House vacation rentals in Ocean Pines

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Top-rated house rentals in Ocean Pines

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Guest favourite

Home in Ocean City

4.94 out of 5 average rating, 219 reviews

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

Jan. 15 – 22

$197 CAD per night

Guest favourite

Home in Ocean Pines

4.89 out of 5 average rating, 141 reviews

Relaxing Home Near the Beach in Ocean Pines, MD

This is a 3 bedroom/2 full bathroom, single-story, home that is ready for you and your dogs if you have them. Guests have use of the entire house, including an outdoor grill. There is a dog door that leads to a fenced backyard. Guests have access to our beach accessories and a free beach parking pass. The house can accommodate 6 people comfortably, and up to 8 with the use of a futon. The house has a stocked kitchen. The community has many amenities that are described in the house manual.

May 14 – 21

$422 CAD per night

Superhost

Home in Rehoboth Beach

4.79 out of 5 average rating, 621 reviews

Contemporary 1 Bedroom 2 level home

The unit has keyless entry system, A/C, brand new full size W/D, large patio w/grill, remote controlled open&close sky lights w/built in shades, new carpet, YoutubeTV/Netflix/Hulu/Amazon Prime Video & walk to the beach and attractions w/out crossing **pet friendly** **LOCATION** Intersection of Washington st & Jefferson St. supplied for guest: sheets blankets bath towels Shampoo/conditioner soap toilet paper paper towels trash bags Back pack type beach chairs (3) Beach umbrella Bikes (2)

Feb. 24 – Mar. 3

$180 CAD per night

Guest favourite

Home in Ocean Pines

4.96 out of 5 average rating, 112 reviews

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.

Dec. 8 – 15

$252 CAD per night

Guest favourite

Home in Berlin

4.78 out of 5 average rating, 174 reviews

OC, Md great amenities in community, near beaches

MERMAID DREAMS where you can just have FUN or just RELAX. We are 5 miles out from OC and Assateague beaches. Our community, Assateague Pointe, is a beautiful gated community, with 2 great pools, baby pool, big splash pool, a 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 stays ONLY

Aug. 14 – 21

$324 CAD per night

Guest favourite

Home in Ocean Pines

4.88 out of 5 average rating, 101 reviews

Cozy home minutes from beach, outlets & casino

Sleeps 8 (1 queen, 1 full, 2 twin, and sleeper sofa) Dogs ok Open living space & deck Fully equipped kitchen Spacious driveway, parking for 6 Minutes away from casino, beach & outlets Ocean Pines community w/ countless amenities (fees may apply) Yacht Club. Live music, tiki bar & restaurant Golf, 5 pools, racquet sports, parks, boat launch & rentals, farmer's market, dog park, fishing & walk/bike trails Beach Club 49th St, Ocean City w/ private parking, showers, game room, bar & cafe

Feb. 10 – 17

$610 CAD per night

Guest favourite

Home in Ocean View

4.92 out of 5 average rating, 530 reviews

Tiny House at Good Earth, near Bethany Beach

A custom-built "Tiny House" located right between our new dinner theater and our garden dining area. True to the show "Tiny House Nation"; cool interior with custom woodwork, stairs to a lofted bed. Fully functioning kitchen. Spacious bathroom & shower. We provide TVs and internet in the units but the quality of service is not guaranteed. We are in a rural area and sometimes it's slow or not working at all. If TV and internet are super important for your stay we may not be the right fit.

Dec. 21 – 28

$190 CAD per night

Guest favourite

Home in Ocean Pines

4.9 out of 5 average rating, 134 reviews

Waterfront Beach Home in the Ocean City, MD Area

There is room for 8 adults (plus 2 kids). Located in the premiere seaside community in the Ocean City area, Ocean Pines, this wonderful waterfront home provides amazing views both day and night. The open floor plan provides guests with lots of room to socialize and bond, but also has secluded bedrooms that provides needed privacy. The outdoor living area is to die for. Sit back and watch the sun set over the canal while you catch up with friends or loved one. Use our bikes!

Dec. 14 – 21

$632 CAD per night

Guest favourite

Home in Rehoboth Beach

4.97 out of 5 average rating, 115 reviews

Charming 1.7 mi to beach,bdwk, restaurants! Quiet

No shared spaces in this Charming 4 room suite in single family home in nice neighborhood, close to Rehoboth Beach, bike/run/walk path to Lewes (4 mi). or Rehoboth, less than 2 miles. Great shopping, in town and TAX FREE! outlets 1/8th mi. large loft, King bedroom after climbing a SPIRAL STAIRCASE with large screen TV's upstairs and down. Bathroom downstairs. Living room with TV and couch and full kitchen. Parking in front. ** Host has her own private suite and entrance.

Oct. 23 – 30

$205 CAD per night

Guest favourite

Home in Ocean City

4.97 out of 5 average rating, 119 reviews

Pet Friendly SFH w/ fenced yard, 2blocks to BEACH!

PET FRIENDLY with fenced in yard, 2 blocks to the beach! 2024 Summer rentals avail. Sunday - Sunday. An 8min walk to the beaches of N. Ocean City! Our home is located in a quiet neighborhood, between the beach & bay! You'll have access to a fenced backyard, full kitchen, smart TV, & WIFI. We expect guests to be courteous to neighbors. Parties & loud music are not permitted. **Not traveling with pets? Check out our ocean side condo near Northside Park!**

Sep. 18 – 25

$541 CAD per night

Guest favourite

Home in Ocean Pines

5.0 out of 5 average rating, 12 reviews

Ocean Pines MD Shady Rest Getaway

We Welcome you to Shady Rest Ocean Pines! My name is HC and I will be hosting you here at Shady Rest Ocean Pines along with my son Elijah. This property was our first family home and turning it into an Airbnb has allowed us to keep it in the family while sharing the tranquility that Ocean Pines has to offer to others. We hope you can create some memories here as we have as a family. Please enjoy your little Shady Rest Gateway! -From The Whaleys'

May 9 – 16

$187 CAD per night

Superhost

Home in Ocean Pines

4.88 out of 5 average rating, 115 reviews

Tortuga Cottage: Your All- Season Getaway

This is an escape to reacquaint with family, nature, and your best self. Come home from the beach just a few miles away to enjoy the gas fire place, outdoor fire pit, and hot tub on chilly nights, fenced in back yard. Take advantage of the parks indoor outdoor pools golf yacht club, just moments from the cottage. Dogs are part of our family, and we are happy to consider canine guests on a case by case basis. Please see policies for breeds.

Oct. 9 – 16

$377 CAD per night