Ocean City Rentals - Flex Stay Homes

Ocean City Flex Stay Rentals

OCMD Weekend & Short Stay Vacations

Here at Seaside Vacations, we understand how busy life is and that you can't always get away for a full week. That's what we LOVE about our Flex Stay Program ~ Arrive when you want, depart when you want, the world is your Oyster!

The homes in our Flex Stay Program have either a 2 or 3 night minimum all year long, not just the Off-Season! Take a weekend getaway to OCMD or stay a few days longer. Whatever your needs or requirements, we have the OCMD rental for you. As always, we're standing by ready to help you find just the right home for your next Beach Break!

Browse these amazing Ocean City Rentals with Flexible Stays so you can check-in on your schedule and not by a schedule set for you. Search and book online today!


Properties Available 158 properties available
When you walk into this first floor condo, it welcomes you right in with its clean and updated, yet still timeless Ocean City Beach House feel. You will enter the home and fall in love with the thoughtful beach decor and open layout of the Living Room, Kitchen and Dining Area - make the most of quality time while relaxing in the Air Conditioning t
Hot HOT 7
The Beach House on 9th St #3
Condominium
$125 - $650 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 9 guests
Tucked back in the quiet North Ocean City neighborhood of Caine Woods is a simply decadent home we call Sea Captain. This much loved 5 Bedroom, 4.5 Bath home with a garage is exactly the perfect space for the family, or families, looking to experience Ocean City, the beach and all our great town has to offer, while still being able to settle in and
Hot HOT 43
Sea Captain
House
$300 - $2,438 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 15 guests
You and your family work hard all year long. Don’t you think you all deserve some time to relax and rejuvenate with some fun in the sun? There’s no better place to connect than Ocean City, and no better place to stay than the fabulous Sea Watch 410 on 115th St.! The Sea Watch is one of the largest condominium buildings in Ocean City, and its amenit
Hot HOT 101
Sea Watch 410
Condominium
$160 - $550 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Golden Sands 1810 - Sky above, Sand below, Peace within! Golden Sands 1810 has everything you need to make precious family memories year after year! *This Property is available for 3 Night minimum during Season*The family-friendly Golden Sands Building is located in the heart of Ocean City, and its Amenities are nothing short of amazing! Featuring
Hot HOT 27
Golden Sands 1810
Condominium
$129 - $970 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Has the hustle and bustle of everyday life gotten to be a boring routine? Are you missing spending that ever important quality time with the ones that matter most? If you’re like the rest of us, it’s easy to fall into those routines and forget to take the time to appreciate what is truly important. Take time to enjoy what you work so hard for each
Hot HOT 26
Golden Sands 211
Condominium
$110 - $665 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Belmont Townhouse 8 - When the warm grains of sand touch our hearts, we know we are in the right place.Bask in Luxury and Style while making treasured Family Memories from the moment you walk in the door of gorgeous Belmont Townhouse 8. This 3 Level Belmont Townhouse, perfectly located in the upscale Belmont Towers, sits right on the Ocean City Boa
Hot HOT 36
Belmont Towers Townhouse 8
Town House
$415 - $1,350 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 12 guests
Is there anything quite like a family Vacation at the Beach?! From watching the Sunrise over the Ocean, to simply listening to the waves crash on the Beach, it's truly what we call paradise. If this is what you're yearning for, Royal Hawaiian 414 is the place for you. This stunning 2 Bedroom/2 Bath Condo is located in the heart of North OCMD on 142
Hot HOT 9
Royal Hawaiian 414
Condominium
$110 - $856 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 7 guests
We travel not to escape Life, but so Life doesn't escape YOU. Isn't it time to relax, rejuvenate, and reconnect with those who matter most? Make the time, because we've got the place! Welcome to Wight Bay 441 - a gorgeous Bay View Condo in the heart of Ocean City. Wight Bay is a fabulous Complex that not only offers a Bay Front Pool, but there is a
Hot HOT 37
Wight Bay 441
Condominium
$125 - $450 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Give me the Sun and the Sea, and a little spot to be…….Welcome to Cab”ANNA Bay at Tiburon 5C - isn’t it time to pull yourself away from the daily grind for a little Beach Break? Make the time, because we’ve got the place! Welcome to family-friendly and affordable Tiburon 5C in OCMD! This adorable condo is located in quiet North Ocean City - away fr
Hot HOT 26
Cab"ANNA" Bay at Tiburon 5C
Condominium
$105 - $375 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 7 guests
Sea Watch 119 - Life is Always Better at the Beach!Have you been dreaming of a beach getaway in a location that won't break the budget? Your search is over - say hello to Sea Watch 119 - in a wonderful, secure, and timeless family community right on the beach, yet still close to everything Ocean City has to offer! The Sea Watch is one of the larges
Hot HOT 106
Sea Watch 119
Condominium
$150 - $500 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Golden Sands 1812 - The best memories are made in Flip-Flops!The family-friendly Golden Sands Building is located in the heart of Ocean City, and its Amenities are nothing short of amazing! Featuring a Penthouse Level Indoor Pool and Fitness Center, as well as a seasonal Recreation Deck with Outdoor Pool, Children’s Pool, Tiki Bar and Grill and eve
Hot HOT 35
Golden Sands 1812
Condominium
$125 - $886 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Has the hustle and bustle of everyday life gotten you into a boring routine? Are you spending that ever important quality time with the ones that matter most? If you’re like the rest of us, it’s easy to fall into those routines and forget to take the time to appreciate what is truly important. Take time to enjoy what you work so hard for each year.
Hot HOT 18
Golden Sands 1108
Condominium
$150 - $585 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests

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