We offer services for vacation rental owners who need assistance managing the details of their rental business. From websites, marketing, housekeeping, and emergency services - we can help you rent with confidence and peace of mind. As a property owner, or potential property owner, you’ve obviously fallen in love with the beach, just as we have. Seaside Vacations was founded with the belief that there was a better way to provide outstanding service, implement market leading technology, and provide the very best Eastern Shore Vacation experience possible all while providing value to both our Partners and Guests.

Are you all about ponies in paradise? If so, you will love comfy and cozy ‘Pony Paradise’ in the very heart of Chincoteague Island! Formerly ever-popular ‘Sunshine and Daydreams’, this Seaside Vacations’ fan-favorite is under New Ownership, and y’all are going to LOVE what they’ve done with the place! This adorable 3 Bedroom/2 Full Bath Cottage is located on Willow Street, just across from where our famous Wild Ponies are penned at the Carnival Grounds. Stroll to the Carnival weekends in July, the Historic Downtown District to shops and dining, or just skip across the street with your morning coffee to watch the ponies graze. What makes vacationing at Pony Paradise even more fun? You get to bring your favorite pup along with no additional fee (Limit 2)! Your pup will especially appreciate the Fully Fenced-in Yard - you can just open the door and they have freedom to play safely in the yard! Pony Paradise has packed a lot of bang into your vacation buck. As you enter through the Screened Front Porch, you’re already thinking you’ll never want to leave. Just imagine curling up here with a good book and taking in that salty, sweet bay bay breeze. Watch the Ponies grazing just across the Street, and you can even enjoy your 4th of July Fireworks right from your Screened Porch! Upon entering Pony Paradise, you’ll be warmly welcomed by serene Colors of Sand and Sea - just breathtaking. With gorgeous flooring reminiscent of a stroll on the Boardwalk and bright and beachy furnishings, you may never want to leave. There’s even a cozy Fireplace for those chilly off-season stays - one of our very favorite times on our Island. You’ll love relaxing after a fun-filled day exploring Assateague in the Living Area with Free WiFi and Flat Screen Apple Streaming TV. There’s plenty of room for all to stretch out, yet still be together. The Chef in your family will love the spacious Eat-in Kitchen with both a Breakfast Bar and Dining Table. Well-stocked with all you need - e...