
Pet-friendly holiday rentals in Assateague Island
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Top-rated pet-friendly home rentals in Assateague Island
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Stunning private waterfront suite
Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, 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. Park in the driveway and step into your own private escape!
PetsOutdoor spacesAir conditioning
4.95 out of 5 average rating, 424 reviews
Home Away from Home , Pet friendly retreat
Welcome to Ocean Pines Getaway, Enter home through a beautiful covered porch with swing for two and lovely seating area. This sweet home has 3 bedrooms & 2 full baths. A fully stocked kitchen , with eat in breakfast nook, Also proper dining room plenty of seating for family Cozy living room with working fireplace. All season sunroom plenty of seating, pub table & bar. Doggie door in sunroom large enough for 100 lb dog, leads to fenced in backyard. $100 pet fee and $125 linens & bath towels.
PetsWalkabilityTV
4.87 out of 5 average rating, 108 reviews
Walk to the Beach! PingPong-Fenced Yard-N64-Bikes!
Escape to the Blue House, a pet-friendly retreat just 6-mins to the beach. - Full kitchen and charcoal grill - Coffee bar (k-cups, espresso, coffee grinder, french press, and pour over) - Fully fenced patio with a fire pit and ping pong - Outdoor shower - 5 Bikes - Northside Park - 2 min walk away - N64 - 48W EV charger - Record player - Pet ramp Sleep 10 (8 Adults 2 Children) in our 3 bedrooms - 1 king, 1 queen, 1 full over full bunk bed, and full sofa bed. NOT POSTED ON C.LIST
WalkabilityOutdoor spacesLayout
4.99 out of 5 average rating, 101 reviews
Jay's Retreat: dock, kayaks, EV charger, bikes
Welcome to Jay’s Retreat, a charming waterfront oasis nestled in scenic Oyster Bay. This beachy 3-bedroom, 2-bathroom home accommodates up to 6 guests and is pet-friendly it an ideal space to vacation with your entire family. The spacious screened porch offers the perfect perch to savor your morning coffee with the sunrise or relax with friends and family while enjoying fresh, locally sourced seafood. End your days by the fire pit, soaking in the peaceful bay views and coastal breeze.
PetsOutdoor spacesBathroom
4.97 out of 5 average rating, 101 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!
WalkabilityPetsSleep quality
4.92 out of 5 average rating, 213 reviews
Sea Dunes King Suite, Exclusive Private Beach - DOG FRIENDLY!
Unwind and chill in this boho coastal inspired guest suite on the ocean side. At Sea Dunes' private guest king suite, the surf and sand are steps away. Get ready to pack your cooler and enjoy a day in the sun on this beautiful, private dog-friendly beach. Sea Dunes is located in Fenwick Island, DE and nestled between protected state nature parks. Just a short trip in the car to a marina with watersports, kayak adventures on the bay, local dining, farm markets and shopping.
WalkabilityPetsAccess
4.83 out of 5 average rating, 138 reviews
"Jolly"- Houseboat Getaway
"Tiny house on the water"! Jolly is a 42ft Holiday Mansion. Baywater Landing buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & deck areas to enjoy! 35 mins from Ocean City & Assateague Island. 45 mins from Chincoteague Island. Jolly remains docked, but guests have access to kayaks and paddle boards at no additional charge. Baywater Landing is secluded- some even say "boring"- but we think that's the whole point!
PetsOutdoor spacesKitchen
4.88 out of 5 average rating, 186 reviews
Cattail's Branch
Enjoy the lovely setting of this romantic spot in nature. Tiny house sits on Widow Hawkins Branch Creek and backs up to Johnson Wildlife Mtg Area. Great for bird watchers and nature lovers. Enjoy sitting by the fire pit or relaxing on spacious deck overlooking creek. Quiet and peaceful. Fully equipped kitchen, Queen bed, bathroom, pull out queen sofa bed with privacy wall to make 2rd bedroom. Close to beaches and town.
PetsOutdoor spacesLong stay
4.84 out of 5 average rating, 251 reviews
Rumbley Cottage on the Tangier Sound-Private Beach
September 12-16 available. Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. Many amenities: WE PROVIDE THE FIREWOOD AND STARTERS, kayaks, paddle boards, MB toiletries.
WalkabilityOutdoor spacesKitchen
4.99 out of 5 average rating, 266 reviews
2 Bedroom Apartment
Centrally located between Chincoteague Island and Ocean City, MD. This pet friendly two bedroom apartment which offers laundry and a spacious kitchen is only steps away from Shad Landing state park and Public Landing. This ground level guesthouse apartment is located 200 feet from our main house is on an over 12 acre partially wooded parcel. Plenty of privacy and room for boat trailer parking.
Outdoor spacesPetsValue
4.94 out of 5 average rating, 193 reviews
Bayfront Modern Retreat • Dock, Kayaks, Views
Wake up to shimmering Chincoteague Bay views in this modern waterfront escape on Virginia’s Eastern Shore. Spend mornings on the water, afternoons by the fire pit, and evenings under glowing sunsets. Kayaks, bikes, pools, golf, pickleball, and trails are moments away, with beaches a short drive. Bring the dog, unplug, and settle in. Your coastal reset starts here.
Outdoor spacesWalkabilityKitchen
4.91 out of 5 average rating, 135 reviews
Highbanks House
Forget your worries in this spacious and serene space. Welcome to your dream home! This stunning 5-bedroom, 3-full-bath rancher is nestled on over 6 acres of private land, offering a perfect blend of comfort and nature. Located just 6 miles from downtown Salisbury and 8 miles from Salisbury University, this property provides both tranquility and convenience.
WalkabilityPetsGetting around
4.83 out of 5 average rating, 181 reviewsPopular amenities for Assateague Island pet-friendly home rentals
Pet-friendly house rentals

Dolores by the Sea- Family Groups ONLY
PetsOutdoor spacesGetting around
4.97 out of 5 average rating, 109 reviews
Ocean Pines Retreat with Beach Club
Outdoor spacesWalkabilityIndoor spaces
4.99 out of 5 average rating, 140 reviews
Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
PetsWalkabilityCheckout
4.93 out of 5 average rating, 290 reviews
Mins to Beach~Walk to Food and Drinks +Beach Gear!
WalkabilityPetsAccuracy
4.99 out of 5 average rating, 149 reviews
Rest A'Shored charming Chincoteague getaway
PetsOutdoor spacesValue
4.92 out of 5 average rating, 221 reviews
Forest Grove Retreat
PetsOutdoor spacesBathroom
4.88 out of 5 average rating, 198 reviews
Escape To A “True” Chesapeake Waterfront Property!
Outdoor spacesPetsCondition
4.88 out of 5 average rating, 102 reviews
Stella
Outdoor spacesWalkabilityComfort
4.9 out of 5 average rating, 145 reviewsPet-friendly home rentals with a pool

Bayside Townhouse w/ amazing amenities
WalkabilityOutdoor spacesHospitality
4.93 out of 5 average rating, 122 reviews
Farmhouse located on a horse farm
PetsWalkabilitySleep quality
4.95 out of 5 average rating, 124 reviews
Beautiful waterview 2B condo w/Dock&Close to Beach
Outdoor spacesWalkabilitySleep quality
5.0 out of 5 average rating, 123 reviews
Berlin Beach House, near Ocean City & Assateague!
Outdoor spacesPetsWifi
4.83 out of 5 average rating, 109 reviews
Direct Oceanfront Newly Renovated W/ Pool 2 Bd
WalkabilityOutdoor spacesCondition
4.99 out of 5 average rating, 107 reviews
Nature's retreat @ the Bug-a-Boo. Beaches nearby
WalkabilityOutdoor spacesAir conditioning
4.81 out of 5 average rating, 169 reviews
3 BR Waterfront Home, Minutes to the Beach
PetsWalkabilityView
4.93 out of 5 average rating, 152 reviews
Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.
Outdoor spacesPetsPool
4.97 out of 5 average rating, 162 reviewsPrivate, pet-friendly home rentals

Hobbs & Rose | A Peaceful Cottage Escape
PetsWalkabilityHiking
5.0 out of 5 average rating, 258 reviews
Uncle Buck's Cottage
Outdoor spacesWalkabilityKitchen
4.91 out of 5 average rating, 109 reviews
Summer's Seaside Cottage | Near Ponies & Beach
Outdoor spacesPetsLaundry
4.95 out of 5 average rating, 195 reviews
Little Red House on a Rural Farm for Stargazing
PetsOutdoor spacesQuiet
4.94 out of 5 average rating, 542 reviews
One Bedroom Beachfront Apartment Mid-Town
WalkabilityPetsWifi
4.9 out of 5 average rating, 137 reviews
New house, Bay views, 4 Beds, Game room
PetsOutdoor spacesFamily
5.0 out of 5 average rating, 25 reviews
Hot Tub. Fire pit. Fenced Yard. Games. Downtown.
Outdoor spacesPetsAccess
4.98 out of 5 average rating, 57 reviews
Captain's Loft
PetsOutdoor spacesParking
5.0 out of 5 average rating, 17 reviewsDestinations to explore
- Rentals with pools Assateague Island
- Waterfront rentals Assateague Island
- House rentals Assateague Island
- Beachfront rentals Assateague Island
- Rentals with a kayak Assateague Island
- Family-friendly rentals Assateague Island
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- Apartment rentals Assateague Island
- Rentals with beach access Assateague Island
- Pet-friendly rentals United States





