Daily fee for guests is $17 for adults 18 & up and $15 for ages 5-17. Pay at door.br* Ocean Pines Beach Club in Ocean City at 49th Street.

5 Bedroom 3 bath Home in Ocean Pines

Ocean Pines, Maryland, United States

Bed

Bath

Sleeps

$450.81

Escape to our charming three-bedroom, two-bathroom vacation rental in beautiful Ocean Pines, MD. Perfectly situated just minutes from the beach, pools, and a variety of restaurants, this family-friendly retreat is ideal for creating unforgettable memories. Enjoy access to nearby yacht clubs, marinas, and a premier golf course, all within a short drive. This is a brand new listing!brbrbrYour host is always available for questions 8:30 a.m. - 5 pm. After hours please email for non emergencies. There is an after hours emergency contact during your stay. Please make sure this is for emergency purpose. If you are going to be checking in after our office closes, please make sure you have all of your check in information with you in order to access condo & for parking instructions. There is a cancellation fee of 99.00 for all cancellations made after 24 hours from reserving. Our cancellation policy is if cancelled 31 days prior, full refund. Anything from 30 days is 50% refunded. brBike, chair & umbrella rentals are available during your visit—please inquire with the host for details.brbrbrWelcome to the Ocean Pines community, a top destination on the Eastern Shore! Dive into a wealth of amenities, including boat ramps, a yacht club, several pools, playgrounds, and lovely nature trails to explore. br Due to community regulations, we cannot purchase pool passes for you. To obtain them, simply bring a copy of your lease and a state-issued ID. For more information on amenities and policies, please visit the Ocean Pines Community website. brWe can’t wait for you to enjoy everything Ocean Pines has to offer! Plus, we have bikes, beach chairs, and umbrella rentals available. Just inquire with your host!brbrAgent will send details no later than 48 hours prior to arrival (4:30 pm) if all documentation is complete. If you do not see it, please check spam folder. brbrStay in this charming Ocean Pines vacation rental near the Yacht Club and marina, just a short drive to Ocean City, MD beaches. This 3-bedroom, 2-bath home features a large living room, enclosed sunroom, and fully equipped kitchen with ample prep space. Enjoy added features like a kids’ room, loft area, and private deck for outdoor relaxation. Located in the desirable Ocean Pines community with access to golf, pools (with pass), parks, walking trails, and waterfront activities, this home is ideal for families seeking comfort, convenience, and a prime coastal location.brbrFeel free to enjoy a run, walk or bike ride in the community. If going to Ocean City, MD beaches, you are approx. 7-9 miles drive. Ocean Pines also has a ferry that goes back and forth to Ocean City for a nice ride via the Assawoman Bay! We do offer bike rentals in 2025. Inquire with host as they are first come first serve.brbr**Description:** brEscape to our charming three-bedroom, two-bathroom vacation rental in beautiful Ocean Pines, MD. Perfectly situated just minutes from the beach, pools, and a variety of restaurants, this family-friendly retreat is ideal for creating unforgettable memories. Enjoy access to nearby yacht clubs, marinas, and a premier golf course, all within a short drive.brbrbr**Features:** br Three Spacious Bedrooms. Comfortably accommodates families or groups.br Two Full Bathrooms: Conveniently designed for your comfort.br Outdoor Deck: Relax and enjoy your morning coffee or evening sunsets.br Parking: Dedicated parking for your convenience.br**Location Highlights:** br- Just a short drive to the beach.br- Close proximity to community pools.br- Nearby restaurants offering diverse dining options.br- Yacht club and marina facilities within reach.br- Golf course for the avid golfer.br**Book your Ocean Pines getaway today and experience the perfect blend of relaxation and adventure!**

Coastal Charm Oasis!

Ocean Pines, Maryland, United States

Bed

Bath

Sleeps

$346.94

Summary:brbrEscape to this stylish, pet-friendly A-frame cottage in a peaceful wooded setting. Perfect for up to 6 guests, this unique sanctuary features a modern kitchen, private deck, and fire pit. Enjoy access to community pools and the beach, all while being a short drive from local dining and golf. A cozy, contemporary retreat with fantastic amenities awaits you.brbrbrbrThe Space:brbrDiscover your own quiet sanctuary in this stylish, pint-sized A-frame cottage. The unique architecture, with its high, wood-beamed ceilings, creates a cozy yet modern atmosphere perfect for a getaway.brbrbrbrThis home comfortably accommodates up to 6 guests, with a recommendation of no more than 4 adults.brbrbrbrKey Features:brbr Living Area: A comfortable living room and dining table, perfect for relaxing after a day of exploring.brbr Kitchen: A full, contemporary kitchen equipped with stainless steel appliances, a dishwasher, and everything you need to prepare a delicious meal.brbr Outdoor Space: Enjoy your private deck with seating, or gather around the gravel patio's fire pit in the evening. A grill is also provided.brbr Amenities: For your convenience, the cottage includes a washer and dryer, yard games, and pickleball equipment.brbrbrbrGuest Access:brbrGuests will enjoy complete and private access to the entire A-frame cottage. Our seamless self check-in system features a smart lock for your convenience and security.brbrbrbrYour private access includes:brbr The entire home and all its interior amenities.brbr A private deck with outdoor seating.brbr A gravel patio with a fire pit and grill.brbrbrbrAs our guest, you also have full access to the fantastic community amenities, including:brbrMultiple swimming pools - fees to accessbrbrCommunity beach accessbrbrbrbrThe Neighborhood:brbrClose to the Woodlands Restaurant & the Pines Public House. Not far from the Ocean Pines Sports Core Pool and the Ocean Pines Golf Club.brbrbrbrOther Things to Note:brbrPet-Friendly: This is a pet-friendly property. We welcome well-behaved pets with a $50 per pet feebrbrCheck-In: This home is equipped with a smart lock for easy, keyless self check-in. Your unique access code will be provided prior to your arrival.brbrbrbrProvided beach access pass for your stay starting in May, allows parking for one car at the Beach (no access to club).brbrOcean Pines has so many options for you to enjoy your vacation. Yacht Club, 5 community pools, golf course. Please check out the Ocean Pines Community site for details on pool and amenity feesbrbrbrbrInteraction with Guests:brbrWe believe in giving our guests space and privacy to enjoy their vacation. While we will not be present at the property during your stay, we are always available and happy to assist with any questions or needs you may have. Please feel free to reach out to us via the app or by phone at any time.

Ocean Pines 2BR 1BA Cottage with Fire Pit

Ocean Pines, Maryland, United States

Bed

1

Bath

6

Sleeps

$466.67

Great for 2 couples (friends/in-laws) and kids. The property is in the Ocean Pines HOA, a 15-minute drive from Ocean City and a bit over 20 minutes from scenic Assateague Island. Hosted directly by owners.brbrCheck ABnB profile for reviews: airbnb.com/h/oceanpines9brbrMust be 25+ years old to rent. No pets policy (due to health/allergies). No smoking.brbrSleeping. The house has two master bedrooms, one on each floor, with king beds and en-suite bathrooms. An additional kids' bedroom with a queen bed and a twin-size bunk bed can comfortably sleep 3 preteens. There is a pack-and-play and an air mattress if needed. Linens and towels are provided.brbrOffice. A separate office and additional dedicated work space makes this ideal for folks who need to work remotely. High speed internet.brbrKitchen. The kitchen is fully stocked, with an expandable dining table that seats up to 8 adults. The screened patio is great for drinks, an alfresco dinner or morning coffee. brbrFamily Fun. Stacks of toys, games and puzzles for the kids. Board games in the office. A pool table (converts into a ping pong table), a retro game console (old Sega, Atari and Nintendo games). brbrBackyard. Firepit, kids swing, hammock.brbrBeach Stuff. Chairs, umbrella, beach cart and tent, kids toys. brbrA parking permit for the Ocean Pines Beach Club on 50th street and Coastal Highway in OC is included.brbrTV: HBO, Netflix, Amazon Prime, Disney+, Hulu (or some combination of).

Down Bimini Lane: Family Retreat (7+) w HomeOffice

Ocean Pines, Maryland, United States

4

Bed

Bath

10

Sleeps

$404.75

Welcome to your relaxing Ocean Pines golf course retreat, a 3-bedroom, 2-bath coastal home ideally located near the Ocean Pines Yacht Club, marina, and community pools (passes required). Set along the fairways, this property offers peaceful views and a quiet, family-friendly atmosphere just a short drive to Ocean City, Maryland. Inside, enjoy an open living space, full kitchen, and comfortable accommodations for families or groups. This is a new listing! Book direct and save. brbrAt Karson’s Keys, your experience matters. Our team provides 24/7 guest support to help with anything during your stay—from property assistance to local recommendations—so you can focus on enjoying your Ocean City getaway. Your host is always available for questions 8:30 a.m. - 5 pm. After hours please email for non emergencies. There is an after hours emergency contact during your stay. Please make sure this is for emergency purpose. If you are going to be checking in after our office closes, please make sure you have all of your check in information with you in order to access condo & for parking instructions. There is a cancellation fee of 99.00 for all cancellations made after 24 hours from reserving. Our cancellation policy is if cancelled 31 days prior, full refund. Anything from 30 days is 50% refunded. brbrBike, chair & umbrella rentals are available during your visit—please inquire with the host for details.brbrbrWelcome to the Ocean Pines community, a top destination on the Eastern Shore! Dive into a wealth of amenities, including boat ramps, a yacht club, several pools, playgrounds, and lovely nature trails to explore. br**Important Note:** brDue to community regulations, we cannot purchase pool passes for you. To obtain them, simply bring a copy of your lease and a state-issued ID. For more information on amenities and policies, please visit the Ocean Pines Community website. brWe can’t wait for you to enjoy everything Ocean Pines has to offer! Plus, we have bikes, beach chairs, and umbrella rentals available. Just inquire with your host!brbrAgent will send details no later than 48 hours prior to arrival (4:30 pm) if all documentation is complete. If you do not see it, please check spam folder. brbrEnjoy easy access to the Ocean Pines Yacht Club and marina, where you can dine waterfront, watch stunning sunsets over the bay, or hop on the seasonal water taxi for a scenic ride toward Ocean City. Multiple Ocean Pines community pools (passes required) provide the perfect way to cool off after a day in the sun, while nearby walking and biking trails make it easy to explore the neighborhood.brbrLocated just minutes from the beaches of Ocean City, the famous Boardwalk, restaurants, mini golf, and family attractions, this home offers the perfect balance of quiet coastal living and easy access to everything OCMD has to offer. Whether you're planning a golf getaway, boating trip, or beach vacation, Ocean Pines delivers a true coastal lifestyle experience.brbrInside the home, enjoy an open-concept living space, fully equipped kitchen, and comfortable accommodations for your group. Relax with peaceful golf course views and unwind in a quiet, family-friendly setting.brbrGuest Notes: 1 designated parking spot. No smoking inside or on property—permitted only at the street. Please dispose of trash in the street dumpster.brbrFeel free to enjoy a run, walk or bike ride in the community. If going to Ocean City, MD beaches, you are approx. 7-9 miles drive. Ocean Pines also has a ferry that goes back and forth to Ocean City for a nice ride via the Assawoman Bay! Bike, beach chairs & umbrella rentals available. Inquire with host.brbrHouse & Condo Rulesbrbrbr1. No Smoking: Smoking of any kind—including cigarettes, cigars, pipes, vapes, and medical marijuana—is strictly prohibited inside the unit.br2. Pet Policy: We maintain a strict no-pet policy. br3. Registered Guests Only: For safety and compliance with State of Maryland regulations, only guests listed on the reservation are permitted overnight. Please disclose the names and ages of all guests. Unapproved extra guests are grounds for immediate eviction without a refund.br4. Liability Waiver: All units are privately owned. The homeowners and management company are not responsible for any accidents, injuries, illnesses, or loss of personal belongings/valuables while on the premises. By accepting this reservation, guests expressly assume the risk of any harm arising from their use of the property.br5. Furniture Care: Please keep the property and furnishings in good order. Do not move furniture for any reason, as it can easily scratch or tear the flooring.br6. Fireplaces: Gas and natural wood-burning fireplaces are strictly off-limits at all times. Only electric fireplaces may be used, and only during the off-season.br7. Appliance Use: Please use all appliances only for their intended purposes. Damage or destruction of appliances is considered a civil issue, and the owner will seek to recover repair or replacement costs.br8. Parking Rules & Fees: There is a $60 parking fee for your first car. A second car is $25 per day or $65 per week. Each unit has specific parking instructions (please see the agent for details). Trailers are not permitted on Ocean City streets without a proper permit.br9. Pool & Parking Passes: Loss or damage of required passes is the sole responsibility of the renter. Please check the property’s “house book” within 4 hours of check-in to ensure all passes are accounted for. If anything is missing, email Kim immediately so you are not charged upon checkout. Unreturned pool passes incur a $30 fee per pass (prices subject to change).br10. Washer & Dryer / Sand Warning: You are welcome to use the washer and dryer; however, you must thoroughly shake out all sand from clothes and towels before washing. Sand causes severe plumbing clogs. If a plumber is required due to sand blockages, a service fee of $95–$300 will be passed on to the guest (depending on the time of call/holidays).br11. Balcony & Walkway Etiquette: The condo association strictly prohibits hanging towels or clothing over railings, as well as grilling of any kind on decks or walkways, unless specifically instructed otherwise.br12. Noise & Parties: We ask that you respect our neighbors. No loud parties, excessive noise, or unregistered overnight guests. If the police or property management are called for a valid noise complaint, guests will be removed from the property with no refund.br13. ID Requirement: All guests must upload a valid Government ID in order to reserve the property and receive access instructions, or present it when checking in at our office.brbrbrbrGuest Notes: 1 designated parking spot. No smoking inside or on property—permitted only at the street. Please dispose of trash in the street dumpster.

3BR/2BA Ocean Pines golf course home near Yacht Club, marina & pools—minutes to Ocean City beaches!

Ocean Pines, Maryland, United States

Bed

Bath

Sleeps

$369.98

- Great Outdoor Spacebr- Off-Street ParkingbrbrWith a hot tub, large deck, and prime location, this 3-bed, 2-bath vacation rental house in Ocean Pines offers a carefree getaway! When you're not visiting nearby attractions, lounge by the fireplace or prepare snacks in the full kitchen. For an additional fee, enjoy access to the Ocean Pines Beach Club amenities like a pool and tennis courts!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTS:br- Bedroom 1: King Bedbr- Bedroom 2: King Bedbr- Bedroom 3: Queen BedbrbrINDOOR LIVING: br- Air conditioning, central heating, ceiling fansbr- 4 Smart TVs (each bedroom & Grand Room)br- Gas fireplacebr- Desk spacebr- Picture windowsbrbrOUTDOOR LIVING: br- Spacious deckbr- Charcoal grill (charcoal not provided)br- Hot tubbr- Private yard, patio furniturebrbrKITCHEN: br- Refrigerator, stove/oven, dishwasherbr- Cooking basicsbr- Coffee maker w/ starter pack of Keurig coffee, pods & creamersbrbrGENERAL: br- Free WiFibr- Washer & dryerbr- Linens & towelsbr- CD playerbr- Hair dryerbrbrOCEAN PINES AMENITIES (w/ additional fees): br- Outdoor pool, clubhouse, playground, tennis courtbrbrACCESSIBILITY:br- Grab rails in the bathroombrbrPARKING: br- Driveway (4 vehicles)br- Street parkingbr- No garage accessbrbr-- THE LOCATION --brbr- 4 miles to Casino at Ocean Downs and Race Trackbr- 7 miles to Baja Amusementsbr- 9 miles to Ocean City Boardwalk & Beachbr- 23 miles to Salisbury Regional Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties or large gatheringsbr- Additional fees and taxes may occurbr- A photo ID will be required before check-in. Guests must email the homeowner a copy of their driver's license before arrivalbr- NOTE: Guests are advised to bring their own beach supplies (chairs, towels, cooler, etc)br- NOTE: Additional fees apply to use the community amenities. Reach out to the homeowner after booking for more informationbr- NOTE: The garage is not available for guests to usebr- NOTE: The property comes with a starter kit of one paper towel roll and a roll of toilet paper per restroom

2 Mi to Golf: Hot Tub Hideaway in Ocean Pines

Ocean Pines, Maryland, United States

Bed

Bath

6

Sleeps

$559.1

Summary:brbr14 Goldeneye CourtbrbrbrbrThe Space:brbrWelcome to your perfect family getaway in Ocean Pines, MD! This charming house offers a delightful blend of comfort and convenience, making it an ideal retreat for families and friends alike. With a spacious layout featuring multiple levels, you'll find plenty of room to relax and unwind. Enjoy the stunning water views from the deck or balcony, where you can sip your morning coffee or host a barbecue on the gas grill. The home is equipped with a variety of amenities to ensure a stress-free stay. Prepare delicious meals in the fully stocked kitchen, complete with a fridge, stove, oven, and dishwasher. After a day of exploring the nearby beaches or theme parks, gather around the dining area or cozy up in the living room with cable TV and board games for family fun. For those who love the outdoors, take advantage of the tennis court, kayaks, and adult bikes available for your use. With comfortable sleeping arrangements, including a king bed, queen bed, double bed, and twin bed, everyone will have a restful night's sleep. Additional conveniences such as a washer/dryer, central AC, and high-speed internet make this home a true haven. Located just steps from the ocean, this family-friendly property is perfect for creating lasting memories. Book your stay today and experience the best of Ocean Pines!

Luxury waterfront retreat w/sunroom, patio, kayaking, grill, and bay views

Ocean Pines, Maryland, United States

Bed

Bath

Sleeps

$416.33

Dog-Friendly Coastal Getaway Near Ocean City, MDbrbrBring your pups! This dog-friendly home welcomes up to 2 dogs with no additional fees and features a relaxing setting just 5 miles from Ocean City, MD off Rt. 90 in the quiet Ocean Pines community. Enjoy ample parking for your boat or jet ski, with a nearby boat ramp for easy water access. Guests also receive an Ocean Pines beach pass and access to community amenities including pools, golf, tennis, parks, and more.brbrbrAt Karson's Keys, we prioritize your comfort and satisfaction during your stay! Our dedicated team is available 24/7 to assist with any guest issues or concerns that may arise. Whether you need assistance with the property, have questions about local attractions, or require maintenance support, just reach out! We’re just a message or call away, ensuring that your vacation is smooth and enjoyable. Your peace of mind is our top priority! There is a cancellation fee of 99.00 for all cancellations made after 24 hours from reserving. Our cancellation policy is if cancelled 31 days prior, full refund. Anything from 30 days is 50% refunded. brbrBike, chair & umbrella rentals are available during your visit—please inquire with the host for details.brbrbrWelcome to the beautiful Ocean Pines community, one of the most sought-after destinations on Maryland’s Eastern Shore and just minutes from Ocean City, MD beaches and the famous boardwalk. Ocean Pines offers a wide variety of amenities designed for families, couples, and vacationers looking for both relaxation and outdoor adventure.brbrGuests can enjoy access to multiple community pools, scenic nature trails, playgrounds, parks, and waterfront areas, perfect for walking, biking, and exploring the natural beauty of the area. Boating enthusiasts will love the convenient boat ramps, marinas, and the Ocean Pines Yacht Club, where you can enjoy waterfront dining, live entertainment, and stunning sunset views over the bay.brbrImportant Community Note:brDue to Ocean Pines community regulations, hosts are not permitted to purchase pool passes in advance. To obtain pool access, guests must visit the Ocean Pines Beach Club or Aquatics office and present a copy of your rental agreement along with a valid state-issued ID. Pool passes can then be purchased directly through the community. For the most up-to-date information on Ocean Pines amenities, pool schedules, and community policies, please visit the official Ocean Pines Community website.brbrDuring your stay, you’ll also be just a short drive from Ocean City’s beautiful sandy beaches, championship golf courses, local restaurants, marinas, wineries, breweries, and family-friendly attractions throughout the Eastern Shore.brbrTo make your beach vacation even easier, we also offer bike, beach chair, and umbrella rentals for your convenience. Simply inquire with your host before or during your stay, and we’ll be happy to help you get everything you need for the perfect coastal getaway.brbrWe look forward to welcoming you and helping you experience everything that Ocean Pines and Ocean City have to offer!brbrThe agent will send all details no later than 48 hours before your arrival. Please note that details will only be sent if your check-in form and rental agreement are fully signed and completed. If these are not submitted, you may not automatically receive your information, which could affect your check-in time. brTo access the pools, please print a copy of your rental agreement. If you have any trouble printing it, just let us know in advance, and we’ll be happy to assist you!brbrWelcome to your home away from home! This charming and spacious 3-bedroom, 2-bath rancher is the perfect getaway for families, groups, and dog lovers looking for a relaxing stay near Ocean City, Maryland.brbrLocated in the peaceful Ocean Pines community just 5 miles from Ocean City off Route 90, this cozy coastal retreat offers comfort, convenience, and access to amazing local amenities.brbrRelax in the bright open-concept living and dining area, featuring comfortable seating and warm décor that invites you to unwind after a day at the beach. Stream your favorite shows on the Smart TV or enjoy quality time with family and friends.brbrPrepare meals with ease in the fully stocked kitchen, complete with appliances, cookware, and essential utensils. The dining table provides plenty of space for everyone to gather and enjoy meals together.brbrEach of the three bedrooms is designed with your comfort in mind, offering plush bedding and ample storage for a peaceful night's sleep after a day exploring Ocean City.brbrTwo full bathrooms help make mornings easy for groups and families. They are stocked with towels and basic toiletries for your convenience.brbrPet-Friendly StaybrbrWe proudly welcome up to 2 dogs with no additional pet fees. The spacious backyard provides room for your pups to stretch their legs, and nearby parks are perfect for walks and exploring.brPlease remember to pick up after your pets.brbrSpend your evenings relaxing on the patio with seating and a grill, perfect for summer barbecues and family gatherings. The yard is a great space for games, relaxing, or enjoying the coastal breeze.brbrOcean Pines AmenitiesbrbrYour stay includes an Ocean Pines Beach Pass and access to the community’s fantastic amenities, including:brbrMultiple community poolsbrbrGolf coursebrbrTennis courtsbrbrParks and playgroundsbrbrScenic walking and biking pathsbrbrBoat ramps nearbybrbrAdditional AmenitiesbrbrHigh-speed Wi-FibrbrSmart TVbrbrAir conditioning & heatingbrbrFree on-site parkingbrbrLINENS INCLUDEDbrbrOptional RentalsbrbrBike, beach chair & umbrella rentals are available during your stay. Please inquire with the host for availability.brbrImportant InformationbrbrFor safety and property protection, non-audio security cameras are located at the front door and backyard. These are only used in case of emergencies and are not actively monitored.brbrbrbrFeel free to enjoy a run, walk or bike ride in the community. If going to Ocean City, MD beaches, you are approx. 7-9 miles drive. Ocean Pines also has a ferry that goes back and forth to Ocean City for a nice ride via the Assawoman Bay! Bike's, beach chairs and umbrella rentals available. Inquire with host.brbrAt Karsons Keys Vacation Rentals, our team is here to support you throughout your entire stay. We provide a smooth and convenient check-in process along with 24-hour emergency contact numbers to ensure assistance is always available if needed. Our goal is to make your Ocean City and Ocean Pines vacation as relaxing and stress-free as possible.brbrIf you plan to arrive after office hours, please make sure you have received and reviewed all of your property details, check-in instructions, and access information before arrival. Having this information readily available will help ensure a seamless check-in experience.brbrWhile our team is always available to help in case of emergencies, guests are responsible for keeping their property address, access codes, and reservation details accessible during their stay. Emergency responders may not have immediate access to these details, so being prepared helps avoid unnecessary delays.brbrAt Karsons Keys, we are committed to providing reliable service, clear communication, and a worry-free vacation experience from check-in to check-out.

Pet-friendly home featuring a private fenced backyard for safe outdoor fun

Ocean Pines, Maryland, United States

Bed

Bath

Sleeps

$301.93

Escape the busy and hurried life in our Ocean Pines home. Nestled among the trees, enjoy your coffee peacefully, sitting on the wrap-around deck. Unwind in our open and bright family room with lots of natural light and huge windows. Equipped with fast WI-FI and lots of other essentials, we know your stay will be easy and relaxing.brbrIt's stocked with everything you need for a family vacation-games, puzzles, books, grilling supplies, kids supplies (pack-n-play, bibs, booster chair), and more!brThe spacebrOur house has three bedrooms. A first-floor and upper-floor bedroom each with a queen bed and an upper-floor bedroom a set of triple bunk beds, and a fourth twin bed. Please note: No adults are allowed in the middle or upper bunks! It's a perfect setup for two families of four to stay.brbrThere is also a desk and computer monitor available for those times that you need to check your email or log into a video meeting.brbrOther things to notebrIt's just a short 10-minute drive to Ocean City and Fenwick Island and 20 minutes to Assateague Island and National Seashore beaches too!brbrThe kitchen includes much more than you’ll need to cook while relaxing during your vacation. We have a toaster, crockpot, small fryer, microwave, and much more.brbrA swingset in the backyard, a basketball hoop in the driveway, kayaks and standup paddle boards are available for use, and so much more!brbrWe’ve also got almost everything you could need for your beach trip: chairs, towels, umbrellas, and beach toys.brbrWithin the community, you can use any of the five pools, tennis courts, yacht club, and golf course for a fee. PLEASE visit oceanpines dot org (www.oceanpines.org) for details about amenities and schedules of activities.brbrUp to 2 dogs weighing 50lbs or less are welcome in our home. No other animals are allowed without pre-approval by owners.

Peaceful, pet and family-friendly beach retreat

Ocean Pines, Maryland, United States

Bed

Bath

Sleeps

$445.89

Summary:brbr14 Clipper on the BaybrbrbrbrThe Space:brbrGet a taste of the waterfront lifestyle here in Ocean Pines and make the best memories here at 14 Clipper on the Bay. This getaway sits in a perfect location to check out the city and beaches while still having a feeling of quiet seclusion on the water. Getting out in the bay will be a breeze with the private dock available for your use, yet you can also stay right at home base and enjoy the fresh air on one of the four decks. Plus, this community boasts a shared pool, skatepark, sports courts, and a playground when you want to have a bit of fun closer to home base. The interior of this gem will welcome each visitor with open arms after full days of excitement. The lower level will be ideal for entertaining and mingling from room to room with the open layout, high-end furnishings, and modern updates throughout. The full kitchen will be a cook's dream, as any recipe will be a breeze with the stainless steel appliances, oversized island, modern cookware, and bar seating. And, the adjacent living area features a TV with streaming capabilities and access to one of the decks with a gas grill. Indulge in that long-awaited getaway and let your worries slip away as you look out to calm waters here in Ocean Pines! bTHINGS TO KNOW/b Streaming is available with guests' own accounts. There are stairs leading to the front door of the home. *Ocean Pines properties offer options to purchase a parking permit for the Ocean Pines Beach Club (located on 49th Street and Coastal Highway in Ocean City) and pool passes to the four Ocean Pines community pools and the Ocean Pines Beach Club pool. Pool passes and parking permits are available for purchase through the Ocean Pines Association. For more information on available package options, pricing, and pool hours, contact the Ocean Pines Association directly.

Waterfront oasis with 4 decks, grill, free WiFi, pool access, dock & central AC

Ocean Pines, Maryland, United States

Bed

Bath

Sleeps

$391.98

Summary:brbrTrinity Place TreasurebrbrbrbrThe Space:brbrTake a break from it all and make your way to the endless excitement of Ocean Pines. Sitting mere minutes from amusement parks, pristine beaches, shopping, and dining, there will be no delay in making the best memories each day. And, when you don't feel like venturing out, the shared pool, tennis courts, and basketball courts will provide plenty of fun close to home. Inside, everyone will love spending downtime reminiscing about the day's fun in the living area boasting soaring ceilings, plush furnishings, and a TV with streaming capabilities to keep up with your favorite shows. When everyone works up an appetite, the adjacent full kitchen is outfitted with all of the major appliances, cookware, and prep space needed to whip up family-favorite recipes in no time. Need to get a bit of remote work done while away The high-speed WiFi has you covered for attending Zoom calls or checking emails if need be. Extra perks include a private washer and dryer, gas grill, and central AC! With all of the comforts of home in a perfect location, this gem is more than ready to welcome you to the Ocean Pines lifestyle! bTHINGS TO KNOW/b Streaming is available with guests' accounts.

Fantastic gem near the beach with fast WiFi, shared pool, grill, central AC & WD

Ocean Pines, Maryland, United States

Bed

Bath

Sleeps

$410.55

Summary:brbrTurtle Shores-22 BostonbrbrbrbrThe Space:brbrMake yourself at home at this fantastic Ocean Pines ranch-style home and get ready to create everlasting memories with your loved ones! This dog and family-friendly home is conveniently located on a beautifully landscaped lot with a dock on the Manklin Creek stream/waterway, which leads to the Bay. This beautiful abode grants you access to endless incredible amenities, which include five swimming pools (indoors and outdoors), parks, a beach club with beachfront parking, a marina, a yacht club, the Ocean Pines Golf Course, sports courts (basketball, volleyball, and tennis), and more. Upon entering, you will find an outstanding and spacious open floor plan with vaulted ceilings and bamboo hardwood floors. The kitchen has been updated with slate gray appliances, custom cabinets, and granite counters. You can easily let your creativity flow and surprise your friends with delicious homemade meals and snacks. Coffee enthusiasts will love the coffee bar section with a Keurig coffee maker and several cups. The living room boasts a two-sided gas fireplace with stone walls on each side, an inviting sofa, and a smart TV. The primary suite is the one that enjoys the other side of the gas fireplace and also features tray ceilings, two closets, an attached workspace with a desk, and an en suite bathroom. The beautiful sunroom offers a wonderful spot to unwind with your loved ones - play board games, enjoy a refreshing beverage, or admire wonderful views using the telescope provided. The custom deck has retractable awnings and overlooks the creek/waterway, which is a nature lovers' paradise. This retreat also is equipped with a former garage turned into a rec room with a Ping-Pong table, electric fireplace, smart TV, and full fridge. bOCEAN PINES AMENITIES/b -Five pools (indoor and outdoor) -Parks -Beach club with beachfront parking -Marina and yacht club -Golf course on-site -Volleyball court -Tennis court -Basketball court bTHINGS TO KNOW/b Streaming is available using your own accounts. Note: Dock is for kayak/paddle board use only. Water is very shallow. *Ocean Pines properties offer options to purchase a parking permit for the Ocean Pines Beach Club (located on 49th Street and Coastal Highway in Ocean City) and pool passes to the four Ocean Pines community pools and the Ocean Pines Beach Club pool. Pool passes and parking permits are available for purchase through the Ocean Pines Association. For more information on available package options, pricing, and pool hours, contact the Ocean Pines Association directly.

Canal-front dog-friendly home, shared pools, sports courts, views

Ocean Pines, Maryland, United States

Bed

Bath

11

Sleeps

$553.46

Summary:brbrThe Point 1437brbrbrbrThe Space:brbrWelcome to your luxurious getaway in Ocean Pines, MD! This stunning 5-bedroom single home is perfectly situated at the point of Ocean Pines, offering a serene retreat just a short drive from local amenities, shopping, and dining. With a spacious deck and an all-season room, you can enjoy the beautiful surroundings year-round, whether you're grilling on the gas grill or relaxing with family and friends. Inside, the home is designed for comfort and convenience. The fully stocked kitchen features modern appliances, including a fridge, stove, oven, and dishwasher, making meal preparation a breeze. After a day of exploring, unwind in the cozy living room by the gas fireplace or indulge in a soothing soak in the jetted tub. With central AC and WiFi, you'll have all the comforts of home at your fingertips. This family-friendly property is equipped with everything you need for a memorable stay, including a washer/dryer, cable TV, and Netflix streaming. The spacious bedrooms, featuring a mix of king, queen, and double beds, ensure everyone has a comfortable place to rest. Enjoy outdoor dining on the patio or take a short drive to the nearby ocean for a day of fun in the sun. Whether you're looking for adventure or relaxation, this Ocean Pines home is the perfect base for your vacation. Book your stay today and experience the best of coastal living! bThings to Know/b Check-in time: 4:00 PM. Check-out time: 10:00 AM. Guests will need to use their own accounts for streaming on the smart TVs. All guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM. No smoking is permitted anywhere on the premises. Ocean City has adopted a noise control ordinance that makes it unlawful to cause or permit noise levels which exceed those established by the Department of the Environment of the State of Maryland (COMAR 26.02.03.02) or are in violation of Chapter 30, Article V of the Town Code. It shall be a violation of this agreement and grounds for eviction under Maryland law if these noise levels are exceeded as a result of activity on this property. Ocean City has other noise ordinances, which are criminal offenses if violated. Learn more about the Ocean Pines area by visiting their web page. Ocean Pines properties offer options to purchase a parking permit for the Ocean Pines Beach Club (located on 49th Street and Coastal Highway in Ocean City) and pool passes to the four Ocean Pines community pools and the Ocean Pines Beach Club pool. Pool passes and parking permits are available for purchase through the Ocean Pines Association. For more information on available package options, pricing, and pool hours, please visit the Ocean Pines website or contact the Ocean Pines Association directly or visit their webpage

Luxury Ocean Pines home w/all season room, private deck, grill & full kitchen

Ocean Pines, Maryland, United States

5

Bed